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Showing metabocard for 5-Methyltetrahydrofolic acid (HMDB0001396)

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IdentificationTaxonomyOntologyPhysical propertiesSpectraBiological propertiesConcentrationsLinksReferencesenzymes (6) Show 6 proteinsXML
enzymes (6) Show 6 proteins
Record Information
Version5.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2021-09-14 15:44:56 UTC
HMDB IDHMDB0001396
Secondary Accession Numbers
  • HMDB01396
Metabolite Identification
Common Name5-Methyltetrahydrofolic acid
Description5 methyltetrahydrofolic acid (5-MTHF) is the most biologically active form of the B-vitamin known as folic acid, also known generically as folate. 5-MTHF functions, in concert with vitamin B12, as a methyl-group donor involved in the conversion of the amino acid homocysteine to methionine. Methyl (CH3) group donation is vital to many bodily processes, including serotonin, melatonin, and DNA synthesis. Therapeutically, 5-MTHF is instrumental in reducing homocysteine levels, preventing neural tube defects, and improving vascular endothelial function. Research on folate supplementation suggests it plays a key role in preventing cervical dysplasia and protecting against neoplasia in ulcerative colitis. Folic acid also shows promise as part of a nutritional protocol to treat vitiligo, and may reduce inflammation of the gingiva. Furthermore, certain neurological, cognitive, and psychiatric presentations may be secondary to folate deficiency. Such presentations include depression, peripheral neuropathy, myelopathy, restless legs syndrome, insomnia, dementia, forgetfulness, irritability, endogenous depression, organic psychosis, and schizophrenia-like syndromes. After ingestion, the process of conversion of folic acid to the metabolically active coenzyme forms is relatively complex. Synthesis of the active forms of folic acid requires several enzymes, adequate liver and intestinal function, and adequate supplies of riboflavin (B2), niacin (B3), pyridoxine (B6), zinc, vitamin C, and serine. After formation of the coenzyme forms of the vitamin in the liver, these metabolically active compounds are secreted into the small intestine with bile (the folate enterohepatic cycle), where they are reabsorbed and distributed to tissues throughout the body. Human pharmacokinetic studies indicate folic acid has high bioavailability, with large oral doses of folic acid substantially raising plasma levels in healthy subjects in a time and dose dependent manner. Red blood cells (RBCs) appear to be the storage depot for folic acid, as RBC levels remain elevated for periods in excess of 40 days following discontinuation of supplementation. Folic acid is poorly transported to the brain and rapidly cleared from the central nervous system. The primary methods of elimination of absorbed folic acid are fecal (through bile) and urinary. Despite the biochemical complexity of this process, evidence suggests oral supplementation with folic acid increases the body's pool of 5-MTHF in healthy individuals. However, enzyme defects, mal-absorption, digestive system pathology, and liver disease can result in impaired ability to activate folic acid. In fact, some individuals have a severe congenital deficiency of the enzyme Methyl tetrahydrofolate reductase (5-MTHFR), which is needed to convert folic acid to 5-MTHF. Milder forms of this enzyme defect likely interact with dietary folate status to determine risk for some disease conditions. In individuals with a genetic defect of this enzyme (whether mild or severe), supplementation with 5- MTHF might be preferable to folic acid supplementation. (PMID: 17176169 ).
Structure
Data?1582752198
MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0001396 (5-Methyltetrahydrofolic acid)


  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
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 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
Download

3D MOL for HMDB0001396 (5-Methyltetrahydrofolic acid)

Download
3D SDF for HMDB0001396 (5-Methyltetrahydrofolic acid)

