Canmetcon
Record Information
Version1.0
Creation date2011-09-21 00:17:59 UTC
Update date2015-07-21 06:57:19 UTC
Primary IDFDB022689
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name5-Formyltetrahydrofolic acid
DescriptionThe active metabolite of folic acid. Leucovorin is used principally as its calcium salt as an antidote to folic acid antagonists which block the conversion of folic acid to folinic acid. [HMDB]
CAS Number58-05-9
Structure
Thumb
Synonyms
SynonymSource
LeucovorinKegg
RescuvolinKegg
5-FormyltetrahydrofolateKegg
L(-)-5-Formyl-5,6,7,8-tetrahydrofolic acidKegg
5-Formyltetrahydrofolic acidGenerator
L(-)-5-Formyl-5,6,7,8-tetrahydrofolateGenerator
FolinateGenerator
(6R,S)-5-FormyltetrahydrofolateHMDB
10-Formyl-7,8-dihydrofolateHMDB
10-Formyl-7,8-dihydrofolic acidHMDB
5-Formyl-5,6,7,8-tetrahydrofolateHMDB
5-Formyl-5,6,7,8-tetrahydrofolic acidHMDB
5-FormyltetrahydropteroylglutamateHMDB
5-Formyltetrahydropteroylglutamic acidHMDB
Folinic acid-SFHMDB
L-LeucovorinHMDB
L-N-[p-[[(2-Amino-5-formyl-5,6,7,8-tetrahydro-4-hydroxy-6-pteridinyl)methyl]amino]benzoyl]-glutamic acidHMDB
LeucalHMDB
LevoleucovorinHMDB
N5-Formyl-5,6,7,8-tetrahydrofolateHMDB
N5-Formyl-5,6,7,8-tetrahydrofolic acidHMDB
N5-FormyltetrahydrofolateHMDB
N5-Formyltetrahydrofolic acidHMDB
WelcovorinHMDB
Acid, folinicHMDB
Folinate, calciumHMDB
Leucovorin, (D)-isomerHMDB
Leucovorin, (DL)-isomerHMDB
Leucovorin, calcium (1:1) saltHMDB
5 FormyltetrahydrofolateHMDB
Citrovorum factorHMDB
Factor, citrovorumHMDB
Folinic acid SFHMDB
Leucovorin, calcium (1:1) salt, pentahydrateHMDB
LeukovorinHMDB
N(5)-FormyltetrahydrofolateHMDB
Leucovorin, (R)-isomerHMDB
Leucovorin, calcium (1:1) salt, (DL)-isomerHMDB
LeukovorumHMDB
Monosodium salt leucovorinHMDB
WellcovorinHMDB
5 FormyltetrahydropteroylglutamateHMDB
Calcium folinateHMDB
Calcium leucovorinHMDB
Leucovorin, calciumHMDB
Leucovorin, monosodium saltHMDB
Folinic acidHMDB, MeSH
Folinic acid-sfHMDB
N5-Formyl-THFhmdb
Predicted Properties
PropertyValueSource
Water Solubility0.18 g/LALOGPS
logP-1.6ALOGPS
logP-2.3ChemAxon
logS-3.4ALOGPS
pKa (Strongest Acidic)3.47ChemAxon
pKa (Strongest Basic)2.81ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count11ChemAxon
Hydrogen Donor Count7ChemAxon
Polar Surface Area215.55 ŲChemAxon
Rotatable Bond Count9ChemAxon
Refractivity126.66 m³·mol⁻¹ChemAxon
Polarizability46.54 ųChemAxon
Number of Rings3ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC20H23N7O7
IUPAC name2-[(4-{[(2-amino-5-formyl-4-oxo-3,4,5,6,7,8-hexahydropteridin-6-yl)methyl]amino}phenyl)formamido]pentanedioic acid
InChI IdentifierInChI=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 KeyVVIAGPKUTFNRDU-UHFFFAOYSA-N
Isomeric SMILESNC1=NC2=C(N(C=O)C(CNC3=CC=C(C=C3)C(=O)NC(CCC(O)=O)C(O)=O)CN2)C(=O)N1
Average Molecular Weight473.4393
Monoisotopic Molecular Weight473.165896125
Classification
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.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassPteridines and derivatives
Sub ClassPterins and derivatives
Direct ParentTetrahydrofolic 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 FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-004i-2332900000-5c40a0014d3bb486cb20View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-0fk9-7225198000-aa48aa22224db36842c7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0031900000-31498c227b611f3360eaView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a6r-0393400000-f81606ae4f4b27aadbacView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-1591000000-825bc8196995ef0bc1e3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0000900000-203ae236b032df3233d7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0umj-1131900000-5174748fd5288f6523fdView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0007-9674000000-192da85bfca095ec870eView in MoNA
ChemSpider ID140
ChEMBL IDCHEMBL69905
KEGG Compound IDC03479
Pubchem Compound ID143
Pubchem Substance IDNot Available
ChEBI ID15640
Phenol-Explorer IDNot Available
DrugBank IDDB00650
HMDB IDHMDB01562
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG ID41929
KNApSAcK IDNot Available
HET ID1KL2
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDFolinic_acid
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
Enzymes
NameGene NameUniProt ID
Aminomethyltransferase, mitochondrialAMTP48728
Formimidoyltransferase-cyclodeaminaseFTCDO95954
Thymidylate synthaseTYMSP04818
Pathways
NameSMPDB LinkKEGG Link
Folate MetabolismSMP00053 map00670
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference