MiMeDB: Showing metabocard for 5,6,7,8-Tetrahydrofolic acid (MMDBc0033003)

Not Available

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-19 04:30:44 UTC

Update Date

2024-10-13 10:55:44 UTC

Metabolite ID

MMDBc0033003

Metabolite Identification

Common Name

5,6,7,8-Tetrahydrofolic acid

Description

5,6,7,8-Tetrahydrofolic acid is a soluble coenzyme (vitamin B9) that is synthesized de novo by plants and microorganisms, and absorbed from the diet by animals. It is composed of three distinct parts: a pterin ring, a p-ABA (p-aminobenzoic acid) and a polyglutamate chain with a number of residues varying between 1 and 8. Only the tetra-reduced form of the molecule serves as a coenzyme for C1 transfer reactions. In biological systems, the C1-units exist under various oxidation states and the different tetrahydrofolate derivatives constitute a family of related molecules named indistinctly under the generic term folate. (PMID 16042593 ). Folate is important for cells and tissues that rapidly divide. Cancer cells divide rapidly, and drugs that interfere with folate metabolism are used to treat cancer. Methotrexate is a drug often used to treat cancer because it inhibits the production of the active form, tetrahydrofolate. Unfortunately, methotrexate can be toxic, producing side effects such as inflammation in the digestive tract that make it difficult to eat normally. -- Wikipedia ; Signs of folic acid deficiency are often subtle. Diarrhea, loss of appetite, and weight loss can occur. Additional signs are weakness, sore tongue, headaches, heart palpitations, irritability, and behavioral disorders. Women with folate deficiency who become pregnant are more likely to give birth to low birth weight and premature infants, and infants with neural tube defects. In adults, anemia is a sign of advanced folate deficiency. In infants and children, folate deficiency can slow growth rate. Some of these symptoms can also result from a variety of medical conditions other than folate deficiency. It is important to have a physician evaluate these symptoms so that appropriate medical care can be given. -- Wikipedia ; Folinic acid is a form of folate that can help 'rescue' or reverse the toxic effects of methotrexate. Folinic acid is not the same as folic acid. Folic acid supplements have little established role in cancer chemotherapy. There have been cases of severe adverse effects of accidental substitution of folic acid for folinic acid in patients receiving methotrexate cancer chemotherapy. It is important for anyone receiving methotrexate to follow medical advice on the use of folic or folinic acid supplements. -- Wikipedia . Low concentrations of folate, vitamin B12, or vitamin B6 may increase the level of homocysteine, an amino acid normally found in blood. There is evidence that an elevated homocysteine level is an independent risk factor for heart disease and stroke. The evidence suggests that high levels of homocysteine may damage coronary arteries or make it easier for blood clotting cells called platelets to clump together and form a clot. However, there is currently no evidence available to suggest that lowering homocysteine with vitamins will reduce your risk of heart disease. Clinical intervention trials are needed to determine whether supplementation with folic acid, vitamin B12 or vitamin B6 can lower your risk of developing coronary heart disease. -- Wikipedia .

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

116
  Mrv0541 02231214272D          

 32 34  0  0  1  0            999 V2000
    3.5220   -0.2143    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.9988    1.0569    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.8598    0.2429    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.1501   -0.9974    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.8502    2.7179    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.4213    2.7124    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9740   -1.0107    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.9740   -2.7179    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.1504   -1.4292    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5220   -2.6894    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8075   -1.4518    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.7180   -0.1779    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0930   -2.6894    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.7214   -1.4347    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7214   -2.2940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4343   -1.0194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2364   -1.4518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2364   -2.2769    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8633   -1.0139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5220   -1.0393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8075   -2.2769    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4309    0.2374    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   11.4277    1.0624    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5793   -1.4236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8601   -0.1888    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2890   -0.1834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2922   -1.0084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5730    0.2264    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1406    1.4777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0019    0.2319    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1469   -0.1723    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1374    2.3027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 20  2  0  0  0  0
  2 30  2  0  0  0  0
  3 31  1  0  0  0  0
  4 31  2  0  0  0  0
  5 32  1  0  0  0  0
  6 32  2  0  0  0  0
  7 14  1  0  0  0  0
  7 17  1  0  0  0  0
  8 15  1  0  0  0  0
  8 18  1  0  0  0  0
  9 16  1  0  0  0  0
  9 19  1  0  0  0  0
 10 18  1  0  0  0  0
 10 21  1  0  0  0  0
 11 20  1  0  0  0  0
 11 21  2  0  0  0  0
 22 12  1  1  0  0  0
 12 30  1  0  0  0  0
 13 21  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
 17 18  2  0  0  0  0
 17 20  1  0  0  0  0
 19 24  2  0  0  0  0
 19 25  1  0  0  0  0
 22 23  1  0  0  0  0
 22 31  1  0  0  0  0
 23 29  1  0  0  0  0
 24 27  1  0  0  0  0
 25 28  2  0  0  0  0
 26 27  2  0  0  0  0
 26 28  1  0  0  0  0
 26 30  1  0  0  0  0
 29 32  1  0  0  0  0
M  END

HMDB0304496
     RDKit          3D
tetrahydrofolate
 55 57  0  0  0  0  0  0  0  0999 V2000
   -8.6290    2.7660   -1.1563 N   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5953    1.8909   -0.7048 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5145    1.5946    0.6040 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5548    0.7805    1.0439 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4430    0.4736    2.2773 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6721    0.2701    0.1171 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7441    0.5657   -1.2262 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7257    1.3899   -1.6274 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7852   -0.0150   -2.1109 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8721   -1.0715   -1.7232 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4826   -0.8790   -0.2678 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8186   -2.1088    0.2552 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6315   -2.3946   -0.4949 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5039   -1.5440   -0.3867 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5771   -1.6852   -1.2624 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6704   -0.8714   -1.1353 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7779    0.1077   -0.1718 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0002    0.9382   -0.0671 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8248    2.1772   -0.0505 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2477    0.3112    0.0082 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.4713    1.0755    0.1046 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.9665    1.0340    1.5079 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2696   -0.2970    2.0819 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3253   -1.0109    1.3488 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0890   -1.8692    0.4943 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.6701   -0.7193    1.6164 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4197    0.6876   -0.9281 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0912   -0.1743   -1.7881 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6812    1.2156   -1.0262 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7164    0.2499    0.6908 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4104   -0.5689    0.5822 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6481   -0.5857    0.5484 N   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4023    3.4768   -1.8601 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.6148    2.6858   -0.7739 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7959    1.6232   -2.6270 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7385    0.3410   -3.0938 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9334   -0.9160   -2.3219 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2340   -2.0740   -1.9531 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8665    0.0377   -0.2577 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5327   -1.9865    1.3406 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5239   -2.9872    0.2616 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5787   -3.2219   -1.1242 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5431   -2.4379   -2.0371 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5398   -0.9565   -1.8089 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3154   -0.7264   -0.0045 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1463    2.1532   -0.1042 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1397    1.4932    2.1367 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8191    1.7509    1.6801 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3601   -0.9699    2.0277 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6209   -0.2289    3.1423 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.3453   -0.5561    0.9030 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8015    2.2068   -1.1170 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7577    1.0148    1.4733 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2227   -0.4274    1.3008 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7130   -1.0283    1.4791 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  2  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  2  0
 24 26  1  0
 21 27  1  0
 27 28  2  0
 27 29  1  0
 17 30  1  0
 30 31  2  0
 11 32  1  0
  8  2  1  0
 31 14  1  0
 32  6  1  0
  1 33  1  0
  1 34  1  0
  8 35  1  0
  9 36  1  0
 10 37  1  0
 10 38  1  0
 11 39  1  0
 12 40  1  0
 12 41  1  0
 13 42  1  0
 15 43  1  0
 16 44  1  0
 20 45  1  0
 21 46  1  6
 22 47  1  0
 22 48  1  0
 23 49  1  0
 23 50  1  0
 26 51  1  0
 29 52  1  0
 30 53  1  0
 31 54  1  0
 32 55  1  0
M  END

