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Identification
Name5-methyltetrahydrofolic acid
Accession NumberDB04789
TypeSmall Molecule
GroupsNutraceutical
Description5-methyltetrahydrofolic acid 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
5-methyltetrahydrofolate
External IDs Not Available
Product Ingredients Not Available
Approved Prescription ProductsNot Available
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International BrandsNot Available
Brand mixtures
NameLabellerIngredients
Prenate EliteAvion Pharmaceuticals, Llc
Prenate EssentialAvion Pharmaceuticals, Llc
Sodium Polysulthionate, 5-mthfSolubiomix
XizflusBasiem
Categories
UNIITYK22LML8F
CAS number134-35-0
WeightAverage: 459.463
Monoisotopic: 459.186631553
Chemical FormulaC20H25N7O6
InChI KeyZNOVTXRBGFNYRX-ABLWVSNPSA-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-{[(2-amino-5-methyl-4-oxo-1,4,5,6,7,8-hexahydropteridin-6-yl)methyl]amino}phenyl)formamido]pentanedioic acid
SMILES
CN1C(CNC2=CC=C(C=C2)C(=O)N[C@@H](CCC(O)=O)C(O)=O)CNC2=C1C(=O)N=C(N)N2
Pharmacology
IndicationNot Available
Structured Indications Not Available
PharmacodynamicsNot Available
Mechanism of action
TargetKindPharmacological actionActionsOrganismUniProt ID
Aminomethyltransferase, mitochondrialProteinunknownNot AvailableHumanP48728 details
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
Pharmacogenomic Effects/ADRs Not Available
Interactions
Drug Interactions Not Available
Food InteractionsNot Available
References
Synthesis ReferenceNot Available
General ReferencesNot Available
External Links
ATC CodesNot Available
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
Clinical Trials
Clinical Trials
PhaseStatusPurposeConditionsCount
Not AvailableCompletedTreatmentHyperhomocysteinaemia / Inflammatory processes / Mortality1
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage forms
FormRouteStrength
Tablet, coatedOral
Capsule, gelatin coatedOral
CapsuleOral
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental PropertiesNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.332 mg/mLALOGPS
logP-0.58ALOGPS
logP-1.9ChemAxon
logS-3.1ALOGPS
pKa (Strongest Acidic)3.48ChemAxon
pKa (Strongest Basic)2.83ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count12ChemAxon
Hydrogen Donor Count7ChemAxon
Polar Surface Area198.48 Å2ChemAxon
Rotatable Bond Count9ChemAxon
Refractivity126.68 m3·mol-1ChemAxon
Polarizability46.19 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
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 )
Spectra
Mass Spec (NIST)Not Available
SpectraNot Available
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
  • 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

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 ]
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Drug created on September 11, 2007 11:49 / Updated on March 05, 2017 20:34