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Human Metabolome Database Version 2.5

 

Showing metabocard for 14,15-DiHETrE (HMDB02265)

Legend: metabolite field enzyme field

Version 2.5
Creation Date 2006-05-22 15:17:45
Update Date 2010-06-02 16:53:25
Accession Number HMDB02265
Secondary Accession Numbers HMDB02342
Common Name 14,15-DiHETrE
Description 14,15-DiHETrE is a Cytochrome P450 (P450) eicosanoid. Eicosanoids generated from arachidonic acid metabolism by cytochrome P450 (P450) enzymes are important autocrine and paracrine factors that have diverse biological functions. P450 eicosanoids are involved in the regulation of vascular tone, renal tubular transport, cardiac contractility, cellular proliferation, and inflammation. Regulation of P450 eicosanoid levels is determined by many factors, including the induction or repression of the P450 enzymes responsible for their formation. Fibrate drugs are part of a diverse group of compounds known as peroxisome proliferators, which also include herbicides and phthalate ester plasticizers. Peroxisome proliferators act via peroxisome proliferator-activated receptor (PPAR ). This receptor is a member of the PPAR nuclear receptor family that also consists of the PPAR and PPAR isoforms. PPAR is mainly expressed in the heart, liver, and kidney, whereas the expression of PPAR is predominantly in the adipose tissue. The biological role of PPAR as a lipid sensor has been well established. 14,15-DiHETrE is a potent activators of PPAR and PPAR . shown to induce the binding of PPAR to a peroxisome proliferator response element (PPRE). Furthermore, 14,15-DiHETrE behaves like peroxisome proliferators in that is able to alter apoA-I and apoA-II mRNA expression. 14,15-DiHETrE is the most potent PPARalpha activator in a COS-7 cell expression system producing a 12-fold increase in PPARalpha-mediated luciferase activity. (PMID: 17431031, 16113065)
Synonyms
  1. 14,15-dihydroxy-5Z,8Z,11Z-eicosatrienoic acid
  2. (+/-)14,15-DiHETrE
  3. (5Z,8Z,11Z)-14,15-Dihydroxyicosa-5,8,11-trienoic acid
  4. (5Z,8Z,11Z)-14,15-Dihydroxyeicosa-5,8,11-trienoic acid
  5. 14,15-dihydroxy-5Z,8Z,11Z-eicosatrienoate
  6. (5Z,8Z,11Z)-14,15-Dihydroxyicosa-5,8,11-trienoate
  7. (5Z,8Z,11Z)-14,15-Dihydroxyeicosa-5,8,11-trienoate
  8. 14,15-dihydroxyeicosatrienoic acid
  9. 14,15-DHET
  10. 14,15-dihydroxyeicosatrienoate
Chemical IUPAC Name (5Z,8Z,11Z)-14,15-dihydroxyicosa-5,8,11-trienoic acid
Chemical Formula C20H34O4
Chemical Structure Structure
Chemical Taxonomy
Kingdom
  • Organic
Super Class
  • Fatty acids
Class
  • Eicosanoids
Sub Class
  • Dihydroxyeicosapolyenoic acids
Family
  • Mammalian Metabolite
Species
  • secondary alcohol
  • 1,2-diol
  • carboxylic acid
  • alkene
Biofunction
—
Application
—
Source
  • Endogenous
Average Molecular Weight 338.482
Monoisotopic Molecular Weight 338.245697
Isomeric SMILES CCCCCC(O)C(O)CC=C/CC=C/CC=C/CCCC(O)=O
Canonical SMILES CCCCCC(O)C(O)CC=CCC=CCC=CCCCC(O)=O
KEGG Compound ID Not Available
BioCyc ID Not Available
BiGG ID Not Available
Wikipedia Link Not Available
NuGOwiki Link HMDB02265 Link Image
Metagene Link HMDB02265 Link Image
METLIN ID Not Available
PubChem Compound 5283147 Link Image
PubChem Substance 4266105 Link Image
ChEBI ID Not Available
CAS Registry Number 77667-09-5
InChI Identifier InChI=1/C20H34O4/c1-2-3-12-15-18(21)19(22)16-13-10-8-6-4-5-7-9-11-14-17-20(23)24/h4,6-7,9-10,13,18-19,21-22H,2-3,5,8,11-12,14-17H2,1H3,(H,23,24)/b6-4-,9-7-,13-10-
Synthesis Reference Not Available
Melting Point (Experimental) Not Available
Experimental Water Solubility Not Available Source: PhysProp
Predicted Water Solubility 0.0139 mg/mL [Predicted by ALOGPS] Calculated using ALOGPS
Physiological Charge -1
State Solid
Experimental LogP/Hydrophobicity Not Available Source: PhysProp
Predicted LogP/Hydrophobicity 5.28 [Predicted by ALOGPS]; 4.1 [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
  • Blood
  • Cerebrospinal Fluid
Tissue Location Not Available
Concentrations (Normal)
Biofluid Blood
Value 0.00122 +/- 0.000705 uM
Age Adult:>18 yrs old
Sex N/A
Patient information Normal
Comments Not Available
References
  • Oxygenated lipids were quantified by Theresa L. Pedersen and John W. Newman at the USDA’s Western Human Nutrition Research Center, Davis, CA, and Lipomics Technologies, Inc.
Biofluid Blood
Value 0.001449 +/- 7.1E-5 uM
Age Adult:>18 yrs old
Sex Both
Patient information Normal
Comments Not Available
References
  • Quehenberger O, Armando AM, Brown AH, Milne SB, Myers DS, Merrill AH, Bandyopadhyay S, Jones KN, Kelly S, Shaner RL, Sullards CM, Wang E, Murphy RC, Barkley RM, Leiker TJ, Raetz CR, Guan Z, Laird GM, Six DA, Russell DW, McDonald JG, Subramaniam S, Fahy E, Dennis EA: Lipidomics reveals a remarkable diversity of lipids in human plasma. J Lipid Res. 2010 Nov;51(11):3299-305. Epub 2010 Jul 29. [PubMed Link Image]
Biofluid CSF
Value 0.00013 +/- 0.00006 uM
Age Adult:>18 yrs old
Sex Both
Patient information Normal
Comments Measured via MS/MS techniques from 4 pooled CSF samples provided by TNO/NuGO – The Netherlands
References
  • John W. Newman, USDA ARS Western Human Nutrition Research Center, Davis CA (personal communication - March 2, 2009)
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. Epoxide hydrolase 2
  2. Epoxide hydrolase 2, cytoplasmic (Epoxide hydrolase 2, cytoplasmic, isoform CRA_b)
Enzyme 1 [top]
Enzyme 1 ID 7147
Enzyme 1 Name Epoxide hydrolase 2
Enzyme 1 Synonyms
  1. Cytosolic epoxide hydrolase
  2. CEH
  3. Epoxide hydratase
  4. Soluble epoxide hydrolase
  5. SEH
Enzyme 1 Gene Name EPHX2
Enzyme 1 Protein Sequence >Epoxide hydrolase 2 
MTLRAAVFDLDGVLALPAVFGVLGRTEEALALPRGLLNDAFQKGGPEGATTRLMKGEITL
SQWIPLMEENCRKCSETAKVCLPKNFSIKEIFDKAISARKINRPMLQAALMLRKKGFTTA
ILTNTWLDDRAERDGLAQLMCELKMHFDFLIESCQVGMVKPEPQIYKFLLDTLKASPSEV
VFLDDIGANLKPARDLGMVTILVQDTDTALKELEKVTGIQLLNTPAPLPTSCNPSDMSHG
YVTVKPRVRLHFVELGSGPAVCLCHGFPESWYSWRYQIPALAQAGYRVLAMDMKGYGESS
APPEIEEYCMEVLCKEMVTFLDKLGLSQAVFIGHDWGGMLVWYMALFYPERVRAVASLNT
PFIPANPNMSPLESIKANPVFDYQLYFQEPGVAEAELEQNLSRTFKSLFRASDESVLSMH
KVCEAGGLFVNSPEEPSLSRMVTEEEIQFYVQQFKKSGFRGPLNWYRNMERNWKWACKSL
GRKILIPALMVTAEKDFVLVPQMSQHMEDWIPHLKRGHIEDCGHWTQMDKPTEVNQILIK
WLDSDARNPPVVSKM
Enzyme 1 Number of Residues 555
Enzyme 1 Molecular Weight 62615.2
Enzyme 1 Theoretical pI 6.21
Enzyme 1 GO Classification
Function
  • catalytic activity
  • hydrolase activity
Process
  • metabolic process
Component
—
Enzyme 1 General Function Involved in catalytic activity
Enzyme 1 Specific Function Acts on epoxides (alkene oxides, oxiranes) and arene oxides. Plays a role in xenobiotic metabolism by degrading potentially toxic epoxides. Also determines steady-state levels of physiological mediators. Has low phosphatase activity
Enzyme 1 Pathways Not Available
Enzyme 1 Reactions
  • an epoxide + H2O = a glycol [RN:R02822]
Enzyme 1 Pfam Domain Function
Enzyme 1 Signals
  • None
Enzyme 1 Transmembrane Regions
  • None
Enzyme 1 Essentiality Not Available
Enzyme 1 GenBank ID Protein 10197680 Link Image
Enzyme 1 UniProtKB/Swiss-Prot ID P34913 Link Image
Enzyme 1 UniProtKB/Swiss-Prot Entry Name HYES_HUMAN Link Image
Enzyme 1 PDB ID 1VJ5 Link Image
Enzyme 1 PDB File Show
Enzyme 1 3D Structure
Enzyme 1 Cellular Location Not Available
Enzyme 1 Gene Sequence >1668 bp 
ATGACGCTGCGCGCGGCCGTCTTCGACCTTGACGGGGTGCTGGCGCTGCCAGCGGTGTTC
GGCGTCCTCGGCCGCACGGAGGAGGCCCTGGCGCTGCCCAGAGGACTTCTGAATGATGCT
TTCCAGAAAGGGGGACCAGAGGGTGCCACTACCCGGCTTATGAAAGGAGAGATCACACTT
TCCCAGTGGATACCACTCATGGAAGAAAACTGCAGGAAGTGCTCCGAGACCGCTAAAGTC
TGCCTCCCCAAGAATTTCTCCATAAAAGAAATCTTTGACAAGGCGATTTCAGCCAGAAAG
ATCAACCGCCCCATGCTCCAGGCAGCTCTCATGCTCAGGAAGAAAGGATTCACTACTGCC
ATCCTCACCAACACCTGGCTGGACGACCGTGCTGAGAGAGATGGCCTGGCCCAGCTGATG
TGTGAGCTGAAGATGCACTTTGACTTCCTGATAGAGTCGTGTCAGGTGGGAATGGTCAAA
CCTGAACCTCAGATCTACAAGTTTCTGCTGGACACCCTGAAGGCCAGCCCCAGTGAGGTC
GTTTTTTTGGATGACATCGGGGCTAATCTGAAGCCAGCCCGTGACTTGGGAATGGTCACC
ATCCTGGTCCAGGACACTGACACGGCCCTGAAAGAACTGGAGAAAGTGACCGGAATCCAG
CTTCTCAATACCCCGGCCCCTCTGCCGACCTCTTGCAATCCAAGTGACATGAGCCATGGG
TACGTGACAGTAAAGCCCAGGGTCCGTCTGCATTTTGTGGAGCTGGGCTCCGGCCCTGCT
GTGTGCCTCTGCCATGGATTTCCCGAGAGTTGGTATTCTTGGAGGTACCAGATCCCTGCT
CTGGCCCAGGCAGGTTACCGGGTCCTAGCTATGGACATGAAAGGCTATGGAGAGTCATCT
GCTCCTCCCGAAATAGAAGAATATTGCATGGAAGTGTTATGTAAGGAGATGGTAACCTTC
CTGGATAAACTGGGCCTCTCTCAAGCAGTGTTCATTGGCCATGACTGGGGTGGCATGCTG
GTGTGGTACATGGCTCTCTTCTACCCCGAGAGAGTGAGGGCGGTGGCCAGTTTGAATACT
CCCTTCATACCAGCAAATCCCAACATGTCCCCTTTGGAGAGTATCAAAGCCAACCCAGTA
TTTGATTACCAGCTCTACTTCCAAGAACCAGGAGTGGCTGAGGCTGAACTGGAACAGAAC
CTGAGTCGGACTTTCAAAAGCCTCTTCAGAGCAAGCGATGAGAGTGTTTTATCCATGCAT
AAAGTCTGTGAAGCGGGAGGACTTTTTGTAAATAGCCCAGAAGAGCCCAGCCTCAGCAGG
ATGGTCACTGAGGAGGAAATCCAGTTCTATGTGCAGCAGTTCAAGAAGTCTGGTTTCAGA
GGTCCTCTAAACTGGTACCGAAACATGGAAAGGAACTGGAAGTGGGCTTGCAAAAGCTTG
GGACGGAAGATCCTGATTCCGGCCCTGATGGTCACGGCGGAGAAGGACTTCGTGCTCGTT
CCTCAGATGTCCCAGCACATGGAGGACTGGATTCCCCACCTGAAAAGGGGACACATTGAG
GACTGTGGGCACTGGACACAGATGGACAAGCCAACCGAGGTGAATCAGATCCTCATTAAG
TGGCTGGATTCTGATGCCCGGAACCCACCGGTGGTCTCAAAGATGTAG
Enzyme 1 GenBank Gene ID AF233334 Link Image
Enzyme 1 GeneCard ID EPHX2 Link Image
Enzyme 1 GenAtlas ID EPHX2 Link Image
Enzyme 1 HGNC ID HGNC:3402 Link Image
Enzyme 1 Chromosome Location 8
Enzyme 1 Locus 8p21
Enzyme 1 SNPs SNPJam Report Link Image
Enzyme 1 General References
  1. Beetham JK, Tian T, Hammock BD: cDNA cloning and expression of a soluble epoxide hydrolase from human liver. Arch Biochem Biophys. 1993 Aug 15;305(1):197-201. [PubMed Link Image]
  2. Sandberg M, Meijer J: Structural characterization of the human soluble epoxide hydrolase gene (EPHX2). Biochem Biophys Res Commun. 1996 Apr 16;221(2):333-9. [PubMed Link Image]
  3. Sandberg M, Hassett C, Adman ET, Meijer J, Omiecinski CJ: Identification and functional characterization of human soluble epoxide hydrolase genetic polymorphisms. J Biol Chem. 2000 Sep 15;275(37):28873-81. [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. Cronin A, Mowbray S, Durk H, Homburg S, Fleming I, Fisslthaler B, Oesch F, Arand M: The N-terminal domain of mammalian soluble epoxide hydrolase is a phosphatase. Proc Natl Acad Sci U S A. 2003 Feb 18;100(4):1552-7. Epub 2003 Feb 6. [PubMed Link Image]
  6. Choudhary C, Kumar C, Gnad F, Nielsen ML, Rehman M, Walther TC, Olsen JV, Mann M: Lysine acetylation targets protein complexes and co-regulates major cellular functions. Science. 2009 Aug 14;325(5942):834-40. Epub 2009 Jul 16. [PubMed Link Image]
  7. Gomez GA, Morisseau C, Hammock BD, Christianson DW: Structure of human epoxide hydrolase reveals mechanistic inferences on bifunctional catalysis in epoxide and phosphate ester hydrolysis. Biochemistry. 2004 Apr 27;43(16):4716-23. [PubMed Link Image]
Enzyme 1 Metabolite References Not Available
Enzyme 2 [top]
Enzyme 2 ID 12992
Enzyme 2 Name Epoxide hydrolase 2, cytoplasmic (Epoxide hydrolase 2, cytoplasmic, isoform CRA_b)
Enzyme 2 Synonyms Not Available
Enzyme 2 Gene Name EPHX2
Enzyme 2 Protein Sequence >Epoxide hydrolase 2 
MTLRAAVFDLDGVLALPAVFGVLGRTEEALALPRGLLNDAFQKGGPEGATTRLMKGEITL
SQWIPLMEENCRKCSETAKVCLPKNFSIKEIFDKAISARKINRPMLQAALMLRKKGFTTA
ILTNTWLDDRAERDGLAQLMCELKMHFDFLIESCQVGMVKPEPQIYKFLLDTLKASPSEV
VFLDDIGANLKPARDLGMVTILVQDTDTALKELEKVTGIQLLNTPAPLPTSCNPSDMSHG
YVTVKPRVRLHFVELGSGPAVCLCHGFPESWYSWRYQIPALAQAGYRVLAMDMKGYGESS
APPEIEEYCMEVLCKEMVTFLDKLGLSQAVFIGHDWGGMLVWYMALFYPERVRAVASLNT
PFIPANPNMSPLESIKANPVFDYQLYFQEPGVAEAELEQNLSRTFKSLFRASDESVLSMH
KVCEAGGLFVNSPEEPSLSRMVTEEEIQFYVQQFKKSGFRGPLNWYRNMERNWKWACKSL
GRKILIPALMVTAEKDFVLVPQMSQHMEDWIPHLKRGHIEDCGHWTQMDKPTEVNQILIK
WLDSDARNPPVVSKM
Enzyme 2 Number of Residues 555
Enzyme 2 Molecular Weight 62616
Enzyme 2 Theoretical pI Not Available
Enzyme 2 GO Classification Not Available
Enzyme 2 General Function Not Available
Enzyme 2 Specific Function Not Available
Enzyme 2 Pathways Not Available
Enzyme 2 Reactions Not Available
Enzyme 2 Pfam Domain Function Not Available
Enzyme 2 Signals
  • None
Enzyme 2 Transmembrane Regions
  • None
Enzyme 2 Essentiality Not Available
Enzyme 2 GenBank ID Protein Not Available
Enzyme 2 UniProtKB/Swiss-Prot ID B2Z3B1 Link Image
Enzyme 2 UniProtKB/Swiss-Prot Entry Name B2Z3B1_HUMAN Link Image
Enzyme 2 PDB ID Not Available
Enzyme 2 Cellular Location Not Available
Enzyme 2 Gene Sequence Not Available
Enzyme 2 GenBank Gene ID Not Available
Enzyme 2 GeneCard ID B2Z3B1 Link Image
Enzyme 2 GenAtlas ID Not Available
Enzyme 2 HGNC ID Not Available
Enzyme 2 Chromosome Location Not Available
Enzyme 2 Locus Not Available
Enzyme 2 SNPs SNPJam Report Link Image
Enzyme 2 General References Not Available
Enzyme 2 Metabolite References Not Available