MiMeDB: Showing metabocard for 5-Methyltetrahydrofolic acid (MMDBc0032836)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-18 21:57:27 UTC

Update Date

2022-08-31 18:52:49 UTC

Metabolite ID

MMDBc0032836

Metabolite Identification

Common Name

5-Methyltetrahydrofolic acid

Description

5 methyltetrahydrofolic acid (5-MTHF) is the most biologically active form of the B-vitamin folic acid, also known generically as folate. It is a methylated derivate of tetrahydrofolate (THF, H4F). It is generated by methylenetetrahydrofolate reductase (M

Structure

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


  Mrv0541 02231219062D          

 33 35  0  0  0  0            999 V2000
   -4.0028    0.6289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0028   -0.2035    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2778    1.0470    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7205    1.0358    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2740   -0.6253    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7205   -0.6289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5712    0.5845    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4345    0.6289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5638   -0.1665    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2481   -1.4428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4345   -0.2035    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7242   -1.4465    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1448    1.0358    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8460   -0.5697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1357   -0.1443    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3219   -0.1443    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1036    0.5697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0851   -0.8915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8879    0.5845    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8583   -0.8915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3392   -0.1591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1567   -0.1553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9892   -0.5919    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1753    0.5882    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1730    0.0296    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.8907   -0.3773    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1693    0.8546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6010    0.0370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8833    1.2690    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4516    1.2616    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3150   -0.3699    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3187   -1.1912    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0253    0.0481    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  3  1  0  0  0  0
  1  4  1  0  0  0  0
  2  5  1  0  0  0  0
  2  6  1  0  0  0  0
  3  7  1  0  0  0  0
  4  8  2  0  0  0  0
  5  9  1  0  0  0  0
  5 10  1  0  0  0  0
  6 11  1  0  0  0  0
  6 12  2  0  0  0  0
  8 13  1  0  0  0  0
  9 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  2  0  0  0  0
 17 19  2  0  0  0  0
 18 20  1  0  0  0  0
 19 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 24  2  0  0  0  0
 25 23  1  1  0  0  0
 25 26  1  0  0  0  0
 25 27  1  0  0  0  0
 26 28  1  0  0  0  0
 27 29  1  0  0  0  0
 27 30  2  0  0  0  0
 28 31  1  0  0  0  0
 31 32  1  0  0  0  0
 31 33  2  0  0  0  0
  7  9  1  0  0  0  0
  8 11  1  0  0  0  0
 20 21  2  0  0  0  0
M  END

HMDB0001396
     RDKit          3D
5-Methyltetrahydrofolic acid
 58 60  0  0  0  0  0  0  0  0999 V2000
    3.4970   -2.2277   -1.4024 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9019   -1.1760   -0.5170 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.2464   -0.7425   -0.4827 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7233    0.0237    0.5890 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9959    0.4436    0.6367 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.8180    0.1057   -0.3870 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1689    0.5254   -0.3815 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.3939   -0.6259   -1.4270 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.1319   -1.0519   -1.4908 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6961   -1.7403   -2.4504 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8062    0.3433    1.6298 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.6163   -0.4577    1.7373 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9491   -0.5381    0.3571 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8104    0.8900   -0.1486 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8805    1.5963    0.6643 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.4992    1.2322    0.6391 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3612    1.7070    1.5985 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6771    1.3807    1.5762 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1688    0.5502    0.5655 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5710    0.1982    0.5495 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2352    0.4604    1.5848 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1294   -0.4078   -0.5909 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5938   -0.7696   -0.5465 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.2998    0.4167   -1.0293 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7518    0.4326   -1.2190 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6894    0.2020   -0.1580 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2485   -0.9510   -0.0874 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0661    1.1136    0.8201 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8431   -1.1540    0.8566 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9367   -1.9159    1.3834 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8825   -0.8027    1.6263 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3235    0.0724   -0.3934 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0235    0.4152   -0.3588 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3677   -1.8634   -2.4609 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1615   -3.1233   -1.3728 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4806   -2.6318   -1.1438 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.4256    1.5094   -0.1518 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.9387   -0.1391   -0.6068 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0278   -0.8905   -2.2238 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9870    1.1184    2.2815 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8827   -1.4752    2.0910 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9082   -0.0137    2.4717 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9987   -1.0617    0.4217 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5149    0.8725   -1.2329 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7981    1.3872   -0.1104 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1433    2.3901    1.3004 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0330    2.3611    2.3910 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3695    1.7549    2.3366 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6149   -0.6194   -1.4531 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6552   -1.6980   -1.1846 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7821    0.8385   -1.9743 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0635    1.2530   -0.2835 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0201    1.4458   -1.7027 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9951   -0.2588   -2.1135 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6891    2.0346    0.9234 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8739   -0.1733    2.4185 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6498   -0.5811   -1.2040 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6648    0.0157   -1.1606 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  6  8  1  0
  8  9  1  0
  9 10  2  0
  4 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 20 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  2  0
 26 28  1  0
 23 29  1  0
 29 30  2  0
 29 31  1  0
 19 32  1  0
 32 33  2  0
 13  2  1  0
 33 16  1  0
  9  3  1  0
  1 34  1  0
  1 35  1  0
  1 36  1  0
  7 37  1  0
  7 38  1  0
  8 39  1  0
 11 40  1  0
 12 41  1  0
 12 42  1  0
 13 43  1  0
 14 44  1  0
 14 45  1  0
 15 46  1  0
 17 47  1  0
 18 48  1  0
 22 49  1  0
 23 50  1  6
 24 51  1  0
 24 52  1  0
 25 53  1  0
 25 54  1  0
 28 55  1  0
 31 56  1  0
 32 57  1  0
 33 58  1  0
M  END


