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Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2016-02-11 01:03:25 UTC
HMDB IDHMDB00854
Secondary Accession NumbersNone
Metabolite Identification
Common NameFormiminoglutamic acid
DescriptionMeasurement of this acid in the urine after oral administration of histidine provides the basis for the diagnostic test of folic acid deficiency and of megaloblastic anemia of pregnancy.
Structure
Thumb
Synonyms
ValueSource
N-Formimidoyl-L-glutamateChEBI
N-formimino-L-GlutamateChEBI
N-Formimidoyl-L-glutamic acidGenerator
FormiminoglutamateGenerator
N-formimino-L-Glutamic acidGenerator
formimino-GluHMDB
formimino-L-GlutamateHMDB
formimino-L-Glutamic acidHMDB
N-(Iminomethyl)-L-glutamic acidHMDB
N-Formimidoyl-glutamic acidHMDB
N-formimino-GlutamateHMDB
Acid, formiminoglutamicMeSH
FIGLUMeSH
Chemical FormulaC6H10N2O4
Average Molecular Weight174.1546
Monoisotopic Molecular Weight174.064056818
IUPAC Name(2S)-2-methanimidamidopentanedioic acid
Traditional NameN-formimino-L-glutamate
CAS Registry Number816-90-0
SMILES
OC(=O)CC[C@H](NC=N)C(O)=O
InChI Identifier
InChI=1S/C6H10N2O4/c7-3-8-4(6(11)12)1-2-5(9)10/h3-4H,1-2H2,(H2,7,8)(H,9,10)(H,11,12)/t4-/m0/s1
InChI KeyInChIKey=NRXIKWMTVXPVEF-BYPYZUCNSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as glutamic acid and derivatives. These 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.
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganic acids and derivatives
Sub ClassCarboxylic acids and derivatives
Direct ParentGlutamic acid and derivatives
Alternative Parents
Substituents
  • Glutamic acid or derivatives
  • Dicarboxylic acid or derivatives
  • Fatty acid
  • Amidine
  • Carboxylic acid amidine
  • Carboxylic acid
  • Carboximidamide
  • Propargyl-type 1,3-dipolar organic compound
  • Organic 1,3-dipolar compound
  • Formamidine
  • Organooxygen compound
  • Carbonyl group
  • Organic nitrogen compound
  • Organonitrogen compound
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Organic oxide
  • Organopnictogen compound
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
Biofunction
  • Protein synthesis, amino acid biosynthesis
ApplicationNot Available
Cellular locations
  • Cytoplasm
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 Solubility2.28 mg/mLALOGPS
logP-1.3ALOGPS
logP-2.8ChemAxon
logS-1.9ALOGPS
pKa (Strongest Acidic)2.49ChemAxon
pKa (Strongest Basic)10.88ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area110.48 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity48.71 m3·mol-1ChemAxon
Polarizability15.61 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
Biological Properties
Cellular Locations
  • Cytoplasm
Biofluid Locations
  • Urine
Tissue LocationNot Available
Pathways
NameSMPDB LinkKEGG Link
Histidine MetabolismSMP00044map00340
HistidinemiaSMP00191Not Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
UrineDetected and Quantified0.47 (0.0-0.80) umol/mmol creatinineAdult (>18 years old)BothNormal
    • Geigy Scientific ...
    • West Cadwell, N.J...
    • Basel, Switzerlan...
details
UrineDetected and Quantified0.90 +/- 0.71 umol/mmol creatinineInfant (0-1 year old)BothNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB022280
KNApSAcK IDNot Available
Chemspider ID388370
KEGG Compound IDC00439
BioCyc IDN-FORMIMINO-L-GLUTAMATE
BiGG ID34986
Wikipedia LinkFormiminoglutamic acid
NuGOwiki LinkHMDB00854
Metagene LinkHMDB00854
METLIN ID5817
PubChem Compound439233
PDB IDNIG
ChEBI ID7274
References
Synthesis ReferenceTabor, Herbert; Rabinowitz, Jesse C. Insts. Formiminoglycine, formimino-L-aspartic acid, and formimino-L-glutamic acid.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Hilton JF, Christensen KE, Watkins D, Raby BA, Renaud Y, de la Luna S, Estivill X, MacKenzie RE, Hudson TJ, Rosenblatt DS: The molecular basis of glutamate formiminotransferase deficiency. Hum Mutat. 2003 Jul;22(1):67-73. [12815595 ]
  2. Haurani FI, Hall CA, Rubin R: Megaloblastic anemia as a result of an abnormal transcobalamin II (Cardeza). J Clin Invest. 1979 Nov;64(5):1253-9. [500809 ]
  3. Perry TL, Applegarth DA, Evans ME, Hansen S, Jellum E: Metabolic studies of a family with massive formiminoglutamic aciduria. Pediatr Res. 1975 Mar;9(3):117-22. [235753 ]
  4. Verhoeven NM, Wanders RJ, Poll-The BT, Saudubray JM, Jakobs C: The metabolism of phytanic acid and pristanic acid in man: a review. J Inherit Metab Dis. 1998 Oct;21(7):697-728. [9819701 ]

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
5-Formiminotetrahydrofolic acid + L-Glutamic acid → Tetrahydrofolic acid + Formiminoglutamic aciddetails
5-Formiminotetrahydrofolic acid + L-Glutamic acid → Tetrahydrofolic acid + Formiminoglutamic aciddetails
General function:
Involved in hydrolase activity, acting on carbon-nitrogen (but not peptide) bonds, in cyclic amides
Specific function:
Not Available
Gene Name:
AMDHD1
Uniprot ID:
Q96NU7
Molecular weight:
46742.505
Reactions
4-Imidazolone-5-propionic acid + Water → Formiminoglutamic acid + Hydrogen Iondetails
4-Imidazolone-5-propionic acid + Water → Formiminoglutamic aciddetails