MiMeDB: Showing metabocard for Tetrahydrofolic acid (MMDBc0029674)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-17 23:37:00 UTC

Update Date

2024-04-30 19:40:29 UTC

Metabolite ID

MMDBc0029674

Metabolite Identification

Common Name

Tetrahydrofolic acid

Description

Tetrahydrofolate 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 )

Structure

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

116
  Mrv1652309042000252D          

 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
    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  2  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
    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
   10.0019    0.2319    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4325    0.2346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4325    1.0596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8491    1.6430    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.1469    1.4721    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.1469   -0.1779    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1469   -1.0029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8614   -1.4154    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8614   -2.2404    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.5759   -1.0029    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1 16  2  0  0  0  0
  2 23  2  0  0  0  0
  3 10  1  0  0  0  0
  3 13  1  0  0  0  0
  4 11  1  0  0  0  0
  4 14  1  0  0  0  0
  5 12  1  0  0  0  0
  5 15  1  0  0  0  0
  6 14  1  0  0  0  0
  6 17  1  0  0  0  0
  7 16  1  0  0  0  0
  7 17  2  0  0  0  0
  8 23  1  0  0  0  0
  9 17  1  0  0  0  0
 10 11  1  0  0  0  0
 13 14  2  0  0  0  0
 13 16  1  0  0  0  0
 15 18  2  0  0  0  0
 15 19  1  0  0  0  0
 18 21  1  0  0  0  0
 19 22  2  0  0  0  0
 20 21  2  0  0  0  0
 20 22  1  0  0  0  0
 20 23  1  0  0  0  0
 10 12  1  1  0  0  0
  8 24  1  6  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 25 27  1  0  0  0  0
 24 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 30 32  2  0  0  0  0
M  END

HMDB0001846
     RDKit          3D
Tetrahydrofolic acid
 55 57  0  0  0  0  0  0  0  0999 V2000
    9.1366    0.4493    1.6665 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.7455    0.5774    1.3745 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2490    1.8070    1.1652 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.9416    2.0038    0.8838 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4491    3.1288    0.6846 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1389    0.8812    0.8214 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6591   -0.3611    1.0367 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9749   -0.5107    1.3155 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.8042   -1.4759    0.9629 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3903   -1.4227    0.7419 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9101   -0.1123    0.1801 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8615   -0.2163   -1.3286 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9884   -1.2337   -1.8236 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5847   -1.2193   -1.7066 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0492   -0.0752   -1.3007 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4467   -0.0902   -1.1766 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1785   -1.2124   -1.4504 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6215   -1.3034   -1.3434 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2457   -2.3612   -1.6535 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3487   -0.1751   -0.8783 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7957   -0.3102   -0.7856 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1707   -0.2309    0.6714 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7318    1.1073    1.2053 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0952    1.2621    2.6374 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6821    0.3354    3.2094 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7785    2.4165    3.2969 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4886    0.7980   -1.4860 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8976    1.7306   -2.0812 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8777    0.7823   -1.4694 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5020   -2.3684   -1.8643 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1297   -2.3886   -1.9966 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7576    0.9970    0.5325 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.4545    0.5355    2.6415 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.7759    0.2685    0.8431 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3279   -1.4842    1.4732 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2346   -2.4286    1.0790 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1202   -2.2506    0.0480 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8862   -1.6707    1.7128 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9206    0.0739    0.6360 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6125    0.7967   -1.7699 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9106   -0.3918   -1.6689 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4401   -2.0655   -2.3194 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5251    0.8105   -1.0945 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9273    0.8067   -0.8602 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8684    0.7048   -0.6291 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1320   -1.2793   -1.2296 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2520   -0.4182    0.8397 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5650   -1.0406    1.1781 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1637    1.8993    0.5624 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6199    1.1749    1.1027 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4867    3.1651    3.3040 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4063    0.1489   -2.0615 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0685   -3.2704   -2.0865 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4039   -3.2887   -2.3194 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3261    1.9459    0.5775 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  1
 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  0
 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
  Mrv1652309042000252D          

