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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2017-03-23 01:41:06 UTC
Update Date2022-03-07 03:17:55 UTC
HMDB IDHMDB0062454
Secondary Accession Numbers
  • HMDB62454
Metabolite Identification
Common Namecholest-5-en-3b-yl (9Z-heptadecenoate)
Descriptioncholesteryl (9Z)-heptadecenoate, also known as ce(17:1(9Z)), belongs to the class of organic compounds known as cholesteryl esters. Cholesteryl esters are compounds containing an esterified cholestane moiety. cholesteryl (9Z)-heptadecenoate is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.
Structure
Data?1563866314
Synonyms
ValueSource
CE(17:1(9Z))ChEBI
Cholesteryl (9Z)-heptadecenoic acidGenerator
17:1 Cholesteryl esterChEBI, HMDB
CE(17:1)ChEBI, HMDB
Cholest-5-en-3b-yl (9Z-heptadecenoic acid)Generator
Chemical FormulaC44H76O2
Average Molecular Weight637.09
Monoisotopic Molecular Weight636.584531687
IUPAC Name(1S,2R,5S,10S,11S,14R,15R)-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-5-yl (9Z)-heptadec-9-enoate
Traditional Name(1S,2R,5S,10S,11S,14R,15R)-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-5-yl (9Z)-heptadec-9-enoate
CAS Registry NumberNot Available
SMILES
[H]\C(CCCCCCC)=C(/[H])CCCCCCCC(=O)O[C@@]1([H])CC[C@@]2(C)C(C1)=CC[C@@]1([H])[C@]3([H])CC[C@]([H])([C@]([H])(C)CCCC(C)C)[C@@]3(C)CC[C@]21[H]
InChI Identifier
InChI=1S/C44H76O2/c1-7-8-9-10-11-12-13-14-15-16-17-18-19-20-24-42(45)46-37-29-31-43(5)36(33-37)25-26-38-40-28-27-39(35(4)23-21-22-34(2)3)44(40,6)32-30-41(38)43/h13-14,25,34-35,37-41H,7-12,15-24,26-33H2,1-6H3/b14-13-/t35-,37+,38+,39-,40+,41+,43+,44-/m1/s1
InChI KeyRLMIGWIAENJHMP-RJRTUNKTSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as cholesteryl esters. Cholesteryl esters are compounds containing an esterified cholestane moiety.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassSteroid esters
Direct ParentCholesteryl esters
Alternative Parents
Substituents
  • Cholesteryl ester
  • Cholesterol
  • Cholestane-skeleton
  • Delta-5-steroid
  • Carboxylic acid ester
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
Ontology
Disposition

Source

Route of exposure

Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility6.2e-06 g/lALOGPS
LogP10.54ALOGPS
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
logP10.54ALOGPS
logP14.12ChemAxon
logS-8ALOGPS
pKa (Strongest Basic)-7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area26.3 ŲChemAxon
Rotatable Bond Count21ChemAxon
Refractivity199.93 m³·mol⁻¹ChemAxon
Polarizability84.5 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M-2H]-305.55630932474
DeepCCS[M+Na]+279.32430932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
cholest-5-en-3b-yl (9Z-heptadecenoate)[H]\C(CCCCCCC)=C(/[H])CCCCCCCC(=O)O[C@@]1([H])CC[C@@]2(C)C(C1)=CC[C@@]1([H])[C@]3([H])CC[C@]([H])([C@]([H])(C)CCCC(C)C)[C@@]3(C)CC[C@]21[H]4287.9Standard polar33892256
cholest-5-en-3b-yl (9Z-heptadecenoate)[H]\C(CCCCCCC)=C(/[H])CCCCCCCC(=O)O[C@@]1([H])CC[C@@]2(C)C(C1)=CC[C@@]1([H])[C@]3([H])CC[C@]([H])([C@]([H])(C)CCCC(C)C)[C@@]3(C)CC[C@]21[H]4801.1Standard non polar33892256
cholest-5-en-3b-yl (9Z-heptadecenoate)[H]\C(CCCCCCC)=C(/[H])CCCCCCCC(=O)O[C@@]1([H])CC[C@@]2(C)C(C1)=CC[C@@]1([H])[C@]3([H])CC[C@]([H])([C@]([H])(C)CCCC(C)C)[C@@]3(C)CC[C@]21[H]4679.9Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - cholest-5-en-3b-yl (9Z-heptadecenoate) GC-MS (Non-derivatized) - 70eV, Positivesplash10-0fkc-6659056000-9c9d3698c5ffc5f5a5c92017-09-20Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - cholest-5-en-3b-yl (9Z-heptadecenoate) 10V, Positive-QTOFsplash10-000i-1165139000-d5887103f81c8183ab2e2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - cholest-5-en-3b-yl (9Z-heptadecenoate) 20V, Positive-QTOFsplash10-06dr-5469040000-5e28f74b95b7cb6ba9c82017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - cholest-5-en-3b-yl (9Z-heptadecenoate) 40V, Positive-QTOFsplash10-0a4i-6479040000-299e7ee65b35c3b2265d2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - cholest-5-en-3b-yl (9Z-heptadecenoate) 10V, Negative-QTOFsplash10-000i-0024009000-be5a4cd89c9ae5abbf982017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - cholest-5-en-3b-yl (9Z-heptadecenoate) 20V, Negative-QTOFsplash10-000i-0049003000-a467a260db980b1a5da62017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - cholest-5-en-3b-yl (9Z-heptadecenoate) 40V, Negative-QTOFsplash10-014u-2029000000-8aac9e09c7cc36306ad22017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - cholest-5-en-3b-yl (9Z-heptadecenoate) 10V, Positive-QTOFsplash10-014r-4019015000-00fa385f5f16f09a06332021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - cholest-5-en-3b-yl (9Z-heptadecenoate) 20V, Positive-QTOFsplash10-052o-9310001000-9c71985b71a1f512a2f02021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - cholest-5-en-3b-yl (9Z-heptadecenoate) 40V, Positive-QTOFsplash10-0a4l-9320000000-8e51f0821c7b6c38354d2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - cholest-5-en-3b-yl (9Z-heptadecenoate) 10V, Negative-QTOFsplash10-000i-0010009000-a7cc0f36b3e7214d75cf2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - cholest-5-en-3b-yl (9Z-heptadecenoate) 20V, Negative-QTOFsplash10-000i-0014009000-a14916448914b132c9f72021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - cholest-5-en-3b-yl (9Z-heptadecenoate) 40V, Negative-QTOFsplash10-001r-2246249000-63fadc37d6fa02af96842021-09-22Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound24779603
PDB IDNot Available
ChEBI ID84329
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. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  2. 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 ]
  3. 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 ]
  4. 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 ]
  5. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.