Legend: enzyme field
| Version | 2.5 | ||||||||||||||||||||||||||||||||||||||||||
| Creation Date | 2005-11-16 15:48:42 | ||||||||||||||||||||||||||||||||||||||||||
| Update Date | 2009-05-05 20:57:50 | ||||||||||||||||||||||||||||||||||||||||||
| Accession Number | HMDB00301 | ||||||||||||||||||||||||||||||||||||||||||
| Secondary Accession Numbers | HMDB02280 | ||||||||||||||||||||||||||||||||||||||||||
| Common Name | Urocanic acid | ||||||||||||||||||||||||||||||||||||||||||
| Description | Urocanic 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 | ||||||||||||||||||||||||||||||||||||||||||
| Synonyms |
|
||||||||||||||||||||||||||||||||||||||||||
| Chemical IUPAC Name | 3-(3H-imidazol-4-yl)prop-2-enoic acid | ||||||||||||||||||||||||||||||||||||||||||
| Chemical Formula | C6H6N2O2 | ||||||||||||||||||||||||||||||||||||||||||
| Chemical Structure | |||||||||||||||||||||||||||||||||||||||||||
| Chemical Taxonomy |
|
||||||||||||||||||||||||||||||||||||||||||
| Average Molecular Weight | 138.124 | ||||||||||||||||||||||||||||||||||||||||||
| Monoisotopic Molecular Weight | 138.042923 | ||||||||||||||||||||||||||||||||||||||||||
| Isomeric SMILES | OC(=O)C=CC1=CNC=N1 | ||||||||||||||||||||||||||||||||||||||||||
| Canonical SMILES | OC(=O)C=CC1=CNC=N1 | ||||||||||||||||||||||||||||||||||||||||||
| KEGG Compound ID | C00785 ![]() |
||||||||||||||||||||||||||||||||||||||||||
| BioCyc ID | UROCANATE ![]() |
||||||||||||||||||||||||||||||||||||||||||
| BiGG ID | 35990 ![]() |
||||||||||||||||||||||||||||||||||||||||||
| Wikipedia Link | Urocanic acid ![]() |
||||||||||||||||||||||||||||||||||||||||||
| NuGOwiki Link | HMDB00301 ![]() |
||||||||||||||||||||||||||||||||||||||||||
| Metagene Link | HMDB00301 ![]() |
||||||||||||||||||||||||||||||||||||||||||
| METLIN ID | 298 ![]() |
||||||||||||||||||||||||||||||||||||||||||
| PubChem Compound | 1178 ![]() |
||||||||||||||||||||||||||||||||||||||||||
| PubChem Substance | 4501799 ![]() |
||||||||||||||||||||||||||||||||||||||||||
| ChEBI ID | 30817 ![]() |
||||||||||||||||||||||||||||||||||||||||||
| CAS Registry Number | 104-98-3 | ||||||||||||||||||||||||||||||||||||||||||
| InChI Identifier | InChI=1/C6H6N2O2/c9-6(10)2-1-5-3-7-4-8-5/h1-4H,(H,7,8)(H,9,10)/b2-1+ | ||||||||||||||||||||||||||||||||||||||||||
