ChemFOnt: Showing chemical card for Levomefolic acid (CFc000233579)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-14 02:03:44 UTC

Chemfont ID

CFc000233579

Molecule Identification

Common Name

Levomefolic acid

Definition

5-methyl-tetrahydrofolate 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. 5-methyl-tetrahydrofolate exists in all living organisms, ranging from bacteria to humans. In humans, 5-methyl-tetrahydrofolate is involved in the sarcosine oncometabolite pathway. 5-methyl-tetrahydrofolate has been detected, but not quantified in, several different foods, such as common beets (Beta vulgaris), peach (var.), brussel sprouts (Brassica oleracea var. gemmifera), kales (Brassica napus var. pabularia), and common buckwheats (Fagopyrum esculentum). This could make 5-methyl-tetrahydrofolate a potential biomarker for the consumption of these foods. 5-methyl-tetrahydrofolate is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. Based on a literature review a significant number of articles have been published on 5-methyl-tetrahydrofolate.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
5-Methyl-tetrahydrofolic acid	Generator
5-Methyltetrahydrofolate	MeSH
5-Methyltetrahydrofolate, (L-glu)-(R)-isomer	MeSH
5-Methyltetrahydrofolate, (L-glu)-(S)-isomer	MeSH
5-Methyltetrahydrofolate, methyl-(14)C-labeled, (DL-glu)-isomer	MeSH
Mefolinate	MeSH
5-Methyltetrahydrofolate, methyl-(14)C-labeled, (L-glu)-isomer	MeSH
CH3-FH4	MeSH
Prefolic a	MeSH
5-Methyltetrahydrofolate, calcium salt (1:1), (L-glu)-isomer	MeSH
L-Methyl folate	MeSH
N(5)-Methyltetrahydrofolic acid	MeSH
5-Methyltetrahydrofolate, (DL-glu)-isomer	MeSH
5-Methyltetrahydropteroylglutamate	MeSH
Methyl folate	MeSH

Chemical Formula

C₂₀H₂₅N₇O₆

Average Molecular Weight

459.4558

Monoisotopic Molecular Weight

459.186631567

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

CN1C(CNC2=CC=C(C=C2)C(=O)NC(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)

InChI Key

ZNOVTXRBGFNYRX-UHFFFAOYSA-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

a small molecule (CPD0-2045 )

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Source

Exogenous

Exogenous (HMDB: HMDB0254053)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.21 g/L	ALOGPS
logP	-1.3	ALOGPS
logP	-4.9	ChemAxon
logS	-3.3	ALOGPS
pKa (Strongest Acidic)	-13	ChemAxon
pKa (Strongest Basic)	15	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	12	ChemAxon
Hydrogen Donor Count	8	ChemAxon
Polar Surface Area	199.47 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	137.7 m³·mol⁻¹	ChemAxon
Polarizability	46.37 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

External Links

HMDB ID

HMDB0257823

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB030576

KNApSAcK ID

C00007252

Chemspider ID

143

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for Levomefolic acid (CFc000233579)

MOL for CFc000233579 (Levomefolic acid)

3D MOL for CFc000233579 (Levomefolic acid)

3D SDF for CFc000233579 (Levomefolic acid)

3D-SDF for CFc000233579 (Levomefolic acid)

PDB for CFc000233579 (Levomefolic acid)

3D PDB for CFc000233579 (Levomefolic acid)

SMILES for CFc000233579 (Levomefolic acid)

INCHI for CFc000233579 (Levomefolic acid)

Structure for CFc000233579 (Levomefolic acid)

3D Structure for CFc000233579 (Levomefolic acid)