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Record Information
Version	2.0
Creation Date	2012-08-09 09:16:15 -0600
Update Date	2015-09-13 12:56:16 -0600
Secondary Accession Numbers	ECMDB21439
Identification
Name:	Imidazolelactic acid
Description	Imidazolelactic acid is a compound that has an imidazole group attached to the beta carbon of lactic acid. (inferred from compound structure) Imidazolelactic acid can be formed from an NADH-assisted reduction of imidazol-5-yl-pyruvate. (KEGG)
Structure	MOLSDFPDBSMILESInChI × Structure for #<Compound:0xaa427a0c> Close
Synonyms:	(S)-3-(Imidazol-5-yl)-lactate (S)-3-(Imidazol-5-yl)-lactic acid 1-Imidazolelactate 1-Imidazolelactic acid 2-Hydroxy-3-[4-imidazolyl]-propanoate 2-Hydroxy-3-[4-imidazolyl]-propanoic acid (S)-3-(imidazol-5-yl)-lactate Imidazol-5-yl-lactate Imidazol-5-yl-lactic acid Imidazole lactate Imidazole lactic acid Imidazolelactate
Chemical Formula:	C6H8N2O3
Weight:	Average: 156.1393 Monoisotopic: 156.053492132
InChI Key:	JTYMXXCJQKGGFG-UHFFFAOYSA-N
InChI:	InChI=1S/C6H8N2O3/c9-5(6(10)11)3-8-2-1-7-4-8/h1-2,4-5,9H,3H2,(H,10,11)
CAS number:	876-19-7
IUPAC Name:	2-hydroxy-3-(1H-imidazol-1-yl)propanoic acid
Traditional IUPAC Name:	2-hydroxy-3-(imidazol-1-yl)propanoic acid
SMILES:	OC(CN1C=CN=C1)C(O)=O
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.
Kingdom	Organic compounds
Super Class	Organoheterocyclic compounds
Class	Azoles
Sub Class	Imidazoles
Direct Parent	Imidazolyl carboxylic acids and derivatives
Alternative Parents	N-substituted imidazoles Alpha hydroxy acids and derivatives Heteroaromatic compounds Secondary alcohols Monocarboxylic acids and derivatives Carboxylic acids Azacyclic compounds Organopnictogen compounds Organonitrogen compounds Organic oxides Hydrocarbon derivatives Carbonyl compounds
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 Framework	Aromatic heteromonocyclic compounds
External Descriptors	imidazolyl carboxylic acid (CHEBI:70808 ) 2-hydroxy monocarboxylic acid (CHEBI:70808 )
Physical Properties
State:	Solid
Charge:	-1
Melting point:	Not Available
Experimental Properties:	Property Value Source
Predicted Properties	Property Value Source Water Solubility 11 g/L ALOGPS logP -1.2 ALOGPS logP -1.7 ChemAxon logS -1.1 ALOGPS pKa (Strongest Acidic) 3.39 ChemAxon pKa (Strongest Basic) 6.77 ChemAxon Physiological Charge -1 ChemAxon Hydrogen Acceptor Count 4 ChemAxon Hydrogen Donor Count 2 ChemAxon Polar Surface Area 75.35 Ų ChemAxon Rotatable Bond Count 3 ChemAxon Refractivity 36.03 m³·mol⁻¹ ChemAxon Polarizability 14.1 ų ChemAxon Number of Rings 1 ChemAxon Bioavailability 1 ChemAxon Rule of Five Yes ChemAxon Ghose Filter Yes ChemAxon Veber's Rule Yes ChemAxon MDDR-like Rule Yes ChemAxon
Biological Properties
Cellular Locations:	Cytoplasm
Reactions:
SMPDB Pathways:	Not Available
KEGG Pathways:	Not Available
EcoCyc Pathways:	Not Available
Concentrations
	Not Available
Spectra
Spectra:	Spectrum Type Description Splash Key Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive splash10-001i-9100000000-af6e1c31ba814d5c0085 View in MoNA Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive splash10-001i-9440000000-51a0a80ace23d0a3d85e View in MoNA Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive Not Available View in JSpectraViewer Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Positive splash10-052r-0900000000-0329a4bafbb746648ef5 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Positive splash10-000i-5900000000-2ceb5bb4c7d0c4d563ae View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Positive splash10-014i-9000000000-af66fc635cd0e0618e4b View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Negative splash10-0a4i-1900000000-e77f735cce68a7f7b4a2 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Negative splash10-014i-9300000000-6a5f23eb647fb89baad5 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Negative splash10-014l-9000000000-4e4a86f260b34da6c02a View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Negative splash10-0aor-9800000000-3a57c8d2b2b5cf3cf713 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Negative splash10-014i-9000000000-a2f57dd2d7faa84a9a49 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Negative splash10-014i-9000000000-281cf185205743f8c55b View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Positive splash10-0bt9-0900000000-81381fab6df16fa55b59 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Positive splash10-00lr-9400000000-eef5c8eb5c6f485c4b70 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Positive splash10-0gb9-9000000000-a7ce72d207b1b75057fd View in MoNA 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer
References
References:	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 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 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 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 van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25. Pubmed: 17765195 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 Winder, C. L., Dunn, W. B., Schuler, S., Broadhurst, D., Jarvis, R., Stephens, G. M., Goodacre, R. (2008). "Global metabolic profiling of Escherichia coli cultures: an evaluation of methods for quenching and extraction of intracellular metabolites." Anal Chem 80:2939-2948. Pubmed: 18331064
Synthesis Reference:	Not Available
Material Safety Data Sheet (MSDS)	Download (PDF)
Links
External Links:	Resource Link CHEBI ID 27487 HMDB ID HMDB02320 Pubchem Compound ID 459122 Kegg ID C05132 ChemSpider ID 404046 Wikipedia ID Not Available BioCyc ID IMIDAZOLE-LACTATE EcoCyc ID IMIDAZOLE-LACTATE