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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2013-05-09 20:55:58 UTC
Update Date2021-09-14 15:48:15 UTC
HMDB IDHMDB0060120
Secondary Accession Numbers
  • HMDB60120
Metabolite Identification
Common Name10-Hydroxy-octadec-12Z-enoate-9-beta-D-glucuronide
Description10-Hydroxy-octadec-12Z-enoate-9-beta-D-glucuronide belongs to the class of organic compounds known as saccharolipids. Saccharolipids are compounds in which fatty acids are linked directly to a sugar backbone, forming structures that are compatible with membrane bilayers. In the saccharolipids, a sugar substitutes for the glycerol backbone that is present in glycerolipids and glycerophospholipids. The most familiar saccharolipids contain an acylated glucosamine. In contrast to others glycolipids, the fatty acid is not glycosidically linked to the sugar moiety. 10-Hydroxy-octadec-12Z-enoate-9-beta-D-glucuronide is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
Data?1563866017
Synonyms
ValueSource
10-Hydroxy-octadec-12Z-enoate-9-b-D-glucuronideGenerator
10-Hydroxy-octadec-12Z-enoate-9-β-D-glucuronideGenerator
10-Hydroxy-octadec-12Z-enoic acid-9-b-D-glucuronideGenerator
10-Hydroxy-octadec-12Z-enoic acid-9-beta-D-glucuronideGenerator
10-Hydroxy-octadec-12Z-enoic acid-9-β-D-glucuronideGenerator
Chemical FormulaC24H42O10
Average Molecular Weight490.5843
Monoisotopic Molecular Weight490.277797564
IUPAC Name(2R,3S,4R,5R,6R)-6-{[(8R,9R,11Z)-1-carboxy-9-hydroxyheptadec-11-en-8-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid
Traditional Name(2R,3S,4R,5R,6R)-6-{[(8R,9R,11Z)-1-carboxy-9-hydroxyheptadec-11-en-8-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid
CAS Registry NumberNot Available
SMILES
CCCCC\C=C/C[C@@H](O)[C@@H](CCCCCCCC(O)=O)O[C@@H]1O[C@H]([C@@H](O)[C@@H](O)[C@H]1O)C(O)=O
InChI Identifier
InChI=1S/C24H42O10/c1-2-3-4-5-7-10-13-16(25)17(14-11-8-6-9-12-15-18(26)27)33-24-21(30)19(28)20(29)22(34-24)23(31)32/h7,10,16-17,19-22,24-25,28-30H,2-6,8-9,11-15H2,1H3,(H,26,27)(H,31,32)/b10-7-/t16-,17-,19-,20+,21-,22-,24-/m1/s1
InChI KeyIRADJQUIAYBZPY-WKVBQAANSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as saccharolipids. Saccharolipids are compounds in which fatty acids are linked directly to a sugar backbone, forming structures that are compatible with membrane bilayers. In the saccharolipids, a sugar substitutes for the glycerol backbone that is present in glycerolipids and glycerophospholipids. The most familiar saccharolipids contain an acylated glucosamine. In contrast to others glycolipids, the fatty acid is not glycosidically linked to the sugar moiety.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSaccharolipids
Sub ClassNot Available
Direct ParentSaccharolipids
Alternative Parents
Substituents
  • Saccharolipid
  • Long-chain fatty acid
  • 1-o-glucuronide
  • O-glucuronide
  • Glucuronic acid or derivatives
  • Hexose monosaccharide
  • Glycosyl compound
  • O-glycosyl compound
  • Beta-hydroxy acid
  • Heterocyclic fatty acid
  • Hydroxy fatty acid
  • Fatty acyl
  • Fatty acid
  • Unsaturated fatty acid
  • Pyran
  • Dicarboxylic acid or derivatives
  • Oxane
  • Monosaccharide
  • Hydroxy acid
  • Secondary alcohol
  • Oxacycle
  • Organoheterocyclic compound
  • Carboxylic acid derivative
  • Carboxylic acid
  • Polyol
  • Acetal
  • Alcohol
  • Carbonyl group
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
Process
Role
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biospecimen Locations
  • Blood
  • Urine
Tissue Locations
  • Kidney
  • Liver
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableNormal
      Not Available
details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableNormal
      Not Available
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB034574
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound131769832
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Thiele I, Swainston N, Fleming RM, Hoppe A, Sahoo S, Aurich MK, Haraldsdottir H, Mo ML, Rolfsson O, Stobbe MD, Thorleifsson SG, Agren R, Bolling C, Bordel S, Chavali AK, Dobson P, Dunn WB, Endler L, Hala D, Hucka M, Hull D, Jameson D, Jamshidi N, Jonsson JJ, Juty N, Keating S, Nookaew I, Le Novere N, Malys N, Mazein A, Papin JA, Price ND, Selkov E Sr, Sigurdsson MI, Simeonidis E, Sonnenschein N, Smallbone K, Sorokin A, van Beek JH, Weichart D, Goryanin I, Nielsen J, Westerhoff HV, Kell DB, Mendes P, Palsson BO: A community-driven global reconstruction of human metabolism. Nat Biotechnol. 2013 May;31(5):419-25. doi: 10.1038/nbt.2488. Epub 2013 Mar 3. [PubMed:23455439 ]
  2. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  3. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
  4. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
  5. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
  6. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.