  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>
HMDB0001396

> <DATABASE_NAME>
hmdb

> <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

$$$$

Download
3D-SDF for HMDB0001396 (5-Methyltetrahydrofolic acid)
https://cactus.nci.nih.gov/chemical/structure/CN1C(CNC2=CC=C(C=C2)C(=O)N%5BC@...
 OpenBabel09142113213D
Jmol version 14.31.45  2021-07-21 05:08 EXTRACT: ({0:57})
 58 60  0  0  0  0  0  0  0  0999 V2000
    5.1827    0.7262   -2.4038 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8235    1.0152   -1.0131 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.0484    2.2186   -0.6703 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6015    1.8304   -0.3592 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0432    1.0821   -1.4881 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7326    0.6204   -1.4361 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2034   -0.0905   -2.5098 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0934   -0.5484   -2.4615 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8794   -0.2994   -1.3325 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3450    0.4145   -0.2559 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0458    0.8652   -0.3081 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2701   -0.7884   -1.2777 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7339   -1.4087   -2.2151 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0267   -0.5476   -0.1886 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4078   -1.0332   -0.1342 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.8497   -0.9841   -1.1294 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2177   -0.1607    0.8271 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3103    1.2613    0.2701 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1080    2.1206    1.2168 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3203    3.4149    0.9314 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5564    1.6445    2.2328 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4199   -2.4599    0.3511 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5843   -3.1149    0.4806 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3814   -3.0142    0.6234 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6909    2.8611    0.5676 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7317    1.8582    1.6414 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.1656    0.5748    1.3481 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2078    0.1427    0.0285 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6445   -1.1572   -0.2478 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6930   -1.5686   -1.3972 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0119   -1.9473    0.7845 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.9547   -1.4762    2.0601 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3346   -2.2949    3.0934 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.5403   -0.2562    2.3279 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.8744    1.5567   -3.0387 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2617    0.5918   -2.4797 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6794   -0.1849   -2.7271 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0702    2.9206   -1.5039 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5765    1.2093    0.5363 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0112    2.7315   -0.1930 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5876    0.9088   -2.2720 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8111   -0.2825   -3.3816 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5036   -1.0992   -3.2950 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9498    0.6083    0.6177 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3678    1.4162    0.5236 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6568   -0.0527    0.5591 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2203   -0.5743    0.9360 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7261   -0.1387    1.7996 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3077    1.6748    0.1611 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8019    1.2392   -0.7026 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8377    3.9259    1.5688 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5416   -4.0283    0.7953 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7040    3.1852    0.3292 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0967    3.7172    0.8872 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4592    2.0913    2.5427 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3168   -2.8526    0.6163 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6393   -3.1974    2.9102 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2985   -1.9712    4.0071 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1 35  1  0  0  0  0
  1 36  1  0  0  0  0
  1 37  1  0  0  0  0
  2  3  1  0  0  0  0
  2 28  1  0  0  0  0
  3  4  1  0  0  0  0
  3 25  1  0  0  0  0
  3 38  1  6  0  0  0
  4  5  1  0  0  0  0
  4 39  1  0  0  0  0
  4 40  1  0  0  0  0
  5  6  1  0  0  0  0
  5 41  1  0  0  0  0
  6  7  2  0  0  0  0
  6 11  1  0  0  0  0
  7  8  1  0  0  0  0
  7 42  1  0  0  0  0
  8  9  2  0  0  0  0
  8 43  1  0  0  0  0
  9 10  1  0  0  0  0
  9 12  1  0  0  0  0
 10 11  2  0  0  0  0
 10 44  1  0  0  0  0
 11 45  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 46  1  0  0  0  0
 15 16  1  6  0  0  0
 15 17  1  0  0  0  0
 15 22  1  0  0  0  0
 17 18  1  0  0  0  0
 17 47  1  0  0  0  0
 17 48  1  0  0  0  0
 18 19  1  0  0  0  0
 18 49  1  0  0  0  0
 18 50  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  2  0  0  0  0
 20 51  1  0  0  0  0
 22 23  1  0  0  0  0
 22 24  2  0  0  0  0
 23 52  1  0  0  0  0
 25 26  1  0  0  0  0
 25 53  1  0  0  0  0
 25 54  1  0  0  0  0
 26 27  1  0  0  0  0
 26 55  1  0  0  0  0
 27 28  2  0  0  0  0
 27 34  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 29 31  1  0  0  0  0
 31 32  1  0  0  0  0
 31 56  1  0  0  0  0
 32 33  1  0  0  0  0
 32 34  2  0  0  0  0
 33 57  1  0  0  0  0
 33 58  1  0  0  0  0
M  END
$$$$