116
  Mrv0541 02231214272D          

 32 34  0  0  1  0            999 V2000
    3.5220   -0.2143    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.9988    1.0569    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.8598    0.2429    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.1501   -0.9974    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.8502    2.7179    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.4213    2.7124    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9740   -1.0107    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.9740   -2.7179    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.1504   -1.4292    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5220   -2.6894    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8075   -1.4518    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.7180   -0.1779    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0930   -2.6894    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.7214   -1.4347    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7214   -2.2940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4343   -1.0194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2364   -1.4518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2364   -2.2769    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8633   -1.0139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5220   -1.0393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8075   -2.2769    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4309    0.2374    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   11.4277    1.0624    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5793   -1.4236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8601   -0.1888    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2890   -0.1834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2922   -1.0084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5730    0.2264    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1406    1.4777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0019    0.2319    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1469   -0.1723    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1374    2.3027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 20  2  0  0  0  0
  2 30  2  0  0  0  0
  3 31  1  0  0  0  0
  4 31  2  0  0  0  0
  5 32  1  0  0  0  0
  6 32  2  0  0  0  0
  7 14  1  0  0  0  0
  7 17  1  0  0  0  0
  8 15  1  0  0  0  0
  8 18  1  0  0  0  0
  9 16  1  0  0  0  0
  9 19  1  0  0  0  0
 10 18  1  0  0  0  0
 10 21  1  0  0  0  0
 11 20  1  0  0  0  0
 11 21  2  0  0  0  0
 22 12  1  1  0  0  0
 12 30  1  0  0  0  0
 13 21  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
 17 18  2  0  0  0  0
 17 20  1  0  0  0  0
 19 24  2  0  0  0  0
 19 25  1  0  0  0  0
 22 23  1  0  0  0  0
 22 31  1  0  0  0  0
 23 29  1  0  0  0  0
 24 27  1  0  0  0  0
 25 28  2  0  0  0  0
 26 27  2  0  0  0  0
 26 28  1  0  0  0  0
 26 30  1  0  0  0  0
 29 32  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0033003

> <DATABASE_NAME>
MIME

> <SMILES>
NC1=NC(=O)C2=C(NCC(CNC3=CC=C(C=C3)C(=O)N[C@@H](CCC(O)=O)C(O)=O)N2)N1

> <INCHI_IDENTIFIER>
InChI=1S/C19H23N7O6/c20-19-25-15-14(17(30)26-19)23-11(8-22-15)7-21-10-3-1-9(2-4-10)16(29)24-12(18(31)32)5-6-13(27)28/h1-4,11-12,21,23H,5-8H2,(H,24,29)(H,27,28)(H,31,32)(H4,20,22,25,26,30)/t11?,12-/m0/s1

> <INCHI_KEY>
MSTNYGQPCMXVAQ-KIYNQFGBSA-N

> <FORMULA>
C19H23N7O6

> <MOLECULAR_WEIGHT>
445.4292

> <EXACT_MASS>
445.170981503

> <JCHEM_ACCEPTOR_COUNT>
12

> <JCHEM_AVERAGE_POLARIZABILITY>
42.9531289011855

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
8

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S)-2-[(4-{[(2-amino-4-oxo-1,4,5,6,7,8-hexahydropteridin-6-yl)methyl]amino}phenyl)formamido]pentanedioic acid

> <ALOGPS_LOGP>
-0.96

> <JCHEM_LOGP>
-4.212630310185438

> <ALOGPS_LOGS>
-3.22

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
3.863700981959142

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.5095693878577654

> <JCHEM_PKA_STRONGEST_BASIC>
3.5846826310688993

> <JCHEM_POLAR_SURFACE_AREA>
207.27000000000004

> <JCHEM_REFRACTIVITY>
121.3866

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.69e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
tetrahydrofolic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0304496
     RDKit          3D
tetrahydrofolate
 55 57  0  0  0  0  0  0  0  0999 V2000
   -8.6290    2.7660   -1.1563 N   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5953    1.8909   -0.7048 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5145    1.5946    0.6040 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5548    0.7805    1.0439 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4430    0.4736    2.2773 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6721    0.2701    0.1171 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7441    0.5657   -1.2262 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7257    1.3899   -1.6274 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7852   -0.0150   -2.1109 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8721   -1.0715   -1.7232 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4826   -0.8790   -0.2678 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8186   -2.1088    0.2552 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6315   -2.3946   -0.4949 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5039   -1.5440   -0.3867 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5771   -1.6852   -1.2624 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6704   -0.8714   -1.1353 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7779    0.1077   -0.1718 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0002    0.9382   -0.0671 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8248    2.1772   -0.0505 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2477    0.3112    0.0082 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.4713    1.0755    0.1046 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.9665    1.0340    1.5079 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2696   -0.2970    2.0819 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3253   -1.0109    1.3488 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0890   -1.8692    0.4943 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.6701   -0.7193    1.6164 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4197    0.6876   -0.9281 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0912   -0.1743   -1.7881 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6812    1.2156   -1.0262 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7164    0.2499    0.6908 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4104   -0.5689    0.5822 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6481   -0.5857    0.5484 N   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4023    3.4768   -1.8601 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.6148    2.6858   -0.7739 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7959    1.6232   -2.6270 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7385    0.3410   -3.0938 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9334   -0.9160   -2.3219 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2340   -2.0740   -1.9531 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8665    0.0377   -0.2577 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5327   -1.9865    1.3406 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5239   -2.9872    0.2616 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5787   -3.2219   -1.1242 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5431   -2.4379   -2.0371 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5398   -0.9565   -1.8089 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3154   -0.7264   -0.0045 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1463    2.1532   -0.1042 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1397    1.4932    2.1367 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8191    1.7509    1.6801 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3601   -0.9699    2.0277 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6209   -0.2289    3.1423 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.3453   -0.5561    0.9030 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8015    2.2068   -1.1170 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7577    1.0148    1.4733 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2227   -0.4274    1.3008 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7130   -1.0283    1.4791 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  2  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  2  0
 24 26  1  0
 21 27  1  0
 27 28  2  0
 27 29  1  0
 17 30  1  0
 30 31  2  0
 11 32  1  0
  8  2  1  0
 31 14  1  0
 32  6  1  0
  1 33  1  0
  1 34  1  0
  8 35  1  0
  9 36  1  0
 10 37  1  0
 10 38  1  0
 11 39  1  0
 12 40  1  0
 12 41  1  0
 13 42  1  0
 15 43  1  0
 16 44  1  0
 20 45  1  0
 21 46  1  6
 22 47  1  0
 22 48  1  0
 23 49  1  0
 23 50  1  0
 26 51  1  0
 29 52  1  0
 30 53  1  0
 31 54  1  0
 32 55  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 116                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0       6.574  -0.400   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      18.664   1.973   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      24.005   0.453   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      22.680  -1.862   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0      23.987   5.073   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0      21.320   5.063   0.000  0.00  0.00           O+0
HETATM    7  N   UNK     0       9.285  -1.887   0.000  0.00  0.00           N+0
HETATM    8  N   UNK     0       9.285  -5.073   0.000  0.00  0.00           N+0
HETATM    9  N   UNK     0      13.347  -2.668   0.000  0.00  0.00           N+0
HETATM   10  N   UNK     0       6.574  -5.020   0.000  0.00  0.00           N+0
HETATM   11  N   UNK     0       5.241  -2.710   0.000  0.00  0.00           N+0
HETATM   12  N   UNK     0      20.007  -0.332   0.000  0.00  0.00           N+0
HETATM   13  N   UNK     0       3.907  -5.020   0.000  0.00  0.00           N+0
HETATM   14  C   UNK     0      10.680  -2.678   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      10.680  -4.282   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      12.011  -1.903   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       7.908  -2.710   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       7.908  -4.250   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      14.678  -1.893   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.574  -1.940   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       5.241  -4.250   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      21.338   0.443   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      21.332   1.983   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      16.015  -2.657   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      14.672  -0.352   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      17.339  -0.342   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      17.345  -1.882   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      16.003   0.423   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      22.662   2.758   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      18.670   0.433   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      22.674  -0.322   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      22.656   4.298   0.000  0.00  0.00           C+0
CONECT    1   20                                                            
CONECT    2   30                                                            
CONECT    3   31                                                            
CONECT    4   31                                                            
CONECT    5   32                                                            
CONECT    6   32                                                            
CONECT    7   14   17                                                       
CONECT    8   15   18                                                       
CONECT    9   16   19                                                       
CONECT   10   18   21                                                       
CONECT   11   20   21                                                       
CONECT   12   22   30                                                       
CONECT   13   21                                                            
CONECT   14    7   15   16                                                  
CONECT   15    8   14                                                       
CONECT   16    9   14                                                       
CONECT   17    7   18   20                                                  
CONECT   18    8   10   17                                                  
CONECT   19    9   24   25                                                  
CONECT   20    1   11   17                                                  
CONECT   21   10   11   13                                                  
CONECT   22   12   23   31                                                  
CONECT   23   22   29                                                       
CONECT   24   19   27                                                       
CONECT   25   19   28                                                       
CONECT   26   27   28   30                                                  
CONECT   27   24   26                                                       
CONECT   28   25   26                                                       
CONECT   29   23   32                                                       
CONECT   30    2   12   26                                                  
CONECT   31    3    4   22                                                  
CONECT   32    5    6   29                                                  
MASTER        0    0    0    0    0    0    0    0   32    0   68    0
END