| 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. | ||||||||||||||||||||||||||||||||||||||||||
| Melting Point (Experimental) | 225 oC | ||||||||||||||||||||||||||||||||||||||||||
| Experimental Water Solubility | 1.5 mg/mL at 17 oC [YALKOWSKY,SH & DANNENFELSER,RM (1992)] Source: PhysProp | ||||||||||||||||||||||||||||||||||||||||||
| Predicted Water Solubility | 42.5 mg/mL [Predicted by ALOGPS] Calculated using ALOGPS | ||||||||||||||||||||||||||||||||||||||||||
| Physiological Charge | -1 | ||||||||||||||||||||||||||||||||||||||||||
| State | Solid | ||||||||||||||||||||||||||||||||||||||||||
| Experimental LogP/Hydrophobicity | Not Available Source: PhysProp | ||||||||||||||||||||||||||||||||||||||||||
| Predicted LogP/Hydrophobicity | 0.14 [MEYLAN,WM & HOWARD,PH (1995)]; 0.22 [Predicted by ALOGPS]; -0.1 [Predicted by PubChem via XLOGP] Calculated using ALOGPS | ||||||||||||||||||||||||||||||||||||||||||
| Material Safety Data Sheet (MSDS) | |||||||||||||||||||||||||||||||||||||||||||
| MOL File | Show ![]() |
||||||||||||||||||||||||||||||||||||||||||
| SDF File | Show ![]() |
||||||||||||||||||||||||||||||||||||||||||
| PDB File | Show ![]() |
||||||||||||||||||||||||||||||||||||||||||
| 2D Structure | |||||||||||||||||||||||||||||||||||||||||||
| 3D Structure | |||||||||||||||||||||||||||||||||||||||||||
| Experimental PDB ID | Not Available | ||||||||||||||||||||||||||||||||||||||||||
| Experimental 1H NMR Spectrum | Download Spectrum Download FID (Varian) Show Experimental Conditions ![]() |
||||||||||||||||||||||||||||||||||||||||||
| Experimental 13C NMR Spectrum | Not Available | ||||||||||||||||||||||||||||||||||||||||||
| Experimental 13C HSQC Spectrum | Download Spectrum Download FID (Bruker) Show Experimental Conditions ![]() |
||||||||||||||||||||||||||||||||||||||||||
| Predicted 1H NMR Spectrum |
Show Image Show Peaklist |
||||||||||||||||||||||||||||||||||||||||||
| Predicted 13C NMR Spectrum |
Show Image Show Peaklist |
||||||||||||||||||||||||||||||||||||||||||
| Mass Spectrum |
|
||||||||||||||||||||||||||||||||||||||||||
| Simplified TOCSY Spectrum | Not Available | ||||||||||||||||||||||||||||||||||||||||||
| BMRB Spectrum | Not Available | ||||||||||||||||||||||||||||||||||||||||||
| Cellular Location |
|
