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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2006-05-22 14:17:47 UTC
Update Date2020-02-26 21:24:03 UTC
HMDB IDHMDB0002320
Secondary Accession Numbers
  • HMDB02320
Metabolite Identification
Common NameImidazolelactic acid
DescriptionImidazolelactic acid is the component of normal human urine. (PMID: 5856262 ). histidine loading causes an increase in the excretion of imidazolelactic acid. (PMID: 6021220 ). 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 ). Urinary excretion of imidazolelactic acid is also an indication for folic acid and vitamin B12 deficiency. (PMID: 4645251 ).
Structure
Data?1582752243
Synonyms
ValueSource
1-Imidazolelactic acidChEBI
2-Hydroxy-3-(1H-imidazol-1-yl)propanoic acidChEBI
1-ImidazolelactateGenerator
2-Hydroxy-3-(1H-imidazol-1-yl)propanoateGenerator
ImidazolelactateGenerator
3-(Imidazol-1-yl)lactateHMDB
2-Hydroxy-3-[4-imidazolyl]-propanoateHMDB
2-Hydroxy-3-[4-imidazolyl]-propanoic acidHMDB
Imidazolelactic acidMeSH
Chemical FormulaC6H8N2O3
Average Molecular Weight156.1393
Monoisotopic Molecular Weight156.053492132
IUPAC Name2-hydroxy-3-(1H-imidazol-1-yl)propanoic acid
Traditional Name2-hydroxy-3-(imidazol-1-yl)propanoic acid
CAS Registry Number876-19-7
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 KeyJTYMXXCJQKGGFG-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as imidazolyl carboxylic acids and derivatives. These are organic compounds containing a carboxylic acid chain (of at least 2 carbon atoms) linked to an imidazole ring.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassAzoles
Sub ClassImidazoles
Direct ParentImidazolyl carboxylic acids and derivatives
Alternative Parents
Substituents
  • Imidazolyl carboxylic acid derivative
  • Alpha-hydroxy acid
  • Hydroxy acid
  • N-substituted imidazole
  • Heteroaromatic compound
  • Secondary alcohol
  • Carboxylic acid derivative
  • Carboxylic acid
  • Azacycle
  • Monocarboxylic acid or derivatives
  • Alcohol
  • Organonitrogen compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Carbonyl group
  • Organic nitrogen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
Physiological effect

Health effect:

Disposition

Source:

Biological location:

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 Solubility11 g/LALOGPS
logP-1.2ALOGPS
logP-1.7ChemAxon
logS-1.2ALOGPS
pKa (Strongest Acidic)3.39ChemAxon
pKa (Strongest Basic)6.77ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area75.35 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity36.03 m³·mol⁻¹ChemAxon
Polarizability14.1 ųChemAxon
Number of Rings1ChemAxon
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, Positivesplash10-001i-9100000000-af6e1c31ba814d5c0085Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-001i-9440000000-51a0a80ace23d0a3d85eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-052r-0900000000-0329a4bafbb746648ef5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-5900000000-2ceb5bb4c7d0c4d563aeSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014i-9000000000-af66fc635cd0e0618e4bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-1900000000-e77f735cce68a7f7b4a2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-9300000000-6a5f23eb647fb89baad5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014l-9000000000-4e4a86f260b34da6c02aSpectrum
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biospecimen Locations
  • Blood
  • Feces
  • Urine
Tissue Locations
  • Placenta
  • Prostate
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot Available
Normal
    details
    BloodDetected but not Quantified Adult (>18 years old)Both
    Normal
    details
    FecesDetected but not Quantified Adult (>18 years old)Both
    Normal
    details
    FecesDetected but not Quantified Adult (>18 years old)Both
    Normal
    details
    UrineDetected and Quantified0.5 (0.17-1.0) umol/mmol creatinineChildren (1-13 years old)BothNormal
      • Geigy Scientific ...
      • West Cadwell, N.J...
      • Basel, Switzerlan...
    details
    UrineDetected and Quantified5.6 (3.5-7.0) umol/mmol creatinineAdult (>18 years old)BothNormal
      • Geigy Scientific ...
      • West Cadwell, N.J...
      • Basel, Switzerlan...
    details
    Abnormal Concentrations
    BiospecimenStatusValueAgeSexConditionReferenceDetails
    BloodDetected but not Quantified Adult (>18 years old)Both
    Schizophrenia
    details
    Associated Disorders and Diseases
    Disease References
    Schizophrenia
    1. Koike S, Bundo M, Iwamoto K, Suga M, Kuwabara H, Ohashi Y, Shinoda K, Takano Y, Iwashiro N, Satomura Y, Nagai T, Natsubori T, Tada M, Yamasue H, Kasai K: A snapshot of plasma metabolites in first-episode schizophrenia: a capillary electrophoresis time-of-flight mass spectrometry study. Transl Psychiatry. 2014 Apr 8;4:e379. doi: 10.1038/tp.2014.19. [PubMed:24713860 ]
    Associated OMIM IDs
    DrugBank IDNot Available
    Phenol Explorer Compound IDNot Available
    FooDB IDFDB022962
    KNApSAcK IDNot Available
    Chemspider ID404046
    KEGG Compound IDC05132
    BioCyc IDNot Available
    BiGG IDNot Available
    Wikipedia LinkNot Available
    METLIN ID6617
    PubChem Compound459122
    PDB IDNot Available
    ChEBI ID70808
    Food Biomarker OntologyNot Available
    VMH IDNot Available
    References
    Synthesis ReferenceNot 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. doi: 10.1038/nature07762. [PubMed:19212411 ]
    2. Dubovsky J, Dubovska E, Formankova J: [Imidazolactic acid in the urine. Method of determination and clinical observations]. Cas Lek Cesk. 1965 Nov 5;104(44):1216-21. [PubMed:5856262 ]
    3. Block WD, Westhoff MH, Steele BF: Histidine metabolism in the human adult: histidine blood tolerance, and the effect of continued free L-histidine ingestion on the concentration of imidazole compounds in blood and urine. J Nutr. 1967 Feb;91(2):189-94. [PubMed:6021220 ]
    4. Hamacher M, Mosebach KO: [Quantitative determination of some imidazole derivatives in the urine of pregnant patients, non-pregnant patients and those with diseases caused by pregnancy]. Hoppe Seylers Z Physiol Chem. 1969 May;350(5):603-8. [PubMed:5789877 ]
    5. van Roon-Djordjevic B, Cerfontain-van Staalen: Urinary excretion of histidine metabolites as an indication for folic acid and vitamin B 12 deficiency. Clin Chim Acta. 1972 Oct;41:55-65. [PubMed:4645251 ]
    6. Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]