  Mrv0541 02231219062D          

 33 35  0  0  0  0            999 V2000
   -4.0028    0.6289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0028   -0.2035    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2778    1.0470    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7205    1.0358    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2740   -0.6253    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7205   -0.6289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5712    0.5845    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4345    0.6289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5638   -0.1665    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2481   -1.4428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4345   -0.2035    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7242   -1.4465    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1448    1.0358    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8460   -0.5697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1357   -0.1443    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3219   -0.1443    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1036    0.5697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0851   -0.8915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8879    0.5845    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8583   -0.8915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3392   -0.1591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1567   -0.1553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9892   -0.5919    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1753    0.5882    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1730    0.0296    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.8907   -0.3773    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1693    0.8546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6010    0.0370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8833    1.2690    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4516    1.2616    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3150   -0.3699    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3187   -1.1912    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0253    0.0481    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  3  1  0  0  0  0
  1  4  1  0  0  0  0
  2  5  1  0  0  0  0
  2  6  1  0  0  0  0
  3  7  1  0  0  0  0
  4  8  2  0  0  0  0
  5  9  1  0  0  0  0
  5 10  1  0  0  0  0
  6 11  1  0  0  0  0
  6 12  2  0  0  0  0
  8 13  1  0  0  0  0
  9 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  2  0  0  0  0
 17 19  2  0  0  0  0
 18 20  1  0  0  0  0
 19 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 24  2  0  0  0  0
 25 23  1  1  0  0  0
 25 26  1  0  0  0  0
 25 27  1  0  0  0  0
 26 28  1  0  0  0  0
 27 29  1  0  0  0  0
 27 30  2  0  0  0  0
 28 31  1  0  0  0  0
 31 32  1  0  0  0  0
 31 33  2  0  0  0  0
  7  9  1  0  0  0  0
  8 11  1  0  0  0  0
 20 21  2  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0032836

> <DATABASE_NAME>
MIME

> <SMILES>
CN1C(CNC2=CC=C(C=C2)C(=O)N[C@H](CCC(O)=O)C(O)=O)CNC2=C1C(=O)NC(N)=N2

> <INCHI_IDENTIFIER>
InChI=1S/C20H25N7O6/c1-27-12(9-23-16-15(27)18(31)26-20(21)25-16)8-22-11-4-2-10(3-5-11)17(30)24-13(19(32)33)6-7-14(28)29/h2-5,12-13,22H,6-9H2,1H3,(H,24,30)(H,28,29)(H,32,33)(H4,21,23,25,26,31)/t12?,13-/m1/s1

> <INCHI_KEY>
ZNOVTXRBGFNYRX-ZGTCLIOFSA-N

> <FORMULA>
C20H25N7O6

> <MOLECULAR_WEIGHT>
459.4558

> <EXACT_MASS>
459.186631567

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_AVERAGE_POLARIZABILITY>
46.12606690283296

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R)-2-[(4-{[(2-amino-5-methyl-4-oxo-3,4,5,6,7,8-hexahydropteridin-6-yl)methyl]amino}phenyl)formamido]pentanedioic acid