Download
PDB for HMDB0001396 (5-Methyltetrahydrofolic acid)
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

Download
3D PDB for HMDB0001396 (5-Methyltetrahydrofolic acid)
COMPND    https://cactus.nci.nih.gov/chemical/structure/CN1C(CNC2=CC=C(C=C2)C(=O)N%5BC@... 
AUTHOR    GENERATED BY OPEN BABEL 3.1.0
HETATM    1  C   UNK A   0       5.183   0.726  -2.404  1.00  0.00           C  
HETATM    2  N   UNK A   0       4.824   1.015  -1.013  1.00  0.00           N  
HETATM    3  C   UNK A   0       4.048   2.219  -0.670  1.00  0.00           C  
HETATM    4  C   UNK A   0       2.602   1.830  -0.359  1.00  0.00           C  
HETATM    5  N   UNK A   0       2.043   1.082  -1.488  1.00  0.00           N  
HETATM    6  C   UNK A   0       0.733   0.620  -1.436  1.00  0.00           C  
HETATM    7  C   UNK A   0       0.203  -0.090  -2.510  1.00  0.00           C  
HETATM    8  C   UNK A   0      -1.093  -0.548  -2.462  1.00  0.00           C  
HETATM    9  C   UNK A   0      -1.879  -0.299  -1.333  1.00  0.00           C  
HETATM   10  C   UNK A   0      -1.345   0.414  -0.256  1.00  0.00           C  
HETATM   11  C   UNK A   0      -0.046   0.865  -0.308  1.00  0.00           C  
HETATM   12  C   UNK A   0      -3.270  -0.788  -1.278  1.00  0.00           C  
HETATM   13  O   UNK A   0      -3.734  -1.409  -2.215  1.00  0.00           O  
ATOM     14  N   GLU A   1      -4.027  -0.548  -0.189  1.00  0.00           N  
ATOM     15  CA  GLU A   1      -5.408  -1.033  -0.134  1.00  0.00           C  
ATOM     16  HA  GLU A   1      -5.850  -0.984  -1.129  1.00  0.00           H  
ATOM     17  CB  GLU A   1      -6.218  -0.161   0.827  1.00  0.00           C  
ATOM     18  CG  GLU A   1      -6.310   1.261   0.270  1.00  0.00           C  
ATOM     19  CD  GLU A   1      -7.108   2.121   1.217  1.00  0.00           C  
ATOM     20  OE1 GLU A   1      -7.320   3.415   0.931  1.00  0.00           O  
ATOM     21  OE2 GLU A   1      -7.556   1.645   2.233  1.00  0.00           O  
ATOM     22  C   GLU A   1      -5.420  -2.460   0.351  1.00  0.00           C  
ATOM     23  O   GLU A   1      -6.584  -3.115   0.481  1.00  0.00           O  
ATOM     24  OXT GLU A   1      -4.381  -3.014   0.623  1.00  0.00           O  
HETATM   25  C   UNK A   0       4.691   2.861   0.568  1.00  0.00           C  
HETATM   26  N   UNK A   0       4.732   1.858   1.641  1.00  0.00           N  
HETATM   27  C   UNK A   0       5.166   0.575   1.348  1.00  0.00           C  
HETATM   28  C   UNK A   0       5.208   0.143   0.029  1.00  0.00           C  
HETATM   29  C   UNK A   0       5.644  -1.157  -0.248  1.00  0.00           C  
HETATM   30  O   UNK A   0       5.693  -1.569  -1.397  1.00  0.00           O  
HETATM   31  N   UNK A   0       6.012  -1.947   0.784  1.00  0.00           N  
HETATM   32  C   UNK A   0       5.955  -1.476   2.060  1.00  0.00           C  
HETATM   33  N   UNK A   0       6.335  -2.295   3.093  1.00  0.00           N  
HETATM   34  N   UNK A   0       5.540  -0.256   2.328  1.00  0.00           N  
HETATM   35  H   UNK A   0       4.874   1.557  -3.039  1.00  0.00           H  
HETATM   36  H   UNK A   0       6.262   0.592  -2.480  1.00  0.00           H  
HETATM   37  H   UNK A   0       4.679  -0.185  -2.727  1.00  0.00           H  
HETATM   38  H   UNK A   0       4.070   2.921  -1.504  1.00  0.00           H  
HETATM   39  H   UNK A   0       2.576   1.209   0.536  1.00  0.00           H  
HETATM   40  H   UNK A   0       2.011   2.732  -0.193  1.00  0.00           H  
HETATM   41  H   UNK A   0       2.588   0.909  -2.272  1.00  0.00           H  
HETATM   42  H   UNK A   0       0.811  -0.282  -3.382  1.00  0.00           H  
HETATM   43  H   UNK A   0      -1.504  -1.099  -3.295  1.00  0.00           H  
HETATM   44  H   UNK A   0      -1.950   0.608   0.618  1.00  0.00           H  
HETATM   45  H   UNK A   0       0.368   1.416   0.524  1.00  0.00           H  
ATOM     46  H   GLU A   1      -3.657  -0.053   0.559  1.00  0.00           H  
ATOM     47  HB1 GLU A   1      -7.220  -0.574   0.936  1.00  0.00           H  
ATOM     48  HB2 GLU A   1      -5.726  -0.139   1.800  1.00  0.00           H  
ATOM     49  HG1 GLU A   1      -5.308   1.675   0.161  1.00  0.00           H  
ATOM     50  HG2 GLU A   1      -6.802   1.239  -0.703  1.00  0.00           H  
ATOM     51  HE1 GLU A   1      -7.838   3.926   1.569  1.00  0.00           H  
ATOM     52  H   GLU A   1      -6.542  -4.028   0.795  1.00  0.00           H  
HETATM   53  H   UNK A   0       5.704   3.185   0.329  1.00  0.00           H  
