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Human Metabolome Database Version 2.5

 

Showing metabocard for 12(R)-HPETE (HMDB04692)

Legend: metabolite field 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
  1. 12R-HpETE
  2. 12R-hydroperoxy-5Z,8Z,10E,14Z-eicosatetraenoic acid
  3. 12R-hydroperoxyeicosatetraenoic acid
  4. 12R-hydroperoxyeicosatetraenoate
  5. 12R-hydroperoxy-5Z,8Z,10E,14Z-eicosatetraenoate
Chemical IUPAC Name (5Z,8Z,10E,12R,14Z)-12-hydroperoxyicosa-5,8,10,14-tetraenoic acid
Chemical Formula C20H32O4
Chemical Structure Structure
Chemical Taxonomy
Kingdom
  • Organic
Super Class
  • Fatty acids
Class
  • Eicosanoids
Sub Class
  • Hydroperoxyeicosatetraenoic acids
Family
  • Mammalian Metabolite
Species
  • hydroperoxide
  • carboxylic acid
  • alkene
Biofunction
—
Application
—
Source
  • Endogenous
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 Link Image
BioCyc ID Not Available
BiGG ID Not Available
Wikipedia Link Not Available
NuGOwiki Link HMDB04692 Link Image
Metagene Link HMDB04692 Link Image
METLIN ID Not Available
PubChem Compound 9548885 Link Image
PubChem Substance 14718420 Link Image
ChEBI ID 34145 Link Image
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 Link Image
SDF File Show Link Image
PDB File Show Link Image
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
Predicted 13C NMR Spectrum Show Image
Show Peaklist
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
Name SMPDB Link KEGG Link
Arachidonic Acid Metabolism SMP00075 Link Image map00590 Link Image
General References Not Available
Metabolic Enzymes
  1. Arachidonate 12-lipoxygenase, 12R-type
Enzyme 1 [top]
Enzyme 1 ID 8675
Enzyme 1 Name Arachidonate 12-lipoxygenase, 12R-type
Enzyme 1 Synonyms
  1. 12R-LOX
  2. 12R-lipoxygenase
  3. Epidermis-type lipoxygenase 12
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
Enzyme 1 Number of Residues 701
Enzyme 1 Molecular Weight 80354.9
Enzyme 1 Theoretical pI 7.68
Enzyme 1 GO Classification
Function
  • binding
  • catalytic activity
  • cation binding
  • ion binding
  • iron ion binding
  • lipoxygenase activity
  • metal ion binding
  • oxidoreductase activity
  • oxidoreductase activity, acting on single donors with incorporation of molecular oxygen
  • oxidoreductase activity, acting on single donors with incorporation of molecular oxygen, incorporation of two atoms of oxygen
  • transition metal ion binding
Process
  • carboxylic acid metabolic process
  • cellular metabolic process
  • fatty acid metabolic process
  • icosanoid metabolic process
  • leukotriene metabolic process
  • metabolic process
  • monocarboxylic acid metabolic process
  • organic acid metabolic process
  • oxidation reduction
  • oxoacid metabolic process
  • unsaturated fatty acid metabolic process
Component
—
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
  • None
Enzyme 1 Transmembrane Regions
  • None
Enzyme 1 Essentiality Not Available
Enzyme 1 GenBank ID Protein Not Available
Enzyme 1 UniProtKB/Swiss-Prot ID O75342 Link Image
Enzyme 1 UniProtKB/Swiss-Prot Entry Name LX12B_HUMAN Link Image
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
Enzyme 1 GenBank Gene ID AF038461 Link Image
Enzyme 1 GeneCard ID ALOX12B Link Image
Enzyme 1 GenAtlas ID ALOX12B Link Image
Enzyme 1 HGNC ID HGNC:430 Link Image
Enzyme 1 Chromosome Location 1
Enzyme 1 Locus 17p13.1
Enzyme 1 SNPs SNPJam Report Link Image
Enzyme 1 General References
  1. Boeglin WE, Kim RB, Brash AR: A 12R-lipoxygenase in human skin: mechanistic evidence, molecular cloning, and expression. Proc Natl Acad Sci U S A. 1998 Jun 9;95(12):6744-9. [PubMed Link Image]
  2. Sun D, McDonnell M, Chen XS, Lakkis MM, Li H, Isaacs SN, Elsea SH, Patel PI, Funk CD: Human 12(R)-lipoxygenase and the mouse ortholog. Molecular cloning, expression, and gene chromosomal assignment. J Biol Chem. 1998 Dec 11;273(50):33540-7. [PubMed Link Image]
  3. Krieg P, Marks F, Furstenberger G: A gene cluster encoding human epidermis-type lipoxygenases at chromosome 17p13.1: cloning, physical mapping, and expression. Genomics. 2001 May 1;73(3):323-30. [PubMed Link Image]
  4. Gerhard DS, Wagner L, Feingold EA, Shenmen CM, Grouse LH, Schuler G, Klein SL, Old S, Rasooly R, Good P, Guyer M, Peck AM, Derge JG, Lipman D, Collins FS, Jang W, Sherry S, Feolo M, Misquitta L, Lee E, Rotmistrovsky K, Greenhut SF, Schaefer CF, Buetow K, Bonner TI, Haussler D, Kent J, Kiekhaus M, Furey T, Brent M, Prange C, Schreiber K, Shapiro N, Bhat NK, Hopkins RF, Hsie F, Driscoll T, Soares MB, Casavant TL, Scheetz TE, Brown-stein MJ, Usdin TB, Toshiyuki S, Carninci P, Piao Y, Dudekula DB, Ko MS, Kawakami K, Suzuki Y, Sugano S, Gruber CE, Smith MR, Simmons B, Moore T, Waterman R, Johnson SL, Ruan Y, Wei CL, Mathavan S, Gunaratne PH, Wu J, Garcia AM, Hulyk SW, Fuh E, Yuan Y, Sneed A, Kowis C, Hodgson A, Muzny DM, McPherson J, Gibbs RA, Fahey J, Helton E, Ketteman M, Madan A, Rodrigues S, Sanchez A, Whiting M, Madari A, Young AC, Wetherby KD, Granite SJ, Kwong PN, Brinkley CP, Pearson RL, Bouffard GG, Blakesly RW, Green ED, Dickson MC, Rodriguez AC, Grimwood J, Schmutz J, Myers RM, Butterfield YS, Griffith M, Griffith OL, Krzywinski MI, Liao N, Morin R, Palmquist D, Petrescu AS, Skalska U, Smailus DE, Stott JM, Schnerch A, Schein JE, Jones SJ, Holt RA, Baross A, Marra MA, Clifton S, Makowski KA, Bosak S, Malek J: The status, quality, and expansion of the NIH full-length cDNA project: the Mammalian Gene Collection (MGC). Genome Res. 2004 Oct;14(10B):2121-7. [PubMed Link Image]
  5. Jobard F, Lefevre C, Karaduman A, Blanchet-Bardon C, Emre S, Weissenbach J, Ozguc M, Lathrop M, Prud'homme JF, Fischer J: Lipoxygenase-3 (ALOXE3) and 12(R)-lipoxygenase (ALOX12B) are mutated in non-bullous congenital ichthyosiform erythroderma (NCIE) linked to chromosome 17p13.1. Hum Mol Genet. 2002 Jan 1;11(1):107-13. [PubMed Link Image]
Enzyme 1 Metabolite References Not Available