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Record Information
Version	2.0
Creation Date	2012-08-03 14:57:54 -0600
Update Date	2015-09-13 15:15:32 -0600
Secondary Accession Numbers	ECMDB21396
Identification
Name:	Urocanic acid
Description	Urocanic acid is a breakdown (deamination) product of histidine from histidase or histidine ammonia lyase (hutS).
Structure	MOLSDF3D-SDFPDBSMILESInChI View 3D Structure × Structure for #<Compound:0xb4883010> Close
Synonyms:	3-(1H-Imidazol-4-yl)-2-propenoate 3-(1H-Imidazol-4-yl)-2-propenoic acid 3-(1H-Imidazol-4-yl)acrylate 3-(1H-Imidazol-4-yl)acrylic acid 3-(4-Imidazolyl)acrylate 3-(4-Imidazolyl)acrylic acid 5-Imidazoleacrylate 5-Imidazoleacrylic acid Imidazole-4-acrylate Imidazole-4-acrylic acid Imidazoleacrylate Imidazoleacrylic acid Urocanate
Chemical Formula:	C6H6N2O2
Weight:	Average: 138.124 Monoisotopic: 138.042927446
InChI Key:	LOIYMIARKYCTBW-OWOJBTEDSA-N
InChI:	InChI=1S/C6H6N2O2/c9-6(10)2-1-5-3-7-4-8-5/h1-4H,(H,7,8)(H,9,10)/b2-1+
CAS number:	104-98-3
IUPAC Name:	(2E)-3-(1H-imidazol-4-yl)prop-2-enoic acid
Traditional IUPAC Name:	trans-urocanic acid
SMILES:	OC(=O)\C=C\C1=CNC=N1
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	Heteroaromatic compounds Monocarboxylic acids and derivatives Carboxylic acids Azacyclic compounds Organopnictogen compounds Organonitrogen compounds Organic oxides Hydrocarbon derivatives Carbonyl compounds
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 )
Physical Properties
State:	Solid
Charge:	-1
Melting point:	225 °C
Experimental Properties:	Property Value Source Water Solubility: 1.5 mg/mL at 17 oC [YALKOWSKY,SH & DANNENFELSER,RM (1992)] PhysProp
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 Ų ChemAxon Rotatable Bond Count 2 ChemAxon Refractivity 35.57 m³·mol⁻¹ ChemAxon Polarizability 13.1 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
	Concentration Strain Media Growth Status Growth System Temperature Details 69± 0 uM BW25113 48 mM Na2HPO4, 22 mM KH2PO4, 10 mM NaCl, 45 mM (NH4)2SO4, supplemented with 1 mM MgSO4, 1 mg/l thiamine·HCl, 5.6 mg/l CaCl2, 8 mg/l FeCl3, 1 mg/l MnCl2·4H2O, 1.7 mg/l ZnCl2, 0.43 mg/l CuCl2·2H2O, 0.6 mg/l CoCl2·2H2O and 0.6 mg/l Na2MoO4·2H2O. 4 g/L Gluco Stationary Phase, glucose limited Bioreactor, pH controlled, O2 and CO2 controlled, dilution rate: 0.2/h 37 oC PMID: 17379776 Find out more about how we convert literature concentrations.