HETATM   54  H   UNK A   0       4.097   3.717   0.887  1.00  0.00           H  
HETATM   55  H   UNK A   0       4.459   2.091   2.543  1.00  0.00           H  
HETATM   56  H   UNK A   0       6.317  -2.853   0.616  1.00  0.00           H  
HETATM   57  H   UNK A   0       6.639  -3.197   2.910  1.00  0.00           H  
HETATM   58  H   UNK A   0       6.298  -1.971   4.007  1.00  0.00           H  
CONECT    1    2   35   36   37                                       
CONECT    2    1    3   28                                            
CONECT    3    2    4   25   38                                       
CONECT    4    3    5   39   40                                       
CONECT    5    4    6   41                                            
CONECT    6    5    7    7   11                                       
CONECT    7    6    6    8   42                                       
CONECT    8    7    9    9   43                                       
CONECT    9    8    8   10   12                                       
CONECT   10    9   11   11   44                                       
CONECT   11   10   10    6   45                                       
CONECT   12    9   13   13   14                                       
CONECT   13   12   12                                                 
CONECT   14   12   15   46                                            
CONECT   15   14   16   17   22                                       
CONECT   16   15                                                      
CONECT   17   15   18   47   48                                       
CONECT   18   17   19   49   50                                       
CONECT   19   18   20   21   21                                       
CONECT   20   19   51                                                 
CONECT   21   19   19                                                 
CONECT   22   15   23   24   24                                       
CONECT   23   22   52                                                 
CONECT   24   22   22                                                 
CONECT   25    3   26   53   54                                       
CONECT   26   25   27   55                                            
CONECT   27   26   28   28   34                                       
CONECT   28   27   27    2   29                                       
CONECT   29   28   30   30   31                                       
CONECT   30   29   29                                                 
CONECT   31   29   32   56                                            
CONECT   32   31   33   34   34                                       
CONECT   33   32   57   58                                            
CONECT   34   32   32   27                                            
CONECT   35    1                                                      
CONECT   36    1                                                      
CONECT   37    1                                                      
CONECT   38    3                                                      
CONECT   39    4                                                      
CONECT   40    4                                                      
CONECT   41    5                                                      
CONECT   42    7                                                      
CONECT   43    8                                                      
CONECT   44   10                                                      
CONECT   45   11                                                      
CONECT   46   14                                                      
CONECT   47   17                                                      
CONECT   48   17                                                      
CONECT   49   18                                                      
CONECT   50   18                                                      
CONECT   51   20                                                      
CONECT   52   23                                                      
CONECT   53   25                                                      
CONECT   54   25                                                      
CONECT   55   26                                                      
CONECT   56   31                                                      
CONECT   57   33                                                      
CONECT   58   33                                                      
MASTER        0    0    0    0    0    0    0    0   58    0   58    0
END

