ContaminantDB: Imidazoleacetic acid

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Targets (1)XML

Record Information

Version

1.0

Creation Date

2014-08-29 06:37:15 UTC

Update Date

2026-04-02 23:56:40 UTC

Accession Number

CHEM003338

Identification

Common Name

Imidazoleacetic acid

Class

Small Molecule

Description

Imidazoleacetic acid is a metabolite product of Histamine metabolism. It is present in normal urine and increased in histidinemic patients. (1).

Contaminant Sources

FooDB Chemicals
HMDB Contaminants - Urine
T3DB toxins

Contaminant Type

Animal Toxin
Food Toxin
Metabolite
Natural Compound
Organic Compound

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
1H-Imidazole-4-acetic acid	ChEBI
4(5)-Imidazoleacetate	ChEBI
4-Imidazoleacetate	ChEBI
Imidazole-4-acetate	ChEBI
1H-Imidazole-4-acetate	Generator
4(5)-Imidazoleacetic acid	Generator
4-Imidazoleacetic acid	Generator
Imidazole-4-acetic acid	Generator
Imidazoleacetate	Generator
1H-Imidazol-4-ylacetic acid	HMDB
IAA	HMDB
IMAC	HMDB
Imidazol-4-ylacetate	HMDB
Imidazol-4-ylacetic acid	HMDB
Imidazole acetate	HMDB
Imidazolyl-4-acetic acid	HMDB
IZC	HMDB
Lopac-I-0375	HMDB
Imidazole-4-acetic acid, sodium salt	HMDB
Imidazole-4-acetic acid hydrochloride	HMDB

Chemical Formula

C₅H₆N₂O₂

Average Molecular Mass

126.113 g/mol

Monoisotopic Mass

126.043 g/mol

CAS Registry Number

645-65-8

IUPAC Name

2-(1H-imidazol-5-yl)acetic acid

Traditional Name

IMAC

SMILES

OC(=O)CC1=CN=CN1

InChI Identifier

InChI=1S/C5H6N2O2/c8-5(9)1-4-2-6-3-7-4/h2-3H,1H2,(H,6,7)(H,8,9)

InChI Key

PRJKNHOMHKJCEJ-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.

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
Heteroaromatic compound
Azacycle
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Carbonyl group
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

imidazolyl carboxylic acid (CHEBI:16974 )

Biological Properties

Status

Detected and Not Quantified

Origin

Endogenous

Cellular Locations

Cytoplasm
Extracellular
Mitochondria

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Name	SMPDB Link	KEGG Link
Histidine Metabolism	SMP00044	map00340
Histidinemia	SMP00191	Not Available

Applications

Not Available

Biological Roles

metabolite

Chemical Roles

Not Available

Physical Properties

State

Solid

Appearance

White powder.

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	53.3 g/L	ALOGPS
logP	-0.5	ALOGPS
logP	-1.4	ChemAxon
logS	-0.37	ALOGPS
pKa (Strongest Acidic)	3.65	ChemAxon
pKa (Strongest Basic)	6.78	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	65.98 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	30.2 m³·mol⁻¹	ChemAxon
Polarizability	11.47 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
GC-MS	GC-MS Spectrum - GC-MS (1 TMS)	splash10-0f89-5900000000-420b0de40d13d8210bbc	Spectrum
GC-MS	GC-MS Spectrum - GC-MS (2 TMS)	splash10-0fc0-5970000000-86a11eed673e756aa38a	Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-0f89-5900000000-420b0de40d13d8210bbc	Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-0fc0-5970000000-86a11eed673e756aa38a	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-001i-9200000000-3560ea9910e3fb51b173	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-00di-8900000000-05046aa1145002d7c5e8	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-003r-9600000000-12712603bcc1f0bea126	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-001i-9000000000-fc527ff9b17df8a45f5d	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-001i-9000000000-f50438c3b380c53358cb	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positive	splash10-004i-0900000000-3e8a5824e3117a9ff630	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positive	splash10-001i-9100000000-bd0eae5cae4e35af3bc9	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positive	splash10-001i-9000000000-029fc71514700cdb7209	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positive	splash10-001i-9000000000-55f8440d265a11022fb9	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positive	splash10-001i-9000000000-2f783a29f0103b0f7b59	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - , negative	splash10-001i-9000000000-536179ad66be87ef6052	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-004i-0900000000-3e8a5824e3117a9ff630	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-001i-9100000000-bd0eae5cae4e35af3bc9	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-001i-9000000000-029fc71514700cdb7209	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-001i-9000000000-55f8440d265a11022fb9	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-001i-9000000000-2f783a29f0103b0f7b59	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 0V, Positive	splash10-004i-1900000000-2df669861c33e046ef52	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-0f89-9000000000-9ab02097fca907a3b75f	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 35V, Negative	splash10-001i-9000000000-8c245e2f0f54c3db08d7	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-001i-9100000000-5976268b58ff0c9c054a	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-001i-9100000000-ffb1202ccd976a3c4ac6	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4i-1900000000-4b77cf695394035f5cb9	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4i-8900000000-3a84b22e5a91324c68a8	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0gc3-9000000000-c43447728a419e4b671a	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-3900000000-d826c494ed679b7cd08e	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0560-9800000000-1d0c114437988870749d	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0kal-9100000000-802d3d5a745c25a2b664	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
2D NMR	[1H,13C] 2D NMR Spectrum	Not Available	Spectrum

Toxicity Profile

Route of Exposure

Not Available

Mechanism of Toxicity

Not Available

Metabolism

Not Available

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

No indication of carcinogenicity to humans (not listed by IARC).