 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
    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  2  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
    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
   10.0019    0.2319    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4325    0.2346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4325    1.0596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8491    1.6430    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.1469    1.4721    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.1469   -0.1779    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1469   -1.0029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8614   -1.4154    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8614   -2.2404    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.5759   -1.0029    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1 16  2  0  0  0  0
  2 23  2  0  0  0  0
  3 10  1  0  0  0  0
  3 13  1  0  0  0  0
  4 11  1  0  0  0  0
  4 14  1  0  0  0  0
  5 12  1  0  0  0  0
  5 15  1  0  0  0  0
  6 14  1  0  0  0  0
  6 17  1  0  0  0  0
  7 16  1  0  0  0  0
  7 17  2  0  0  0  0
  8 23  1  0  0  0  0
  9 17  1  0  0  0  0
 10 11  1  0  0  0  0
 13 14  2  0  0  0  0
 13 16  1  0  0  0  0
 15 18  2  0  0  0  0
 15 19  1  0  0  0  0
 18 21  1  0  0  0  0
 19 22  2  0  0  0  0
 20 21  2  0  0  0  0
 20 22  1  0  0  0  0
 20 23  1  0  0  0  0
 10 12  1  1  0  0  0
  8 24  1  6  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 25 27  1  0  0  0  0
 24 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 30 32  2  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0029674

> <DATABASE_NAME>
MIME

> <SMILES>
NC1=NC(=O)C2=C(NC[C@H](CNC3=CC=C(C=C3)C(=O)NC(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-PXYINDEMSA-N