COMPND    HMDB0304496
HETATM    1  N1  UNL     1      -8.629   2.766  -1.156  1.00  0.00           N  
HETATM    2  C1  UNL     1      -7.595   1.891  -0.705  1.00  0.00           C  
HETATM    3  N2  UNL     1      -7.514   1.595   0.604  1.00  0.00           N  
HETATM    4  C2  UNL     1      -6.555   0.780   1.044  1.00  0.00           C  
HETATM    5  O1  UNL     1      -6.443   0.474   2.277  1.00  0.00           O  
HETATM    6  C3  UNL     1      -5.672   0.270   0.117  1.00  0.00           C  
HETATM    7  C4  UNL     1      -5.744   0.566  -1.226  1.00  0.00           C  
HETATM    8  N3  UNL     1      -6.726   1.390  -1.627  1.00  0.00           N  
HETATM    9  N4  UNL     1      -4.785  -0.015  -2.111  1.00  0.00           N  
HETATM   10  C5  UNL     1      -3.872  -1.071  -1.723  1.00  0.00           C  
HETATM   11  C6  UNL     1      -3.483  -0.879  -0.268  1.00  0.00           C  
HETATM   12  C7  UNL     1      -2.819  -2.109   0.255  1.00  0.00           C  
HETATM   13  N5  UNL     1      -1.632  -2.395  -0.495  1.00  0.00           N  
HETATM   14  C8  UNL     1      -0.504  -1.544  -0.387  1.00  0.00           C  
HETATM   15  C9  UNL     1       0.577  -1.685  -1.262  1.00  0.00           C  
HETATM   16  C10 UNL     1       1.670  -0.871  -1.135  1.00  0.00           C  
HETATM   17  C11 UNL     1       1.778   0.108  -0.172  1.00  0.00           C  
HETATM   18  C12 UNL     1       3.000   0.938  -0.067  1.00  0.00           C  
HETATM   19  O2  UNL     1       2.825   2.177  -0.050  1.00  0.00           O  
HETATM   20  N6  UNL     1       4.248   0.311   0.008  1.00  0.00           N  
HETATM   21  C13 UNL     1       5.471   1.075   0.105  1.00  0.00           C  
HETATM   22  C14 UNL     1       5.966   1.034   1.508  1.00  0.00           C  
HETATM   23  C15 UNL     1       6.270  -0.297   2.082  1.00  0.00           C  
HETATM   24  C16 UNL     1       7.325  -1.011   1.349  1.00  0.00           C  
HETATM   25  O3  UNL     1       7.089  -1.869   0.494  1.00  0.00           O  
HETATM   26  O4  UNL     1       8.670  -0.719   1.616  1.00  0.00           O  
HETATM   27  C17 UNL     1       6.420   0.688  -0.928  1.00  0.00           C  
HETATM   28  O5  UNL     1       6.091  -0.174  -1.788  1.00  0.00           O  
HETATM   29  O6  UNL     1       7.681   1.216  -1.026  1.00  0.00           O  
HETATM   30  C18 UNL     1       0.716   0.250   0.691  1.00  0.00           C  
HETATM   31  C19 UNL     1      -0.410  -0.569   0.582  1.00  0.00           C  
HETATM   32  N7  UNL     1      -4.648  -0.586   0.548  1.00  0.00           N  
HETATM   33  H1  UNL     1      -8.402   3.477  -1.860  1.00  0.00           H  
HETATM   34  H2  UNL     1      -9.615   2.686  -0.774  1.00  0.00           H  
HETATM   35  H3  UNL     1      -6.796   1.623  -2.627  1.00  0.00           H  
HETATM   36  H4  UNL     1      -4.738   0.341  -3.094  1.00  0.00           H  
HETATM   37  H5  UNL     1      -2.933  -0.916  -2.322  1.00  0.00           H  
HETATM   38  H6  UNL     1      -4.234  -2.074  -1.953  1.00  0.00           H  
HETATM   39  H7  UNL     1      -2.866   0.038  -0.258  1.00  0.00           H  
HETATM   40  H8  UNL     1      -2.533  -1.986   1.341  1.00  0.00           H  
HETATM   41  H9  UNL     1      -3.524  -2.987   0.262  1.00  0.00           H  
HETATM   42  H10 UNL     1      -1.579  -3.222  -1.124  1.00  0.00           H  
HETATM   43  H11 UNL     1       0.543  -2.438  -2.037  1.00  0.00           H  
HETATM   44  H12 UNL     1       2.540  -0.956  -1.809  1.00  0.00           H  
HETATM   45  H13 UNL     1       4.315  -0.726  -0.004  1.00  0.00           H  
HETATM   46  H14 UNL     1       5.146   2.153  -0.104  1.00  0.00           H  
HETATM   47  H15 UNL     1       5.140   1.493   2.137  1.00  0.00           H  
HETATM   48  H16 UNL     1       6.819   1.751   1.680  1.00  0.00           H  
HETATM   49  H17 UNL     1       5.360  -0.970   2.028  1.00  0.00           H  
HETATM   50  H18 UNL     1       6.621  -0.229   3.142  1.00  0.00           H  
HETATM   51  H19 UNL     1       9.345  -0.556   0.903  1.00  0.00           H  
HETATM   52  H20 UNL     1       7.801   2.207  -1.117  1.00  0.00           H  
HETATM   53  H21 UNL     1       0.758   1.015   1.473  1.00  0.00           H  
HETATM   54  H22 UNL     1      -1.223  -0.427   1.301  1.00  0.00           H  
HETATM   55  H23 UNL     1      -4.713  -1.028   1.479  1.00  0.00           H  
CONECT    1    2   33   34
CONECT    2    3    3    8
CONECT    3    4
CONECT    4    5    5    6
CONECT    6    7    7   32
CONECT    7    8    9
CONECT    8   35
CONECT    9   10   36
CONECT   10   11   37   38
CONECT   11   12   32   39
CONECT   12   13   40   41
CONECT   13   14   42
CONECT   14   15   15   31
CONECT   15   16   43
CONECT   16   17   17   44
CONECT   17   18   30
CONECT   18   19   19   20
CONECT   20   21   45
CONECT   21   22   27   46
CONECT   22   23   47   48
CONECT   23   24   49   50
CONECT   24   25   25   26
CONECT   26   51
CONECT   27   28   28   29
CONECT   29   52
CONECT   30   31   31   53
CONECT   31   54
CONECT   32   55
END

HMDB0304496
     RDKit          3D
tetrahydrofolate
 55 57  0  0  0  0  0  0  0  0999 V2000
   -8.6290    2.7660   -1.1563 N   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5953    1.8909   -0.7048 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5145    1.5946    0.6040 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5548    0.7805    1.0439 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4430    0.4736    2.2773 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6721    0.2701    0.1171 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7441    0.5657   -1.2262 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7257    1.3899   -1.6274 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7852   -0.0150   -2.1109 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8721   -1.0715   -1.7232 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4826   -0.8790   -0.2678 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8186   -2.1088    0.2552 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6315   -2.3946   -0.4949 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5039   -1.5440   -0.3867 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5771   -1.6852   -1.2624 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6704   -0.8714   -1.1353 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7779    0.1077   -0.1718 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0002    0.9382   -0.0671 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8248    2.1772   -0.0505 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2477    0.3112    0.0082 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.4713    1.0755    0.1046 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.9665    1.0340    1.5079 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2696   -0.2970    2.0819 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3253   -1.0109    1.3488 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0890   -1.8692    0.4943 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.6701   -0.7193    1.6164 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4197    0.6876   -0.9281 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0912   -0.1743   -1.7881 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6812    1.2156   -1.0262 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7164    0.2499    0.6908 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4104   -0.5689    0.5822 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6481   -0.5857    0.5484 N   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4023    3.4768   -1.8601 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.6148    2.6858   -0.7739 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7959    1.6232   -2.6270 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7385    0.3410   -3.0938 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9334   -0.9160   -2.3219 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2340   -2.0740   -1.9531 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8665    0.0377   -0.2577 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5327   -1.9865    1.3406 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5239   -2.9872    0.2616 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5787   -3.2219   -1.1242 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5431   -2.4379   -2.0371 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5398   -0.9565   -1.8089 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3154   -0.7264   -0.0045 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1463    2.1532   -0.1042 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1397    1.4932    2.1367 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8191    1.7509    1.6801 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3601   -0.9699    2.0277 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6209   -0.2289    3.1423 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.3453   -0.5561    0.9030 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8015    2.2068   -1.1170 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7577    1.0148    1.4733 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2227   -0.4274    1.3008 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7130   -1.0283    1.4791 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  2  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  2  0
 24 26  1  0
 21 27  1  0
 27 28  2  0
 27 29  1  0
 17 30  1  0
 30 31  2  0
 11 32  1  0
  8  2  1  0
 31 14  1  0
 32  6  1  0
  1 33  1  0
  1 34  1  0
  8 35  1  0
  9 36  1  0
 10 37  1  0
 10 38  1  0
 11 39  1  0
 12 40  1  0
 12 41  1  0
 13 42  1  0
 15 43  1  0
 16 44  1  0
 20 45  1  0
 21 46  1  6
 22 47  1  0
 22 48  1  0
 23 49  1  0
 23 50  1  0
 26 51  1  0
 29 52  1  0
 30 53  1  0
 31 54  1  0
 32 55  1  0
M  END