> <ALOGPS_LOGP>
-1.26

> <JCHEM_LOGP>
-2.843842352810261

> <ALOGPS_LOGS>
-3.12

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
3.8684582575504742

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.2189752579192654

> <JCHEM_PKA_STRONGEST_BASIC>
4.637989856477614

> <JCHEM_POLAR_SURFACE_AREA>
198.47999999999996

> <JCHEM_REFRACTIVITY>
126.88129999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.46e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2R)-2-[(4-{[(2-amino-5-methyl-4-oxo-3,6,7,8-tetrahydropteridin-6-yl)methyl]amino}phenyl)formamido]pentanedioic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0001396
     RDKit          3D
5-Methyltetrahydrofolic acid
 58 60  0  0  0  0  0  0  0  0999 V2000
    3.4970   -2.2277   -1.4024 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9019   -1.1760   -0.5170 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.2464   -0.7425   -0.4827 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7233    0.0237    0.5890 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9959    0.4436    0.6367 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.8180    0.1057   -0.3870 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1689    0.5254   -0.3815 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.3939   -0.6259   -1.4270 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.1319   -1.0519   -1.4908 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6961   -1.7403   -2.4504 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8062    0.3433    1.6298 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.6163   -0.4577    1.7373 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9491   -0.5381    0.3571 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8104    0.8900   -0.1486 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8805    1.5963    0.6643 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.4992    1.2322    0.6391 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3612    1.7070    1.5985 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6771    1.3807    1.5762 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1688    0.5502    0.5655 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5710    0.1982    0.5495 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2352    0.4604    1.5848 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1294   -0.4078   -0.5909 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5938   -0.7696   -0.5465 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.2998    0.4167   -1.0293 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7518    0.4326   -1.2190 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6894    0.2020   -0.1580 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2485   -0.9510   -0.0874 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0661    1.1136    0.8201 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8431   -1.1540    0.8566 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9367   -1.9159    1.3834 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8825   -0.8027    1.6263 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3235    0.0724   -0.3934 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0235    0.4152   -0.3588 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3677   -1.8634   -2.4609 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1615   -3.1233   -1.3728 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4806   -2.6318   -1.1438 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.4256    1.5094   -0.1518 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.9387   -0.1391   -0.6068 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0278   -0.8905   -2.2238 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9870    1.1184    2.2815 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8827   -1.4752    2.0910 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9082   -0.0137    2.4717 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9987   -1.0617    0.4217 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5149    0.8725   -1.2329 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7981    1.3872   -0.1104 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1433    2.3901    1.3004 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0330    2.3611    2.3910 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3695    1.7549    2.3366 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6149   -0.6194   -1.4531 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6552   -1.6980   -1.1846 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7821    0.8385   -1.9743 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0635    1.2530   -0.2835 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0201    1.4458   -1.7027 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9951   -0.2588   -2.1135 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6891    2.0346    0.9234 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8739   -0.1733    2.4185 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6498   -0.5811   -1.2040 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6648    0.0157   -1.1606 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  6  8  1  0
  8  9  1  0
  9 10  2  0
  4 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 20 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  2  0
 26 28  1  0
 23 29  1  0
 29 30  2  0
 29 31  1  0
 19 32  1  0
 32 33  2  0
 13  2  1  0
 33 16  1  0
  9  3  1  0
  1 34  1  0
  1 35  1  0
  1 36  1  0
  7 37  1  0
  7 38  1  0
  8 39  1  0
 11 40  1  0
 12 41  1  0
 12 42  1  0
 13 43  1  0
 14 44  1  0
 14 45  1  0
 15 46  1  0
 17 47  1  0
 18 48  1  0
 22 49  1  0
 23 50  1  6
 24 51  1  0
 24 52  1  0
 25 53  1  0
 25 54  1  0
 28 55  1  0
 31 56  1  0
 32 57  1  0
 33 58  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  C   UNK     0      -7.472   1.174   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -7.472  -0.380   0.000  0.00  0.00           C+0
HETATM    3  N   UNK     0      -6.119   1.954   0.000  0.00  0.00           N+0
HETATM    4  N   UNK     0      -8.812   1.933   0.000  0.00  0.00           N+0
HETATM    5  N   UNK     0      -6.111  -1.167   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0      -8.812  -1.174   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -4.800   1.091   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0     -10.144   1.174   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -4.786  -0.311   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -6.063  -2.693   0.000  0.00  0.00           C+0
HETATM   11  N   UNK     0     -10.144  -0.380   0.000  0.00  0.00           N+0
HETATM   12  O   UNK     0      -8.819  -2.700   0.000  0.00  0.00           O+0
HETATM   13  N   UNK     0     -11.470   1.933   0.000  0.00  0.00           N+0
HETATM   14  C   UNK     0      -3.446  -1.063   0.000  0.00  0.00           C+0
HETATM   15  N   UNK     0      -2.120  -0.269   0.000  0.00  0.00           N+0
HETATM   16  C   UNK     0      -0.601  -0.269   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.193   1.063   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.159  -1.664   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.657   1.091   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       1.602  -1.664   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.500  -0.297   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       4.026  -0.290   0.000  0.00  0.00           C+0
HETATM   23  N   UNK     0       5.580  -1.105   0.000  0.00  0.00           N+0
HETATM   24  O   UNK     0       4.061   1.098   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       7.790   0.055   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       9.129  -0.704   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       7.783   1.595   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      10.455   0.069   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       9.115   2.369   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0       6.443   2.355   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      11.788  -0.690   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      11.795  -2.224   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0      13.114   0.090   0.000  0.00  0.00           O+0
CONECT    1    2    3    4                                                  
CONECT    2    1    5    6                                                  
CONECT    3    1    7                                                       
CONECT    4    1    8                                                       
CONECT    5    2    9   10                                                  
CONECT    6    2   11   12                                                  
CONECT    7    3    9                                                       
CONECT    8    4   13   11                                                  
CONECT    9    5   14    7                                                  
CONECT   10    5                                                            
CONECT   11    6    8                                                       
CONECT   12    6                                                            
CONECT   13    8                                                            
CONECT   14    9   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16   19                                                       
CONECT   18   16   20                                                       
CONECT   19   17   21                                                       
CONECT   20   18   21                                                       
CONECT   21   19   22   20                                                  
CONECT   22   21   23   24                                                  
CONECT   23   22   25                                                       
CONECT   24   22                                                            
CONECT   25   23   26   27                                                  
CONECT   26   25   28                                                       
CONECT   27   25   29   30                                                  
CONECT   28   26   31                                                       
CONECT   29   27                                                            
CONECT   30   27                                                            
CONECT   31   28   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31                                                            
MASTER        0    0    0    0    0    0    0    0   33    0   70    0
END