> <FORMULA>
C19H23N7O6

> <MOLECULAR_WEIGHT>
445.4292

> <EXACT_MASS>
445.170981503

> <JCHEM_ACCEPTOR_COUNT>
12

> <JCHEM_ATOM_COUNT>
55

> <JCHEM_AVERAGE_POLARIZABILITY>
44.5670153862625

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
9

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
-0.96

> <JCHEM_LOGP>
-3.636316241831437

> <ALOGPS_LOGS>
-3.22

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
3.882650266532847

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.0444825037700194

> <JCHEM_PKA_STRONGEST_BASIC>
5.760080233502614

> <JCHEM_POLAR_SURFACE_AREA>
208.25999999999996

> <JCHEM_REFRACTIVITY>
132.4011

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.69e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-{[4-({[(6S)-4-hydroxy-2-imino-5,6,7,8-tetrahydro-1H-pteridin-6-yl]methyl}amino)phenyl]formamido}pentanedioic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0001846
     RDKit          3D
Tetrahydrofolic acid
 55 57  0  0  0  0  0  0  0  0999 V2000
    9.1366    0.4493    1.6665 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.7455    0.5774    1.3745 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2490    1.8070    1.1652 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.9416    2.0038    0.8838 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4491    3.1288    0.6846 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1389    0.8812    0.8214 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6591   -0.3611    1.0367 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9749   -0.5107    1.3155 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.8042   -1.4759    0.9629 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3903   -1.4227    0.7419 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9101   -0.1123    0.1801 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8615   -0.2163   -1.3286 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9884   -1.2337   -1.8236 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5847   -1.2193   -1.7066 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0492   -0.0752   -1.3007 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4467   -0.0902   -1.1766 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1785   -1.2124   -1.4504 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6215   -1.3034   -1.3434 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2457   -2.3612   -1.6535 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3487   -0.1751   -0.8783 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7957   -0.3102   -0.7856 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1707   -0.2309    0.6714 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7318    1.1073    1.2053 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0952    1.2621    2.6374 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6821    0.3354    3.2094 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7785    2.4165    3.2969 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4886    0.7980   -1.4860 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8976    1.7306   -2.0812 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8777    0.7823   -1.4694 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5020   -2.3684   -1.8643 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1297   -2.3886   -1.9966 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7576    0.9970    0.5325 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.4545    0.5355    2.6415 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.7759    0.2685    0.8431 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3279   -1.4842    1.4732 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2346   -2.4286    1.0790 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1202   -2.2506    0.0480 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8862   -1.6707    1.7128 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9206    0.0739    0.6360 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6125    0.7967   -1.7699 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9106   -0.3918   -1.6689 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4401   -2.0655   -2.3194 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5251    0.8105   -1.0945 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9273    0.8067   -0.8602 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8684    0.7048   -0.6291 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1320   -1.2793   -1.2296 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2520   -0.4182    0.8397 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5650   -1.0406    1.1781 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1637    1.8993    0.5624 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6199    1.1749    1.1027 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4867    3.1651    3.3040 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4063    0.1489   -2.0615 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0685   -3.2704   -2.0865 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4039   -3.2887   -2.3194 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3261    1.9459    0.5775 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  1
 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  0
 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                                 04-SEP-20   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 116                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-20         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  N   UNK     0       9.285  -1.887   0.000  0.00  0.00           N+0
HETATM    4  N   UNK     0       9.285  -5.073   0.000  0.00  0.00           N+0
HETATM    5  N   UNK     0      13.347  -2.668   0.000  0.00  0.00           N+0
HETATM    6  N   UNK     0       6.574  -5.020   0.000  0.00  0.00           N+0
HETATM    7  N   UNK     0       5.241  -2.710   0.000  0.00  0.00           N+0
HETATM    8  N   UNK     0      20.007  -0.332   0.000  0.00  0.00           N+0
HETATM    9  N   UNK     0       3.907  -5.020   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0      10.680  -2.678   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      10.680  -4.282   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      12.011  -1.903   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.908  -2.710   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.908  -4.250   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      14.678  -1.893   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.574  -1.940   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.241  -4.250   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      16.015  -2.657   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      14.672  -0.352   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      17.339  -0.342   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      17.345  -1.882   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      16.003   0.423   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      18.670   0.433   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      21.341   0.438   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      21.341   1.978   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      20.252   3.067   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0      22.674   2.748   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      22.674  -0.332   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      22.674  -1.872   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      24.008  -2.642   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      24.008  -4.182   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0      25.342  -1.872   0.000  0.00  0.00           O+0
CONECT    1   16                                                            
CONECT    2   23                                                            
CONECT    3   10   13                                                       
CONECT    4   11   14                                                       
CONECT    5   12   15                                                       
CONECT    6   14   17                                                       
CONECT    7   16   17                                                       
CONECT    8   23   24                                                       
CONECT    9   17                                                            
CONECT   10    3   11   12                                                  
CONECT   11    4   10                                                       
CONECT   12    5   10                                                       
CONECT   13    3   14   16                                                  
CONECT   14    4    6   13                                                  
CONECT   15    5   18   19                                                  
CONECT   16    1    7   13                                                  
CONECT   17    6    7    9                                                  
CONECT   18   15   21                                                       
CONECT   19   15   22                                                       
CONECT   20   21   22   23                                                  
CONECT   21   18   20                                                       
CONECT   22   19   20                                                       
CONECT   23    2    8   20                                                  
CONECT   24    8   25   28                                                  
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25                                                            
CONECT   28   24   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30                                                            
MASTER        0    0    0    0    0    0    0    0   32    0   68    0
END

