Legend: enzyme field
| Version | 2.5 | ||||||||||||||||||
| Creation Date | 2006-08-14 01:36:18 | ||||||||||||||||||
| Update Date | 2009-05-05 21:00:08 | ||||||||||||||||||
| Accession Number | HMDB04692 | ||||||||||||||||||
| Secondary Accession Numbers | Not Available | ||||||||||||||||||
| Common Name | 12(R)-HPETE | ||||||||||||||||||
| Description | 12(R)-HPETE is a hydroperoxyeicosatetraenoic acid eicosanoid derived from arachidonic acid. The epidermal lipoxygenases 12R-LOX and eLOX3 act in sequence to convert arachidonic acid via 12(R)-HPETE to 12(R)-HETE and the corresponding epoxyalcohol, 8(R)-hydroxy-11(R),12(R)-epoxyeicosatrienoic acid. The epidermal lipoxygenases 12R-LOX and eLOX3 are the gene products of ALOX12B and ALOXE3. Mutations in ALOXE3 or ALOX12B have been found in families with autosomal-recessive congenital ichthyosis (ARCI). ARCI is a clinically and genetically heterogeneous group of severe hereditary keratinization disorders characterized by intense scaling of the whole integument, and differences in color and shape, often associated with erythema. Mutations in ALOXE3 and ALOX12B on chromosome 17p13, which code for two different epidermal lipoxygenases, were found in patients with ichthyosiform erythroderma. Genetic studies indicated that 12R-lipoxygenase (12R-LOX) or epidermal lipoxygenase-3 (eLOX3) was mutated in six families affected by non-bullous congenital ichthyosiform erythroderma (NCIE), one of the main clinical forms of ichthyosis. (PMID: 16116617, 15629692) | ||||||||||||||||||
| Synonyms |
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| Chemical IUPAC Name | (5Z,8Z,10E,12R,14Z)-12-hydroperoxyicosa-5,8,10,14-tetraenoic acid | ||||||||||||||||||
| Chemical Formula | C20H32O4 | ||||||||||||||||||
| Chemical Structure | |||||||||||||||||||
| Chemical Taxonomy |
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| Average Molecular Weight | 336.466 | ||||||||||||||||||
| Monoisotopic Molecular Weight | 336.230072 | ||||||||||||||||||
| Isomeric SMILES | CCCCCC=C/C[C@@H](OO)C=CC=C/CC=C/CCCC(O)=O | ||||||||||||||||||
| Canonical SMILES | CCCCCC=CCC(OO)C=CC=CCC=CCCCC(O)=O | ||||||||||||||||||
| KEGG Compound ID | C14812 ![]() |
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| BioCyc ID | Not Available | ||||||||||||||||||
| BiGG ID | Not Available | ||||||||||||||||||
| Wikipedia Link | Not Available | ||||||||||||||||||
| NuGOwiki Link | HMDB04692 ![]() |
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| Metagene Link | HMDB04692 ![]() |
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| METLIN ID | Not Available | ||||||||||||||||||
| PubChem Compound | 9548885 ![]() |
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| PubChem Substance | 14718420 ![]() |
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| ChEBI ID | 34145 ![]() |
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| CAS Registry Number | 126873-49-2 | ||||||||||||||||||
| InChI Identifier | InChI=1/C20H32O4/c1-2-3-4-5-10-13-16-19(24-23)17-14-11-8-6-7-9-12-15-18-20(21)22/h7-11,13-14,17,19,23H,2-6,12,15-16,18H2,1H3,(H,21,22)/b9-7-,11-8-,13-10-,17-14+/t19-/m1/s1 | ||||||||||||||||||
| Synthesis Reference | Porter, Ned A.; Dussault, Patrick; Breyer, Robert A.; Kaplan, Jere; Morelli, Joseph. The resolution of racemic hydroperoxides: a chromatography-based separation of perketals derived from arachidonic, linoleic, and oleic acid hydroperoxides. Chemical Research in Toxicology (1990), 3(3), 236-43. | ||||||||||||||||||
| Melting Point (Experimental) | Not Available | ||||||||||||||||||
| Experimental Water Solubility | Not Available Source: PhysProp | ||||||||||||||||||