COMPND    HMDB0001396
HETATM    1  C1  UNL     1       3.497  -2.228  -1.402  1.00  0.00           C  
HETATM    2  N1  UNL     1       3.902  -1.176  -0.517  1.00  0.00           N  
HETATM    3  C2  UNL     1       5.246  -0.743  -0.483  1.00  0.00           C  
HETATM    4  C3  UNL     1       5.723   0.024   0.589  1.00  0.00           C  
HETATM    5  N2  UNL     1       6.996   0.444   0.637  1.00  0.00           N  
HETATM    6  C4  UNL     1       7.818   0.106  -0.387  1.00  0.00           C  
HETATM    7  N3  UNL     1       9.169   0.525  -0.382  1.00  0.00           N  
HETATM    8  N4  UNL     1       7.394  -0.626  -1.427  1.00  0.00           N  
HETATM    9  C5  UNL     1       6.132  -1.052  -1.491  1.00  0.00           C  
HETATM   10  O1  UNL     1       5.696  -1.740  -2.450  1.00  0.00           O  
HETATM   11  N5  UNL     1       4.806   0.343   1.630  1.00  0.00           N  
HETATM   12  C6  UNL     1       3.616  -0.458   1.737  1.00  0.00           C  
HETATM   13  C7  UNL     1       2.949  -0.538   0.357  1.00  0.00           C  
HETATM   14  C8  UNL     1       2.810   0.890  -0.149  1.00  0.00           C  
HETATM   15  N6  UNL     1       1.880   1.596   0.664  1.00  0.00           N  
HETATM   16  C9  UNL     1       0.499   1.232   0.639  1.00  0.00           C  
HETATM   17  C10 UNL     1      -0.361   1.707   1.598  1.00  0.00           C  
HETATM   18  C11 UNL     1      -1.677   1.381   1.576  1.00  0.00           C  
HETATM   19  C12 UNL     1      -2.169   0.550   0.566  1.00  0.00           C  
HETATM   20  C13 UNL     1      -3.571   0.198   0.550  1.00  0.00           C  
HETATM   21  O2  UNL     1      -4.235   0.460   1.585  1.00  0.00           O  
HETATM   22  N7  UNL     1      -4.129  -0.408  -0.591  1.00  0.00           N  
HETATM   23  C14 UNL     1      -5.594  -0.770  -0.547  1.00  0.00           C  
HETATM   24  C15 UNL     1      -6.300   0.417  -1.029  1.00  0.00           C  
HETATM   25  C16 UNL     1      -7.752   0.433  -1.219  1.00  0.00           C  
HETATM   26  C17 UNL     1      -8.689   0.202  -0.158  1.00  0.00           C  
HETATM   27  O3  UNL     1      -9.249  -0.951  -0.087  1.00  0.00           O  
HETATM   28  O4  UNL     1      -9.066   1.114   0.820  1.00  0.00           O  
HETATM   29  C18 UNL     1      -5.843  -1.154   0.857  1.00  0.00           C  
HETATM   30  O5  UNL     1      -4.937  -1.916   1.383  1.00  0.00           O  
HETATM   31  O6  UNL     1      -6.883  -0.803   1.626  1.00  0.00           O  
HETATM   32  C19 UNL     1      -1.323   0.072  -0.393  1.00  0.00           C  
HETATM   33  C20 UNL     1       0.023   0.415  -0.359  1.00  0.00           C  
HETATM   34  H1  UNL     1       3.368  -1.863  -2.461  1.00  0.00           H  
HETATM   35  H2  UNL     1       4.161  -3.123  -1.373  1.00  0.00           H  
HETATM   36  H3  UNL     1       2.481  -2.632  -1.144  1.00  0.00           H  
HETATM   37  H4  UNL     1       9.426   1.509  -0.152  1.00  0.00           H  
HETATM   38  H5  UNL     1       9.939  -0.139  -0.607  1.00  0.00           H  
HETATM   39  H6  UNL     1       8.028  -0.890  -2.224  1.00  0.00           H  
HETATM   40  H7  UNL     1       4.987   1.118   2.282  1.00  0.00           H  
HETATM   41  H8  UNL     1       3.883  -1.475   2.091  1.00  0.00           H  
HETATM   42  H9  UNL     1       2.908  -0.014   2.472  1.00  0.00           H  
HETATM   43  H10 UNL     1       1.999  -1.062   0.422  1.00  0.00           H  
HETATM   44  H11 UNL     1       2.515   0.873  -1.233  1.00  0.00           H  
HETATM   45  H12 UNL     1       3.798   1.387  -0.110  1.00  0.00           H  
HETATM   46  H13 UNL     1       2.143   2.390   1.300  1.00  0.00           H  
HETATM   47  H14 UNL     1       0.033   2.361   2.391  1.00  0.00           H  
HETATM   48  H15 UNL     1      -2.369   1.755   2.337  1.00  0.00           H  
HETATM   49  H16 UNL     1      -3.615  -0.619  -1.453  1.00  0.00           H  
HETATM   50  H17 UNL     1      -5.655  -1.698  -1.185  1.00  0.00           H  
HETATM   51  H18 UNL     1      -5.782   0.838  -1.974  1.00  0.00           H  
HETATM   52  H19 UNL     1      -6.063   1.253  -0.284  1.00  0.00           H  
HETATM   53  H20 UNL     1      -8.020   1.446  -1.703  1.00  0.00           H  
HETATM   54  H21 UNL     1      -7.995  -0.259  -2.113  1.00  0.00           H  
HETATM   55  H22 UNL     1      -8.689   2.035   0.923  1.00  0.00           H  
HETATM   56  H23 UNL     1      -6.874  -0.173   2.418  1.00  0.00           H  
HETATM   57  H24 UNL     1      -1.650  -0.581  -1.204  1.00  0.00           H  
HETATM   58  H25 UNL     1       0.665   0.016  -1.161  1.00  0.00           H  
CONECT    1    2   34   35   36
CONECT    2    3   13
CONECT    3    4    4    9
CONECT    4    5   11
CONECT    5    6    6
CONECT    6    7    8
CONECT    7   37   38
CONECT    8    9   39
CONECT    9   10   10
CONECT   11   12   40
CONECT   12   13   41   42
CONECT   13   14   43
CONECT   14   15   44   45
CONECT   15   16   46
CONECT   16   17   17   33
CONECT   17   18   47
CONECT   18   19   19   48
CONECT   19   20   32
CONECT   20   21   21   22
CONECT   22   23   49
CONECT   23   24   29   50
CONECT   24   25   51   52
CONECT   25   26   53   54
CONECT   26   27   27   28
CONECT   28   55
CONECT   29   30   30   31
CONECT   31   56
CONECT   32   33   33   57
CONECT   33   58
END