Download
SMILES for HMDB0001396 (5-Methyltetrahydrofolic acid)
CN1C(CNC2=CC=C(C=C2)C(=O)N[C@H](CCC(O)=O)C(O)=O)CNC2=C1C(=O)NC(N)=N2
Download
INCHI for HMDB0001396 (5-Methyltetrahydrofolic acid)
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
Download
View in JSmolView Stereo Labels
Synonyms
ValueSource
5-MethyltetrahydrofolateGenerator
5-Methyl tetrahydrofolateHMDB
5-Methyl-5,6,7,8-tetrahydrofolateHMDB
5-Methyl-tetrahydrofolateHMDB
5-MethyltetrahydropteroylglutamateHMDB
Methyl folateHMDB
Methyl-tetrahydrofolateHMDB
N( 5)-MethyltetrahydrofolateHMDB
N-(4-(((2-Amino-1,4,5,6,7,8-hexahydro-5-methyl-4-oxo-6-pteridinyl)methyl)amino)benzoyl)-L-glutamateHMDB
N-(4-(((2-Amino-1,4,5,6,7,8-hexahydro-5-methyl-4-oxo-6-pteridinyl)methyl)amino)benzoyl)-L-glutamic acidHMDB
N-(5-Methyl-5,6,7,8-tetrahydropteroyl)-L-glutamateHMDB
N-(5-Methyl-5,6,7,8-tetrahydropteroyl)-L-glutamic acidHMDB
N5-Methyl-tetrahydrofolateHMDB
N5-Methyl-tetrahydrofolic acidHMDB
N5-MethyltetrahydrofolateHMDB
N5-Methyltetrahydropteroyl mono-L-glutamateHMDB
[(6S)-5-Methyl-5,6,7,8-tetrahydropteroyl]glutamateHMDB
5-Methyltetrahydrofolate, (DL-glu)-isomerHMDB
5-Methyltetrahydrofolate, (L-glu)-(R)-isomerHMDB
5-Methyltetrahydrofolate, (L-glu)-(S)-isomerHMDB
5-Methyltetrahydrofolate, calcium salt (1:1), (L-glu)-isomerHMDB
5-Methyltetrahydrofolate, methyl-(14)C-labeled, (DL-glu)-isomerHMDB
5-Methyltetrahydrofolate, methyl-(14)C-labeled, (L-glu)-isomerHMDB
CH3-FH4HMDB
L-Methyl folateHMDB
N(5)-Methyltetrahydrofolic acidHMDB
Prefolic aHMDB
MefolinateHMDB
Levomefolic acidHMDB
L-MethylfolateHMDB
DeplinHMDB
Chemical FormulaC20H25N7O6
Average Molecular Weight459.4558
Monoisotopic Molecular Weight459.186631567
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 Number134-35-0
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 KeyZNOVTXRBGFNYRX-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.
KingdomOrganic compounds  
Super ClassOrganoheterocyclic compounds  
ClassPteridines and derivatives  
Sub ClassPterins and derivatives  
Direct ParentTetrahydrofolic 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 FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Physiological effect
Health effect:
Disposition
Source:
Biological location:
Process
Naturally occurring process:
Role
Biological role:
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.35 g/LALOGPS
logP-1.3ALOGPS
logP-2.8ChemAxon
logS-3.1ALOGPS
pKa (Strongest Acidic)3.22ChemAxon
pKa (Strongest Basic)4.64ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count11ChemAxon
Hydrogen Donor Count7ChemAxon
Polar Surface Area198.48 ŲChemAxon
Rotatable Bond Count9ChemAxon
Refractivity126.88 m³·mol⁻¹ChemAxon
Polarizability46.13 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
GC-MS
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-03di-2645900000-0472550b7df0d95d47182017-09-01View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-059i-4532290000-8e3b1526c05a0a70d9712017-10-06View Spectrum
MSMass Spectrum (Electron Ionization)splash10-03di-2645900000-0472550b7df0d95d47182021-09-05View Spectrum
LC-MS/MS
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum -  10V, Positivesplash10-03dl-0313900000-d4f9d7f9d8c65a2e04282016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum -  20V, Positivesplash10-01ox-0924300000-2f133db2f48bd5b14a8d2016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum -  40V, Positivesplash10-000f-0920000000-298e8f3cd55b0fe42bad2016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum -  10V, Negativesplash10-0a4i-0001900000-b1b1292a418283f61ea92016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum -  20V, Negativesplash10-0900-1256900000-32c1cf48970dead32f602016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum -  40V, Negativesplash10-0006-9641100000-b5468bf27455b7e5ee392016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum -  10V, Negativesplash10-0a4i-0001900000-ba41f53e73f5102d5c042021-09-06View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum -  20V, Negativesplash10-0a4u-3419800000-385454b6189707f5e6842021-09-06View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum -  40V, Negativesplash10-0zg0-3931100000-ccab9c792ff1e540a4e82021-09-06View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum -  10V, Positivesplash10-03di-0108900000-f5ef3a5a71a48db8560b2021-09-07View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum -  20V, Positivesplash10-03di-0209100000-ac8dd1f905331a1f84bb2021-09-07View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum -  40V, Positivesplash10-000x-0912000000-e973388138222d0175172021-09-07View Spectrum
Biological Properties
Cellular Locations
  • Extracellular
Biospecimen Locations
  • Blood
    • 

