Np mrd loader

You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on NP-MRD.
Record Information
Version1.0
Created at2005-11-16 15:48:42 UTC
Updated at2021-08-10 02:54:38 UTC
NP-MRD IDNP0000209
Secondary Accession NumbersNone
Natural Product Identification
Common NameUrocanic acid
DescriptionUrocanic acid is a breakdown (deamination) product of histidine. In the liver, urocanic acid is an intermediate in the conversion of histidine to glutamic acid, whereas in the epidermis, it accumulates and may be both a UV protectant and an immunoregulator. Urocanic acid (UA) exists as a trans isomer (t-UA, approximately 30 mg/cm2) in the uppermost layer of the skin (stratum corneum). T-UA is formed as the cells of the second layer of skin become metabolically inactive. During this process, proteins and membranes degrade, histidine is released, and histidase (histidine ammonia lyase) catalyzes the deamination of histidine to form t-UA. T-UA accumulates in the epidermis until removal by either the monthly skin renewal cycle or sweat. Upon absorption of UV light, the naturally occurring t-UA isomerizes to its cis form, c-UA. Because DNA lesions (e.G., Pyrimidine dimers) in the lower epidermis can result from UV-B absorption, initial research proposed that t-UA acted as a natural sunscreen absorbing UV-B in the stratum corneum before the damaging rays could penetrate into lower epidermal zones. Researchers have found that c-UA also suppresses contact hypersensitivity and delayed hypersensitivity, reduces the Langerhans cell count in the epidermis, prolongs skin-graft survival time, and affects natural killer cell activity.
Structure
Data?1628564078
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 Mass138.1240 Da
Monoisotopic Mass138.04293 Da
IUPAC Name(2E)-3-(1H-imidazol-4-yl)prop-2-enoic acid
Traditional Nametrans-urocanic acid
CAS Registry Number104-98-3
SMILES
[H]OC(=O)C(\[H])=C(/[H])C1=C([H])N=C([H])N1[H]
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 KeyLOIYMIARKYCTBW-OWOJBTEDSA-N
Spectra
Spectrum TypeDescriptionDepositor IDDeposition DateView
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 25 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Wishart Lab2021-06-20View Spectrum
Species
Species of Origin
  • Animalia
  • Species Where Detected
    Species NameSourceReference
    Saccharomyces cerevisiaeKNApSAcK Database
    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
    Physical Properties
    StateSolid
    Experimental Properties
    PropertyValueReference
    Melting Point225 °CNot Available
    Boiling PointNot AvailableNot Available
    Water Solubility1.5 mg/mL at 17 °CNot Available
    LogPNot AvailableNot Available
    Predicted Properties
    PropertyValueSource
    Water Solubility42.5 g/LALOGPS
    logP0ALOGPS
    logP-1ChemAxon
    logS-0.82ALOGPS
    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
    BioavailabilityYesChemAxon
    Rule of FiveYesChemAxon
    Ghose FilterNoChemAxon
    Veber's RuleNoChemAxon
    MDDR-like RuleNoChemAxon
    HMDB IDHMDB0000301
    DrugBank IDDB01971
    Phenol Explorer Compound IDNot Available
    FoodDB IDFDB007506
    KNApSAcK IDC00051902
    Chemspider ID643824
    KEGG Compound IDC00785
    BioCyc IDNot Available
    BiGG ID35990
    Wikipedia LinkUrocanic_acid
    METLIN ID298
    PubChem Compound736715
    PDB IDNot Available
    ChEBI ID30817
    Good Scents IDNot Available
    References
    General References
    1. 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 ]
    2. 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 ]
    3. 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 ]
    4. 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 ]
    5. 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 ]
    6. 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 ]
    7. 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 ]
    8. Morrison H: Photochemistry and photobiology of urocanic acid. Photodermatol. 1985 Jun;2(3):158-65. [PubMed:3895185 ]