ChemFOnt: Showing chemical card for (6S)-5-formyltetrahydrofolate(2-) (CFc000043169)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 19:46:06 UTC

Chemfont ID

CFc000043169

Molecule Identification

Common Name

(6S)-5-formyltetrahydrofolate(2-)

Definition

(6S)-5-formyltetrahydrofolate(2-) is also known as Leucovorin, calcium (1:1) salt, pentahydrate or 5-Formyltetrahydrofolic acid. (6S)-5-formyltetrahydrofolate(2-) is considered to be practically insoluble (in water) and acidic

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Leucovorin	Kegg
Rescuvolin	Kegg
5-Formyltetrahydrofolate	Kegg
L(-)-5-Formyl-5,6,7,8-tetrahydrofolic acid	Kegg
5-Formyltetrahydrofolic acid	Generator
L(-)-5-Formyl-5,6,7,8-tetrahydrofolate	Generator
(6R,S)-5-Formyltetrahydrofolate	HMDB
10-Formyl-7,8-dihydrofolate	HMDB
10-Formyl-7,8-dihydrofolic acid	HMDB
5-Formyl-5,6,7,8-tetrahydrofolate	HMDB
5-Formyl-5,6,7,8-tetrahydrofolic acid	HMDB
5-Formyltetrahydropteroylglutamate	HMDB
5-Formyltetrahydropteroylglutamic acid	HMDB
Folinate	HMDB, Generator
Folinic acid	HMDB, MeSH
Folinic acid-SF	HMDB
L-Leucovorin	HMDB
L-N-[P-[[(2-amino-5-Formyl-5,6,7,8-tetrahydro-4-hydroxy-6-pteridinyl)methyl]amino]benzoyl]-glutamic acid	HMDB
Leucal	HMDB
Levoleucovorin	HMDB
N5-Formyl-5,6,7,8-tetrahydrofolate	HMDB
N5-Formyl-5,6,7,8-tetrahydrofolic acid	HMDB
N5-Formyltetrahydrofolate	HMDB
N5-Formyltetrahydrofolic acid	HMDB
Welcovorin	HMDB
Acid, folinic	MeSH, HMDB
Folinate, calcium	MeSH, HMDB
Leucovorin, (D)-isomer	MeSH, HMDB
Leucovorin, (DL)-isomer	MeSH, HMDB
Leucovorin, calcium (1:1) salt	MeSH, HMDB
5 Formyltetrahydrofolate	MeSH, HMDB
Citrovorum factor	MeSH, HMDB
Factor, citrovorum	MeSH, HMDB
Folinic acid SF	MeSH, HMDB
Leucovorin, calcium (1:1) salt, pentahydrate	MeSH, HMDB
Leukovorin	MeSH, HMDB
N(5)-Formyltetrahydrofolate	MeSH, HMDB
Leucovorin, (R)-isomer	MeSH, HMDB
Leucovorin, calcium (1:1) salt, (DL)-isomer	MeSH, HMDB
Leukovorum	MeSH, HMDB
Monosodium salt leucovorin	MeSH, HMDB
Wellcovorin	MeSH, HMDB
5 Formyltetrahydropteroylglutamate	MeSH, HMDB
Calcium folinate	MeSH, HMDB
Calcium leucovorin	MeSH, HMDB
Leucovorin, calcium	MeSH, HMDB
Leucovorin, monosodium salt	MeSH, HMDB
5-Formlyl-5,6,7,8-tetrahydrofolate,calcium salt	Generator

Chemical Formula

C₂₀H₂₃N₇O₇

Average Molecular Weight

473.4393

Monoisotopic Molecular Weight

473.165896125

IUPAC Name

2-[(4-{[(2-amino-5-formyl-4-oxo-3,4,5,6,7,8-hexahydropteridin-6-yl)methyl]amino}phenyl)formamido]pentanedioic acid

Traditional Name

2-[(4-{[(2-amino-5-formyl-4-oxo-3,6,7,8-tetrahydropteridin-6-yl)methyl]amino}phenyl)formamido]pentanedioic acid

CAS Registry Number

58-05-9

SMILES

OC(=O)CCC(NC(=O)C1=CC=C(NCC2CNC3=C(N2C=O)C(O)=NC(=N)N3)C=C1)C(O)=O

InChI Identifier

InChI=1S/C20H23N7O7/c21-20-25-16-15(18(32)26-20)27(9-28)12(8-23-16)7-22-11-3-1-10(2-4-11)17(31)24-13(19(33)34)5-6-14(29)30/h1-4,9,12-13,22H,5-8H2,(H,24,31)(H,29,30)(H,33,34)(H4,21,23,25,26,32)

InChI Key

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

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Exogenous (HMDB: HMDB0062757)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.18 g/L	ALOGPS
logP	-1.6	ALOGPS
logP	-2.3	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Acidic)	3.47	ChemAxon
pKa (Strongest Basic)	2.81	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	215.55 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	126.66 m³·mol⁻¹	ChemAxon
Polarizability	46.54 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

HMDB0258132

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB022689

KNApSAcK ID

Not Available

Chemspider ID

140

KEGG Compound ID

C03479

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 (6S)-5-formyltetrahydrofolate(2-) (CFc000043169)

MOL for CFc000043169 ((6S)-5-formyltetrahydrofolate(2-))

3D MOL for CFc000043169 ((6S)-5-formyltetrahydrofolate(2-))

3D SDF for CFc000043169 ((6S)-5-formyltetrahydrofolate(2-))

3D-SDF for CFc000043169 ((6S)-5-formyltetrahydrofolate(2-))

PDB for CFc000043169 ((6S)-5-formyltetrahydrofolate(2-))

3D PDB for CFc000043169 ((6S)-5-formyltetrahydrofolate(2-))

SMILES for CFc000043169 ((6S)-5-formyltetrahydrofolate(2-))

INCHI for CFc000043169 ((6S)-5-formyltetrahydrofolate(2-))

Structure for CFc000043169 ((6S)-5-formyltetrahydrofolate(2-))

3D Structure for CFc000043169 ((6S)-5-formyltetrahydrofolate(2-))