Uses/Sources

This is an endogenously produced metabolite found in the human body. It is used in metabolic reactions, catabolic reactions or waste generation.

Minimum Risk Level

Not Available

Health Effects

Not Available

Symptoms

Not Available

Treatment

Not Available

Concentrations

Not Available

External Links

DrugBank ID

Not Available

HMDB ID

HMDB0002024

FooDB ID

FDB030508

Phenol Explorer ID

Not Available

KNApSAcK ID

Not Available

BiGG ID

40666

BioCyc ID

4-IMIDAZOLEACETATE

METLIN ID

6445

PDB ID

Not Available

Wikipedia Link

Not Available

Chemspider ID

ChEBI ID

PubChem Compound ID

Kegg Compound ID

YMDB ID

Not Available

ECMDB ID

M2MDB004224

References

Synthesis Reference

Madsen Christian; Jensen Anders A; Liljefors Tommy; Kristiansen Uffe; Nielsen Birgitte; Hansen Camilla P; Larsen Mogens; Ebert Bjarke; Bang-Andersen Benny; Krogsgaard-Larsen Povl; Frolund Bente 5-Substituted imidazole-4-acetic acid analogues: synthesis, modeling, and pharmacological characterization of a series of novel gamma-aminobutyric acid(C) receptor agonists. Journal of medicinal chemistry (2007), 50(17), 4147-61.

MSDS

Link

General References

1. Mung D, Li L: Applying quantitative metabolomics based on chemical isotope labeling LC-MS for detecting potential milk adulterant in human milk. Anal Chim Acta. 2018 Feb 25;1001:78-85. doi: 10.1016/j.aca.2017.11.019. Epub 2017 Nov 14.

2. Madsen Christian; Jensen Anders A; Liljefors Tommy; Kristiansen Uffe; Nielsen Birgitte; Hansen Camilla P; Larsen Mogens; Ebert Bjarke; Bang-Andersen Benny; Krogsgaard-Larsen Povl; Frolund Bente 5-Substituted imidazole-4-acetic acid analogues: synthesis, modeling, and pharmacological characterization of a series of novel gamma-aminobutyric acid(C) receptor agonists. Journal of medicinal chemistry (2007), 50(17), 4147-61.

3. Khandelwal JK, Prell GD, Morrishow AM, Green JP: Presence and measurement of imidazoleacetic acid, a gamma-aminobutyric acid agonist, in rat brain and human cerebrospinal fluid. J Neurochem. 1989 Apr;52(4):1107-13.

4. Tsuruta Y, Tomida H, Kohashi K, Ohkura Y: Simultaneous determination of imidazoleacetic acid and N tau- and N pi-methylimidazoleacetic acids in human urine by high-performance liquid chromatography with fluorescence detection. J Chromatogr. 1987 Apr 24;416(1):63-9.

5. Khandelwal JK, Hough LB, Pazhenchevsky B, Morrishow AM, Green JP: Presence and measurement of methylimidazoleacetic acids in brain and body fluids. J Biol Chem. 1982 Nov 10;257(21):12815-9.

6. Sondergaard I: Quantitative determination of 1,4-methyl-imidazoleacetic acid in urine by high performance liquid chromatography. Allergy. 1982 Nov;37(8):581-6.

7. Imamura I, Watanabe T, Hase Y, Sakamoto Y, Fukuda Y, Yamamoto H, Tsuruhara T, Wada H: Histamine metabolism in patients with histidinemia: determination of urinary levels of histamine, N tau-methylhistamine, imidazole acetic acid, and its conjugate(s). J Biochem. 1984 Dec;96(6):1925-9.

8. Thiele I, Swainston N, Fleming RM, Hoppe A, Sahoo S, Aurich MK, Haraldsdottir H, Mo ML, Rolfsson O, Stobbe MD, Thorleifsson SG, Agren R, Bolling C, Bordel S, Chavali AK, Dobson P, Dunn WB, Endler L, Hala D, Hucka M, Hull D, Jameson D, Jamshidi N, Jonsson JJ, Juty N, Keating S, Nookaew I, Le Novere N, Malys N, Mazein A, Papin JA, Price ND, Selkov E Sr, Sigurdsson MI, Simeonidis E, Sonnenschein N, Smallbone K, Sorokin A, van Beek JH, Weichart D, Goryanin I, Nielsen J, Westerhoff HV, Kell DB, Mendes P, Palsson BO: A community-driven global reconstruction of human metabolism. Nat Biotechnol. 2013 May;31(5):419-25. doi: 10.1038/nbt.2488. Epub 2013 Mar 3.

9. 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.

10. https://www.ncbi.nlm.nih.gov/pubmed/?term=22770225

Imidazoleacetic acid (CHEM003338)

Structure for CHEM003338: Imidazoleacetic acid