| Predicted Water Solubility | 1.69e-03 mg/mL [Predicted by ALOGPS] Calculated using ALOGPS | ||||||||||||||||||
| Physiological Charge | -1 | ||||||||||||||||||
| State | Solid | ||||||||||||||||||
| Experimental LogP/Hydrophobicity | Not Available Source: PhysProp | ||||||||||||||||||
| Predicted LogP/Hydrophobicity | 5.90 [Predicted by ALOGPS]; 5 [Predicted by PubChem via XLOGP] Calculated using ALOGPS | ||||||||||||||||||
| Material Safety Data Sheet (MSDS) | Not Available | ||||||||||||||||||
| MOL File | Show ![]() |
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| SDF File | Show ![]() |
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| PDB File | Show ![]() |
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| 2D Structure | |||||||||||||||||||
| 3D Structure | |||||||||||||||||||
| Experimental PDB ID | Not Available | ||||||||||||||||||
| Experimental 1H NMR Spectrum | Not Available | ||||||||||||||||||
| Experimental 13C NMR Spectrum | Not Available | ||||||||||||||||||
| Experimental 13C HSQC Spectrum | Not Available | ||||||||||||||||||
| Predicted 1H NMR Spectrum |
Show Image Show Peaklist |
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| Predicted 13C NMR Spectrum |
Show Image Show Peaklist |
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| Mass Spectrum | Not Available | ||||||||||||||||||
| Simplified TOCSY Spectrum | Not Available | ||||||||||||||||||
| BMRB Spectrum | Not Available | ||||||||||||||||||
| Cellular Location | Not Available | ||||||||||||||||||
| Biofluid Location | Not Available | ||||||||||||||||||
| Tissue Location | Not Available | ||||||||||||||||||
| Concentrations (Normal) | Not Available | ||||||||||||||||||
| Concentrations (Abnormal) | Not Available | ||||||||||||||||||
| Associated Disorders | Not Available | ||||||||||||||||||
| OMIM ID | Not Available | ||||||||||||||||||
| Pathways |
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| General References | Not Available | ||||||||||||||||||
| Metabolic Enzymes |
| Enzyme 1 [top] | |||||||
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| Enzyme 1 ID | 8675 | ||||||
| Enzyme 1 Name | Arachidonate 12-lipoxygenase, 12R-type | ||||||
| Enzyme 1 Synonyms |
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| Enzyme 1 Gene Name | ALOX12B | ||||||
| Enzyme 1 Protein Sequence |
>Arachidonate 12-lipoxygenase, 12R-type
MATYKVRVATGTDLLSGTRDSISLTIVGTQGESHKQLLNHFGRDFATGAVGQYTVQCPQD LGELIIIRLHKERYAFFPKDPWYCNYVQICAPNGRIYHFPAYQWMDGYETLALREATGKT TADDSLPVLLEHRKEEIRAKQDFYHWRVFLPGLPSYVHIPSYRPPVRRHRNPNRPEWNGY IPGFPILINFKATKFLNLNLRYSFLKTASFFVRLGPMALAFKVRGLLDCKHSWKRLKDIR KIFPGKKSVVSEYVAEHWAEDTFFGYQYLNGVNPGLIRRCTRIPDKFPVTDDMVAPFLGE GTCLQAELEKGNIYLADYRIMEGIPTVELSGRKQHHCAPLCLLHFGPEGKMMPIAIQLSQ TPGPDCPIFLPSDSEWDWLLAKTWVRYAEFYSHEAIAHLLETHLIAEAFCLALLRNLPMC HPLYKLLIPHTRYTVQINSIGRAVLLNEGGLSAKGMSLGVEGFAGVMVRALSELTYDSLY LPNDFVERGVQDLPGYYYRDDSLAVWNALEKYVTEIITYYYPSDAAVEGDPELQSWVQEI FKECLLGRESSGFPRCLRTVPELIRYVTIVIYTCSAKHAAVNTGQMEFTAWMPNFPASMR NPPIQTKGLTTLETFMDTLPDVKTTCITLLVLWTLSREPDDRRPLGHFPDIHFVEEAPRR SIEAFRQRLNQISHDIRQRNKCLPIPYYYLDPVLIENSISI |
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| Enzyme 1 Number of Residues | 701 | ||||||
| Enzyme 1 Molecular Weight | 80354.9 | ||||||
| Enzyme 1 Theoretical pI | 7.68 | ||||||
| Enzyme 1 GO Classification |
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| Enzyme 1 General Function | Involved in metal ion binding | ||||||
| Enzyme 1 Specific Function | Converts arachidonic acid to 12R- hydroperoxyeicosatetraenoic acid (12R-HPETE) | ||||||
| Enzyme 1 Pathways | Not Available | ||||||