HMDB0001396
     RDKit          3D
5-Methyltetrahydrofolic acid
 58 60  0  0  0  0  0  0  0  0999 V2000
    3.4970   -2.2277   -1.4024 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9019   -1.1760   -0.5170 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.2464   -0.7425   -0.4827 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7233    0.0237    0.5890 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9959    0.4436    0.6367 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.8180    0.1057   -0.3870 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1689    0.5254   -0.3815 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.3939   -0.6259   -1.4270 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.1319   -1.0519   -1.4908 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6961   -1.7403   -2.4504 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8062    0.3433    1.6298 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.6163   -0.4577    1.7373 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9491   -0.5381    0.3571 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8104    0.8900   -0.1486 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8805    1.5963    0.6643 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.4992    1.2322    0.6391 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3612    1.7070    1.5985 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6771    1.3807    1.5762 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1688    0.5502    0.5655 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5710    0.1982    0.5495 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2352    0.4604    1.5848 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1294   -0.4078   -0.5909 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5938   -0.7696   -0.5465 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.2998    0.4167   -1.0293 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7518    0.4326   -1.2190 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6894    0.2020   -0.1580 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2485   -0.9510   -0.0874 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0661    1.1136    0.8201 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8431   -1.1540    0.8566 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9367   -1.9159    1.3834 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8825   -0.8027    1.6263 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3235    0.0724   -0.3934 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0235    0.4152   -0.3588 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3677   -1.8634   -2.4609 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1615   -3.1233   -1.3728 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4806   -2.6318   -1.1438 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.4256    1.5094   -0.1518 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.9387   -0.1391   -0.6068 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0278   -0.8905   -2.2238 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9870    1.1184    2.2815 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8827   -1.4752    2.0910 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9082   -0.0137    2.4717 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9987   -1.0617    0.4217 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5149    0.8725   -1.2329 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7981    1.3872   -0.1104 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1433    2.3901    1.3004 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0330    2.3611    2.3910 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3695    1.7549    2.3366 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6149   -0.6194   -1.4531 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6552   -1.6980   -1.1846 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7821    0.8385   -1.9743 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0635    1.2530   -0.2835 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0201    1.4458   -1.7027 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9951   -0.2588   -2.1135 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6891    2.0346    0.9234 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8739   -0.1733    2.4185 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6498   -0.5811   -1.2040 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6648    0.0157   -1.1606 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  6  8  1  0
  8  9  1  0
  9 10  2  0
  4 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 20 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  2  0
 26 28  1  0
 23 29  1  0
 29 30  2  0
 29 31  1  0
 19 32  1  0
 32 33  2  0
 13  2  1  0
 33 16  1  0
  9  3  1  0
  1 34  1  0
  1 35  1  0
  1 36  1  0
  7 37  1  0
  7 38  1  0
  8 39  1  0
 11 40  1  0
 12 41  1  0
 12 42  1  0
 13 43  1  0
 14 44  1  0
 14 45  1  0
 15 46  1  0
 17 47  1  0
 18 48  1  0
 22 49  1  0
 23 50  1  6
 24 51  1  0
 24 52  1  0
 25 53  1  0
 25 54  1  0
 28 55  1  0
 31 56  1  0
 32 57  1  0
 33 58  1  0
M  END