Synonyms

Value	Source
(6S)-Tetrahydrofolate	ChEBI
(6S)-Tetrahydrofolic acid	ChEBI
(6S)-THFA	ChEBI
5,6,7,8-Tetrahydrofolate	ChEBI
Tetrahydrofolate	ChEBI
THF	ChEBI
5,6,7,8-Tetrahydrofolic acid	Generator
5,6,7,8-Tetrahydrofolic acid, (D-(-))-isomer	MeSH
5,6,7,8-Tetrahydrofolic acid, (L)-isomer	MeSH
5,6,7,8-Tetrahydrofolic acid, ion (2-)-isomer	MeSH
Tetrahydropteroylglutamate	MeSH
Tetrahydrofolic acid	ChEBI, KEGG

Molecular Formula

C₁₉H₂₃N₇O₆

Average Mass

445.4292

Monoisotopic Mass

445.170981503

IUPAC Name

(2S)-2-[(4-{[(2-amino-4-oxo-1,4,5,6,7,8-hexahydropteridin-6-yl)methyl]amino}phenyl)formamido]pentanedioic acid

Traditional Name

tetrahydrofolic acid

CAS Registry Number

135-16-0

SMILES

NC1=NC(=O)C2=C(NCC(CNC3=CC=C(C=C3)C(=O)N[C@@H](CCC(O)=O)C(O)=O)N2)N1

InChI Identifier

InChI=1S/C19H23N7O6/c20-19-25-15-14(17(30)26-19)23-11(8-22-15)7-21-10-3-1-9(2-4-10)16(29)24-12(18(31)32)5-6-13(27)28/h1-4,11-12,21,23H,5-8H2,(H,24,29)(H,27,28)(H,31,32)(H4,20,22,25,26,30)/t11?,12-/m0/s1

InChI Key

MSTNYGQPCMXVAQ-KIYNQFGBSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as enals. These are an alpha,beta-unsaturated aldehyde of general formula RC=C-CH=O in which the aldehydic C=O function is conjugated to a C=C triple bond at the alpha,beta position.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbonyl compounds

Direct Parent

Enals

Alternative Parents

Substituents

Enal
Organic oxide
Hydrocarbon derivative
Short-chain aldehyde
Aldehyde
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

enal (CHEBI:61722 )
monounsaturated fatty acid aldehyde (CHEBI:61722 )
an aldehyde (CPD-13228 )

Functional Ontology

Not Available

Physical Properties

State

Solid

Predicted Properties

Property	Value	Source
Water Solubility	0.27 g/L	ALOGPS
logP	-0.96	ALOGPS
logP	-4.2	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Acidic)	3.51	ChemAxon
pKa (Strongest Basic)	3.58	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	12	ChemAxon
Hydrogen Donor Count	8	ChemAxon
Polar Surface Area	207.27 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	121.39 m³·mol⁻¹	ChemAxon
Polarizability	42.95 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_3_54) - 70eV, Positive	Not Available	2022-08-08	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0032-0431900000-ff1f3948e47561161293	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-001i-0952300000-ed9d84bc39d490f6210e	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-001i-0920000000-0d0efcb6c323340d20b9	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0006-0001900000-abb4cec0eb79b0bd2de1	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0v4l-2356900000-2fd17d2f587bbd5e882c	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9441000000-8c630c7a3633467d6bb3	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0002-0080900000-73480c24ce118e5e02f3	2021-10-21	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0002-0390100000-9f24528058374fc56c6d	2021-10-21	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0089-0962000000-9a988cf519f340f5d7cf	2021-10-21	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-005c-0002900000-9587282a39f915386f95	2021-10-21	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0zi3-2807900000-28355749389d1e225f7b	2021-10-21	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0udi-3911000000-e7b1ccb0c9f2d7c8269a	2021-10-21	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-22	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Lysosome
Mitochondria

Biospecimen Locations

Blood
Brain
Epidermis
Erythrocyte
Fibroblasts
Intestine
Kidney
Liver
Neuron
Pancreas
Placenta
Platelet
Prostate
Testis

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Not Available

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Eukaryota/Fungi	Ascomycota	1	Human feces; Human saliva	Unknown

