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Human Metabolome Database Version 3.5

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Showing metabocard for Imidazolelactic acid (HMDB02320)

Record Information
Version 3.5
Creation Date 2006-05-22 08:17:47 -0600
Update Date 2013-02-08 17:11:44 -0700
HMDB ID HMDB02320
Secondary Accession Numbers None
Metabolite Identification
Common Name Imidazolelactic acid
Description Imidazolelactic acid is the component of normal human urine. (PMID: 5856262 Link_out). histidine loading causes an increase in the excretion of imidazolelactic acid. (PMID: 6021220 Link_out). During pregnancy the values for imidazolelactic acid in urine is increased 3-fold. An interaction of allergic reactions and anomalies in the metabolism of the sex hormones are considered to form the basis of the pregnancy-specific illnesses that were studied. (PMID: 5789877 Link_out). Urinary excretion of imidazolelactic acid is also an indication for folic acid and vitamin B12 deficiency. (PMID: 4645251 Link_out).
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. 1-Imidazolelactate
  2. 1-Imidazolelactic acid
  3. 2-Hydroxy-3-[4-imidazolyl]-propanoate
  4. 2-Hydroxy-3-[4-imidazolyl]-propanoic acid
Chemical Formula C6H8N2O3
Average Molecular Weight 156.1393
Monoisotopic Molecular Weight 156.053492132
IUPAC Name 2-hydroxy-3-(1H-imidazol-1-yl)propanoic acid
Traditional IUPAC Name 2-hydroxy-3-(imidazol-1-yl)propanoic acid
CAS Registry Number 876-19-7
SMILES OC(CN1C=CN=C1)C(O)=O
InChI Identifier InChI=1S/C6H8N2O3/c9-5(6(10)11)3-8-2-1-7-4-8/h1-2,4-5,9H,3H2,(H,10,11)
InChI Key JTYMXXCJQKGGFG-UHFFFAOYSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Aromatic Heteromonocyclic Compounds
Class Azoles
Sub Class Imidazoles
Other Descriptors
  • Aromatic Heteromonocyclic Compounds
Substituents
  • Alpha Hydroxy Acid
  • Carboxylic Acid
  • Secondary Alcohol
Direct Parent Imidazolyl Carboxylic Acids and Derivatives
Ontology
Status Detected and Quantified
Origin
  • Endogenous
Biofunction Not Available
Application Not Available
Cellular locations
  • Cytoplasm (predicted from logP)
Physical Properties
State Solid
Experimental Properties
Property Value Reference
Melting Point Not Available Not Available
Boiling Point Not Available Not Available
Water Solubility Not Available Not Available
LogP Not Available Not Available
Predicted Properties
Property Value Source
Water Solubility 11 g/L ALOGPS
LogP -1.18 ALOGPS
LogP -1.7 ChemAxon
LogS -1.15 ALOGPS
pKa (strongest acidic) 3.39 ChemAxon
pKa (strongest basic) 6.77 ChemAxon
Hydrogen Acceptor Count 4 ChemAxon
Hydrogen Donor Count 2 ChemAxon
Polar Surface Area 75.35 A2 ChemAxon
Rotatable Bond Count 3 ChemAxon
Refractivity 36.03 ChemAxon
Polarizability 14.1 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge -1 ChemAxon
Spectra
Not Available
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Prostate
Pathways Not Available
Normal Concentrations
Biofluid Status Value Age Sex Condition Comments
Blood Expected and not Quantified
Not Applicable Not Available Not Available Normal Inferred from detection in urine
Urine Detected and Quantified
Article_icon
0.5 (0.17-1.0) umol/mmol creatinine Children (1-13 year old) Both Normal Not Available
Urine Detected and Quantified
Article_icon
5.6 (3.5-7.0) umol/mmol creatinine Adult (>18 years old) Both Normal Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease References None
Associated OMIM IDs None
DrugBank ID Not Available
Phenol Explorer Compound ID Not Available
Phenol Explorer Metabolite ID Not Available
FoodDB ID FDB022962
KNApSAcK ID Not Available
Chemspider ID 404046 Link_out
KEGG Compound ID C05132 Link_out
BioCyc ID Not Available
BiGG ID Not Available
Wikipedia Link Not Available
NuGOwiki Link HMDB02320 Link_out
Metagene Link HMDB02320 Link_out
METLIN ID 6617 Link_out
PubChem Compound 459122 Link_out
PDB ID Not Available
ChEBI ID 27487 Link_out
References
Synthesis Reference Not Available
Material Safety Data Sheet (MSDS) Download (PDF)
General References
  1. Sreekumar A, Poisson LM, Rajendiran TM, Khan AP, Cao Q, Yu J, Laxman B, Mehra R, Lonigro RJ, Li Y, Nyati MK, Ahsan A, Kalyana-Sundaram S, Han B, Cao X, Byun J, Omenn GS, Ghosh D, Pennathur S, Alexander DC, Berger A, Shuster JR, Wei JT, Varambally S, Beecher C, Chinnaiyan AM: Metabolomic profiles delineate potential role for sarcosine in prostate cancer progression. Nature. 2009 Feb 12;457(7231):910-4. Pubmed: 19212411 Link_out