ChemFOnt: Showing chemical card for (6R)-5,10-methenyltetrahydrofolate (CFc000043035)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 19:45:53 UTC

Chemfont ID

CFc000043035

Molecule Identification

Common Name

(6R)-5,10-methenyltetrahydrofolate

Definition

(6R)-5,10-methenyltetrahydrofolate is also known as Anhydroleucovorin. (6R)-5,10-methenyltetrahydrofolate is considered to be practically insoluble (in water) and acidic

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
5,10-Methenyltetrahydrofolate	ChEBI
5,10-Methenyltetrahydrofolic acid	Generator
5,10-Methenyltetrahydrofolic acid mono-L-glutamic acid	Generator
Anhydroleucovorin	MeSH, HMDB
5,10-Methenyltetrahydropteroylglutamate	MeSH, HMDB
N5,N10-Methenyl tetrahydrofolate	MeSH, HMDB
(6R)-5,10-Methenyltetrahydrofolic acid	Generator

Chemical Formula

C₂₀H₂₀N₇O₆

Average Molecular Weight

454.424

Monoisotopic Molecular Weight

454.148054972

IUPAC Name

(6aR)-3-amino-8-(4-{[(1S)-1,3-dicarboxypropyl]carbamoyl}phenyl)-1-oxo-1H,2H,5H,6H,6aH,7H,8H-10lambda5-imidazo[1,5-f]pteridin-10-ylium

Traditional Name

(6aR)-3-amino-8-(4-{[(1S)-1,3-dicarboxypropyl]carbamoyl}phenyl)-1-oxo-2H,5H,6H,6aH,7H-10lambda5-imidazo[1,5-f]pteridin-10-ylium

CAS Registry Number

Not Available

SMILES

[H][C@@]12CN(C=[N+]1C1=C(NC2)N=C(N)NC1=O)C1=CC=C(C=C1)C(=O)N[C@@H](CCC([O-])=O)C([O-])=O

InChI Identifier

InChI=1S/C20H21N7O6/c21-20-24-16-15(18(31)25-20)27-9-26(8-12(27)7-22-16)11-3-1-10(2-4-11)17(30)23-13(19(32)33)5-6-14(28)29/h1-4,9,12-13H,5-8H2,(H6-,21,22,23,24,25,28,29,30,31,32,33)/p-1/t12-,13+/m1/s1

InChI Key

MEANFMOQMXYMCT-OLZOCXBDSA-M

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

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

dicarboxylic acid anion (CHEBI:57455 )
tetrahydrofolate (CHEBI:57455 )

Functional Ontology

Not Available

Exogenous (HMDB: HMDB0062623)

Process

Naturally occurring process

Biological process

Biochemical pathway

Metabolic pathway

Pyrimidine Metabolism (PathBank: SMP0121324)
Pyrimidine Metabolism (PathBank: SMP0002370)

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.24 g/L	ALOGPS
logP	-1	ALOGPS
logP	-4.6	ChemAxon
logS	-3.3	ALOGPS
pKa (Strongest Acidic)	3.21	ChemAxon
pKa (Strongest Basic)	-0.92	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	195.12 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	156.05 m³·mol⁻¹	ChemAxon
Polarizability	44.98 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

HMDB0062623

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

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

57455

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for (6R)-5,10-methenyltetrahydrofolate (CFc000043035)

MOL for CFc000043035 ((6R)-5,10-methenyltetrahydrofolate)

3D MOL for CFc000043035 ((6R)-5,10-methenyltetrahydrofolate)

3D SDF for CFc000043035 ((6R)-5,10-methenyltetrahydrofolate)

3D-SDF for CFc000043035 ((6R)-5,10-methenyltetrahydrofolate)

PDB for CFc000043035 ((6R)-5,10-methenyltetrahydrofolate)

3D PDB for CFc000043035 ((6R)-5,10-methenyltetrahydrofolate)

SMILES for CFc000043035 ((6R)-5,10-methenyltetrahydrofolate)

INCHI for CFc000043035 ((6R)-5,10-methenyltetrahydrofolate)

Structure for CFc000043035 ((6R)-5,10-methenyltetrahydrofolate)

3D Structure for CFc000043035 ((6R)-5,10-methenyltetrahydrofolate)