2.02012-08-03 14:57:54 -06002015-09-13 15:15:32 -0600ECMDB21396M2MDB001791Urocanic acidUrocanic acid is a breakdown (deamination) product of histidine from histidase or histidine ammonia lyase (hutS).3-(1H-Imidazol-4-yl)-2-propenoate3-(1H-Imidazol-4-yl)-2-propenoic acid3-(1H-Imidazol-4-yl)acrylate3-(1H-Imidazol-4-yl)acrylic acid3-(4-Imidazolyl)acrylate3-(4-Imidazolyl)acrylic acid5-Imidazoleacrylate5-Imidazoleacrylic acidImidazole-4-acrylateImidazole-4-acrylic acidImidazoleacrylateImidazoleacrylic acidUrocanateC6H6N2O2138.124138.042927446(2E)-3-(1H-imidazol-4-yl)prop-2-enoic acidtrans-urocanic acid104-98-3OC(=O)\C=C\C1=CNC=N1InChI=1S/C6H6N2O2/c9-6(10)2-1-5-3-7-4-8-5/h1-4H,(H,7,8)(H,9,10)/b2-1+LOIYMIARKYCTBW-OWOJBTEDSA-NSolidCytoplasmlogp0.22logs-0.51solubility4.25e+01 g/lmelting_point225 oClogp-1pka_strongest_acidic3.85pka_strongest_basic6.13iupac(2E)-3-(1H-imidazol-4-yl)prop-2-enoic acidaverage_mass138.124mono_mass138.042927446smilesOC(=O)\C=C\C1=CNC=N1formulaC6H6N2O2inchiInChI=1S/C6H6N2O2/c9-6(10)2-1-5-3-7-4-8-5/h1-4H,(H,7,8)(H,9,10)/b2-1+inchikeyLOIYMIARKYCTBW-OWOJBTEDSA-Npolar_surface_area65.98refractivity35.57polarizability13.1rotatable_bond_count2acceptor_count3donor_count2physiological_charge-1formal_charge0Specdb::CMs531Specdb::CMs532Specdb::CMs533Specdb::CMs1728Specdb::CMs8610Specdb::CMs29558Specdb::CMs30237Specdb::CMs30711Specdb::CMs30921Specdb::CMs31121Specdb::CMs32123Specdb::CMs32124Specdb::CMs37411Specdb::CMs151786Specdb::CMs1057495Specdb::CMs1057497Specdb::CMs1057498Specdb::NmrOneD1322Specdb::NmrOneD6522Specdb::NmrOneD6523Specdb::NmrOneD6524Specdb::NmrOneD6525Specdb::NmrOneD6526Specdb::NmrOneD6527Specdb::NmrOneD6528Specdb::NmrOneD6529Specdb::NmrOneD6530Specdb::NmrOneD6531Specdb::NmrOneD6532Specdb::NmrOneD6533Specdb::NmrOneD6534Specdb::NmrOneD6535Specdb::NmrOneD6536Specdb::NmrOneD6537Specdb::NmrOneD6538Specdb::NmrOneD6539Specdb::NmrOneD6540Specdb::NmrOneD6541Specdb::MsMs513Specdb::MsMs514Specdb::MsMs515Specdb::MsMs3975Specdb::MsMs3976Specdb::MsMs3977Specdb::MsMs3978Specdb::MsMs3979Specdb::MsMs3980Specdb::MsMs3984Specdb::MsMs3985Specdb::MsMs260679Specdb::MsMs260680Specdb::MsMs260681Specdb::MsMs280614Specdb::MsMs280615Specdb::MsMs280616Specdb::MsMs438573Specdb::MsMs438574Specdb::MsMs438575Specdb::MsMs438576Specdb::MsMs438577Specdb::MsMs439163Specdb::MsMs448111Specdb::MsMs2226226Specdb::NmrTwoD1264HMDB003011178643824C0078530817UROUrocanic acidIshii, 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 316:593-597.17379776Sastry 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):1.16409897Hug 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):117-23.9757593Snellman 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):862-5.9155258Schwarz 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):188-92.6501514Hermann 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):41-7.11129077Kinuta 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):3212-8.14518047Yokoya 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):330-2.6628454Morrison H: Photochemistry and photobiology of urocanic acid. Photodermatol. 1985 Jun;2(3):158-65.3895185Yamamoto, 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.http://hmdb.ca/system/metabolites/msds/000/000/220/original/HMDB00301.pdf?135846196148 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 GlucoBioreactor, pH controlled, O2 and CO2 controlled, dilution rate: 0.2/h68.9uM0.037 oCBW25113Stationary Phase, glucose limited2756000Ishii, 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 316:593-597.17379776