Synonyms

Value	Source
5-Methyltetrahydrofolate	Generator
5-Methyl tetrahydrofolate	HMDB
5-Methyl-5,6,7,8-tetrahydrofolate	HMDB
5-Methyl-tetrahydrofolate	HMDB
5-Methyltetrahydropteroylglutamate	HMDB
Methyl folate	HMDB
Methyl-tetrahydrofolate	HMDB
N( 5)-Methyltetrahydrofolate	HMDB
N-(4-(((2-Amino-1,4,5,6,7,8-hexahydro-5-methyl-4-oxo-6-pteridinyl)methyl)amino)benzoyl)-L-glutamate	HMDB
N-(4-(((2-Amino-1,4,5,6,7,8-hexahydro-5-methyl-4-oxo-6-pteridinyl)methyl)amino)benzoyl)-L-glutamic acid	HMDB
N-(5-Methyl-5,6,7,8-tetrahydropteroyl)-L-glutamate	HMDB
N-(5-Methyl-5,6,7,8-tetrahydropteroyl)-L-glutamic acid	HMDB
N5-Methyl-tetrahydrofolate	HMDB
N5-Methyl-tetrahydrofolic acid	HMDB
N5-Methyltetrahydrofolate	HMDB
N5-Methyltetrahydropteroyl mono-L-glutamate	HMDB
[(6S)-5-Methyl-5,6,7,8-tetrahydropteroyl]glutamate	HMDB
5-Methyltetrahydrofolate, (DL-glu)-isomer	HMDB
5-Methyltetrahydrofolate, (L-glu)-(R)-isomer	HMDB
5-Methyltetrahydrofolate, (L-glu)-(S)-isomer	HMDB
5-Methyltetrahydrofolate, calcium salt (1:1), (L-glu)-isomer	HMDB
5-Methyltetrahydrofolate, methyl-(14)C-labeled, (DL-glu)-isomer	HMDB
5-Methyltetrahydrofolate, methyl-(14)C-labeled, (L-glu)-isomer	HMDB
CH3-FH4	HMDB
L-Methyl folate	HMDB
N(5)-Methyltetrahydrofolic acid	HMDB
Prefolic a	HMDB
Mefolinate	HMDB
Levomefolic acid	HMDB
L-Methylfolate	HMDB
Deplin	HMDB

Molecular Formula

C₂₀H₂₅N₇O₆

Average Mass

459.4558

Monoisotopic Mass

459.186631567

IUPAC Name

(2R)-2-[(4-{[(2-amino-5-methyl-4-oxo-3,4,5,6,7,8-hexahydropteridin-6-yl)methyl]amino}phenyl)formamido]pentanedioic acid

Traditional Name

(2R)-2-[(4-{[(2-amino-5-methyl-4-oxo-3,6,7,8-tetrahydropteridin-6-yl)methyl]amino}phenyl)formamido]pentanedioic acid

CAS Registry Number

134-35-0

SMILES

CN1C(CNC2=CC=C(C=C2)C(=O)N[C@H](CCC(O)=O)C(O)=O)CNC2=C1C(=O)NC(N)=N2

InChI Identifier

InChI=1S/C20H25N7O6/c1-27-12(9-23-16-15(27)18(31)26-20(21)25-16)8-22-11-4-2-10(3-5-11)17(30)24-13(19(32)33)6-7-14(28)29/h2-5,12-13,22H,6-9H2,1H3,(H,24,30)(H,28,29)(H,32,33)(H4,21,23,25,26,31)/t12?,13-/m1/s1

InChI Key

ZNOVTXRBGFNYRX-ZGTCLIOFSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as tetrahydrofolic acids. These are heterocyclic compounds based on the 5,6,7,8-tetrahydropteroic acid skeleton conjugated with at least one L-glutamic acid unit.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Pteridines and derivatives

Sub Class

Pterins and derivatives

Direct Parent

Tetrahydrofolic acids

Alternative Parents

Substituents

Tetrahydrofolic acid
Glutamic acid or derivatives
Hippuric acid or derivatives
Hippuric acid
N-acyl-alpha-amino acid
N-acyl-alpha amino acid or derivatives
Alpha-amino acid or derivatives
Aminobenzamide
Aminobenzoic acid or derivatives
Benzoic acid or derivatives
Benzamide
Benzoyl
Phenylalkylamine
Tertiary aliphatic/aromatic amine
Aniline or substituted anilines
Dialkylarylamine
Secondary aliphatic/aromatic amine
Pyrimidone
Aminopyrimidine
Dicarboxylic acid or derivatives
Benzenoid
Pyrimidine
Monocyclic benzene moiety
Vinylogous amide
Heteroaromatic compound
Secondary carboxylic acid amide
Tertiary amine
Amino acid or derivatives
Amino acid
Carboxamide group
Secondary amine
Carboxylic acid
Carboxylic acid derivative
Azacycle
Organic nitrogen compound
Carbonyl group
Organonitrogen compound
Organooxygen compound
Primary amine
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic oxygen compound
Amine
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Physical Properties

State

Solid

Predicted Properties

Property	Value	Source
Water Solubility	0.35 g/L	ALOGPS
logP	-1.3	ALOGPS
logP	-2.8	ChemAxon
logS	-3.1	ALOGPS
pKa (Strongest Acidic)	3.22	ChemAxon
pKa (Strongest Basic)	4.64	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	198.48 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	126.88 m³·mol⁻¹	ChemAxon
Polarizability	46.13 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	splash10-03di-2645900000-0472550b7df0d95d4718	2017-09-01	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive	splash10-059i-4532290000-8e3b1526c05a0a70d971	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
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03dl-0313900000-d4f9d7f9d8c65a2e0428	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-01ox-0924300000-2f133db2f48bd5b14a8d	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-000f-0920000000-298e8f3cd55b0fe42bad	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-0001900000-b1b1292a418283f61ea9	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0900-1256900000-32c1cf48970dead32f60	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9641100000-b5468bf27455b7e5ee39	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-0001900000-ba41f53e73f5102d5c04	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4u-3419800000-385454b6189707f5e684	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0zg0-3931100000-ccab9c792ff1e540a4e8	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03di-0108900000-f5ef3a5a71a48db8560b	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03di-0209100000-ac8dd1f905331a1f84bb	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-000x-0912000000-e973388138222d017517	2021-09-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 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, 1000 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, 200 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, 300 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, 400 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, 500 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, 600 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, 700 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, 800 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-29	View Spectrum