| Enzyme 1 Reactions | Not Available | ||||||
| Enzyme 1 Pfam Domain Function | |||||||
| Enzyme 1 Signals |
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| Enzyme 1 Transmembrane Regions |
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| Enzyme 1 Essentiality | Not Available | ||||||
| Enzyme 1 GenBank ID Protein | Not Available | ||||||
| Enzyme 1 UniProtKB/Swiss-Prot ID | O75342 ![]() |
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| Enzyme 1 UniProtKB/Swiss-Prot Entry Name | LX12B_HUMAN ![]() |
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| Enzyme 1 PDB ID | Not Available | ||||||
| Enzyme 1 Cellular Location | Not Available | ||||||
| Enzyme 1 Gene Sequence |
>2106 bp
ATGGCCACCTACAAAGTCAGGGTGGCCACAGGCACCGACCTCTTGTCGGGAACACGGGAC TCCATCTCACTGACCATTGTGGGGACACAAGGAGAGAGCCATAAGCAGCTGCTGAACCAC TTTGGGAGAGACTTTGCAACTGGGGCGGTGGGCCAGTACACCGTGCAGTGCCCTCAGGAC CTGGGTGAGCTCATCATCATCCGCCTGCACAAAGAGCGGTACGCCTTCTTCCCCAAGGAC CCTTGGTACTGCAACTATGTGCAGATCTGTGCCCCCAACGGCCGTATCTACCACTTCCCC GCCTACCAGTGGATGGATGGCTACGAGACCCTGGCACTCCGGGAGGCCACAGGAAAGACA ACAGCAGATGACTCGCTCCCCGTCCTCCTGGAGCACAGAAAAGAGGAGATCAGAGCCAAG CAGGACTTCTACCACTGGCGAGTCTTTCTTCCTGGCCTGCCCAGCTATGTGCACATTCCC AGTTACCGCCCTCCGGTGCGGAGGCATCGCAACCCCAACCGGCCTGAGTGGAATGGCTAT ATTCCGGGATTCCCAATTCTCATCAACTTTAAGGCCACCAAGTTCCTGAACTTAAATCTC CGCTACTCCTTCCTCAAGACGGCCTCCTTCTTCGTCCGCCTGGGGCCCATGGCACTGGCT TTCAAAGTCCGCGGCCTGTTGGACTGCAAACATTCGTGGAAGAGGCTGAAGGACATTAGG AAAATTTTCCCTGGCAAGAAATCTGTCGTCTCCGAGTACGTGGCCGAGCACTGGGCAGAG GACACCTTCTTTGGGTACCAGTACCTCAACGGCGTCAACCCCGGCCTGATCCGCCGCTGC ACGCGGATCCCAGACAAGTTCCCCGTCACAGACGACATGGTGGCTCCGTTCCTGGGCGAG GGAACGTGCTTGCAAGCGGAGCTGGAGAAGGGGAACATTTACCTGGCCGACTACCGCATC ATGGAGGGCATCCCCACCGTGGAGCTCAGCGGCCGGAAGCAGCACCACTGCGCCCCCCTC TGCCTGCTGCACTTTGGACCCGAGGGCAAGATGATGCCCATCGCCATCCAGCTCAGCCAG ACCCCTGGGCCAGATTGCCCCATCTTCCTGCCCAGTGATTCTGAGTGGGACTGGCTGCTA GCCAAGACGTGGGTACGCTATGCGGAGTTCTACAGCCACGAGGCCATCGCCCACCTGCTG GAGACACACCTCATTGCTGAGGCCTTCTGCCTGGCCTTGCTGAGGAACCTGCCCATGTGC CACCCCCTCTACAAGCTCCTCATCCCCCATACCCGATACACCGTCCAGATCAACAGCATT GGCCGGGCCGTTCTCCTCAATGAGGGGGGGCTCTCTGCCAAGGGCATGTCCCTGGGCGTG GAAGGCTTTGCTGGGGTGATGGTACGGGCTCTGTCGGAGCTCACCTATGACAGCCTCTAC CTCCCCAATGACTTTGTGGAGCGTGGGGTCCAGGACCTGCCTGGATATTACTACCGCGAT GACAGCTTGGCGGTGTGGAATGCACTGGAGAAGTATGTGACGGAGATCATCACCTATTAT TACCCGAGTGACGCAGCCGTGGAGGGTGATCCGGAATTGCAGTCTTGGGTGCAGGAAATA TTTAAAGAGTGCCTCCTGGGGCGGGAGAGCTCAGGCTTCCCTAGGTGCTTGCGAACCGTG CCTGAGCTGATCCGATATGTCACTATAGTCATCTACACCTGCTCTGCCAAGCACGCTGCT GTCAACACAGGCCAGATGGAGTTCACCGCCTGGATGCCCAACTTCCCAGCGTCCATGCGG AATCCACCGATTCAGACTAAGGGGCTGACCACTCTGGAGACCTTCATGGACACGTTGCCG GATGTGAAGACCACGTGCATCACGCTGCTGGTGCTCTGGACCCTCAGCCGAGAGCCTGAC GACAGGCGGCCCCTGGGACACTTCCCGGACATTCACTTCGTGGAGGAGGCCCCGCGGAGG AGCATAGAGGCGTTCCGCCAGCGCCTGAACCAGATCTCACACGACATCCGCCAGCGCAAC AAGTGCCTTCCCATCCCCTACTACTACCTGGACCCGGTGCTGATTGAGAACAGCATTTCT ATTTAG |
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| Enzyme 1 GenBank Gene ID | AF038461 ![]() |
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| Enzyme 1 GeneCard ID | ALOX12B ![]() |
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| Enzyme 1 GenAtlas ID | ALOX12B ![]() |
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| Enzyme 1 HGNC ID | HGNC:430 ![]() |
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| Enzyme 1 Chromosome Location | 1 | ||||||
| Enzyme 1 Locus | 17p13.1 | ||||||
| Enzyme 1 SNPs | SNPJam Report ![]() |
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| Enzyme 1 General References |
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| Enzyme 1 Metabolite References | Not Available | ||||||