Spectra
Spectra:	Spectrum Type Description Splash Key GC-MS GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS) splash10-014m-1930000000-25b091170cc3ea73bcf7 View in MoNA GC-MS GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized) splash10-00l5-1930000000-5c3c875338a517d52729 View in MoNA GC-MS GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS) splash10-00di-9410000000-b58e1b2cdd5c12a6ba24 View in MoNA GC-MS GC-MS Spectrum - GC-MS (2 TMS) splash10-0159-3950000000-433e50271e182f8408fd View in MoNA GC-MS GC-MS Spectrum - EI-B (Non-derivatized) splash10-000f-9200000000-cb7f9025a0f6adf740c1 View in MoNA GC-MS GC-MS Spectrum - GC-EI-TOF (Non-derivatized) splash10-014m-1930000000-25b091170cc3ea73bcf7 View in MoNA GC-MS GC-MS Spectrum - GC-EI-TOF (Non-derivatized) splash10-00l5-1930000000-5c3c875338a517d52729 View in MoNA GC-MS GC-MS Spectrum - GC-EI-TOF (Non-derivatized) splash10-00di-9410000000-b58e1b2cdd5c12a6ba24 View in MoNA GC-MS GC-MS Spectrum - GC-MS (Non-derivatized) splash10-0159-3950000000-433e50271e182f8408fd View in MoNA GC-MS GC-MS Spectrum - GC-EI-TOF (Non-derivatized) splash10-014m-1930000000-3815ef1f1f386e091dc3 View in MoNA GC-MS GC-MS Spectrum - GC-EI-TOF (Non-derivatized) splash10-00dm-2900000000-aaefc749352097679e8f View in MoNA Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive splash10-000f-9500000000-7f0462e0ef244d2118a8 View in MoNA Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive splash10-00di-6910000000-b1e081746388d0700ce0 View in MoNA Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive Not Available View in JSpectraViewer Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive Not Available View in JSpectraViewer Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive Not Available View in JSpectraViewer Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, Positive Not Available View in JSpectraViewer LC-MS/MS LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated) splash10-00di-3900000000-8c1c060d06c1ce3fb5f7 View in MoNA LC-MS/MS LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated) splash10-00kf-9000000000-ae9de21d4642045fb96c View in MoNA LC-MS/MS LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated) splash10-014l-9000000000-8e6978d7f104386d2e82 View in MoNA LC-MS/MS LC-MS/MS Spectrum - EI-B (HITACHI M-80) , Positive splash10-000f-9200000000-cb7f9025a0f6adf740c1 View in MoNA LC-MS/MS LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative splash10-000i-1900000000-c628b05706544cb1ebdc View in MoNA LC-MS/MS LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative splash10-0006-9300000000-bc4c631410a5cbb3c2f5 View in MoNA LC-MS/MS LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative splash10-0006-9000000000-ccac569cbc78a632da48 View in MoNA LC-MS/MS LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative splash10-0006-9000000000-a22c861e4f2551a3f582 View in MoNA LC-MS/MS LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative splash10-00kf-9000000000-37421b473ba575d307fd View in MoNA LC-MS/MS LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive splash10-00du-5900000000-29dc15087c785a19c0ee View in MoNA LC-MS/MS LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative splash10-0006-9200000000-1cc9b0a66b83ca383ebd View in MoNA LC-MS/MS LC-MS/MS Spectrum - LC-ESI-QQ , negative splash10-000i-1900000000-c628b05706544cb1ebdc View in MoNA LC-MS/MS LC-MS/MS Spectrum - LC-ESI-QQ , negative splash10-0006-9300000000-bc4c631410a5cbb3c2f5 View in MoNA LC-MS/MS LC-MS/MS Spectrum - LC-ESI-QQ , negative splash10-0006-9000000000-ccac569cbc78a632da48 View in MoNA LC-MS/MS LC-MS/MS Spectrum - LC-ESI-QQ , negative splash10-0006-9000000000-a22c861e4f2551a3f582 View in MoNA LC-MS/MS LC-MS/MS Spectrum - LC-ESI-QQ , negative splash10-00kf-9000000000-37421b473ba575d307fd View in MoNA