COMPND    HMDB0001846
HETATM    1  N1  UNL     1       9.137   0.449   1.666  1.00  0.00           N  
HETATM    2  C1  UNL     1       7.745   0.577   1.374  1.00  0.00           C  
HETATM    3  N2  UNL     1       7.249   1.807   1.165  1.00  0.00           N  
HETATM    4  C2  UNL     1       5.942   2.004   0.884  1.00  0.00           C  
HETATM    5  O1  UNL     1       5.449   3.129   0.685  1.00  0.00           O  
HETATM    6  C3  UNL     1       5.139   0.881   0.821  1.00  0.00           C  
HETATM    7  C4  UNL     1       5.659  -0.361   1.037  1.00  0.00           C  
HETATM    8  N3  UNL     1       6.975  -0.511   1.315  1.00  0.00           N  
HETATM    9  N4  UNL     1       4.804  -1.476   0.963  1.00  0.00           N  
HETATM   10  C5  UNL     1       3.390  -1.423   0.742  1.00  0.00           C  
HETATM   11  C6  UNL     1       2.910  -0.112   0.180  1.00  0.00           C  
HETATM   12  C7  UNL     1       2.862  -0.216  -1.329  1.00  0.00           C  
HETATM   13  N5  UNL     1       1.988  -1.234  -1.824  1.00  0.00           N  
HETATM   14  C8  UNL     1       0.585  -1.219  -1.707  1.00  0.00           C  
HETATM   15  C9  UNL     1      -0.049  -0.075  -1.301  1.00  0.00           C  
HETATM   16  C10 UNL     1      -1.447  -0.090  -1.177  1.00  0.00           C  
HETATM   17  C11 UNL     1      -2.178  -1.212  -1.450  1.00  0.00           C  
HETATM   18  C12 UNL     1      -3.621  -1.303  -1.343  1.00  0.00           C  
HETATM   19  O2  UNL     1      -4.246  -2.361  -1.653  1.00  0.00           O  
HETATM   20  N6  UNL     1      -4.349  -0.175  -0.878  1.00  0.00           N  
HETATM   21  C13 UNL     1      -5.796  -0.310  -0.786  1.00  0.00           C  
HETATM   22  C14 UNL     1      -6.171  -0.231   0.671  1.00  0.00           C  
HETATM   23  C15 UNL     1      -5.732   1.107   1.205  1.00  0.00           C  
HETATM   24  C16 UNL     1      -6.095   1.262   2.637  1.00  0.00           C  
HETATM   25  O3  UNL     1      -6.682   0.335   3.209  1.00  0.00           O  
HETATM   26  O4  UNL     1      -5.778   2.416   3.297  1.00  0.00           O  
HETATM   27  C17 UNL     1      -6.489   0.798  -1.486  1.00  0.00           C  
HETATM   28  O5  UNL     1      -5.898   1.731  -2.081  1.00  0.00           O  
HETATM   29  O6  UNL     1      -7.878   0.782  -1.469  1.00  0.00           O  
HETATM   30  C18 UNL     1      -1.502  -2.368  -1.864  1.00  0.00           C  
HETATM   31  C19 UNL     1      -0.130  -2.389  -1.997  1.00  0.00           C  
HETATM   32  N7  UNL     1       3.758   0.997   0.532  1.00  0.00           N  
HETATM   33  H1  UNL     1       9.454   0.536   2.641  1.00  0.00           H  
HETATM   34  H2  UNL     1       9.776   0.269   0.843  1.00  0.00           H  
HETATM   35  H3  UNL     1       7.328  -1.484   1.473  1.00  0.00           H  
HETATM   36  H4  UNL     1       5.235  -2.429   1.079  1.00  0.00           H  
HETATM   37  H5  UNL     1       3.120  -2.251   0.048  1.00  0.00           H  
HETATM   38  H6  UNL     1       2.886  -1.671   1.713  1.00  0.00           H  
HETATM   39  H7  UNL     1       1.921   0.074   0.636  1.00  0.00           H  
HETATM   40  H8  UNL     1       2.613   0.797  -1.770  1.00  0.00           H  
HETATM   41  H9  UNL     1       3.911  -0.392  -1.669  1.00  0.00           H  
HETATM   42  H10 UNL     1       2.440  -2.065  -2.319  1.00  0.00           H  
HETATM   43  H11 UNL     1       0.525   0.810  -1.094  1.00  0.00           H  
HETATM   44  H12 UNL     1      -1.927   0.807  -0.860  1.00  0.00           H  
HETATM   45  H13 UNL     1      -3.868   0.705  -0.629  1.00  0.00           H  
HETATM   46  H14 UNL     1      -6.132  -1.279  -1.230  1.00  0.00           H  
HETATM   47  H15 UNL     1      -7.252  -0.418   0.840  1.00  0.00           H  
HETATM   48  H16 UNL     1      -5.565  -1.041   1.178  1.00  0.00           H  
HETATM   49  H17 UNL     1      -6.164   1.899   0.562  1.00  0.00           H  
HETATM   50  H18 UNL     1      -4.620   1.175   1.103  1.00  0.00           H  
HETATM   51  H19 UNL     1      -6.487   3.165   3.304  1.00  0.00           H  
HETATM   52  H20 UNL     1      -8.406   0.149  -2.061  1.00  0.00           H  
HETATM   53  H21 UNL     1      -2.069  -3.270  -2.087  1.00  0.00           H  
HETATM   54  H22 UNL     1       0.404  -3.289  -2.319  1.00  0.00           H  
HETATM   55  H23 UNL     1       3.326   1.946   0.577  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

HMDB0001846
     RDKit          3D
Tetrahydrofolic acid
 55 57  0  0  0  0  0  0  0  0999 V2000
    9.1366    0.4493    1.6665 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.7455    0.5774    1.3745 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2490    1.8070    1.1652 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.9416    2.0038    0.8838 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4491    3.1288    0.6846 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1389    0.8812    0.8214 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6591   -0.3611    1.0367 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9749   -0.5107    1.3155 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.8042   -1.4759    0.9629 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3903   -1.4227    0.7419 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9101   -0.1123    0.1801 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8615   -0.2163   -1.3286 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9884   -1.2337   -1.8236 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5847   -1.2193   -1.7066 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0492   -0.0752   -1.3007 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4467   -0.0902   -1.1766 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1785   -1.2124   -1.4504 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6215   -1.3034   -1.3434 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2457   -2.3612   -1.6535 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3487   -0.1751   -0.8783 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7957   -0.3102   -0.7856 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1707   -0.2309    0.6714 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7318    1.1073    1.2053 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0952    1.2621    2.6374 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6821    0.3354    3.2094 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7785    2.4165    3.2969 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4886    0.7980   -1.4860 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8976    1.7306   -2.0812 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8777    0.7823   -1.4694 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5020   -2.3684   -1.8643 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1297   -2.3886   -1.9966 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7576    0.9970    0.5325 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.4545    0.5355    2.6415 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.7759    0.2685    0.8431 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3279   -1.4842    1.4732 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2346   -2.4286    1.0790 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1202   -2.2506    0.0480 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8862   -1.6707    1.7128 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9206    0.0739    0.6360 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6125    0.7967   -1.7699 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9106   -0.3918   -1.6689 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4401   -2.0655   -2.3194 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5251    0.8105   -1.0945 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9273    0.8067   -0.8602 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8684    0.7048   -0.6291 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1320   -1.2793   -1.2296 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2520   -0.4182    0.8397 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5650   -1.0406    1.1781 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1637    1.8993    0.5624 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6199    1.1749    1.1027 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4867    3.1651    3.3040 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4063    0.1489   -2.0615 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0685   -3.2704   -2.0865 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4039   -3.2887   -2.3194 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3261    1.9459    0.5775 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  1
 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  0
 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
Tetrahydrofolate	Generator
(6S)-Tetrahydrofolate	HMDB
(6S)-Tetrahydrofolic acid	HMDB
5,6,7,8-Tetrahydrofolate	HMDB
5,6,7,8-Tetrahydrofolic acid	HMDB
Tetra-H-folate	HMDB
Tetrahydrafolate	HMDB
Tetrahydropteroyl mono-L-glutamate	HMDB
Tetrahydropteroylglutamate	HMDB

Molecular Formula

C₁₉H₂₃N₇O₆

Average Mass

445.4292

Monoisotopic Mass

445.170981503

IUPAC Name

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

Traditional Name

2-{[4-({[(6S)-4-hydroxy-2-imino-5,6,7,8-tetrahydro-1H-pteridin-6-yl]methyl}amino)phenyl]formamido}pentanedioic acid

CAS Registry Number

135-16-0

SMILES

NC1=NC(=O)C2=C(NC[C@H](CNC3=CC=C(C=C3)C(=O)NC(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-PXYINDEMSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as xanthines. These are purine derivatives with a ketone group conjugated at carbons 2 and 6 of the purine moiety.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Imidazopyrimidines

Sub Class

Purines and purine derivatives

Direct Parent

Xanthines

Alternative Parents

Substituents

Xanthine
Purinone
6-oxopurine
Alkaloid or derivatives
Pyrimidone
Pyrimidine
N-substituted imidazole
Heteroaromatic compound
Vinylogous amide
Imidazole
Azole
Urea
Lactam
Azacycle
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

purine alkaloid (CHEBI:27732 )
trimethylxanthine (CHEBI:27732 )
Purine alkaloids (C07481 )
a small molecule (1-3-7-TRIMETHYLXANTHINE )