||||||||||||||||||||||||||||||||||||||||||
| Biofluid Location |
|
||||||||||||||||||||||||||||||||||||||||||
| Tissue Location |
|
||||||||||||||||||||||||||||||||||||||||||
| Concentrations (Normal) |
|
||||||||||||||||||||||||||||||||||||||||||
| Concentrations (Abnormal) |
|
||||||||||||||||||||||||||||||||||||||||||
| Associated Disorders |
|
||||||||||||||||||||||||||||||||||||||||||
| OMIM ID |
|
||||||||||||||||||||||||||||||||||||||||||
| Pathways |
|
||||||||||||||||||||||||||||||||||||||||||
| General References |
|
||||||||||||||||||||||||||||||||||||||||||
| Metabolic Enzymes |
| Enzyme 1 [top] | |||||||
|---|---|---|---|---|---|---|---|
| Enzyme 1 ID | 5956 | ||||||
| Enzyme 1 Name | Histidine ammonia-lyase | ||||||
| Enzyme 1 Synonyms |
|
||||||
| Enzyme 1 Gene Name | HAL | ||||||
| Enzyme 1 Protein Sequence |
>Histidine ammonia-lyase
MPRYTVHVRGEWLAVPCQDAQLTVGWLGREAVRRYIKNKPDNGGFTSVDDAHFLVRRCKG LGLLDNEDRLEVALENNEFVEVVIEGDAMSPDFIPSQPEGVYLYSKYREPEKYIELDGDR LTTEDLVNLGKGRYKIKLTPTAEKRVQKSREVIDSIIKEKTVVYGITTGFGKFARTVIPI NKLQELQVNLVRSHSSGVGKPLSPERCRMLLALRINVLAKGYSGISLETLKQVIEMFNAS CLPYVPEKGTVGASGDLAPLSHLALGLVGEGKMWSPKSGWADAKYVLEAHGLKPVILKPK EGLALINGTQMITSLGCEAVERASAIARQADIVAALTLEVLKGTTKAFDTDIHALRPHRG QIEVAFRFRSLLDSDHHPSEIAESHRFCDRVQDAYTLRCCPQVHGVVNDTIAFVKNIITT ELNSATDNPMVFANRGETVSGGNFHGEYPAKALDYLAIGIHELAAISERRIERLCNPSLS ELPAFLVAEGGLNSGFMIAHCTAAALVSENKALCHPSSVDSLSTSAATEDHVSMGGWAAR KALRVIEHVEQVLAIELLAACQGIEFLRPLKTTTPLEKVYDLVRSVVRPWIKDRFMAPDI EAAHRLLLEQKVWEVAAPYIEKYRMEHIPESRPLSPTAFSLQFLHKKSTKIPESEDL |
||||||
| Enzyme 1 Number of Residues | 657 | ||||||
| Enzyme 1 Molecular Weight | 72696.9 | ||||||
| Enzyme 1 Theoretical pI | 6.95 | ||||||
| Enzyme 1 GO Classification |
|
||||||
| Enzyme 1 General Function | Involved in histidine ammonia-lyase activity | ||||||
| Enzyme 1 Specific Function | L-histidine = urocanate + NH(3) | ||||||
| Enzyme 1 Pathways | |||||||
| Enzyme 1 Reactions |
|
||||||
| Enzyme 1 Pfam Domain Function |
|
||||||
| Enzyme 1 Signals |
|
||||||
| Enzyme 1 Transmembrane Regions |
|
||||||
| Enzyme 1 Essentiality | Not Available | ||||||
| Enzyme 1 GenBank ID Protein | Not Available | ||||||
| Enzyme 1 UniProtKB/Swiss-Prot ID | P42357 ![]() |
||||||
| Enzyme 1 UniProtKB/Swiss-Prot Entry Name | HUTH_HUMAN ![]() |
||||||