Biological Properties

Cellular Locations

Extracellular

Biospecimen Locations

Blood
Cerebrospinal Fluid (CSF)
Feces
Kidney
Liver
Placenta
Urine

Tissue Locations

Kidney
Liver
Placenta

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
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

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference
MMDBr0000123	5-Methyltetrahydrofolic acid	5-Methyltetrahydrofolic acid	Folate receptor 1 (adult)	5-Methyltetrahydrofolate Transport via Receptor Binding And Protolysis	VMH	15094208
MMDBr0000124	5-Methyltetrahydrofolic acid	5-Methyltetrahydrofolic acid	Solute carrier family 19 (folate transporter), member 1	5-Methyltetrahydrofolate Transport via Anion Exchange	VMH	11375437 14770311
MMDBr0000683	5-Methyltetrahydrofolic acid	Hydrogen Ion	Not Available	6, 7-Dihydropteridine Reduction	VMH	3735413
MMDBr0001646	5-Methyltetrahydrofolic acid	Hydrogen Ion	Not Available	Methionine Synthase	VMH	30371894
MMDBr0004976	5-Methyltetrahydrofolic acid	Hydrogen Ion	Not Available	Methionine Synthase	VMH	30371894
MMDBr0004977	5-Methyltetrahydrofolic acid	Hydrogen Ion	Not Available	Methionine Synthase	VMH	30371894
MMDBr0005382	5-Methyltetrahydrofolic acid	5-Methyltetrahydrofolic acid	Not Available	Transport of Thf, Extracellular	VMH	30371894
MMDBr0005420	5-Methyltetrahydrofolic acid	5-Methyltetrahydrofolic acid	Not Available	5-Methyltetrahydrofolate Transport via Anion Antiport	VMH	30371894
MMDBr0005500	Hydrogen Ion	5-Methyltetrahydrofolic acid	Methylenetetrahydrofolate reductase (nad(p)h)	5, 10-Methylenetetrahydrofolatereductase (NADPH)	VMH	30371894
MMDBr0006953	5-Methyltetrahydrofolic acid	Hydrogen Ion	Not Available	5-MethyltetrahydrofolateL-homocysteine S-methyltransferase	VMH	30371894
MMDBr0007126	5-Methyltetrahydrofolic acid	Hydrogen Ion	Not Available	Methylenetetrahydrofolate reductase NADPH2	VMH	30371894
MMDBr0008016	5-Methyltetrahydrofolic acid	Hydrogen Ion	Not Available	5-Methyltetrahydrofolate:NAD+ Oxidoreductase / Ec:1.5.1.20	VMH	30371894
MMDBr0010265	S-Adenosylmethionine	5-Methyltetrahydrofolic acid	Histamine n-methyltransferase	Histamine N-Methyltransferase	VMH	30371894
MMDBr0018070	Hydrogen Ion	NADP	5,10-methylenetetrahydrofolate reductase	Reduction	PathBank	31602464
MMDBr0018071	Homocysteine	L-Methionine	Methionine synthase	Synthesis	PathBank	31602464
MMDBr0019774	Hydrogen Ion	NADP	Not Available		PathBank	31602464
MMDBr0019775	Homocysteine	L-Methionine	Not Available		PathBank	31602464

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference
Aids		Association	Human Cerebrospinal Fluid (CSF)	HMDB	1969014
Rett syndrome	Slight Decrease	Association	Human Cerebrospinal Fluid (CSF)	HMDB	16429378

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria	Proteobacteria	177	Human ; Human sputum; Human subgingival plaque; Human feces; 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	385	Human feces; Human pleural fluid plaque; Pig ; Human sputum; Human ; Human subgingival plaque; Human saliva; Human urine; Human mucosa; Cattle ; Human stool	Metabolic reconstruction
Bacteria	Actinobacteria	148	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	4		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

Source Type	Source Sub-type	Species	Data Source	Reference
Plant		Lactuca sativa	FooDB	31437929

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference
Human Feces	Detected but not Quantified									HMDB
Human Cerebrospinal fluid (csf)	Detected and Quantified	0.026	0.007			uM	Children (1-13 years old)	Not Specified	AIDS	HMDB	1969014
Human Cerebrospinal fluid (csf)	Detected and Quantified			0.00700	0.0110	uM	Children (1-13 years old)	Both	Cerebral folate transport deficiency	HMDB	25274592
Human Cerebrospinal fluid (csf)	Detected and Quantified	0.053		0.02	0.09	uM	Adult (>18 years old)	Not Specified	Rett syndrome	HMDB	16429378
Human Cerebrospinal fluid (csf)	Detected and Quantified			0.0400	0.128	uM	Children (1-13 years old)	Both	Normal	HMDB	25274592
Human Cerebrospinal fluid (csf)	Detected and Quantified	0.075		0.045	0.13	uM	Adult (>18 years old)	Not Specified	Normal	HMDB	16429378
Human Cerebrospinal fluid (csf)	Detected and Quantified	0.12		0.04	0.20	uM	Adult (>18 years old)	Both	Normal	HMDB	9870205
Human Blood	Detected and Quantified	0.3		0.094	0.7	uM	Adult (>18 years old)	Both	Normal	HMDB	18160726
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 Placenta	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Urine	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	32966057
Human Blood	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	32966057

