Urocanic acid (CED0006163)

Record Information

Version

1.0

Creation Date

2016-05-22 04:30:42 UTC

Update Date

2026-05-14 17:22:54 UTC

Accession Number

CHEM017647

Identification

Common Name

Urocanic acid

Class

Small Molecule

Description

Urocanic acid is an organic compound with the chemical formula C6H6N2O2 and an average molecular weight of 138.12 g/mol. Urocanic acid belongs to the imidazoles, a subclass of azoles within the organic compounds. In an industrial context, the compound is utilized as a UV stabilizer. The substance is found in or released from five recorded sources. Within the category of food, food processing, and cookware, it is associated with the processing of meats, the processing of fish, and the preparation of vinegar. Additionally, it is found in electrical and electronic equipment, specifically in antennas and auxiliary devices. Regarding its biological activity, urocanic acid has one recorded protein target, which is urocanate hydratase (hutU).

Contaminant Type

Not Available

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(2E)-3-(1H-Imidazol-4-yl)acrylic acid	ChEBI
(e)-3-(1H-Imidazol-4-yl)-2-propenoic acid	ChEBI
(2E)-3-(1H-Imidazol-4-yl)acrylate	Generator
(e)-3-(1H-Imidazol-4-yl)-2-propenoate	Generator
Urocanate	Generator
3-(1H-Imidazol-4-yl)-2-propenoate	HMDB
3-(1H-Imidazol-4-yl)-2-propenoic acid	HMDB
3-(1H-Imidazol-4-yl)acrylate	HMDB
3-(1H-Imidazol-4-yl)acrylic acid	HMDB
3-(4-Imidazolyl)acrylate	HMDB
3-(4-Imidazolyl)acrylic acid	HMDB
5-Imidazoleacrylate	HMDB
5-Imidazoleacrylic acid	HMDB
Imidazole-4-acrylate	HMDB
Imidazole-4-acrylic acid	HMDB
Imidazoleacrylic acid	HMDB
Acid, glyoxalinylacrylic	HMDB
Acid, urocanic	HMDB
Glyoxalinylacrylic acid	HMDB
(2E)-3-(1H-Imidazol-5-yl)-2-propenoic acid	HMDB
(e)-3-(4-Imidazolyl)acrylic acid	HMDB
(e)-3-(Imidazol-4-yl)-2-propenoic acid	HMDB
(e)-Urocanic acid	HMDB
trans-Urocanic acid	HMDB

Chemical Formula

C₆H₆N₂O₂

Average Molecular Mass

138.124 g/mol

Monoisotopic Mass

138.043 g/mol

CAS Registry Number

104-98-3

IUPAC Name

(2E)-3-(1H-imidazol-4-yl)prop-2-enoic acid

Traditional Name

trans-urocanic acid

SMILES

OC(=O)\C=C\C1=CNC=N1

InChI Identifier

InChI=1S/C6H6N2O2/c9-6(10)2-1-5-3-7-4-8-5/h1-4H,(H,7,8)(H,9,10)/b2-1+

InChI Key

LOIYMIARKYCTBW-OWOJBTEDSA-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

urocanic acid (CHEBI:30817 )

Biological Properties

Status

Detected and Not Quantified

Origin

Not Available

Cellular Locations

Not Available

Biofluid Locations

Not Available

Tissue Locations

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Organoleptic Effects

Not Available

Physical Properties

State

Not Available

Appearance

Not Available

Experimental Properties

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

Predicted Properties

Property	Value	Source
Water Solubility	42.5 g/L	ALOGPS
logP	0.22	ALOGPS
logP	-1	ChemAxon
logS	-0.51	ALOGPS
pKa (Strongest Acidic)	3.85	ChemAxon
pKa (Strongest Basic)	6.13	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	65.98 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	35.57 m³·mol⁻¹	ChemAxon
Polarizability	13.1 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	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	Deposition Date	View
GC-MS	GC-MS Spectrum	splash10-014m-1930000000-25b091170cc3ea73bcf7	Not Available	View Spectrum
GC-MS	GC-MS Spectrum	splash10-00l5-1930000000-5c3c875338a517d52729	Not Available	View Spectrum
GC-MS	GC-MS Spectrum	splash10-00di-9410000000-b58e1b2cdd5c12a6ba24	Not Available	View Spectrum
GC-MS	GC-MS Spectrum	splash10-0159-3950000000-433e50271e182f8408fd	Not Available	View Spectrum
GC-MS	GC-MS Spectrum	splash10-000f-9200000000-cb7f9025a0f6adf740c1	Not Available	View Spectrum
GC-MS	GC-MS Spectrum	splash10-014m-1930000000-25b091170cc3ea73bcf7	Not Available	View Spectrum
GC-MS	GC-MS Spectrum	splash10-00l5-1930000000-5c3c875338a517d52729	Not Available	View Spectrum
GC-MS	GC-MS Spectrum	splash10-00di-9410000000-b58e1b2cdd5c12a6ba24	Not Available	View Spectrum
GC-MS	GC-MS Spectrum	splash10-0159-3950000000-433e50271e182f8408fd	Not Available	View Spectrum
GC-MS	GC-MS Spectrum	splash10-014m-1930000000-3815ef1f1f386e091dc3	Not Available	View Spectrum
GC-MS	GC-MS Spectrum	splash10-00dm-2900000000-aaefc749352097679e8f	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	splash10-000f-9500000000-7f0462e0ef244d2118a8	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	splash10-00di-6910000000-b1e081746388d0700ce0	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	Not Available	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	Not Available	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	Not Available	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	Not Available	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-00di-3900000000-8c1c060d06c1ce3fb5f7	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-00kf-9000000000-ae9de21d4642045fb96c	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-014l-9000000000-8e6978d7f104386d2e82	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-000f-9200000000-cb7f9025a0f6adf740c1	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-000i-1900000000-c628b05706544cb1ebdc	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0006-9300000000-bc4c631410a5cbb3c2f5	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0006-9000000000-ccac569cbc78a632da48	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0006-9000000000-a22c861e4f2551a3f582	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-00kf-9000000000-37421b473ba575d307fd	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-00du-5900000000-29dc15087c785a19c0ee	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0006-9200000000-1cc9b0a66b83ca383ebd	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-000i-1900000000-c628b05706544cb1ebdc	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0006-9300000000-bc4c631410a5cbb3c2f5	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0006-9000000000-ccac569cbc78a632da48	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0006-9000000000-a22c861e4f2551a3f582	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-00kf-9000000000-37421b473ba575d307fd	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0006-9200000000-1cc9b0a66b83ca383ebd	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-00du-5900000000-29dc15087c785a19c0ee	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0006-9000000000-853f5ec98c651c09e3db	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0w29-9000000000-44d309d3e0e56bbb9680	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-000i-0900000000-134c65f0d4d973daa316	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-000i-0900000000-0b27055a09a3ef32509d	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-002f-9200000000-c783c391a7c2289bd411	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-00kf-9000000000-5a6aa3817637eb7f111b	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-000i-3900000000-0d430c4fc4bd7f1d1670	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-00kf-9000000000-f2d70873af244fbec955	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-014l-9000000000-31462c3e83bebf9a1225	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0006-9100000000-fa874c48d3170a59d1b8	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-00ku-9000000000-43276ca3f0799ffcd202	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-006x-9500000000-a3283ca7230e33343005	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0006-9000000000-033705db77ccb32c7d88	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0006-9000000000-4dc261a6b83e77aa29a8	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-00dl-8900000000-ce506cc87ae1f0533aa1	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0079-1900000000-5e51f64ba1845b0937fb	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-03di-9000000000-f9046ab0200660a5a10b	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0079-2900000000-bc76f0e644ed0868c081	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-00kf-9000000000-95a84f1e10f025a7d47f	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-006x-9300000000-20dd6d9b76b78bd9a3a0	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-00kf-9000000000-5bfe4323ce73dca9720b	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-00di-4900000000-213f550edda0d0d083f7	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-00ko-9000000000-a047a4e3a3513df90f3e	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-014l-9000000000-83c762ef5a215a2ad602	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0079-1900000000-928d60d45ff2c49d6af6	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-000i-0900000000-0f247674727412e79606	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-006x-9300000000-e7933ed4100c41603ba7	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0079-1900000000-dac4165382f541a26a03	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0076-8900000000-6da8eb6b76055856b714	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-014i-9000000000-ab76de8a8f1873f63de6	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-000i-1900000000-173e1f32b118424e132d	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-000l-5900000000-b1ebc285fc95a34dc7b1	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-00kf-9200000000-66f717c0018108bc7769	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0006-9100000000-058e97cab302e3106c14	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-00kf-9000000000-2b7478e2a5a03d1bfa3b	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-014l-9000000000-4fe0932f7f117477bc74	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-00di-0900000000-8a1dddb6aabb5fb9243f	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-006x-9600000000-00d2fa6d6455f3b28850	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-00kf-9000000000-2c3b0f7d1c263d6b66a4	Not Available	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, D₂O, predicted)	Not Available	Not Available	View Spectrum
1D NMR	¹H NMR Spectrum (1D, D₂O, predicted)	Not Available	Not Available	View Spectrum