Exposure Sources

Source Type	Species	Data Source	Reference
Animal	Laminaria	FooDB	Manually Annotated
Animal	Haliotis	FooDB	Manually Annotated
Animal	Strombidae	FooDB	Manually Annotated
Animal	Clupea harengus harengus	FooDB	Manually Annotated
Animal	Undaria pinnatifida	FooDB	Manually Annotated
Animal	Peprilus triacanthus	FooDB	Manually Annotated
Animal	Rhodophyta	FooDB	Manually Annotated
Animal	Myoxocephalus	FooDB	Manually Annotated
Animal	Eucheuma	FooDB	Manually Annotated
Animal	Saccharina japonica	FooDB	Manually Annotated
Animal	Spirulina	FooDB	Manually Annotated
Animal	Lota lota	FooDB	Manually Annotated
Animal	Porphyra umbilicalis	FooDB	Manually Annotated
Animal	Chondrus crispus	FooDB	Manually Annotated
Plant	Rubus arcticus	FooDB	Manually Annotated
Plant	Agaricus bisporus	FooDB	Manually Annotated
Plant	Cajanus cajan	FooDB	Manually Annotated
Plant	Origanum majorana	FooDB	Manually Annotated
Plant	Rumex articus	FooDB	Manually Annotated
Plant	Armoracia rusticana	FooDB	Manually Annotated
Plant	Prunus persica	FooDB	Manually Annotated
Plant	Hibiscus sabdariffa	FooDB	Manually Annotated
Plant	Benincasa hispida	FooDB	Manually Annotated
Plant	Cucurbita pepo var. cylindrica	FooDB	Manually Annotated
Plant		FooDB	Manually Annotated
Plant	Canarium ovatum	FooDB	Manually Annotated
Plant	Ribes aureum var. villosum	FooDB	Manually Annotated
Plant	Brassica oleracea var. gemmifera	FooDB	Manually Annotated
Plant	Foeniculum vulgare	FooDB	Manually Annotated
Plant	Brassica oleracea var. gongylodes	FooDB	Manually Annotated
Plant	Phoenix dactylifera	FooDB	Manually Annotated
Plant	Vaccinium macrocarpon	FooDB	Manually Annotated
Plant	Arctium lappa	FooDB	Manually Annotated
Plant	Juglans cinerea	FooDB	Manually Annotated
Plant	Prunus cerasus	FooDB	Manually Annotated
Plant	Artocarpus altilis	FooDB	Manually Annotated
Plant	Eruca vesicaria ssp. sativa	FooDB	Manually Annotated
Plant	Citrus x paradisi	FooDB	Manually Annotated
Plant	Rosmarinus officinalis	FooDB	Manually Annotated
Plant	Cynara scolymus	FooDB	Manually Annotated
Plant	Vigna unguiculata	FooDB	Manually Annotated
Plant	Ficus carica	FooDB	Manually Annotated
Plant	Lentinus edodes	FooDB	Manually Annotated
Plant	Cyathea	FooDB	Manually Annotated
Plant	Metroxylon sagu	FooDB	Manually Annotated
Plant	Vitis rotundifolia	FooDB	Manually Annotated
Plant	Brosimum alicastrum	FooDB	Manually Annotated
Plant	Psidium cattleianum	FooDB	Manually Annotated
Plant	Beta vulgaris var. rubra	FooDB	Manually Annotated
Plant	Lepidium sativum	FooDB	Manually Annotated
Plant	Castanea mollissima	FooDB	Manually Annotated
Plant	Helianthus tuberosus	FooDB	Manually Annotated
Plant	Morus	FooDB	Manually Annotated
Plant	Grifola frondosa	FooDB	Manually Annotated
Plant	Phytolacca americana	FooDB	Manually Annotated
Plant	Vitis labrusca	FooDB	Manually Annotated
Plant		FooDB	Manually Annotated
Plant	Artemisia vulgaris	FooDB	Manually Annotated
Plant	Tetragonia tetragonioides	FooDB	Manually Annotated
Plant	Cucumis metuliferus	FooDB	Manually Annotated
Plant	Nephelium lappaceum	FooDB	Manually Annotated
Plant	Myrica	FooDB	Manually Annotated
Plant	Corylus avellana	FooDB	Manually Annotated
Plant	Castanea crenata	FooDB	Manually Annotated
Plant	Litchi chinensis	FooDB	Manually Annotated
Plant	Juglans regia	FooDB	Manually Annotated
Plant	Quercus	FooDB	Manually Annotated
Plant	Trigonella foenum-graecum	FooDB	Manually Annotated
Plant	Vaccinium angustifolium	FooDB	Manually Annotated
Plant	Physalis	FooDB	Manually Annotated
Plant	Malpighia emarginata	FooDB	Manually Annotated
Plant	Brassica oleracea var. sabauda	FooDB	Manually Annotated
Plant	Brassica napus	FooDB	Manually Annotated
Plant	Thelesperma	FooDB	Manually Annotated
Plant	Asparagus officinalis	FooDB	Manually Annotated
Plant	Chamerion angustifolium	FooDB	Manually Annotated
Plant	Levisticum officinale	FooDB	Manually Annotated
Plant	Pimpinella anisum	FooDB	Manually Annotated
Plant	Citrus aurantiifolia	FooDB	Manually Annotated
Plant	Lactuca sativa	FooDB	Manually Annotated
Plant	Vaccinium elliottii	FooDB	Manually Annotated
Plant	Artemisia dracunculus	FooDB	Manually Annotated
Plant	Matricaria recutita	FooDB	Manually Annotated
Plant	Ziziphus zizyphus	FooDB	Manually Annotated
Plant	Dimocarpus longan	FooDB	Manually Annotated
Plant	Eragrostis tef	FooDB	Manually Annotated
Plant	Salvia hispanica	FooDB	Manually Annotated
Plant	Pistacia vera	FooDB	Manually Annotated
Plant	Malus pumila	FooDB	Manually Annotated
Plant	Vitellaria paradoxa	FooDB	Manually Annotated
Plant	Pangium edule	FooDB	Manually Annotated
Plant	Cynara cardunculus	FooDB	Manually Annotated
Plant	Allium	FooDB	Manually Annotated
Plant		FooDB	Manually Annotated
Plant	Brassica oleracea var. viridis	FooDB	Manually Annotated
Plant	Punica granatum	FooDB	Manually Annotated
Plant	Agave	FooDB	Manually Annotated
Plant	Diospyros	FooDB	Manually Annotated
Plant	Hedysarum alpinum	FooDB	Manually Annotated
Plant	Gossypium	FooDB	Manually Annotated
Plant	Vigna aconitifolia	FooDB	Manually Annotated
Plant	Amaranthus	FooDB	Manually Annotated
Plant	Beta vulgaris	FooDB	Manually Annotated
Plant	Mammea americana	FooDB	Manually Annotated
Plant	Annona squamosa	FooDB	Manually Annotated
Plant	Cucumis sativus	FooDB	Manually Annotated
Plant	Brassica alboglabra	FooDB	Manually Annotated
Plant	Vitis	FooDB	Manually Annotated
Plant	Apium graveolens var. dulce	FooDB	Manually Annotated
Plant	Xanthosoma sagittifolium	FooDB	Manually Annotated
Plant	Basella alba	FooDB	Manually Annotated
Plant	Carya illinoinensis	FooDB	Manually Annotated
Plant	Citrus latifolia	FooDB	Manually Annotated
Plant	Capsicum baccatum var. baccatum	FooDB	Manually Annotated
Plant	Byrsonima crassifolia	FooDB	Manually Annotated
Plant	Ribes rubrum	FooDB	Manually Annotated
Plant	Cinnamomum aromaticum	FooDB	Manually Annotated
Plant	Capsicum pubescens	FooDB	Manually Annotated
Plant	Crateva religiosa	FooDB	Manually Annotated
Plant	Brassica rapa var. chinensis	FooDB	Manually Annotated
Plant		FooDB	Manually Annotated
Plant	Portulaca oleracea	FooDB	Manually Annotated
Plant	Ipomoea batatas	FooDB	Manually Annotated
Plant	Mentha arvensis	FooDB	Manually Annotated
Plant	Vitis aestivalis	FooDB	Manually Annotated
Plant	Eugenia javanica	FooDB	Manually Annotated
Plant	Pastinaca sativa	FooDB	Manually Annotated
Plant	Cucurbita maxima	FooDB	Manually Annotated
Plant	Chenopodium album	FooDB	Manually Annotated
Plant	Psophocarpus tetragonolobus	FooDB	Manually Annotated
Plant	Vaccinium stamineum	FooDB	Manually Annotated
Plant	Solanum lycopersicum var. cerasiforme	FooDB	Manually Annotated
Plant	Allium ampeloprasum	FooDB	Manually Annotated
Plant	Brassica oleracea	FooDB	Manually Annotated
Plant	Sechium edule	FooDB	Manually Annotated
Plant	Lactuca sativa l. var. longifolia	FooDB	Manually Annotated
Plant	Grataegosorbus mitschurinii	FooDB	Manually Annotated
Plant	Diospyros virginiana	FooDB	Manually Annotated
Plant	Origanum x majoricum	FooDB	Manually Annotated
Plant	Rubus x loganobaccus	FooDB	Manually Annotated
Plant	Taraxacum officinale	FooDB	Manually Annotated
Plant	Tragopogon porrifolius	FooDB	Manually Annotated
Plant	Rumex	FooDB	Manually Annotated
Plant	Allium ascalonicum	FooDB	Manually Annotated
Plant	Curcuma longa	FooDB	Manually Annotated
Plant	Ananas comosus	FooDB	Manually Annotated
Plant	Rubus chamaemorus	FooDB	Manually Annotated
Plant	Persea americana	FooDB	Manually Annotated
Plant	Elettaria cardamomum	FooDB	Manually Annotated
Plant	Citrullus lanatus var. fistulosus	FooDB	Manually Annotated
Plant	Amelanchier alnifolia	FooDB	Manually Annotated
Plant	Eugenia uniflora	FooDB	Manually Annotated
Plant	Annona reticulata	FooDB	Manually Annotated
Plant	Cichorium intybus	FooDB	Manually Annotated
Plant	Sesbania bispinosa	FooDB	Manually Annotated
Plant	Brassica oleracea var. botrytis	FooDB	Manually Annotated
Plant	Chenopodium quinoa	FooDB	Manually Annotated
Plant	Cucumis melo	FooDB	Manually Annotated
Plant	Ribes x nidigrolaria	FooDB	Manually Annotated
Plant	Garcinia mangostana	FooDB	Manually Annotated
Plant	Corchorus olitorius	FooDB	Manually Annotated
Plant	Juglans nigra	FooDB	Manually Annotated
Plant	Glycine max	FooDB	Manually Annotated
Plant	Dioscorea pentaphylla	FooDB	Manually Annotated
Plant	Cinnamomum verum	FooDB	Manually Annotated
Plant	Lathyrus sativus	FooDB	Manually Annotated
Plant	Allium tuberosum	FooDB	Manually Annotated
Plant	Petasites japonicus	FooDB	Manually Annotated
Plant	Gaylussacia baccata	FooDB	Manually Annotated
Plant	Prunus tomentosa	FooDB	Manually Annotated
Plant	Mentha x piperita	FooDB	Manually Annotated
Plant	Ocimum basilicum	FooDB	Manually Annotated
Plant	Maranta arundinacea	FooDB	Manually Annotated
Plant	Citrus limon	FooDB	Manually Annotated
Plant	Matteuccia struthiopteris	FooDB	Manually Annotated
Plant	Cucurbita moschata	FooDB	Manually Annotated
Plant	Macadamia	FooDB	Manually Annotated
Plant	Tilia	FooDB	Manually Annotated
Plant	Apium graveolens var. rapaceum	FooDB	Manually Annotated
Plant	Papaver	FooDB	Manually Annotated
Plant	Vaccinium myrtilloides	FooDB	Manually Annotated
Plant	Rosa	FooDB	Manually Annotated
Plant	Capsicum annuum var. annuum	FooDB	Manually Annotated
Plant	Sesamum orientale	FooDB	Manually Annotated
Plant	Nelumbo	FooDB	Manually Annotated
Plant	Brassica oleracea var. conica	FooDB	Manually Annotated
Plant	Annona cherimola	FooDB	Manually Annotated
Plant	Brassica rapa var. pekinensis	FooDB	Manually Annotated
Plant	Brassica rapa	FooDB	Manually Annotated
Plant	Lippia graveolens	FooDB	Manually Annotated
Plant	Prunus	FooDB	Manually Annotated
Plant	Citrus sinensis	FooDB	Manually Annotated
Plant	Capparis spinosa	FooDB	Manually Annotated
Plant	Lens culinaris	FooDB	Manually Annotated
Plant	Vaccinium deliciosum	FooDB	Manually Annotated
Plant	Phaseolus lunatus	FooDB	Manually Annotated
Plant	Artocarpus heterophyllus	FooDB	Manually Annotated
Plant	Prunus virginiana	FooDB	Manually Annotated
Plant	Linum usitatissimum	FooDB	Manually Annotated
Plant	Musa acuminata	FooDB	Manually Annotated
Plant	Citrullus lanatus	FooDB	Manually Annotated
Plant	Vigna unguiculata ssp. unguiculata	FooDB	Manually Annotated
Plant	Macadamia tetraphylla	FooDB	Manually Annotated
Plant	Prunus domestica	FooDB	Manually Annotated
Plant	Prunus armeniaca	FooDB	Manually Annotated
Plant	Phyllostachys edulis	FooDB	Manually Annotated
Plant	Lagenaria siceraria	FooDB	Manually Annotated
Plant	Carum carvi	FooDB	Manually Annotated
Plant	Allium schoenoprasum	FooDB	Manually Annotated
