Urocanic acid (CHEM017647)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-22 04:30:42 UTC
Update Date2016-11-09 01:15:38 UTC
Accession NumberCHEM017647
Identification
Common NameUrocanic acid
ClassSmall Molecule
Description
Contaminant Sources
  • FooDB Chemicals
  • HMDB Contaminants - Feces
  • HMDB Contaminants - Urine
  • ToxCast & Tox21 Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
(2E)-3-(1H-Imidazol-4-yl)acrylic acidChEBI
(e)-3-(1H-Imidazol-4-yl)-2-propenoic acidChEBI
(2E)-3-(1H-Imidazol-4-yl)acrylateGenerator
(e)-3-(1H-Imidazol-4-yl)-2-propenoateGenerator
UrocanateGenerator
3-(1H-Imidazol-4-yl)-2-propenoateHMDB
3-(1H-Imidazol-4-yl)-2-propenoic acidHMDB
3-(1H-Imidazol-4-yl)acrylateHMDB
3-(1H-Imidazol-4-yl)acrylic acidHMDB
3-(4-Imidazolyl)acrylateHMDB
3-(4-Imidazolyl)acrylic acidHMDB
5-ImidazoleacrylateHMDB
5-Imidazoleacrylic acidHMDB
Imidazole-4-acrylateHMDB
Imidazole-4-acrylic acidHMDB
Imidazoleacrylic acidHMDB
Acid, glyoxalinylacrylicHMDB
Acid, urocanicHMDB
Glyoxalinylacrylic acidHMDB
(2E)-3-(1H-Imidazol-5-yl)-2-propenoic acidHMDB
(e)-3-(4-Imidazolyl)acrylic acidHMDB
(e)-3-(Imidazol-4-yl)-2-propenoic acidHMDB
(e)-Urocanic acidHMDB
trans-Urocanic acidHMDB
Chemical FormulaC6H6N2O2
Average Molecular Mass138.124 g/mol
Monoisotopic Mass138.043 g/mol
CAS Registry Number104-98-3
IUPAC Name(2E)-3-(1H-imidazol-4-yl)prop-2-enoic acid
Traditional Nametrans-urocanic acid
SMILESOC(=O)\C=C\C1=CNC=N1
InChI IdentifierInChI=1S/C6H6N2O2/c9-6(10)2-1-5-3-7-4-8-5/h1-4H,(H,7,8)(H,9,10)/b2-1+
InChI KeyLOIYMIARKYCTBW-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.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassAzoles
Sub ClassImidazoles
Direct ParentImidazolyl 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 FrameworkAromatic heteromonocyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility42.5 g/LALOGPS
logP0.22ALOGPS
logP-1ChemAxon
logS-0.51ALOGPS
pKa (Strongest Acidic)3.85ChemAxon
pKa (Strongest Basic)6.13ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area65.98 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity35.57 m³·mol⁻¹ChemAxon
Polarizability13.1 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)splash10-014m-1930000000-25b091170cc3ea73bcf7Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-00l5-1930000000-5c3c875338a517d52729Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)splash10-00di-9410000000-b58e1b2cdd5c12a6ba24Spectrum
GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-0159-3950000000-433e50271e182f8408fdSpectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-000f-9200000000-cb7f9025a0f6adf740c1Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-014m-1930000000-25b091170cc3ea73bcf7Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00l5-1930000000-5c3c875338a517d52729Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00di-9410000000-b58e1b2cdd5c12a6ba24Spectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0159-3950000000-433e50271e182f8408fdSpectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-014m-1930000000-3815ef1f1f386e091dc3Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00dm-2900000000-aaefc749352097679e8fSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-000f-9500000000-7f0462e0ef244d2118a8Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00di-6910000000-b1e081746388d0700ce0Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-00di-3900000000-8c1c060d06c1ce3fb5f7Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-00kf-9000000000-ae9de21d4642045fb96cSpectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-014l-9000000000-8e6978d7f104386d2e82Spectrum
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-80) , Positivesplash10-000f-9200000000-cb7f9025a0f6adf740c1Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-000i-1900000000-c628b05706544cb1ebdcSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-0006-9300000000-bc4c631410a5cbb3c2f5Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-0006-9000000000-ccac569cbc78a632da48Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-0006-9000000000-a22c861e4f2551a3f582Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-00kf-9000000000-37421b473ba575d307fdSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-00du-5900000000-29dc15087c785a19c0eeSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-0006-9200000000-1cc9b0a66b83ca383ebdSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-000i-1900000000-c628b05706544cb1ebdcSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0006-9300000000-bc4c631410a5cbb3c2f5Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0006-9000000000-ccac569cbc78a632da48Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0006-9000000000-a22c861e4f2551a3f582Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-00kf-9000000000-37421b473ba575d307fdSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0006-9200000000-1cc9b0a66b83ca383ebdSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-00du-5900000000-29dc15087c785a19c0eeSpectrum
LC-MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-0006-9000000000-853f5ec98c651c09e3dbSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0079-1900000000-dac4165382f541a26a03Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0076-8900000000-6da8eb6b76055856b714Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014i-9000000000-ab76de8a8f1873f63de6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-1900000000-173e1f32b118424e132dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000l-5900000000-b1ebc285fc95a34dc7b1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00kf-9200000000-66f717c0018108bc7769Spectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDDB01971
HMDB IDHMDB0000301
FooDB IDFDB007506
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG ID35990
BioCyc IDNot Available
METLIN ID298
PDB IDNot Available
Wikipedia LinkUrocanic_acid
Chemspider ID643824
ChEBI ID30817
PubChem Compound ID736715
Kegg Compound IDC00785
YMDB IDNot Available
ECMDB IDECMDB21396
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. 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.
2. 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.
3. 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.
4. 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.
5. 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.
6. 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.
7. 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.
8. 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.
9. 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.
10. Morrison H: Photochemistry and photobiology of urocanic acid. Photodermatol. 1985 Jun;2(3):158-65.
11. Oesterwitz H, Gruner S, Diezel W, Schneider W: Inhibition of rat heart allograft rejection by a PUVA treatment of the graft recipient. Role of cisurocanic acid. Transpl Int. 1990 May;3(1):8-11.
12. 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.
13. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.
14. https://www.ncbi.nlm.nih.gov/pubmed/?term=9724745