Toxicity Profile

Mechanism of Toxicity

Not Available

Carcinogenicity (IARC Classification)

Not Available

Minimum Risk Level

Not Available

Symptoms

Not Available

Treatment

Not Available

Toxicity Values

Toxicity Value	Unit	Value Range	Organism	Dose Descriptor	Route of Exposure	Predicted or Experimental	Reference
1031.0	Log mg/kg	[580:1800]	Rat	LD50	oral	predicted	Not Available

Health Effects

Health Effect	Relationship	Direction	Reference

Exposure Sources

Source ID	Source	Sector	Reference
506	Antennas	Electrical & Electronic Equipment	Not Available
507	Auxiliary Devices	Electrical & Electronic Equipment	Not Available
548	Preparation Of Vinegar	Food, food processing & cookware	Not Available
551	Processing Fish	Food, food processing & cookware	Not Available
552	Processing Meats	Food, food processing & cookware	Not Available
612	Body Washing Or Cleaning Implements	Personal care & cosmetics	Not Available
616	Face Mask Cosmetics	Personal care & cosmetics	Not Available
619	Manicure Pedicure	Personal care & cosmetics	Not Available

Pathways

5 pathways

Targets

Structure	Protein	UniProt ID	Organism	Relationship	Details
Click to view 3D structure	Histamine H3 receptor	Q9JI35	Cavia porcellus	Predicted (SEA)	15.4141
Click to view 3D structure	Histamine H2 receptor	P47747	Cavia porcellus	Predicted (SEA)	8.64126
Click to view 3D structure	Histamine H3 receptor	Q9QYN8	Rattus norvegicus	Predicted (SEA)	35.4214
Click to view 3D structure	Histamine H3 receptor	Q9Y5N1	Humans	Predicted (SEA)	181.856
Click to view 3D structure	Histidinol dehydrogenase	P06988	Escherichia coli (strain K12)	Predicted (SEA)	6.69503
Click to view 3D structure	Histamine H1 receptor	P31389	Cavia porcellus	Predicted (SEA)	120.121
Click to view 3D structure	Histidine decarboxylase	P16453	Rattus norvegicus	Predicted (SEA)	8.09632
Click to view 3D structure	Carbonic anhydrase 2	P00918	Humans	Predicted (SEA)	558.179
Click to view 3D structure	Carbonic anhydrase 5A, mitochondrial	P35218	Humans	Predicted (SEA)	200.929
Click to view 3D structure	Histamine H4 receptor	Q9H3N8	Humans	Predicted (SEA)	169.166
Click to view 3D structure	Carbonic anhydrase 14	Q9ULX7	Humans	Predicted (SEA)	228.098
Click to view 3D structure	Carbonic anhydrase 9	Q16790	Humans	Predicted (SEA)	525.871
Click to view 3D structure	Carbonic anhydrase 1	P00915	Humans	Predicted (SEA)	572.892
Click to view 3D structure	Histamine H2 receptor	P25021	Humans	Predicted (SEA)	391.348
Click to view 3D structure	Histidinol dehydrogenase	Q8G2R2	Brucella suis biovar 1 (strain 1330)	Predicted (SEA)	11.0546
Click to view 3D structure	Carbonic anhydrase 7	P43166	Humans	Predicted (SEA)	401.78
Click to view 3D structure	Carbonic anhydrase 6	P23280	Humans	Predicted (SEA)	222.182
Click to view 3D structure	Carbonic anhydrase 12	O43570	Humans	Predicted (SEA)	635.172
Click to view 3D structure	Histidinol dehydrogenase, chloroplastic	P24226	Brassica oleracea var. capitata	Predicted (SEA)	11.366
Click to view 3D structure	Histamine H1 receptor	P35367	Humans	Predicted (SEA)	1102.34
Click to view 3D structure	Carbonic anhydrase 3	P07451	Humans	Predicted (SEA)	193.845
Click to view 3D structure	Histamine H4 receptor	Q91ZY2	Mus musculus	Predicted (SEA)	25.4567
Click to view 3D structure	Carbonic anhydrase 5B, mitochondrial	Q9Y2D0	Humans	Predicted (SEA)	465.538
Click to view 3D structure	Casein kinase II subunit alpha	P68400	Humans	Predicted (SEA)	2680.82
Click to view 3D structure	Cytochrome P450 3A4	P08684	Humans	Predicted (SEA)	5171.91