| Enzyme 1 PDB ID | Not Available | ||||||
| Enzyme 1 Cellular Location | Not Available | ||||||
| Enzyme 1 Gene Sequence |
>1974 bp
ATGCCCAGATACACGGTGCACGTACGTGGGGAATGGCTGGCAGTGCCCTGCCAGGACGCG CAGCTCACTGTGGGCTGGCTGGGCCGGGAGGCCGTGAGGCGCTATATCAAGAATAAGCCC GACAATGGTGGCTTCACCTCCGTGGATGACGCGCACTTCCTTGTGCGCCGGTGCAAGGGC CTGGGCCTGCTGGACAACGAGGACCGGCTCGAGGTGGCCCTAGAGAACAACGAGTTCGTG GAAGTGGTTATAGAGGGTGATGCCATGTCTCCTGACTTCATTCCATCTCAACCAGAAGGA GTTTATCTATACAGCAAGTACCGGGAGCCTGAAAAGTACATCGAGTTAGATGGAGACCGT CTGACCACGGAGGATCTGGTCAACTTGGGAAAGGGACGCTACAAAATAAAGCTCACCCCA ACAGCTGAGAAGAGGGTGCAGAAATCCAGGGAGGTCATAGATAGCATCATAAAAGAGAAA ACAGTTGTTTACGGTATTACTACAGGTTTTGGGAAATTTGCCAGAACTGTAATTCCTATC AATAAGCTACAGGAGCTTCAGGTCAACTTAGTACGCTCACATTCTTCAGGTGTTGGGAAA CCACTAAGTCCTGAGAGGTGTCGGATGCTCTTGGCTTTAAGGATCAATGTCTTAGCCAAA GGATACAGTGGCATTTCCCTGGAGACCCTCAAACAAGTCATAGAAATGTTTAATGCCTCC TGCCTGCCCTATGTCCCAGAGAAAGGAACCGTTGGTGCCAGTGGAGACCTTGCCCCACTC TCTCATCTTGCTCTTGGGCTAGTTGGAGAAGGGAAGATGTGGTCTCCGAAGAGTGGCTGG GCTGATGCTAAATACGTGCTAGAAGCCCATGGATTGAAACCAGTTATTTTAAAACCAAAA GAGGGCCTGGCACTCATCAATGGGACGCAGATGATCACATCCCTGGGCTGTGAAGCTGTA GAGCGAGCCAGTGCTATTGCACGGCAGGCTGACATTGTGGCAGCCCTGACCCTTGAGGTG CTGAAGGGCACCACCAAAGCCTTTGACACTGACATTCATGCTCTTCGACCTCACCGTGGG CAAATTGAAGTTGCTTTTCGGTTTCGGTCACTCTTGGACTCAGATCACCACCCATCAGAA ATAGCAGAGAGTCACAGGTTCTGTGATCGCGTCCAGGATGCATACACCTTGCGCTGCTGT CCACAGGTCCATGGTGTGGTGAATGATACAATAGCATTTGTGAAGAACATCATTACCACA GAACTGAACAGCGCAACAGATAATCCTATGGTCTTTGCCAATAGGGGAGAGACAGTTTCT GGAGGAAACTTCCATGGTGAATACCCAGCCAAAGCCCTAGACTACTTGGCCATTGGCATC CATGAACTTGCTGCAATCAGTGAGAGAAGAATCGAGCGGCTCTGCAATCCCTCCCTCAGT GAGCTGCCTGCCTTCCTGGTGGCTGAAGGTGGTCTGAACTCTGGGTTCATGATAGCTCAC TGCACGGCAGCAGCCCTTGTTTCTGAGAACAAGGCTCTGTGCCATCCCTCGTCTGTTGAC TCCCTCTCCACCAGCGCAGCCACGGAGGACCACGTCTCCATGGGAGGATGGGCAGCAAGG AAAGCCCTCAGGGTCATCGAGCATGTGGAGCAAGTGCTGGCCATCGAGCTCCTTGCAGCC TGCCAGGGCATAGAGTTTCTACGTCCCCTGAAAACAACCACTCCGCTGGAGAAGGTCTAT GACCTGGTGCGCTCTGTTGTAAGGCCCTGGATAAAAGATCGCTTCATGGCCCCGGACATC GAGGCAGCCCACAGGCTGCTCCTGGAGCAGAAGGTTTGGGAAGTAGCTGCTCCATACATT GAAAAATACAGAATGGAGCATATTCCAGAATCAAGACCTCTTTCTCCAACAGCCTTTTCA CTGCAATTTCTGCACAAGAAATCCACCAAAATCCCGGAGTCTGAGGACCTTTAA |
||||||
| Enzyme 1 GenBank Gene ID | D16626 ![]() |
||||||
| Enzyme 1 GeneCard ID | HAL ![]() |
||||||
| Enzyme 1 GenAtlas ID | HAL ![]() |
||||||
