Showing metabocard for N10-Formyl-THF (BMDB0000972)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (5) Show 5 proteinsXML
Record Information
Version1.0
Creation Date2016-09-30 22:39:19 UTC
Update Date2020-05-21 16:28:32 UTC
BMDB IDBMDB0000972
Secondary Accession Numbers
  • BMDB00972
Metabolite Identification
Common NameN10-Formyl-THF
Description10-Formyltetrahydrofolate, also known as 10-formyl-THF or 10-formyl-H4pteglu1, 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. 10-Formyltetrahydrofolate is a strong basic compound (based on its pKa). 10-Formyltetrahydrofolate exists in all eukaryotes, ranging from yeast to humans.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
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
Chemical FormulaC20H23N7O7
Average Molecular Weight473.4393
Monoisotopic Molecular Weight473.165896125
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
Traditional Name(2S)-2-[(4-{N-[(4-hydroxy-2-imino-5,6,7,8-tetrahydro-1H-pteridin-6-yl)methyl]formamido}phenyl)formamido]pentanedioic acid
CAS Registry Number2800-34-2
SMILES
NC1=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
InChI Identifier
InChI=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
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.
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
StatusExpected but not Quantified
OriginNot Available
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cytoplasm
  • Lysosome
  • Mitochondria
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP-1.5ALOGPS
logP-4ChemAxon
logS-3.2ALOGPS
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Biological Properties
Cellular Locations
  • Cytoplasm
  • Lysosome
  • Mitochondria
Biospecimen LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
HMDB IDHMDB0000972
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB030256
KNApSAcK IDNot Available
Chemspider ID109092
KEGG Compound IDC00234
BioCyc IDNot Available
BiGG ID34337
Wikipedia Link10-Formyltetrahydrofolate
METLIN ID5912
PubChem Compound122347
PDB IDNot Available
ChEBI ID15637
References
Synthesis ReferenceDenis V; Daignan-Fornier B Synthesis of glutamine, glycine and 10-formyl tetrahydrofolate is coregulated with purine biosynthesis in Saccharomyces cerevisiae. Molecular & general genetics : MGG (1998), 259(3), 246-55.
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

Enzyme Details
1. Monofunctional C1-tetrahydrofolate synthase, mitochondrial
General function:
Nucleotide transport and metabolism
Specific function:
May provide the missing metabolic reaction required to link the mitochondria and the cytoplasm in the mammalian model of one-carbon folate metabolism in embryonic an transformed cells complementing thus the enzymatic activities of MTHFD2.
Gene Name:
MTHFD1L
Uniprot ID:
Q0VCR7
Molecular weight:
105227.0
Enzyme Details
2. Bifunctional purine biosynthesis protein PURH
General function:
Nucleotide transport and metabolism
Specific function:
Bifunctional enzyme that catalyzes 2 steps in purine biosynthesis.
Gene Name:
ATIC
Uniprot ID:
Q0VCK0
Molecular weight:
64483.0
Reactions
N10-Formyl-THF + AICAR → Tetrahydrofolic acid + Phosphoribosyl formamidocarboxamidedetails
Enzyme Details
3. Methionyl-tRNA formyltransferase, mitochondrial
General function:
Translation, ribosomal structure and biogenesis
Specific function:
Formylates methionyl-tRNA in mitochondria. A single tRNA(Met) gene gives rise to both an initiator and an elongator species via an unknown mechanism.
Gene Name:
MTFMT
Uniprot ID:
O77480
Molecular weight:
43620.0
Reactions
N10-Formyl-THF + L-Methionyl-tRNA(Met) → Tetrahydrofolic acid + N-formylmethionyl-tRNA(fMet)details
Enzyme Details
4. Trifunctional purine biosynthetic protein adenosine-3
General function:
Nucleotide transport and metabolism
Specific function:
Not Available
Gene Name:
GART
Uniprot ID:
Q59A32
Molecular weight:
107907.0
Reactions
N10-Formyl-THF + Glycineamideribotide → Tetrahydrofolic acid + 5'-Phosphoribosyl-N-formylglycinamidedetails
Enzyme Details
5. Retinal dehydrogenase 1
General function:
Energy production and conversion
Specific function:
Can convert/oxidize retinaldehyde to retinoic acid. Binds free retinal and cellular retinol-binding protein-bound retinal. May have a broader specificity and oxidize other aldehydes in vivo.
Gene Name:
ALDH1A1
Uniprot ID:
P48644
Molecular weight:
54806.0
Reactions
N10-Formyl-THF + NADP + Water → Tetrahydrofolic acid + Carbon dioxide + NADPHdetails