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	-3.6	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Acidic)	2.04	ChemAxon
pKa (Strongest Basic)	5.76	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	12	ChemAxon
Hydrogen Donor Count	9	ChemAxon
Polar Surface Area	208.26 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	132.4 m³·mol⁻¹	ChemAxon
Polarizability	44.57 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 (Non-derivatized) - 70eV, Positive	splash10-0uka-4676900000-780e78301e85c240ab73	2017-09-01	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive	splash10-006x-1311190000-af98cc8be4da08f9b782	2017-10-06	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-0002-7796610000-0937514a7f23431b726e	2018-05-25	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-0nor-3269210000-20105ed6a7a6e24e2441	2018-05-25	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-00kr-1935200000-a9449c19c1ae3b0d70da	2018-05-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0032-0431900000-ff1f3948e47561161293	2016-06-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-001i-0952300000-ed9d84bc39d490f6210e	2016-06-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-001i-0920000000-0d0efcb6c323340d20b9	2016-06-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0006-0001900000-abb4cec0eb79b0bd2de1	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0v4l-2356900000-2fd17d2f587bbd5e882c	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9441000000-8c630c7a3633467d6bb3	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0002-0080900000-73480c24ce118e5e02f3	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0002-0491100000-0b5df4d0f168f8f15275	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0089-0962000000-9a988cf519f340f5d7cf	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-005c-0002900000-9587282a39f915386f95	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0zi3-2807900000-28355749389d1e225f7b	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0udi-3911000000-e7b1ccb0c9f2d7c8269a	2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, experimental)		2018-05-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-29	View Spectrum
2D NMR	[¹H, ¹H]-TOCSY. Unexported temporarily by An Chi on Oct 15, 2021 until json or nmrML file is generated. 2D NMR Spectrum (experimental)		2018-05-25	View Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)		2018-05-25	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Lysosome
Mitochondria

Biospecimen Locations

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

Tissue Locations

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

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species
MMDBp0191831	Methionine synthase	Unknown	Q99707	Homo sapiens
MMDBp0191859	Methylenetetrahydrofolate reductase	Unknown	P42898	Homo sapiens
MMDBp0191999	Trifunctional purine biosynthetic protein adenosine-3	Enzyme	P22102	Homo sapiens
MMDBp0192325	Formimidoyltransferase-cyclodeaminase	Enzyme	O95954	Homo sapiens
MMDBp0192327	Aminomethyltransferase, mitochondrial	Enzyme	P48728	Homo sapiens
MMDBp0192410	Dihydrofolate reductase	Enzyme	P00374	Homo sapiens
MMDBp0192412	Serine hydroxymethyltransferase, mitochondrial	Enzyme	P34897	Homo sapiens
MMDBp0192414	Serine hydroxymethyltransferase, cytosolic	Enzyme	P34896	Homo sapiens
MMDBp0192469	Folylpolyglutamate synthase, mitochondrial	Enzyme	Q05932	Homo sapiens
MMDBp0192500	Bifunctional purine biosynthesis protein PURH	Enzyme	P31939	Homo sapiens
MMDBp0192538	Bifunctional methylenetetrahydrofolate dehydrogenase/cyclohydrolase, mitochondrial	Unknown	P13995	Homo sapiens
MMDBp0192541	C-1-tetrahydrofolate synthase, cytoplasmic	Enzyme	P11586	Homo sapiens
MMDBp0192555	Cytosolic 10-formyltetrahydrofolate dehydrogenase	Enzyme	O75891	Homo sapiens
MMDBp0193789	Glycine cleavage system H protein, mitochondrial	Enzyme	P23434	Homo sapiens
MMDBp0193878	Gamma-glutamyl hydrolase	Enzyme	Q92820	Homo sapiens
MMDBp0194067	Mitochondrial 10-formyltetrahydrofolate dehydrogenase	Enzyme	Q3SY69	Homo sapiens
MMDBp0194161	Dihydrofolate reductase	Enzyme	B0YJ76	Homo sapiens
MMDBp0194162	Methionyl-tRNA formyltransferase, mitochondrial	Enzyme	Q96DP5	Homo sapiens
MMDBp0194163	Monofunctional C1-tetrahydrofolate synthase, mitochondrial	Enzyme	Q6UB35	Homo sapiens
MMDBp0194164	Methylenetetrahydrofolate dehydrogenase (NADP+ dependent) 2, methenyltetrahydrofolate cyclohydrolase	Enzyme	Q7Z650	Homo sapiens
MMDBp0196796	Dihydrofolate reductase, mitochondrial	Unknown	Q86XF0
MMDBp0196837	HemK methyltransferase family member 1	Unknown	Q9Y5R4
MMDBp0196881	Methyltransferase-like protein 2B	Unknown	Q6P1Q9
MMDBp0196882	Methyltransferase-like protein 6	Unknown	Q8TCB7
MMDBp0197020	Uncharacterized methyltransferase WBSCR22	Unknown	O43709