Plant	Citrus reticulata	FooDB	Manually Annotated
Plant	Carissa macrocarpa	FooDB	Manually Annotated
Plant	Averrhoa carambola	FooDB	Manually Annotated
Plant	Satureja hortensis	FooDB	Manually Annotated
Plant	Brassica rapa var. rapa	FooDB	Manually Annotated
Plant	Anethum graveolens	FooDB	Manually Annotated
Plant	Sorbus aucuparia	FooDB	Manually Annotated
Plant	Coriandrum sativum	FooDB	Manually Annotated
Plant	Nelumbo nucifera	FooDB	Manually Annotated
Plant	Bertholletia excelsa	FooDB	Manually Annotated
Plant	Cymbopogon citratus	FooDB	Manually Annotated
Plant	Brassica oleracea var. costata	FooDB	Manually Annotated
Plant	Panax	FooDB	Manually Annotated
Plant	Ceratonia siliqua	FooDB	Manually Annotated
Plant	Luffa aegyptiaca	FooDB	Manually Annotated
Plant	Anacardium occidentale	FooDB	Manually Annotated
Plant	Carthamus tinctorius	FooDB	Manually Annotated
Plant	Cicer arietinum	FooDB	Manually Annotated
Plant	Camellia sinensis	FooDB	Manually Annotated
Plant	Rubus occidentalis	FooDB	Manually Annotated
Plant	Vigna umbellata	FooDB	Manually Annotated
Plant	Allium fistulosum	FooDB	Manually Annotated
Plant	Capsicum	FooDB	Manually Annotated
Plant	Vaccinium alaskaense	FooDB	Manually Annotated
Plant	Solanum lycopersicum var. lycopersicum	FooDB	Manually Annotated
Plant	Lupinus	FooDB	Manually Annotated
Plant	Tilia cordata	FooDB	Manually Annotated
Plant	Prunus persica var. nucipersica	FooDB	Manually Annotated
Plant	Eriobotrya japonica	FooDB	Manually Annotated
Plant	Durio zibethinus	FooDB	Manually Annotated
Plant	Brassica napus var. pabularia	FooDB	Manually Annotated
Plant	Phaseolus vulgaris	FooDB	Manually Annotated
Plant	Oenothera biennis	FooDB	Manually Annotated
Plant	Diospyros kaki	FooDB	Manually Annotated
Plant	Ribes glandulosum	FooDB	Manually Annotated
Plant	Theobroma cacao	FooDB	Manually Annotated
Plant	Daucus carota ssp. sativus	FooDB	Manually Annotated
Plant	Virola surinamensis	FooDB	Manually Annotated
Plant	Verbena officinalis	FooDB	Manually Annotated
Plant	Rumex acetosa	FooDB	Manually Annotated
Plant	Vaccinium oxycoccos	FooDB	Manually Annotated
Plant	Vaccinium myrtillus	FooDB	Manually Annotated
Plant	Brassica oleracea var. capitata	FooDB	Manually Annotated
Plant	Syzygium aromaticum	FooDB	Manually Annotated
Plant	Pyrus pyrifolia	FooDB	Manually Annotated
Plant	Vicia faba	FooDB	Manually Annotated
Plant	Vaccinium parvifolium	FooDB	Manually Annotated
Plant	Aloysia triphylla	FooDB	Manually Annotated
Plant	Capsicum chinense	FooDB	Manually Annotated
Plant	Theobroma grandiflorum	FooDB	Manually Annotated
Plant	Vaccinium reticulatum	FooDB	Manually Annotated
Plant	Solanum quitoense	FooDB	Manually Annotated
Plant	Ginkgo biloba	FooDB	Manually Annotated
Plant	Vigna unguiculata ssp. cylindrica	FooDB	Manually Annotated
Plant	Flammulina velutipes	FooDB	Manually Annotated
Plant	Satureja montana	FooDB	Manually Annotated
Plant	Citrus japonica	FooDB	Manually Annotated
Plant		FooDB	Manually Annotated
Plant	Vitis vinifera	FooDB	Manually Annotated
Plant	Prunus avium	FooDB	Manually Annotated
Plant	Capsicum annuum	FooDB	Manually Annotated
Plant	Perideridia oregana	FooDB	Manually Annotated
Plant	Vaccinium arboreum	FooDB	Manually Annotated
Plant	Pouteria sapota	FooDB	Manually Annotated
Plant	Wasabia japonica	FooDB	Manually Annotated
Plant	Piper nigrum	FooDB	Manually Annotated
Plant	Origanum onites	FooDB	Manually Annotated
Plant	Origanum vulgare	FooDB	Manually Annotated
Plant	Viburnum edule	FooDB	Manually Annotated
Plant	Dioscorea	FooDB	Manually Annotated
Plant	Momordica charantia	FooDB	Manually Annotated
Plant	Brassica oleracea var. italica	FooDB	Manually Annotated
Plant	Vaccinium uliginosum	FooDB	Manually Annotated
Plant	Castanea	FooDB	Manually Annotated
Plant	Rubus ursinus x idaeus	FooDB	Manually Annotated
Plant	Solanum melongena	FooDB	Manually Annotated
Plant	Cirsium	FooDB	Manually Annotated
Plant	Pleurotus ostreatus	FooDB	Manually Annotated
Plant	Opuntia	FooDB	Manually Annotated
Plant	Anthriscus cerefolium	FooDB	Manually Annotated
Plant	Raphanus sativus var. sativus	FooDB	Manually Annotated
Plant	Colocasia esculenta	FooDB	Manually Annotated
Plant	Prunus persica var. persica	FooDB	Manually Annotated
Plant	Myristica fragrans	FooDB	Manually Annotated
Plant	Nuphar lutea	FooDB	Manually Annotated
Plant	Lupinus albus	FooDB	Manually Annotated
Plant	Pachyrhizus erosus	FooDB	Manually Annotated
Plant	Cichorium endivia	FooDB	Manually Annotated
Plant	Apium graveolens	FooDB	Manually Annotated
Plant	Elaeis	FooDB	Manually Annotated
Plant	Cinnamomum	FooDB	Manually Annotated
Plant	Ribes uva-crispa	FooDB	Manually Annotated
Plant	Feijoa sellowiana	FooDB	Manually Annotated
Plant	Dysphania ambrosioides	FooDB	Manually Annotated
Plant	Raphanus sativus var. niger	FooDB	Manually Annotated
Plant	Photinia melanocarpa	FooDB	Manually Annotated
Plant	Salvia officinalis	FooDB	Manually Annotated
Plant	Rheum rhabarbarum	FooDB	Manually Annotated
Plant	Vaccinium	FooDB	Manually Annotated
Plant	Lablab purpureus	FooDB	Manually Annotated
Plant	Crocus sativus	FooDB	Manually Annotated
Plant	Cydonia oblonga	FooDB	Manually Annotated
Plant	Citrus maxima	FooDB	Manually Annotated
Plant	Syzygium jambos	FooDB	Manually Annotated
Plant	Annona muricata	FooDB	Manually Annotated
Plant	Salix pulchra	FooDB	Manually Annotated
Plant	Castanea sativa	FooDB	Manually Annotated
Plant	Cucurbita	FooDB	Manually Annotated
Plant	Fagus	FooDB	Manually Annotated
Plant	Opuntia cochenillifera	FooDB	Manually Annotated
Plant	Vaccinium ovatum	FooDB	Manually Annotated
Plant	Cocos nucifera	FooDB	Manually Annotated
Plant	Tamarindus indica	FooDB	Manually Annotated
Plant	Phaseolus coccineus	FooDB	Manually Annotated
Plant	Thymus pulegioides	FooDB	Manually Annotated
Plant	Mespilus germanica	FooDB	Manually Annotated
Plant	Cucurbita pepo var. cylindrica	FooDB	Manually Annotated
Plant	Brassica rapa var. perviridis	FooDB	Manually Annotated
Plant	Mentha aquatica	FooDB	Manually Annotated
Plant	Solanum tuberosum	FooDB	Manually Annotated
Plant	Salvia elegans	FooDB	Manually Annotated
Plant	Mentha	FooDB	Manually Annotated
Plant	Psidium guajava	FooDB	Manually Annotated
Plant	Sagittaria latifolia	FooDB	Manually Annotated
Plant	Olea europaea	FooDB	Manually Annotated
Plant	Sambucus	FooDB	Manually Annotated
Plant	Pinus	FooDB	Manually Annotated
Plant	Syzygium cumini	FooDB	Manually Annotated
Plant	Tilia tomentosa	FooDB	Manually Annotated
Plant	Daucus carota	FooDB	Manually Annotated
Plant	Typha angustifolia	FooDB	Manually Annotated
Plant	Vaccinium vitis-idaea	FooDB	Manually Annotated
Plant	Empetrum nigrum	FooDB	Manually Annotated
Plant	Valerianella locusta	FooDB	Manually Annotated
Plant	Myrica rubra	FooDB	Manually Annotated
Plant	Vaccinium angustifolium x vaccinium corymbosum	FooDB	Manually Annotated
Plant	Sisymbrium	FooDB	Manually Annotated
Plant	Brassica oleracea l. var. capitata l. f. alba dc.	FooDB	Manually Annotated
Plant	Vanilla	FooDB	Manually Annotated
Plant	Raphanus sativus	FooDB	Manually Annotated
Plant	Vigna radiata	FooDB	Manually Annotated
Plant	Carya	FooDB	Manually Annotated
Plant	Prunus dulcis	FooDB	Manually Annotated
Plant	Manihot esculenta	FooDB	Manually Annotated
Plant	Physalis philadelphica var. immaculata	FooDB	Manually Annotated
Plant	Borago officinalis	FooDB	Manually Annotated
Plant	Hyssopus officinalis	FooDB	Manually Annotated
Plant	Beta vulgaris ssp. cicla	FooDB	Manually Annotated
Plant	Scorzonera hispanica	FooDB	Manually Annotated
Plant	Vigna unguiculata ssp. sesquipedalis	FooDB	Manually Annotated
Plant	Angelica keiskei	FooDB	Manually Annotated
Plant	Ipomoea aquatica	FooDB	Manually Annotated
Plant	Musa x paradisiaca	FooDB	Manually Annotated
Plant	Cuminum cyminum	FooDB	Manually Annotated
Plant	Rubus spectabilis	FooDB	Manually Annotated
Plant	Allium sativum	FooDB	Manually Annotated
Plant	Arachis hypogaea	FooDB	Manually Annotated
Plant	Rubus idaeus	FooDB	Manually Annotated
Plant	Cantharellus cibarius	FooDB	Manually Annotated
Plant	Fragaria x ananassa	FooDB	Manually Annotated
Plant	Pyrus communis	FooDB	Manually Annotated
Plant	Sinapis alba	FooDB	Manually Annotated
Plant	Apium graveolens var. secalinum	FooDB	Manually Annotated
Plant	Brassica ruvo	FooDB	Manually Annotated
Plant	Morus nigra	FooDB	Manually Annotated
Plant	Solanum lycopersicum	FooDB	Manually Annotated
Plant	Abelmoschus esculentus	FooDB	Manually Annotated
Plant	Moringa oleifera	FooDB	Manually Annotated
Plant	Pinus edulis	FooDB	Manually Annotated
Plant	Passiflora edulis	FooDB	Manually Annotated
Plant	Mentha spicata	FooDB	Manually Annotated
Plant	Vigna angularis	FooDB	Manually Annotated
Plant	Helianthus annuus	FooDB	Manually Annotated
Plant	Opuntia macrorhiza	FooDB	Manually Annotated
Plant	Cucurbita pepo var. clypeata	FooDB	Manually Annotated
Plant	Manilkara zapota	FooDB	Manually Annotated
Plant	Pisum sativum	FooDB	Manually Annotated
Plant	Corylus	FooDB	Manually Annotated
Plant	Malus	FooDB	Manually Annotated
Plant	Juglans	FooDB	Manually Annotated
Plant	Zingiber officinale	FooDB	Manually Annotated
Plant	Petroselinum crispum	FooDB	Manually Annotated
Plant	Sambucus nigra	FooDB	Manually Annotated
Plant	Allium cepa	FooDB	Manually Annotated
Plant	Ribes nigrum	FooDB	Manually Annotated
Plant	Mangifera indica	FooDB	Manually Annotated
Plant	Illicium verum	FooDB	Manually Annotated
Plant	Chamaemelum nobile	FooDB	Manually Annotated
Plant	Laurus nobilis	FooDB	Manually Annotated
Plant		FooDB	Manually Annotated
Plant	Auricularia auricula-judae	FooDB	Manually Annotated
Plant	Attalea speciosa	FooDB	Manually Annotated
Plant	Juglans ailanthifolia	FooDB	Manually Annotated
Plant	Melissa officinalis	FooDB	Manually Annotated
Plant	Hippophae rhamnoides	FooDB	Manually Annotated
Plant	Spinacia oleracea	FooDB	Manually Annotated
Plant	Polygonum alpinum	FooDB	Manually Annotated
Plant	Brassica juncea	FooDB	Manually Annotated
Plant	Pediomelum esculentum	FooDB	Manually Annotated
Plant	Auricularia polytricha	FooDB	Manually Annotated
Plant	Camellia oleifera	FooDB	Manually Annotated
Plant	Carica papaya	FooDB	Manually Annotated
Plant	Vaccinium corymbosum	FooDB	Manually Annotated
Plant	Actinidia chinensis	FooDB	Manually Annotated
Plant	Chrysanthemum coronarium	FooDB	Manually Annotated
Plant	Eleocharis dulcis	FooDB	Manually Annotated
Plant	Thymus vulgaris	FooDB	Manually Annotated
Plant	Medicago sativa	FooDB	Manually Annotated
Plant	Vigna mungo	FooDB	Manually Annotated
Plant	Pimenta dioica	FooDB	Manually Annotated