External Links

HMDB ID

HMDB0001396

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB022600

KNApSAcK ID

Not Available

Chemspider ID

388371

KEGG Compound ID

C00440

BioCyc ID

Not Available

BiGG ID

Wikipedia Link

METLIN ID

PubChem Compound

PDB ID

Not Available

ChEBI ID

15641

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Surtees R, Leonard J, Austin S: Association of demyelination with deficiency of cerebrospinal-fluid S-adenosylmethionine in inborn errors of methyl-transfer pathway. Lancet. 1991 Dec 21-28;338(8782-8783):1550-4. doi: 10.1016/0140-6736(91)92373-a. [PubMed:1683972 ]
Surtees R, Hyland K, Smith I: Central-nervous-system methyl-group metabolism in children with neurological complications of HIV infection. Lancet. 1990 Mar 17;335(8690):619-21. doi: 10.1016/0140-6736(90)90409-x. [PubMed:1969014 ]
Kane MA, Roth E, Raptis G, Schreiber C, Waxman S: Effect of intracellular folate concentration on the modulation of 5-fluorouracil cytotoxicity by the elevation of phosphoribosylpyrophosphate in cultured human KB cells. Cancer Res. 1987 Dec 15;47(24 Pt 1):6444-50. [PubMed:2445472 ]
Straw JA, Szapary D, Wynn WT: Pharmacokinetics of the diastereoisomers of leucovorin after intravenous and oral administration to normal subjects. Cancer Res. 1984 Jul;44(7):3114-9. [PubMed:6609768 ]
Prasad PD, Mahesh VB, Leibach FH, Ganapathy V: Functional coupling between a bafilomycin A1-sensitive proton pump and a probenecid-sensitive folate transporter in human placental choriocarcinoma cells. Biochim Biophys Acta. 1994 Jun 30;1222(2):309-14. doi: 10.1016/0167-4889(94)90184-8. [PubMed:8031869 ]
Camilo E, Zimmerman J, Mason JB, Golner B, Russell R, Selhub J, Rosenberg IH: Folate synthesized by bacteria in the human upper small intestine is assimilated by the host. Gastroenterology. 1996 Apr;110(4):991-8. doi: 10.1053/gast.1996.v110.pm8613033. [PubMed:8613033 ]
Evans MI, Duquette DA, Rinaldo P, Bawle E, Rosenblatt DS, Whitty J, Quintero RA, Johnson MP: Modulation of B12 dosage and response in fetal treatment of methylmalonic aciduria (MMA): titration of treatment dose to serum and urine MMA. Fetal Diagn Ther. 1997 Jan-Feb;12(1):21-3. doi: 10.1159/000264418. [PubMed:9101216 ]
Van Hove JL, Lazeyras F, Zeisel SH, Bottiglieri T, Hyland K, Charles HC, Gray L, Jaeken J, Kahler SG: One-methyl group metabolism in non-ketotic hyperglycinaemia: mildly elevated cerebrospinal fluid homocysteine levels. J Inherit Metab Dis. 1998 Dec;21(8):799-811. doi: 10.1023/a:1005462400552. [PubMed:9870205 ]
Chladek J, Sispera L, Martinkova J: High-performance liquid chromatographic assay for the determination of 5-methyltetrahydrofolate in human plasma. J Chromatogr B Biomed Sci Appl. 2000 Jul 21;744(2):307-13. doi: 10.1016/s0378-4347(00)00257-7. [PubMed:10993519 ]
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 ]
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 ]
Kim TH, Yang J, Darling PB, O'Connor DL: A large pool of available folate exists in the large intestine of human infants and piglets. J Nutr. 2004 Jun;134(6):1389-94. doi: 10.1093/jn/134.6.1389. [PubMed:15173401 ]
Irizarry MC: Biomarkers of Alzheimer disease in plasma. NeuroRx. 2004 Apr;1(2):226-34. doi: 10.1602/neurorx.1.2.226. [PubMed:15717023 ]
Ormazabal A, Artuch R, Vilaseca MA, Aracil A, Pineda M: Cerebrospinal fluid concentrations of folate, biogenic amines and pterins in Rett syndrome: treatment with folinic acid. Neuropediatrics. 2005 Dec;36(6):380-5. doi: 10.1055/s-2005-873078. [PubMed:16429378 ]
Authors unspecified: 5-methyltetrahydrofolate. Monograph. Altern Med Rev. 2006 Dec;11(4):330-7. [PubMed:17176169 ]

Showing metabocard for 5-Methyltetrahydrofolic acid (MMDBc0032836)

MOL for #<Metabolite:0x000055d24b192cd8>

3D MOL for #<Metabolite:0x000055d24b192cd8>

3D SDF for #<Metabolite:0x000055d24b192cd8>

3D-SDF for #<Metabolite:0x000055d24b192cd8>

PDB for #<Metabolite:0x000055d24b192cd8>

3D PDB for #<Metabolite:0x000055d24b192cd8>

SMILES for #<Metabolite:0x000055d24b192cd8>

INCHI for #<Metabolite:0x000055d24b192cd8>

Structure for #<Metabolite:0x000055d24b192cd8>

3D Structure for #<Metabolite:0x000055d24b192cd8>