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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2018-05-20 09:42:13 UTC
HMDB IDHMDB0000854
Secondary Accession Numbers
  • HMDB00854
Metabolite Identification
Common NameFormiminoglutamic acid
DescriptionFormiminoglutamic acid, also known as N-formimino-L-glutamate or acid, formiminoglutamic, 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. Formiminoglutamic acid is slightly soluble (in water) and a moderately acidic compound (based on its pKa). Formiminoglutamic acid has been detected in multiple biofluids, such as feces and urine. Within the cell, formiminoglutamic acid is primarily located in the cytoplasm. Formiminoglutamic acid participates in a number of enzymatic reactions. In particular, Formiminoglutamic acid can be biosynthesized from 4-imidazolone-5-propionic acid through its interaction with the enzyme probable imidazolonepropionase. In addition, Tetrahydrofolic acid and formiminoglutamic acid can be converted into 5-formiminotetrahydrofolic acid and L-glutamic acid through the action of the enzyme formimidoyltransferase-cyclodeaminase. In humans, formiminoglutamic acid is involved in the histidine metabolism pathway. Formiminoglutamic acid is also involved in the metabolic disorder called the histidinemia pathway.
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 KeyNRXIKWMTVXPVEF-BYPYZUCNSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds 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.
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
  • 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
Disposition

Source:

Biological location:

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 Solubility2.28 g/LALOGPS
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 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity48.71 m³·mol⁻¹ChemAxon
Polarizability15.61 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-056u-9400000000-6cceb3db80c1c51b5798View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-0fg9-9230000000-65123e05e539b5af2388View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-056r-0900000000-92c0f47c419298fb78a2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004j-5900000000-8b915dd10756167a4003View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0012-9100000000-313b0983e834934e5682View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00fr-1900000000-b264a846efb94105ac49View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0f97-5900000000-2f4ec838a8ef46f9428dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-002f-9200000000-a518077a6ec2f6a6c6c5View in MoNA
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen Locations
  • Feces
  • Urine
Tissue LocationNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not Quantified Adult (>18 years old)Both
Normal
details
UrineDetected and Quantified13.400-21.800 umol/mmol creatinineAdult (>18 years old)Both
Normal
details
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
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not Quantified Adult (>18 years old)BothColorectal Cancer details
UrineDetected and Quantified780.114-1876.796 umol/mmol creatinineChildren (1-13 years old)BothGlutamate formiminotransferase deficiency details
Associated Disorders and Diseases
Disease References
Colorectal cancer
  1. Brown DG, Rao S, Weir TL, O'Malia J, Bazan M, Brown RJ, Ryan EP: Metabolomics and metabolic pathway networks from human colorectal cancers, adjacent mucosa, and stool. Cancer Metab. 2016 Jun 6;4:11. doi: 10.1186/s40170-016-0151-y. eCollection 2016. [PubMed:27275383 ]
Glutamate formiminotransferase deficiency
  1. 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. [PubMed:235753 ]
Associated OMIM IDs
  • 114500 (Colorectal cancer)
  • 229100 (Glutamate formiminotransferase deficiency)
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB022280
KNApSAcK IDNot Available
Chemspider ID388370
KEGG Compound IDC00439
BioCyc IDN-FORMIMINO-L-GLUTAMATE
BiGG ID34986
Wikipedia LinkFormiminoglutamic acid
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. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed: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