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reactions

Reaction ID	Precursor	Product	Enzyme	Data Source	Reference
MMDBr0001238	L-Glutamic acid	Pentaglutamyl Folate (Thf)	folylpolyglutamate synthase	VMH	10777604
MMDBr0001242	10-Formyltetrahydrofolic acid	Tetrahydrofolic acid	aldehyde dehydrogenase 1 family, member L1	VMH; KEGG	2733692
MMDBr0001243	Formic acid	10-Formyltetrahydrofolic acid	methylenetetrahydrofolate dehydrogenase (NADP+ dependent) 1, methenyltetrahydrofolate cyclohydrolase, formyltetrahydrofolate synthetase	VMH	12937168
MMDBr0001270	10-Formyltetrahydrofolic acid	5'-Phosphoribosyl-N-formylglycineamide	phosphoribosylglycinamide formyltransferase, phosphoribosylglycinamide synthetase, phosphoribosylaminoimidazole synthetase	VMH; KEGG	12450384 2183217 9328467 9473452
MMDBr0001273	S(8)-aminomethyldihydrolipoamide	Dihydrolipoamide	aminomethyltransferase	VMH	15355973
MMDBr0001290	Pentaglutamyl Folate (Thf)	L-Glutamic acid	gamma-glutamyl hydrolase (conjugase, folylpolygammaglutamyl hydrolase)	VMH	11375437 2867095 9614206
MMDBr0001291	Pentaglutamyl Folate (Thf)	L-Glutamic acid	gamma-glutamyl hydrolase (conjugase, folylpolygammaglutamyl hydrolase)	VMH	11375437 2867095 9614206
MMDBr0001305	L-Serine	Glycine	serine hydroxymethyltransferase 1 (soluble)	VMH; KEGG	8505317 8611185 9038835
MMDBr0001339	Formiminoglutamic acid	5-Formiminotetrahydrofolic acid	Not Available	VMH; KEGG	30371894
MMDBr0001646	5-Methyltetrahydrofolic acid	L-Methionine	Not Available	VMH; KEGG	30371894
MMDBr0002094	Sarcosine	Glycine	sarcosine dehydrogenase	VMH	10444331
MMDBr0002489	Dihydrofolic acid	Tetrahydrofolic acid	dihydrofolate reductase	VMH	15153070 1631094 6882460
MMDBr0002490	Dihydrofolic acid	Tetrahydrofolic acid	dihydrofolate reductase	VMH	15153070 16171773 1631094 6882460 962851
MMDBr0002938	L-Glutamic acid	Heptaglutamyl Folate (Thf)	folylpolyglutamate synthase	VMH	16859665 2645826 2695555 7027025 7142207
MMDBr0002939	Heptaglutamyl Folate (Thf)	L-Glutamic acid	gamma-glutamyl hydrolase (conjugase, folylpolygammaglutamyl hydrolase)	VMH	12909365 16859665
MMDBr0004976	5-Methyltetrahydrofolic acid	Selenomethionine	Not Available	VMH	30371894
MMDBr0004977	5-Methyltetrahydrofolic acid	Selenomethionine	Not Available	VMH	30371894
MMDBr0006743	Formaldehyde	5,10-Methylene-THF	Not Available	VMH	30371894
MMDBr0006939	10-Formyltetrahydrofolic acid	5'-Phosphoribosyl-N-formylglycineamide	Not Available	VMH	30371894
MMDBr0006943	5-Formiminotetrahydrofolic acid	Formiminoglutamic acid	Not Available	VMH	30371894
MMDBr0006953	5-Methyltetrahydrofolic acid	L-Methionine	Not Available	VMH	30371894
MMDBr0007191	10-Formyltetrahydrofolic acid	Formic acid	Not Available	VMH	30371894
MMDBr0007202	alpha-Ketoisovaleric acid	2-Dehydropantoate	Not Available	VMH	30371894
MMDBr0007309	Dihydrofolic acid	Tetrahydrofolic acid	Not Available	VMH; KEGG	30371894
MMDBr0007406	L-Glutamic acid	Tetrahydrofolyl-[Glu](2)	Not Available	VMH	30371894
MMDBr0007427	L-Serine	Glycine	Not Available	VMH; KEGG	30371894
MMDBr0007618	L-Glutamic acid	Pentaglutamyl Folate (Thf)	Not Available	VMH	30371894
MMDBr0007706	10-Formyltetrahydrofolic acid	Phosphoribosyl formamidocarboxamide	Not Available	VMH; KEGG	30371894
MMDBr0008072	Formic acid	10-Formyltetrahydrofolic acid	Not Available	VMH	30371894
MMDBr0008126	dUMP	5-Thymidylic acid	Not Available	VMH	30371894
MMDBr0008291	Glycine	5,10-Methylene-THF	Not Available	VMH	30371894
MMDBr0008389	Folic acid	Tetrahydrofolic acid	Not Available	VMH	30371894
MMDBr0008413	Tetrahydrofolic acid	Folic acid	Not Available	VMH	30371894
MMDBr0010265	S-Adenosylmethionine	5-Methyltetrahydrofolic acid	histamine N-methyltransferase	VMH	30371894
MMDBr0010755	Folinic acid	Formiminoglutamic acid	formimidoyltransferase cyclodeaminase	VMH; KEGG	30371894
MMDBr0010939	L-Serine	Glycine	Not Available	VMH	30371894
MMDBr0011016	dUMP	5-Thymidylic acid	Not Available	VMH	30371894

