ECMDB: Imidazolelactic acid (ECMDB21439) (M2MDB001834)

Identification Taxonomy Physical Properties Biological Properties Spectra Concentrations Links References XML

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

MOL SDF PDB SMILES InChI

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

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 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	36.03 m³·mol⁻¹	ChemAxon
Polarizability	14.1 Å³	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

Imidazolelactic acid (ECMDB21439) (M2MDB001834)

Structure for #<Compound:0xa58b1884>