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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2006-08-12 21:36:15 UTC
Update Date2020-02-26 21:24:38 UTC
HMDB IDHMDB0003470
Secondary Accession Numbers
  • HMDB03470
Metabolite Identification
Common NameN-Formyl-L-glutamic acid
DescriptionN-Formyl-L-glutamic acid, also known as N-formyl-L-glutamate, belongs to the class of organic compounds known as glutamic acid and derivatives. Glutamic acid and derivatives are compounds containing glutamic acid or a derivative thereof resulting from reaction of glutamic acid at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom. N-Formyl-L-glutamic acid is an extremely weak basic (essentially neutral) compound (based on its pKa). N-Formyl-L-glutamic acid exists in all living organisms, ranging from bacteria to humans. tetrahydrofolic acid and N-formyl-L-glutamic acid can be biosynthesized from N5-formyl-THF and L-glutamic acid; which is catalyzed by the enzyme formimidoyltransferase-cyclodeaminase. In humans, N-formyl-L-glutamic acid is involved in folate metabolism. N-Formyl-L-glutamic acid is an intermediate in the histidine metabolism, in a reaction mediated by the enzyme formiminotransferase cyclodeaminase , a bifunctional enzyme that channels 1-carbon units from formiminoglutamate to the folate pool.
Structure
Data?1582752278
Synonyms
ValueSource
(2S)-2-(Formylamino)pentanedioic acidChEBI
N-Formyl-L-glutamateChEBI
(2S)-2-(Formylamino)pentanedioateGenerator
(2S)-2-FormamidopentanedioateHMDB
(2S)-2-Formamidopentanedioic acidHMDB
N-FormylglutamateHMDB
N-Formylglutamate, ion(2-)HMDB
Chemical FormulaC6H9NO5
Average Molecular Weight175.1394
Monoisotopic Molecular Weight175.048072403
IUPAC Name(2S)-2-formamidopentanedioic acid
Traditional NameN-formyl-L-glutamic acid
CAS Registry Number1681-96-5
SMILES
OC(=O)CC[C@H](NC=O)C(O)=O
InChI Identifier
InChI=1S/C6H9NO5/c8-3-7-4(6(11)12)1-2-5(9)10/h3-4H,1-2H2,(H,7,8)(H,9,10)(H,11,12)/t4-/m0/s1
InChI KeyADZLWSMFHHHOBV-BYPYZUCNSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as glutamic acid and derivatives. Glutamic acid and derivatives are compounds containing glutamic acid or a derivative thereof resulting from reaction of glutamic acid at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentGlutamic acid and derivatives
Alternative Parents
Substituents
  • Glutamic acid or derivatives
  • N-acyl-l-alpha-amino acid
  • N-formyl-alpha-amino acid
  • N-formyl-alpha amino acid or derivatives
  • Dicarboxylic acid or derivatives
  • Fatty acid
  • Secondary carboxylic acid amide
  • Carboxamide group
  • Carboxylic acid
  • Organopnictogen compound
  • Carbonyl group
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Disposition

Source:

Process

Naturally occurring process:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility24.5 g/LALOGPS
logP-0.86ALOGPS
logP-1.2ChemAxon
logS-0.85ALOGPS
pKa (Strongest Acidic)3.3ChemAxon
pKa (Strongest Basic)-0.91ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area103.7 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity36.24 m³·mol⁻¹ChemAxon
Polarizability15.42 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-055f-9500000000-87e21ed84f3e07a0525eSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-0udi-5090000000-9bdfed547fb095a666a7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a59-0900000000-56d7b5efa61129bb9f2aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0f89-1900000000-f0cf3aae7ee3fc5cdc38Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ue9-9700000000-81fd656d12663befc16eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-05fs-0900000000-e09e113f64d6b1d6f838Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0fba-1900000000-df4e50eec3cd34d33f16Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-002f-9300000000-0e7670e199ce4fc65a9aSpectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB023180
KNApSAcK IDNot Available
Chemspider ID388496
KEGG Compound IDC01045
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID6939
PubChem Compound439376
PDB IDNot Available
ChEBI ID48309
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceBorek, Blanche Ann; Waelsch, Heinrich. The enzymic degradation of histidine. Journal of Biological Chemistry (1953), 205 459-74.
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

General function:
Involved in catalytic activity
Specific function:
Folate-dependent enzyme, that displays both transferase and deaminase activity. Serves to channel one-carbon units from formiminoglutamate to the folate pool. Binds and promotes bundling of vimentin filaments originating from the Golgi (By similarity).
Gene Name:
FTCD
Uniprot ID:
O95954
Molecular weight:
58925.93
Reactions
Folinic acid + L-Glutamic acid → Tetrahydrofolic acid + N-Formyl-L-glutamic aciddetails
Folinic acid + L-Glutamic acid → Tetrahydrofolic acid + N-Formyl-L-glutamic aciddetails