LC-MS/MS LC-MS/MS Spectrum - LC-ESI-QTOF , negative splash10-0006-9200000000-1cc9b0a66b83ca383ebd View in MoNA LC-MS/MS LC-MS/MS Spectrum - LC-ESI-QTOF , positive splash10-00du-5900000000-29dc15087c785a19c0ee View in MoNA LC-MS/MS LC-MS/MS Spectrum - 20V, Negative splash10-0006-9000000000-853f5ec98c651c09e3db View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Positive splash10-0079-1900000000-dac4165382f541a26a03 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Positive splash10-0076-8900000000-6da8eb6b76055856b714 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Positive splash10-014i-9000000000-ab76de8a8f1873f63de6 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Negative splash10-000i-1900000000-173e1f32b118424e132d View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Negative splash10-000l-5900000000-b1ebc285fc95a34dc7b1 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Negative splash10-00kf-9200000000-66f717c0018108bc7769 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 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 2D NMR [1H,13C] 2D NMR Spectrum Not Available View in JSpectraViewer
References
References:	Hermann K, Abeck D: Determination of histidine and urocanic acid isomers in the human skin by high-performance capillary electrophoresis. J Chromatogr B Biomed Sci Appl. 2000 Nov 10;749(1):41-7. Pubmed: 11129077 Hug DH, Hunter JK, Dunkerson DD: The potential role for urocanic acid and sunlight in the immune suppression associated with protein malnutrition. J Photochem Photobiol B. 1998 Jul 10;44(2):117-23. Pubmed: 9757593 Ishii, N., Nakahigashi, K., Baba, T., Robert, M., Soga, T., Kanai, A., Hirasawa, T., Naba, M., Hirai, K., Hoque, A., Ho, P. Y., Kakazu, Y., Sugawara, K., Igarashi, S., Harada, S., Masuda, T., Sugiyama, N., Togashi, T., Hasegawa, M., Takai, Y., Yugi, K., Arakawa, K., Iwata, N., Toya, Y., Nakayama, Y., Nishioka, T., Shimizu, K., Mori, H., Tomita, M. (2007). "Multiple high-throughput analyses monitor the response of E. coli to perturbations." Science 316:593-597. Pubmed: 17379776 Kinuta M, Kinuta K, Yamada H, Abe T, Yoshida Y, Araki K, Li SA, Otsuka A, Nakanishi A, Moriyama Y, Takei K: Formation of S-[2-carboxy-1-(1H-imidazol-4-yl) ethyl]glutathione, a new metabolite of L-histidine, from cis-urocanic acid and glutathione by the action of glutathione S-transferase. Electrophoresis. 2003 Sep;24(18):3212-8. Pubmed: 14518047 Morrison H: Photochemistry and photobiology of urocanic acid. Photodermatol. 1985 Jun;2(3):158-65. Pubmed: 3895185 Sastry CM, Whitmore SE, Breysse PN, Morison WL, Strickland PT: The effect of clinical UVA/B exposures on urinary urocanic acid isomer levels in individuals with caucasian type (II/III) skin types. Dermatol Online J. 2005 Dec 1;11(3):1. Pubmed: 16409897 Schwarz W, Langer K, Haag A: High-performance liquid chromatographic determination of (Z)-and (E)-urocanic acid in human skin. J Chromatogr. 1984 Sep 14;310(1):188-92. Pubmed: 6501514 Snellman E, Jansen CT, Laihia JK, Milan T, Koulu L, Leszczynski K, Pasanen P: Urocanic acid concentration and photoisomerization in Caucasian skin phototypes. Photochem Photobiol. 1997 May;65(5):862-5. Pubmed: 9155258 Yokoya S, Tokuhiro E, Suwa S, Maesaka H: Measurement of the skin urocanic acid content in normal and histidinemic infants. Eur J Pediatr. 1983 Sep;140(4):330-2. Pubmed: 6628454
Synthesis Reference:	Yamamoto, Kozo; Sato, Tadashi; Tosa, Tetsuya; Chibata, Ichiro. Continuous production of urocanic acid by immobilized Achromobacter liquidum cells. Biotechnology and Bioengineering (1974), 16(12), 1601-10.
Material Safety Data Sheet (MSDS)	Download (PDF)
Links
External Links:	Resource Link CHEBI ID 30817 HMDB ID HMDB00301 Pubchem Compound ID 1178 Kegg ID C00785 ChemSpider ID 643824 Wikipedia Urocanic acid BioCyc ID Not Available Ligand Expo URO