Source Type	Activity	Data Source	Reference
Drugs	Antimicrobial	U.S. Environmental Protection Agency	CompTox
Cosmetics	Not Available	U.S. Environmental Protection Agency	CompTox
Domestics	Not Available	U.S. Environmental Protection Agency	CompTox

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Units	Age	Sex	Health Condition	Data Source	Reference
Human Blood	Detected and Quantified	0.0025	0.0044	uM	Adult (>18 years old)	Both	Normal	HMDB	17272488
Human Blood	Detected but not Quantified				Not Specified	Not Specified	Normal	HMDB	31557052
Human Brain	Detected but not Quantified				Not Specified	Not Specified	Normal	HMDB	34986597
Human Epidermis	Detected but not Quantified				Not Specified	Not Specified	Normal	HMDB	34986597
Human Erythrocyte	Detected but not Quantified				Not Specified	Not Specified	Normal	HMDB	34986597
Human Fibroblasts	Detected but not Quantified				Not Specified	Not Specified	Normal	HMDB	34986597
Human Intestine	Detected but not Quantified				Not Specified	Not Specified	Normal	HMDB	34986597
Human Kidney	Detected but not Quantified				Not Specified	Not Specified	Normal	HMDB	34986597
Human Liver	Detected but not Quantified				Not Specified	Not Specified	Normal	HMDB	34986597
Human Neuron	Detected but not Quantified				Not Specified	Not Specified	Normal	HMDB	34986597
Human Pancreas	Detected but not Quantified				Not Specified	Not Specified	Normal	HMDB	34986597
Human Placenta	Detected but not Quantified				Not Specified	Not Specified	Normal	HMDB	34986597
Human Platelet	Detected but not Quantified				Not Specified	Not Specified	Normal	HMDB	34986597
Human Prostate	Detected but not Quantified				Not Specified	Not Specified	Normal	HMDB	34986597
Human Testis	Detected but not Quantified				Not Specified	Not Specified	Normal	HMDB	34986597