  • Cerebrospinal Fluid (CSF)
    • 

  • Urine
Tissue Locations
  • Kidney
    • 

  • Liver
    • 

  • Placenta
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal  details
BloodDetected and Quantified0.3 (0.094-0.7) uMAdult (>18 years old)BothNormal  details
Cerebrospinal Fluid (CSF)Detected and Quantified0.12 (0.04-0.20) uMAdult (>18 years old)BothNormal  details
Cerebrospinal Fluid (CSF)Detected and Quantified0.0400-0.128 uMChildren (1-13 years old)BothNormal  details
Cerebrospinal Fluid (CSF)Detected and Quantified0.075 (0.045 - 0.13) uMAdult (>18 years old)Not SpecifiedNormal  details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableNormal
      Not Available
  details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal  details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
Cerebrospinal Fluid (CSF)Detected and Quantified0.00700-0.0110 uMChildren (1-13 years old)BothCerebral folate transport deficiency  details
Cerebrospinal Fluid (CSF)Detected and Quantified0.053 (0.02 - 0.09) uMAdult (>18 years old)Not SpecifiedRett syndrome  details
Cerebrospinal Fluid (CSF)Detected and Quantified0.026 +/- 0.007 uMChildren (1-13 years old)Not Specified
 
AIDS		  details
Associated Disorders and Diseases
Disease References
Rett syndrome
  1. 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. [PubMed:16429378  ] 
AIDS
  1. 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. [PubMed:1969014  ] 
Cerebral folate transport deficiency
  1. Al-Baradie RS, Chaudhary MW: Diagnosis and management of cerebral folate deficiency. A form of folinic acid-responsive seizures. Neurosciences (Riyadh). 2014 Oct;19(4):312-6. [PubMed:25274592  ] 
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022600  
KNApSAcK IDNot Available
Chemspider ID388371  
KEGG Compound IDC00440  
BioCyc IDNot Available
BiGG ID34988  
Wikipedia LinkLevomefolic acid  
METLIN ID6215  
PubChem Compound439234  
PDB IDNot Available
ChEBI ID15641  
Food Biomarker OntologyNot Available
VMH ID5MTHF  
MarkerDB IDMDB00000321  
References
Synthesis ReferenceGennari, Federico.  Process for producing 5-methyltetrahydrofolic acid and its salts.    U.S.  (1992),     6 pp.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. 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. [PubMed:11816560  ] 
  2. 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. [PubMed:16429378  ] 
  3. 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. [PubMed:10993519  ] 
  4. 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. [PubMed:8031869  ] 
  5. 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. [PubMed:15173401  ] 
  6. 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. [PubMed:8613033  ] 
  7. 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. [PubMed:15094208  ] 
  8. 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. [PubMed:1683972  ] 
  9. 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. [PubMed:1969014  ] 
  10. 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. [PubMed:9101216  ] 