| Enzyme 1 HGNC ID | HGNC:4806 ![]() |
||||||
| Enzyme 1 Chromosome Location | 1 | ||||||
| Enzyme 1 Locus | 12q22-q24.1 | ||||||
| Enzyme 1 SNPs | SNPJam Report ![]() |
||||||
| Enzyme 1 General References |
|
||||||
| Enzyme 1 Metabolite References | Not Available | ||||||
| Enzyme 2 [top] | |||||||
| Enzyme 2 ID | 6202 | ||||||
| Enzyme 2 Name | Urocanate hydratase | ||||||
| Enzyme 2 Synonyms |
|
||||||
| Enzyme 2 Gene Name | UROC1 | ||||||
| Enzyme 2 Protein Sequence |
>Urocanate hydratase
MSSLQALCSGLPLRPLPENRGRQAGVPHAPVRTPSLSPVEKQLALRNALRYFPPDVQELL APEFAQELQLYGHIYMYRFCPDIEMRAYPIEQYPCQTKVAAAIMHMIMNNLDPAVAQFPQ ELVTYGGNGQVFSNWAQFWLTMFYLSKMTEEQTLVMYSGHPLGLFPSSRSAPRLVITNGM VIPNYSSRTEYEKLFALGVTMYGQMTAGSYCYIGPQGIVHGTVLTVLNAARRYLGIEDLA GKVFVTSGLGGMSGAQAKAAVIVGCIGVIAEVDKAALEKRHRQGWLMEVTDSLDRCIQRL REARKKKEVLSLGYHGNVVALWERLVHELDTTGECLVDLGSDQTSCHNPFNGGYYPVQLS FTEAQSLMASNPAVFKDLVQESLRRQVSAINRLAEEKFFFWDYGNAFLLEAQRAGADVEK KGAGRTEFRYPSYVQHIMGDIFSQGFGPFRWVCTSGDPQDLAVTDELATSVLEEAIADGV KVSVKLQYMDNIRWIREAARHRLVVGSQARILYSDQKGRVAIAVAINQAIACRRIKAPVV LSRDHHDVSGTDSPFRETSNIYDGSAFCADMAVQNFVGDACRGATWVALHNGGGVGWGEV INGGFGLVLDGTPEAEGRARLMLSWDVSNGVARRCWSGNQKAYEIICQTMQENSTLVVTL PHKVEDERVLQQALQL |
||||||
| Enzyme 2 Number of Residues | 676 | ||||||
| Enzyme 2 Molecular Weight | 74830.0 | ||||||
| Enzyme 2 Theoretical pI | 6.78 | ||||||
| Enzyme 2 GO Classification |
|
||||||
| Enzyme 2 General Function | Involved in urocanate hydratase activity | ||||||
| Enzyme 2 Specific Function | 3-(5-oxo-4,5-dihydro-3H-imidazol-4- yl)propanoate = urocanate + H(2)O | ||||||
| Enzyme 2 Pathways |
|
||||||
| Enzyme 2 Reactions |
|
||||||
| Enzyme 2 Pfam Domain Function |
|
||||||
| Enzyme 2 Signals |
|
||||||
| Enzyme 2 Transmembrane Regions |
|
||||||
| Enzyme 2 Essentiality | Not Available | ||||||
| Enzyme 2 GenBank ID Protein | Not Available | ||||||
| Enzyme 2 UniProtKB/Swiss-Prot ID | Q96N76 ![]() |
||||||
| Enzyme 2 UniProtKB/Swiss-Prot Entry Name | HUTU_HUMAN ![]() |
||||||
| Enzyme 2 PDB ID | Not Available | ||||||
| Enzyme 2 Cellular Location | Not Available | ||||||
| Enzyme 2 Gene Sequence |
>2031 bp