External Links

HMDB ID

HMDB0304496

DrugBank ID

DB00116

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

91443

PDB ID

Not Available

ChEBI ID

20506

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Taber LD, O'Brien P, Bowsher RR, Sportsman JR: Competitive particle concentration fluorescence immunoassay for measuring 5,10-dideaza-5,6,7,8-tetrahydrofolic acid (lometrexol) in serum. Clin Chem. 1991 Feb;37(2):254-60. [PubMed:1993335 ]
Pieniazek D, Kubalska J, Pronicka E, Stecko E: Disturbances in histidine metabolism in children with speech abnormalities. Acta Anthropogenet. 1985;9(1-3):117-21. [PubMed:2887178 ]
Baggott JE, Johanning GL, Branham KE, Prince CW, Morgan SL, Eto I, Vaughn WH: Cofactor role for 10-formyldihydrofolic acid. Biochem J. 1995 Jun 15;308 ( Pt 3):1031-6. doi: 10.1042/bj3081031. [PubMed:8948466 ]
Wang S, Low PS: Folate-mediated targeting of antineoplastic drugs, imaging agents, and nucleic acids to cancer cells. J Control Release. 1998 Apr 30;53(1-3):39-48. doi: 10.1016/s0168-3659(97)00236-8. [PubMed:9741912 ]
Zhu WY, Alliegro MA, Melera PW: The rate of folate receptor alpha (FR alpha) synthesis in folate depleted CHL cells is regulated by a translational mechanism sensitive to media folate levels, while stable overexpression of its mRNA is mediated by gene amplification and an increase in transcript half-life. J Cell Biochem. 2001 Mar 26;81(2):205-19. doi: 10.1002/1097-4644(20010501)81:2<205::aid-jcb1036>3.0.co;2-s. [PubMed:11241661 ]
Garbis SD, Melse-Boonstra A, West CE, van Breemen RB: Determination of folates in human plasma using hydrophilic interaction chromatography-tandem mass spectrometry. Anal Chem. 2001 Nov 15;73(22):5358-64. doi: 10.1021/ac010741y. [PubMed:11816560 ]
Greenwald P, Milner JA, Anderson DE, McDonald SS: Micronutrients in cancer chemoprevention. Cancer Metastasis Rev. 2002;21(3-4):217-30. doi: 10.1023/a:1021202709003. [PubMed:12549762 ]
Mattson MP: Will caloric restriction and folate protect against AD and PD? Neurology. 2003 Feb 25;60(4):690-5. doi: 10.1212/01.wnl.0000042785.02850.11. [PubMed:12601113 ]
Lu S, Chen GL, Ren C, Kwabi-Addo B, Epner DE: Methionine restriction selectively targets thymidylate synthase in prostate cancer cells. Biochem Pharmacol. 2003 Sep 1;66(5):791-800. doi: 10.1016/s0006-2952(03)00406-4. [PubMed:12948860 ]
Mattson MP: Gene-diet interactions in brain aging and neurodegenerative disorders. Ann Intern Med. 2003 Sep 2;139(5 Pt 2):441-4. doi: 10.7326/0003-4819-139-5_part_2-200309021-00012. [PubMed:12965973 ]
Verwei M, Arkbage K, Mocking H, Havenaar R, Groten J: The binding of folic acid and 5-methyltetrahydrofolate to folate-binding proteins during gastric passage differs in a dynamic in vitro gastrointestinal model. J Nutr. 2004 Jan;134(1):31-7. doi: 10.1093/jn/134.1.31. [PubMed:14704289 ]
Makino Y, Nagano M, Tamura K, Kawarabayashi T: Pregnancy complicated with pure red cell aplasia: a case report. J Perinat Med. 2003;31(6):530-4. doi: 10.1515/JPM.2003.082. [PubMed:14711112 ]
Kamen BA, Smith AK: A review of folate receptor alpha cycling and 5-methyltetrahydrofolate accumulation with an emphasis on cell models in vitro. Adv Drug Deliv Rev. 2004 Apr 29;56(8):1085-97. doi: 10.1016/j.addr.2004.01.002. [PubMed:15094208 ]
Wolters M, Strohle A, Hahn A: [Age-associated changes in the metabolism of vitamin B(12) and folic acid: prevalence, aetiopathogenesis and pathophysiological consequences]. Z Gerontol Geriatr. 2004 Apr;37(2):109-35. doi: 10.1007/s00391-004-0169-6. [PubMed:15103481 ]
Pljesa S: [Possible complications of erythropoietin therapy in patients with chronic renal failure]. Med Pregl. 2004 May-Jun;57(5-6):254-7. doi: 10.2298/mpns0406254p. [PubMed:15503795 ]
Siega-Riz AM, Savitz DA, Zeisel SH, Thorp JM, Herring A: Second trimester folate status and preterm birth. Am J Obstet Gynecol. 2004 Dec;191(6):1851-7. doi: 10.1016/j.ajog.2004.07.076. [PubMed:15592264 ]
Hankey GJ, Eikelboom JW, Loh K, Tang M, Pizzi J, Thom J, Yi Q: Sustained homocysteine-lowering effect over time of folic acid-based multivitamin therapy in stroke patients despite increasing folate status in the population. Cerebrovasc Dis. 2005;19(2):110-6. doi: 10.1159/000082788. Epub 2004 Dec 17. [PubMed:15608435 ]
Pufulete M, Al-Ghnaniem R, Khushal A, Appleby P, Harris N, Gout S, Emery PW, Sanders TA: Effect of folic acid supplementation on genomic DNA methylation in patients with colorectal adenoma. Gut. 2005 May;54(5):648-53. doi: 10.1136/gut.2004.054718. [PubMed:15831910 ]
Ozer B, Serin E, Gumurdulu Y, Kayaselcuk F, Anarat R, Gur G, Kul K, Guclu M, Boyacioglu S: Helicobacter pylori eradication lowers serum homocysteine level in patients without gastric atrophy. World J Gastroenterol. 2005 May 14;11(18):2764-7. doi: 10.3748/wjg.v11.i18.2764. [PubMed:15884118 ]
Ramaekers VT, Rothenberg SP, Sequeira JM, Opladen T, Blau N, Quadros EV, Selhub J: Autoantibodies to folate receptors in the cerebral folate deficiency syndrome. N Engl J Med. 2005 May 12;352(19):1985-91. doi: 10.1056/NEJMoa043160. [PubMed:15888699 ]
Stuerenburg HJ, Ganzer S, Arlt S, Muller-Thomsen T: The influence of smoking on plasma folate and lipoproteins in Alzheimer disease, mild cognitive impairment and depression. Neuro Endocrinol Lett. 2005 Jun;26(3):261-3. [PubMed:15990733 ]
Sahr T, Ravanel S, Rebeille F: Tetrahydrofolate biosynthesis and distribution in higher plants. Biochem Soc Trans. 2005 Aug;33(Pt 4):758-62. doi: 10.1042/BST0330758. [PubMed:16042593 ]
Asrar FM, O'Connor DL: Bacterially synthesized folate and supplemental folic acid are absorbed across the large intestine of piglets. J Nutr Biochem. 2005 Oct;16(10):587-93. doi: 10.1016/j.jnutbio.2005.02.006. [PubMed:16081276 ]
Dietrich M, Brown CJ, Block G: The effect of folate fortification of cereal-grain products on blood folate status, dietary folate intake, and dietary folate sources among adult non-supplement users in the United States. J Am Coll Nutr. 2005 Aug;24(4):266-74. doi: 10.1080/07315724.2005.10719474. [PubMed:16093404 ]
Ahmed F, Khan MR, Akhtaruzzaman M, Karim R, Marks GC, Banu CP, Nahar B, Williams G: Efficacy of twice-weekly multiple micronutrient supplementation for improving the hemoglobin and micronutrient status of anemic adolescent schoolgirls in Bangladesh. Am J Clin Nutr. 2005 Oct;82(4):829-35. doi: 10.1093/ajcn/82.4.829. [PubMed:16210713 ]
Omura Y: Excessive use of Steroid Hormone & beneficial effects of True St. 36 acupuncture on malignant brain tumors--part I; how to estimate non-invasively presence of excess dose of Steroid Hormone in patients, baseball players & other professional athletes from its toxic effects on heart & pancreas, as well as persistent or recurrent infection--part II. Acupunct Electrother Res. 2005;30(1-2):57-102. doi: 10.3727/036012905815901398. [PubMed:16231633 ]
Paulionis L, Kane SL, Meckling KA: Vitamin status and cognitive function in a long-term care population. BMC Geriatr. 2005 Dec 13;5:16. doi: 10.1186/1471-2318-5-16. [PubMed:16351716 ]
Durga J, van Boxtel MP, Schouten EG, Bots ML, Kok FJ, Verhoef P: Folate and the methylenetetrahydrofolate reductase 677C-->T mutation correlate with cognitive performance. Neurobiol Aging. 2006 Feb;27(2):334-43. doi: 10.1016/j.neurobiolaging.2005.01.003. Epub 2005 Feb 24. [PubMed:16399216 ]
Authors unspecified: Pemetrexed: new drug. Pleural mesothelioma: a first encouraging trial. Prescrire Int. 2005 Dec;14(80):212-4. [PubMed:16400741 ]
Smith DE, Kok RM, Teerlink T, Jakobs C, Smulders YM: Quantitative determination of erythrocyte folate vitamer distribution by liquid chromatography-tandem mass spectrometry. Clin Chem Lab Med. 2006;44(4):450-9. doi: 10.1515/CCLM.2006.085. [PubMed:16599840 ]
Tchantchou F: Homocysteine metabolism and various consequences of folate deficiency. J Alzheimers Dis. 2006 Aug;9(4):421-7. doi: 10.3233/jad-2006-9408. [PubMed:16917151 ]

Showing metabocard for 5,6,7,8-Tetrahydrofolic acid (MMDBc0033003)

MOL for #<Metabolite:0x00007fdb0db14258>

3D MOL for #<Metabolite:0x00007fdb0db14258>

3D SDF for #<Metabolite:0x00007fdb0db14258>

3D-SDF for #<Metabolite:0x00007fdb0db14258>

PDB for #<Metabolite:0x00007fdb0db14258>

3D PDB for #<Metabolite:0x00007fdb0db14258>

SMILES for #<Metabolite:0x00007fdb0db14258>

INCHI for #<Metabolite:0x00007fdb0db14258>

Structure for #<Metabolite:0x00007fdb0db14258>

3D Structure for #<Metabolite:0x00007fdb0db14258>