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
Bacteria	Proteobacteria	182	Human feces; Human sputum; Human ; Human unknown; Pig ; Human pleural fluid plaque; Human dental plaque; Human nasal swab; Human stool; Human feces; pleural fluid plaque; bal	Unknown; Metabolic reconstruction
Bacteria	Firmicutes	409	Human feces; Human pleural fluid plaque; Pig ; Human sputum; Human ; Human subgingival plaque; Human saliva; Human urine; Human mucosa; Human supragingival plaque; Cattle ; Human stool	Metabolic reconstruction
Bacteria	Actinobacteria	149	Human feces; Human sputum; Human bronchial brush; Human nasopharyngeal swab; Human pleural fluid plaque; Human dental plaque; Human ; Human supragingival plaque; Human mucosa; Human subgingival plaque; Human saliva	Metabolic reconstruction
Bacteria	Verrucomicrobia	1	Human ; Human feces	Metabolic reconstruction
Bacteria	Bacteroidetes	126	Human feces; Human appendix biopsy; Human ; Human stool; Human saliva; Human gastric fluid; Human urine; Human subgingival plaque; Human supragingival plaque	Metabolic reconstruction
Bacteria	Synergistetes	4	Human feces	Metabolic reconstruction
Bacteria	Spirochaetes	1	Human feces	Metabolic reconstruction
Archaea	Thaumarchaeota	1		Metabolic reconstruction
Bacteria	Fusobacteria	20	Human feces; Human	Metabolic reconstruction
Archaea	Euryarchaeota	5		Metabolic reconstruction
Bacteria	Candidatus melainabacteria	1	Human feces	Metabolic reconstruction
Bacteria	Tenericutes	4	Human feces	Metabolic reconstruction
Bacteria	Planctomycetes	1	Human feces	Metabolic reconstruction
Archaea	Crenarchaeota	1		Metabolic reconstruction
Eukaryota/Fungi	Ascomycota	1	Human feces; Human saliva	Unknown

Exposure Sources

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Units	Age	Sex	Health Condition	Data Source	Reference
Human Feces	Detected but not Quantified							HMDB
Human Blood	Detected and Quantified	0.0025	0.0044	uM	Adult (>18 years old)	Both	Normal	HMDB	17272488
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

HMDB0001846

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB022705

KNApSAcK ID

Not Available

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Wikipedia Link

METLIN ID

PubChem Compound

PDB ID

Not Available

ChEBI ID

20506

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

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Showing metabocard for Tetrahydrofolic acid (MMDBc0029674)

MOL for #<Metabolite:0x00007fdaf8bb2f80>

3D MOL for #<Metabolite:0x00007fdaf8bb2f80>

3D SDF for #<Metabolite:0x00007fdaf8bb2f80>

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PDB for #<Metabolite:0x00007fdaf8bb2f80>

3D PDB for #<Metabolite:0x00007fdaf8bb2f80>

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Structure for #<Metabolite:0x00007fdaf8bb2f80>

3D Structure for #<Metabolite:0x00007fdaf8bb2f80>