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Identification
Name5-methyltetrahydrofolate
Accession NumberDB04789
TypeSmall Molecule
GroupsExperimental
Description

5-Methyltetrahydrofolate is a methylated derivate of tetrahydrofolate. It is generated by methylenetetrahydrofolate reductase from 5,10-methylenetetrahydrofolate and used to recycle homocysteine back to methionine by 5-methyltetrahydrofolate-homocysteine methyltransferases (also called methionine synthases).

Structure
Thumb
Synonyms
[(6S)-5-methyl-5,6,7,8-tetrahydropteroyl]glutamate
5-methyltetrahydrofolate
N-(5-methyl-5,6,7,8-tetrahydropteroyl)-L-glutamic acid
External Identifiers Not Available
Approved Prescription ProductsNot Available
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
L-methylfolate Calciumtablet, coated15 mg/1oralVirtus Pharmaceuticals2012-03-15Not applicableUs
International BrandsNot Available
Brand mixtures
NameLabellerIngredients
Virt-PN DHAVirtus Pharmaceuticals
Vitafol NanoEverett Laboratories, Inc.
Vitafol UltraEverett Laboratories, Inc.
Yasmin PlusBayer Inc
Yaz PlusBayer Inc
Salts
Name/CASStructureProperties
Levomefolate calcium
151533-22-1
Thumb
  • InChI Key: VWBBRFHSPXRJQD-QNTKWALQSA-L
  • Monoisotopic Mass: 497.1335724
  • Average Mass: 497.525
DBSALT001276
CategoriesNot Available
UNIITYK22LML8F
CAS number134-35-0
WeightAverage: 459.4558
Monoisotopic: 459.186631567
Chemical FormulaC20H25N7O6
InChI KeyInChIKey=ZNOVTXRBGFNYRX-STQMWFEESA-N
InChI
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-/m0/s1
IUPAC Name
(2S)-2-{[4-({[(6S)-2-amino-5-methyl-4-oxo-1,4,5,6,7,8-hexahydropteridin-6-yl]methyl}amino)phenyl]formamido}pentanedioic acid
SMILES
CN1[C@@H](CNC2=CC=C(C=C2)C(=O)N[C@@H](CCC(O)=O)C(O)=O)CNC2=C1C(=O)N=C(N)N2
Taxonomy
DescriptionThis compound 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
  • N-acyl-alpha amino acid or derivatives
  • N-acyl-alpha-amino acid
  • Hippuric acid
  • Hippuric acid or derivatives
  • Aminobenzoic acid or derivatives
  • Alpha-amino acid or derivatives
  • N-substituted-alpha-amino acid
  • Benzoic acid or derivatives
  • Benzamide
  • Aminobenzamide
  • Phenylalkylamine
  • Substituted aniline
  • Dialkylarylamine
  • Benzoyl
  • Secondary aliphatic/aromatic amine
  • Pyrimidone
  • Aniline
  • Amino fatty acid
  • Fatty acyl
  • Benzenoid
  • Pyrimidine
  • Primary aromatic amine
  • Dicarboxylic acid or derivatives
  • Monocyclic benzene moiety
  • Heteroaromatic compound
  • Vinylogous amide
  • Tertiary amine
  • Secondary carboxylic acid amide
  • Carboxamide group
  • Azacycle
  • Secondary amine
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Amine
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Pharmacology
IndicationNot Available
PharmacodynamicsNot Available
Mechanism of actionNot Available
Related Articles
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
MetabolismNot Available
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organismsNot Available
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption-0.5477
Blood Brain Barrier-0.9162
Caco-2 permeable-0.8516
P-glycoprotein substrateSubstrate0.8413
P-glycoprotein inhibitor INon-inhibitor0.9223
P-glycoprotein inhibitor IINon-inhibitor0.9933
Renal organic cation transporterNon-inhibitor0.8623
CYP450 2C9 substrateNon-substrate0.7153
CYP450 2D6 substrateNon-substrate0.8217
CYP450 3A4 substrateNon-substrate0.5221
CYP450 1A2 substrateNon-inhibitor0.8546
CYP450 2C9 inhibitorNon-inhibitor0.8537
CYP450 2D6 inhibitorNon-inhibitor0.9295
CYP450 2C19 inhibitorNon-inhibitor0.8801
CYP450 3A4 inhibitorNon-inhibitor0.9463
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9338
Ames testNon AMES toxic0.7803
CarcinogenicityNon-carcinogens0.9459
BiodegradationNot ready biodegradable0.8995
Rat acute toxicity2.6188 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9337
hERG inhibition (predictor II)Inhibitor0.5
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage forms
FormRouteStrength
Tablet, coatedoral15 mg/1
Capsule, gelatin coatedoral
Tablet, coatedoral
Capsule, liquid filledoral
Tabletoral
PricesNot Available
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)
US5798338 No1995-07-102015-07-10Us
US6441168 No2002-07-302022-07-30Us
US6958326 No2001-12-202021-12-20Us
US7163931 No2002-03-032022-03-03Us
US8617597 No2010-02-082030-02-08Us
Properties
StateSolid
Experimental PropertiesNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.332 mg/mLALOGPS
logP-0.58ALOGPS
logP-3.8ChemAxon
logS-3.1ALOGPS
pKa (Strongest Acidic)3.5ChemAxon
pKa (Strongest Basic)3.54ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count12ChemAxon
Hydrogen Donor Count7ChemAxon
Polar Surface Area198.48 Å2ChemAxon
Rotatable Bond Count9ChemAxon
Refractivity126.68 m3·mol-1ChemAxon
Polarizability46.56 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01ox-0312900000-1e7ffc57c6bfdc0e8fe9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01ox-0924300000-c9fa222e5e77153ca411View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-1921000000-012fee21d119d325c696View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0001900000-dd3b789dceaf2f1cb9a7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0904-1245900000-aa2092d5d8304fe7f772View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-7951200000-24cf3f653b8a2e0b9b29View in MoNA
References
Synthesis ReferenceNot Available
General ReferencesNot Available
External Links
ATC CodesNot Available
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available

Targets

Kind
Protein
Organism
Human
Pharmacological action
unknown
General Function:
Transaminase activity
Specific Function:
The glycine cleavage system catalyzes the degradation of glycine.
Gene Name:
AMT
Uniprot ID:
P48728
Molecular Weight:
43945.65 Da

Transporters

Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inhibitor
General Function:
Organic anion transmembrane transporter activity
Specific Function:
Mediates hepatobiliary excretion of numerous organic anions. May function as a cellular cisplatin transporter.
Gene Name:
ABCC2
Uniprot ID:
Q92887
Molecular Weight:
174205.64 Da
References
  1. Kusuhara H, Han YH, Shimoda M, Kokue E, Suzuki H, Sugiyama Y: Reduced folate derivatives are endogenous substrates for cMOAT in rats. Am J Physiol. 1998 Oct;275(4 Pt 1):G789-96. [PubMed:9756510 ]
Comments
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Drug created on September 11, 2007 11:49 / Updated on May 28, 2016 02:12