ATGTCTAGCCTCCAGGCGCTGTGCTCTGGCCTGCCCCTGCGGCCCCTCCCAGAGAACCGG GGACGCCAGGCTGGGGTGCCCCATGCCCCTGTCAGGACCCCCAGCCTCAGCCCTGTGGAG AAACAGCTGGCGCTGAGGAACGCCCTGCGCTACTTCCCCCCGGATGTCCAGGAGCTGCTG GCCCCAGAGTTTGCCCAGGAGCTGCAACTGTACGGACACATCTACATGTACCGGTTTTGC CCCGACATTGAAATGAGGGCCTACCCGATTGAGCAGTACCCCTGCCAGACGAAAGTGGCT GCCGCCATCATGCACATGATTATGAACAACCTGGATCCTGCCGTGGCCCAGTTTCCCCAG GAGCTGGTGACCTATGGAGGAAATGGGCAGGTGTTCAGCAACTGGGCTCAGTTCTGGCTG ACCATGTTCTACTTGTCGAAGATGACAGAGGAGCAGACTTTGGTCATGTACAGTGGGCAC CCACTTGGCCTCTTTCCCAGCAGCCGCAGTGCCCCACGGCTCGTCATCACCAATGGGATG GTCATTCCCAACTACTCCTCCCGGACGGAGTATGAGAAGCTCTTTGCCTTGGGGGTTACA ATGTACGGCCAGATGACAGCAGGTAGCTACTGCTACATCGGTCCCCAGGGAATCGTTCAT GGCACTGTGCTCACCGTGTTGAATGCTGCACGTCGGTACCTGGGCATCGAGGACTTGGCT GGGAAGGTCTTTGTCACCTCTGGGCTCGGCGGAATGAGTGGGGCTCAGGCCAAGGCCGCA GTCATCGTGGGGTGCATCGGTGTGATAGCAGAGGTGGATAAAGCAGCCCTTGAGAAACGC CACAGGCAGGGCTGGCTGATGGAAGTGACTGACAGCTTGGACCGCTGCATCCAGAGGCTC AGGGAAGCAAGGAAAAAAAAGGAGGTGCTCAGCCTTGGTTACCATGGCAACGTGGTGGCT CTTTGGGAGCGCCTGGTCCACGAATTGGACACGACGGGGGAGTGCTTGGTGGACCTGGGG TCAGATCAGACATCCTGCCACAACCCGTTCAATGGCGGCTACTACCCTGTGCAGCTCAGC TTCACGGAGGCCCAGAGCCTCATGGCCTCCAACCCTGCTGTGTTCAAGGACCTGGTCCAG GAAAGCCTGAGGAGGCAAGTCTCAGCCATCAACAGGTTGGCCGAGGAGAAGTTCTTCTTC TGGGACTACGGCAATGCCTTCCTCTTGGAGGCCCAGAGAGCAGGAGCGGATGTGGAGAAG AAAGGTGCTGGCAGGACAGAGTTCCGCTACCCTTCCTATGTGCAGCACATCATGGGGGAC ATATTCTCCCAGGGATTTGGGCCTTTCCGCTGGGTGTGCACATCGGGGGACCCCCAGGAC CTGGCGGTCACAGACGAACTGGCCACATCTGTGCTGGAGGAAGCCATTGCTGATGGAGTG AAGGTGTCTGTGAAGCTGCAGTACATGGACAACATCCGCTGGATCCGGGAGGCCGCCAGG CACCGGCTGGTGGTGGGCTCCCAGGCAAGGATCTTGTACTCAGACCAGAAGGGCCGCGTG GCCATCGCTGTGGCCATTAACCAGGCCATCGCCTGCAGGAGGATCAAGGCGCCGGTGGTC CTGAGCCGAGATCACCATGACGTGAGCGGCACCGACAGCCCCTTTAGGGAGACCTCCAAC ATTTACGACGGCTCTGCCTTCTGTGCAGACATGGCTGTGCAGAACTTCGTGGGAGATGCC TGTCGCGGAGCCACCTGGGTCGCCCTTCACAACGGAGGGGGCGTGGGCTGGGGTGAGGTG ATCAACGGGGGATTCGGCCTCGTGCTGGACGGTACCCCGGAGGCCGAGGGGAGAGCCAGG CTGATGCTCAGCTGGGATGTCTCCAATGGTGTGGCCCGGCGCTGCTGGTCAGGGAACCAG AAGGCCTATGAGATCATCTGCCAGACCATGCAGGAGAACAGCACCTTGGTGGTGACACTG CCTCACAAGGTGGAGGACGAGCGGGTGCTCCAGCAGGCCCTGCAGCTCTGA |
||||||
| Enzyme 2 GenBank Gene ID | AK055862 ![]() |
||||||
| Enzyme 2 GeneCard ID | UROC1 ![]() |
||||||
| Enzyme 2 GenAtlas ID | UROC1 ![]() |
||||||
| Enzyme 2 HGNC ID | HGNC:26444 ![]() |
||||||
| Enzyme 2 Chromosome Location | 3 | ||||||
| Enzyme 2 Locus | 3q21.3 | ||||||
| Enzyme 2 SNPs | SNPJam Report ![]() |
||||||
| Enzyme 2 General References |
|
||||||
| Enzyme 2 Metabolite References | Not Available | ||||||