2.0 2012-08-03 14:57:54 -0600 2015-09-13 15:15:32 -0600 ECMDB21396 M2MDB001791 Urocanic acid Urocanic acid is a breakdown (deamination) product of histidine from histidase or histidine ammonia lyase (hutS). 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 C6H6N2O2 138.124 138.042927446 (2E)-3-(1H-imidazol-4-yl)prop-2-enoic acid trans-urocanic acid 104-98-3 OC(=O)\C=C\C1=CNC=N1 InChI=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-N Solid Cytoplasm logp 0.22 ALOGPS logs -0.51 ALOGPS solubility 4.25e+01 g/l ALOGPS melting_point 225 oC logp -1 ChemAxon pka_strongest_acidic 3.85 ChemAxon pka_strongest_basic 6.13 ChemAxon iupac (2E)-3-(1H-imidazol-4-yl)prop-2-enoic acid ChemAxon average_mass 138.124 ChemAxon mono_mass 138.042927446 ChemAxon smiles OC(=O)\C=C\C1=CNC=N1 ChemAxon formula C6H6N2O2 ChemAxon 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+ ChemAxon inchikey LOIYMIARKYCTBW-OWOJBTEDSA-N ChemAxon polar_surface_area 65.98 ChemAxon refractivity 35.57 ChemAxon polarizability 13.1 ChemAxon rotatable_bond_count 2 ChemAxon acceptor_count 3 ChemAxon donor_count 2 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon Specdb::CMs 531 Specdb::CMs 532 Specdb::CMs 533 Specdb::CMs 1728 Specdb::CMs 8610 Specdb::CMs 29558 Specdb::CMs 30237 Specdb::CMs 30711 Specdb::CMs 30921 Specdb::CMs 31121 Specdb::CMs 32123 Specdb::CMs 32124 Specdb::CMs 37411 Specdb::CMs 151786 Specdb::CMs 1057495 Specdb::CMs 1057497 Specdb::CMs 1057498 Specdb::NmrOneD 1322 Specdb::NmrOneD 6522 Specdb::NmrOneD 6523 Specdb::NmrOneD 6524 Specdb::NmrOneD 6525 Specdb::NmrOneD 6526 Specdb::NmrOneD 6527 Specdb::NmrOneD 6528 Specdb::NmrOneD 6529 Specdb::NmrOneD 6530 Specdb::NmrOneD 6531 Specdb::NmrOneD 6532 Specdb::NmrOneD 6533 Specdb::NmrOneD 6534 Specdb::NmrOneD 6535 Specdb::NmrOneD 6536 Specdb::NmrOneD 6537 Specdb::NmrOneD 6538 Specdb::NmrOneD 6539 Specdb::NmrOneD 6540 Specdb::NmrOneD 6541 Specdb::MsMs 513 Specdb::MsMs 514 Specdb::MsMs 515 Specdb::MsMs 3975 Specdb::MsMs 3976 Specdb::MsMs 3977 Specdb::MsMs 3978 Specdb::MsMs 3979 Specdb::MsMs 3980 Specdb::MsMs 3984 Specdb::MsMs 3985 Specdb::MsMs 260679 Specdb::MsMs 260680 Specdb::MsMs 260681 Specdb::MsMs 280614 Specdb::MsMs 280615 Specdb::MsMs 280616 Specdb::MsMs 438573 Specdb::MsMs 438574 Specdb::MsMs 438575 Specdb::MsMs 438576 Specdb::MsMs 438577 Specdb::MsMs 439163 Specdb::MsMs 448111 Specdb::MsMs 2226226 Specdb::NmrTwoD 1264 HMDB00301 1178 643824 C00785 30817 URO Urocanic acid 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. 17379776 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. 16409897 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. 9757593 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. 9155258 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. 6501514 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. 11129077 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. 14518047 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. 6628454 Morrison H: Photochemistry and photobiology of urocanic acid. Photodermatol. 1985 Jun;2(3):158-65. 3895185 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. http://hmdb.ca/system/metabolites/msds/000/000/220/original/HMDB00301.pdf?1358461961 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 Bioreactor, pH controlled, O2 and CO2 controlled, dilution rate: 0.2/h 68.9 uM 0.0 37 oC BW25113 Stationary Phase, glucose limited 275600 0 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. 17379776