Record Information
Version1.0
Creation date2015-05-07 18:54:34 UTC
Update date2019-11-26 03:21:40 UTC
Primary IDFDB030256
Secondary Accession Numbers
  • FDB022345
Chemical Information
FooDB Name10-formyl-tetrahydrofolate
Description10-formyltetrahydrofolate, also known as 10-formyl-thf or 10-formyltetrahydropteroylglutamic acid, is a member of the class of compounds known as tetrahydrofolic acids. Tetrahydrofolic acids are heterocyclic compounds based on the 5,6,7,8-tetrahydropteroic acid skeleton conjugated with at least one L-glutamic acid unit. 10-formyltetrahydrofolate is practically insoluble (in water) and a moderately acidic compound (based on its pKa). 10-formyltetrahydrofolate can be found in a number of food items such as agave, black salsify, white cabbage, and lemon, which makes 10-formyltetrahydrofolate a potential biomarker for the consumption of these food products. 10-formyltetrahydrofolate exists in all eukaryotes, ranging from yeast to humans. In humans, 10-formyltetrahydrofolate is involved in several metabolic pathways, some of which include mercaptopurine action pathway, methionine metabolism, purine metabolism, and folate malabsorption, hereditary. 10-formyltetrahydrofolate is also involved in several metabolic disorders, some of which include myoadenylate deaminase deficiency, adenine phosphoribosyltransferase deficiency (APRT), molybdenum cofactor deficiency, and cystathionine beta-synthase deficiency. 10-Formyltetrahydrofolate (10-CHO-THF) is a form of tetrahydrofolate that acts as a donor of formyl groups in anabolism. In these reactions 10-CHO-THF is used as a substrate in formyltransferase reactions. This is important in purine biosynthesis, where 10-CHO-THF is a substrate for phosphoribosylaminoimidazolecarboxamide formyltransferase, as well as in the formylation of the methionyl initiator tRNA (fMet-tRNA), when 10-CHO-THF is a substrate for methionyl-tRNA formyltransferase .
CAS Number2800-34-2
Structure
Thumb
Synonyms
SynonymSource
10-Formyl-THFKegg
10-Formyltetrahydrofolic acidGenerator
10-Formyl-(6Rs)-tetrahydrofolic acidHMDB
10-Formyl-H4pteglu1HMDB
10-Formyl-tetrahydrofolateHMDB
10-FormyltetrahydropteroylglutamateHMDB
10-Formyltetrahydropteroylglutamic acidHMDB
10-FTHFHMDB
N-[p-[N-[(2-Amino-5,6,7,8-tetrahydro-4-hydroxy-6-pteridinyl)methyl]formamido]benzoyl]-glutamateHMDB
N-[p-[N-[(2-Amino-5,6,7,8-tetrahydro-4-hydroxy-6-pteridinyl)methyl]formamido]benzoyl]-glutamic acidHMDB
N-[p-[N-[(2-Amino-5,6,7,8-tetrahydro-4-hydroxy-6-pteridinyl)methyl]formamido]benzoyl]-L-glutamateHMDB
N-[p-[N-[(2-Amino-5,6,7,8-tetrahydro-4-hydroxy-6-pteridinyl)methyl]formamido]benzoyl]-L-glutamic acidHMDB
N10-Formyl-5,6,7,8-tetrahydrofolateHMDB
N10-Formyl-5,6,7,8-tetrahydrofolic acidHMDB
N10-Formyl-H4FHMDB
N10-Formyl-THFHMDB
N10-FormyltetrahydrofolateHMDB
N10-Formyltetrahydrofolic acidHMDB
N10-FormyltetrahydropteroylglutamateHMDB
Predicted Properties
PropertyValueSource
Water Solubility0.34 g/LALOGPS
logP-1.5ALOGPS
logP-4ChemAxon
logS-3.1ALOGPS
pKa (Strongest Acidic)2.95ChemAxon
pKa (Strongest Basic)5.75ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count12ChemAxon
Hydrogen Donor Count8ChemAxon
Polar Surface Area216.54 ŲChemAxon
Rotatable Bond Count9ChemAxon
Refractivity135.7 m³·mol⁻¹ChemAxon
Polarizability46.38 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC20H23N7O7
IUPAC name(2S)-2-[(4-{N-[(4-hydroxy-2-imino-1,2,5,6,7,8-hexahydropteridin-6-yl)methyl]formamido}phenyl)formamido]pentanedioic acid
InChI IdentifierInChI=1S/C20H23N7O7/c21-20-25-16-15(18(32)26-20)23-11(7-22-16)8-27(9-28)12-3-1-10(2-4-12)17(31)24-13(19(33)34)5-6-14(29)30/h1-4,9,11,13,23H,5-8H2,(H,24,31)(H,29,30)(H,33,34)(H4,21,22,25,26,32)/t11?,13-/m0/s1
InChI KeyAUFGTPPARQZWDO-YUZLPWPTSA-N
Isomeric SMILESNC1=NC(=O)C2=C(NCC(CN(C=O)C3=CC=C(C=C3)C(=O)N[C@@H](CCC(O)=O)C(O)=O)N2)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
  • Acylaminobenzoic acid or derivatives
  • Alpha-amino acid or derivatives
  • Anilide
  • Benzoic acid or derivatives
  • Benzamide
  • Benzoyl
  • Pyrimidone
  • Aminopyrimidine
  • Secondary aliphatic/aromatic amine
  • Dicarboxylic acid or derivatives
  • Benzenoid
  • Pyrimidine
  • Monocyclic benzene moiety
  • Heteroaromatic compound
  • Vinylogous amide
  • Tertiary carboxylic acid amide
  • Amino acid or derivatives
  • Amino acid
  • Carboxamide group
  • Secondary carboxylic acid amide
  • Azacycle
  • Carboxylic acid
  • Carboxylic acid derivative
  • Secondary amine
  • Organic oxygen compound
  • Organic nitrogen compound
  • Carbonyl group
  • Hydrocarbon derivative
  • Amine
  • Organic oxide
  • Organopnictogen compound
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
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
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MS10-Formyltetrahydrofolic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-004j-2733900000-d416b73a1673d1220b87Spectrum
Predicted GC-MS10-Formyltetrahydrofolic acid, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0v4i-2913374000-7b894dbf7f83fe5cd9d7Spectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-05cr-0401900000-21104c38dc03ca4e7a0eSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-003r-0935700000-2f12524764eca10dcf15Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001i-0910000000-03f41886e7967d0201ebSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0000900000-1244cea99701ed75f41cSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00bc-1123900000-cdcadc51a3f47cb93886Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9842000000-62efadef6701421ce2c5Spectrum
NMRNot Available
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound IDNot Available
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
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
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference