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Human Metabolome Database Version 2.5

 

Showing metabocard for 9,10-DHOME (HMDB04704)

Legend: metabolite field enzyme field

Version 2.5
Creation Date 2006-08-14 02:38:14
Update Date 2010-06-02 09:57:02
Accession Number HMDB04704
Secondary Accession Numbers Not Available
Common Name 9,10-DHOME
Description 9,10-DHOME is a derivative of linoleic acid diol that have been reported to be toxic in human's tissue preparations. 9,10-DHOME is a naturally occurring proliferator-activated receptor (PPAR) gamma2 ligand, which stimulates adipocytes and inhibits osteoblast differentiation. 9,10-DHOME is the epoxide hydrolase metabolite of the leukotoxin 9,10--EpOME. 9,10-EpOMEs act as a protoxin, with the corresponding epoxide hydrolase 9,10-DiHOME specifically exerting toxicity. Both the 9,10-EpOME and the 9,10-DiHOME are shown to have neutrophil chemotactic activity. 9,10-DiHOME suppress the neutrophil respiratory burst by a mechanism distinct from that of respiratory burst inhibitors such as cyclosporin H or lipoxin A4,which inhibit multiple aspects of neutrophil activation. (PMID: 12021203, 12127265, 17435320)
Synonyms
  1. 9,10-DiHOME
  2. 9,10-dihydroxy-12Z-octadecenoic acid
  3. (12Z)-9,10-Dihydroxyoctadec-12-enoic acid
  4. 9,10-dihydroxy-12Z-octadecenoate
  5. (12Z)-9,10-Dihydroxyoctadec-12-enoate
  6. 9,10-hydroxyoctadec-12(Z)-enoate
  7. leukotoxin
  8. 9,10-hydroxyoctadec-12(Z)-enoic acid
Chemical IUPAC Name (Z)-9,10-dihydroxyoctadec-12-enoic acid
Chemical Formula C18H34O4
Chemical Structure Structure
Chemical Taxonomy
Kingdom
  • Organic
Super Class
  • Organic acids
Class
  • Fatty Acids
Sub Class
  • Long chain fatty acids
Family
  • Mammalian Metabolite
Species
  • secondary alcohol
  • 1,2-diol
  • carboxylic acid
  • alkene
Biofunction
—
Application
—
Source
  • Endogenous
Average Molecular Weight 314.460
Monoisotopic Molecular Weight 314.245697
Isomeric SMILES CCCCCC=C/CC(O)C(O)CCCCCCCC(O)=O
Canonical SMILES CCCCCC=CCC(O)C(O)CCCCCCCC(O)=O
KEGG Compound ID C14828 Link Image
BioCyc ID Not Available
BiGG ID Not Available
Wikipedia Link Not Available
NuGOwiki Link HMDB04704 Link Image
Metagene Link HMDB04704 Link Image
METLIN ID Not Available
PubChem Compound 9966640 Link Image
PubChem Substance 24701141 Link Image
ChEBI ID Not Available
CAS Registry Number Not Available
InChI Identifier InChI=1/C18H34O4/c1-2-3-4-5-7-10-13-16(19)17(20)14-11-8-6-9-12-15-18(21)22/h7,10,16-17,19-20H,2-6,8-9,11-15H2,1H3,(H,21,22)/b10-7-
Synthesis Reference Not Available
Melting Point (Experimental) Not Available
Experimental Water Solubility Not Available Source: PhysProp
Predicted Water Solubility 0.0401 mg/mL [Predicted by ALOGPS] Calculated using ALOGPS
Physiological Charge -1
State Solid
Experimental LogP/Hydrophobicity Not Available Source: PhysProp
Predicted LogP/Hydrophobicity 5.18 [Predicted by ALOGPS]; 4.9 [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 0.0605 +/- 0.00382 uM
Age Adult:>18 yrs old
Sex N/A
Patient information Normal
Comments Not Available
References
  • Wishart DS, Knox C, Guo AC, Eisner R, Young N, Gautam B, Hau DD, Psychogios N, Dong E, Bouatra S, Mandal R, Sinelnikov I, Xia J, Jia L, Cruz JA, Lim E, Sobsey CA, Shrivastava S, Huang P, Liu P, Fang L, Peng J, Fradette R, Cheng D, Tzur D, Clements M, Lewis A, De Souza A, Zuniga A, Dawe M, Xiong Y, Clive D, Greiner R, Nazyrova A, Shaykhutdinov R, Li L, Vogel HJ, Forsythe I: HMDB: a knowledgebase for the human metabolome. Nucleic Acids Res. 2008 Oct 25. [PubMed Link Image]
Biofluid CSF
Value 0.00049 +/- 0.00044 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 Not Available
General References Not Available