  11. 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  ] 
  12. Irizarry MC: Biomarkers of Alzheimer disease in plasma. NeuroRx. 2004 Apr;1(2):226-34. [PubMed:15717023  ] 
  13. 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. [PubMed:9870205  ] 
  14. 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  ] 
  15. Authors unspecified: 5-methyltetrahydrofolate. Monograph. Altern Med Rev. 2006 Dec;11(4):330-7. [PubMed:17176169  ] 
Enzymes
  Enzyme Details
1. Methionine synthase
General function:
Involved in cobalamin binding
Specific function:
Catalyzes the transfer of a methyl group from methyl-cobalamin to homocysteine, yielding enzyme-bound cob(I)alamin and methionine. Subsequently, remethylates the cofactor using methyltetrahydrofolate (By similarity).

Gene Name:
MTR
Uniprot ID:
Q99707  
Molecular weight:
140525.91
Reactions
5-Methyltetrahydrofolic acid + Homocysteine → Tetrahydrofolic acid + L-Methioninedetails
  Enzyme Details
2. Methylenetetrahydrofolate reductase
General function:
Involved in methylenetetrahydrofolate reductase (NADPH) activity
Specific function:
Catalyzes the conversion of 5,10-methylenetetrahydrofolate to 5-methyltetrahydrofolate, a co-substrate for homocysteine remethylation to methionine.

Gene Name:
MTHFR
Uniprot ID:
P42898  
Molecular weight:
74595.895
Reactions
5-Methyltetrahydrofolic acid + NAD(P)(+) → 5,10-Methylene-THF + NAD(P)Hdetails
5-Methyltetrahydrofolic acid + NADP → 5,10-Methylene-THF + NADPH + Hydrogen Iondetails
5-Methyltetrahydrofolic acid + NAD → 5,10-Methylene-THF + NADH + Hydrogen Iondetails
  Enzyme Details
3. HemK methyltransferase family member 1
General function:
Not Available
Specific function:
N5-glutamine methyltransferase responsible for the methylation of the GGQ triplet of the mitochondrial translation release factor MTRF1L.

Gene Name:
HEMK1
Uniprot ID:
Q9Y5R4  
Molecular weight:
Not Available
Reactions
Serotonin + 5-Methyltetrahydrofolic acid → 5-Methoxytryptamine + Tetrahydrofolic aciddetails
  Enzyme Details
4. Methyltransferase-like protein 2B
General function:
Not Available
Specific function:
Probable methyltransferase (By similarity).

Gene Name:
METTL2B
Uniprot ID:
Q6P1Q9  
Molecular weight:
Not Available
Reactions
Serotonin + 5-Methyltetrahydrofolic acid → 5-Methoxytryptamine + Tetrahydrofolic aciddetails
  Enzyme Details
5. Methyltransferase-like protein 6
General function:
Not Available
Specific function:
Probable methyltransferase (By similarity).

Gene Name:
METTL6
Uniprot ID:
Q8TCB7  
Molecular weight:
Not Available
Reactions
Serotonin + 5-Methyltetrahydrofolic acid → 5-Methoxytryptamine + Tetrahydrofolic aciddetails
  Enzyme Details
6. Uncharacterized methyltransferase WBSCR22
General function:
Not Available
Specific function:
Methyltransferase that may act on DNA.

Gene Name:
WBSCR22
Uniprot ID:
O43709  
Molecular weight:
Not Available
Reactions
Serotonin + 5-Methyltetrahydrofolic acid → 5-Methoxytryptamine + Tetrahydrofolic aciddetails