ChemFOnt: Showing chemical card for Folinic acid (CFc000001199)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:45:47 UTC

Chemfont ID

CFc000001199

Molecule Identification

Common Name

Folinic acid

Definition

731

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(6S)-5-Formyl-5,6,7,8-tetrahydrofolic acid	ChEBI
(6S)-Folinic acid	ChEBI
(6S)-Leucovorin	ChEBI
(S)-Leucovorin	ChEBI
Citrovorum factor	ChEBI
L-Folinic acid	ChEBI
Levofolene	ChEBI
Levofolinic acid	ChEBI
Levoleucovorin	ChEBI
N-[4-({[(6S)-2-amino-5-formyl-4-oxo-1,4,5,6,7,8-hexahydropteridin-6-yl]methyl}amino)benzoyl]-L-glutamic acid	ChEBI
(6S)-5-Formyl-5,6,7,8-tetrahydrofolate	Generator
(6S)-Folinate	Generator
L-Folinate	Generator
Levofolinate	Generator
N-[4-({[(6S)-2-amino-5-formyl-4-oxo-1,4,5,6,7,8-hexahydropteridin-6-yl]methyl}amino)benzoyl]-L-glutamate	Generator
Folinate	Generator
5-Formyltetrahydrofolate	HMDB
Pteroyl-D-glutamate	HMDB
5 Formyltetrahydropteroylglutamate	HMDB
5-Formyltetrahydropteroylglutamate	HMDB
Calcium folinate	HMDB
Folinic acid-SF	HMDB
Leucovorin	HMDB
Leucovorin, (S)-isomer	HMDB
Leucovorin, monosodium salt	HMDB
Leucovorin, (R)-isomer	HMDB
Leucovorin, calcium	HMDB
Leucovorin, calcium (1:1) salt, (DL)-isomer	HMDB
Leucovorin, calcium (1:1) salt, (S)-isomer	HMDB
Leukovorin	HMDB
Leukovorum	HMDB
Monosodium salt leucovorin	HMDB
Wellcovorin	HMDB
Levo leucovorin	HMDB
6 S Leucovorin	HMDB
Acid, folinic	HMDB
Factor, citrovorum	HMDB
Folinic acid SF	HMDB
Fusilev	HMDB
Leucovorin, calcium (1:1) salt, pentahydrate	HMDB
Leucovorin, monopotassium salt, (S)-isomer	HMDB
N(5)-Formyltetrahydrofolate	HMDB
S-Leucovorin	HMDB
5 Formyltetrahydrofolate	HMDB
6-S-Leucovorin	HMDB
6S Leucovorin	HMDB
6S-Leucovorin	HMDB
Calcium leucovorin	HMDB
Folinate, calcium	HMDB
Leucovorin, (D)-isomer	HMDB
Leucovorin, (DL)-isomer	HMDB
Leucovorin, calcium (1:1) salt	HMDB
Leucovorin, monosodium salt, (S)-isomer	HMDB
S Leucovorin	HMDB
Levo-leucovorin	HMDB
5-Formyl-(6S)-tetrahydrofolic acid	HMDB
5-Formyl-5,6,7,8-tetrahydrofolic acid	HMDB
5-Formyltetrahydrofolic acid	HMDB
5-Formyltetrahydropteroylglutamic acid	HMDB
CF	HMDB
Kunyrin	HMDB
Leucoverin	HMDB
N5-Formyl-5,6,7,8-tetrahydrofolic acid	HMDB
N5-Formyl-THF	HMDB
N5-Formyltetrahydrofolic acid	HMDB
Welcovorin	HMDB
(6S)-5-Formyltetrahydrofolate	HMDB
(6S)-5-Formyltetrahydrofolic acid	HMDB
Folinic acid	MeSH

Chemical Formula

C₂₀H₂₃N₇O₇

Average Molecular Weight

473.4393

Monoisotopic Molecular Weight

473.165896125

IUPAC Name

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

Traditional Name

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

CAS Registry Number

68538-85-2

SMILES

NC1=NC(=O)C2=C(NC[C@H](CNC3=CC=C(C=C3)C(=O)N[C@@H](CCC(O)=O)C(O)=O)N2C=O)N1

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)/t12-,13-/m0/s1

InChI Key

VVIAGPKUTFNRDU-STQMWFEESA-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

5-formyltetrahydrofolic acid (CHEBI:63606 )

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 17272488)

Organ

Cell

Fibroblasts (HMDB: HMDB0001562)

Cellular substructure

Extracellular (HMDB: HMDB0001562)

Source

Exogenous

Exogenous (HMDB: HMDB0001562)

Food

Animal origin

Poultry

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Endogenous

Endogenous (HMDB: HMDB0001562)

Process

Naturally occurring process

Biological process

Biochemical pathway

Metabolic pathway

Folate Metabolism (PathBank: SMP0000801)
One Carbon Pool by Folate (PathBank: SMP0122040)
One Carbon Pool by Folate I (PathBank: SMP0002369)

Disease pathway

Methylenetetrahydrofolate Reductase Deficiency (MTHFRD) (PathBank: SMP0120522)
Folate Malabsorption, Hereditary (PathBank: SMP0120656)

Drug action pathway

Methotrexate Action Pathway (PathBank: SMP0000432)

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.3 g/L	ALOGPS
logP	-1.1	ALOGPS
logP	-2.7	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Acidic)	3.47	ChemAxon
pKa (Strongest Basic)	2.81	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	12	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	215.55 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	126.46 m³·mol⁻¹	ChemAxon
Polarizability	46.34 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