(3S,5R,6R,6'S)-6,7-Didehydro-5,6-dihydro-3,5,6'-trihydroxy-13,14,20-trinor-3'-oxo-beta,epsilon-caroten-19',11'-olide 3-acetate (CHEM031239)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 02:30:11 UTC
Update Date2016-11-09 01:19:13 UTC
Accession NumberCHEM031239
Identification
Common Name(3S,5R,6R,6'S)-6,7-Didehydro-5,6-dihydro-3,5,6'-trihydroxy-13,14,20-trinor-3'-oxo-beta,epsilon-caroten-19',11'-olide 3-acetate
ClassSmall Molecule
Description(3S,5R,6R,6'S)-6,7-Didehydro-5,6-dihydro-3,5,6'-trihydroxy-13,14,20-trinor-3'-oxo-beta,epsilon-caroten-19',11'-olide 3-acetate is found in mollusks. (3S,5R,6R,6'S)-6,7-Didehydro-5,6-dihydro-3,5,6'-trihydroxy-13,14,20-trinor-3'-oxo-beta,epsilon-caroten-19',11'-olide 3-acetate is a constituent of the oyster Crassostrea gigas.
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(3S,5R,6R,6's)-6,7-Didehydro-5,6-dihydro-3,5,6'-trihydroxy-13,14,20-trinor-3'-oxo-b,epsilon-caroten-19',11'-olide 3-acetateGenerator
(3S,5R,6R,6's)-6,7-Didehydro-5,6-dihydro-3,5,6'-trihydroxy-13,14,20-trinor-3'-oxo-b,epsilon-caroten-19',11'-olide 3-acetic acidGenerator
(3S,5R,6R,6's)-6,7-Didehydro-5,6-dihydro-3,5,6'-trihydroxy-13,14,20-trinor-3'-oxo-beta,epsilon-caroten-19',11'-olide 3-acetic acidGenerator
(3S,5R,6R,6's)-6,7-Didehydro-5,6-dihydro-3,5,6'-trihydroxy-13,14,20-trinor-3'-oxo-β,epsilon-caroten-19',11'-olide 3-acetateGenerator
(3S,5R,6R,6's)-6,7-Didehydro-5,6-dihydro-3,5,6'-trihydroxy-13,14,20-trinor-3'-oxo-β,epsilon-caroten-19',11'-olide 3-acetic acidGenerator
3-Hydroxy-4-[(3E,5E,7E,9E)-10-{[(2Z)-4-[(e)-2-(1-hydroxy-2,6,6-trimethyl-4-oxocyclohex-2-en-1-yl)ethenyl]-5-oxo-2,5-dihydrofuran-2-ylidene]methyl}-3-methylundeca-1,3,5,7,9-pentaen-1-ylidene]-3,5,5-trimethylcyclohexyl acetic acidHMDB
Chemical FormulaC39H48O7
Average Molecular Mass628.794 g/mol
Monoisotopic Mass628.340 g/mol
CAS Registry Number256505-50-7
IUPAC Name3-hydroxy-4-[(3E,5E,7E,9E)-10-{[(2Z)-4-[(E)-2-(1-hydroxy-2,6,6-trimethyl-4-oxocyclohex-2-en-1-yl)ethenyl]-5-oxo-2,5-dihydrofuran-2-ylidene]methyl}-3-methylundeca-1,3,5,7,9-pentaen-1-ylidene]-3,5,5-trimethylcyclohexyl acetate
Traditional Name3-hydroxy-4-[(3E,5E,7E,9E)-10-{[(2Z)-4-[(E)-2-(1-hydroxy-2,6,6-trimethyl-4-oxocyclohex-2-en-1-yl)ethenyl]-5-oxofuran-2-ylidene]methyl}-3-methylundeca-1,3,5,7,9-pentaen-1-ylidene]-3,5,5-trimethylcyclohexyl acetate
SMILESCC(=O)OC1CC(C)(C)C(=C=C\C(C)=C\C=C\C=C\C=C(/C)\C=C2/OC(=O)C(\C=C\C3(O)C(C)=CC(=O)CC3(C)C)=C2)C(C)(O)C1
InChI IdentifierInChI=1S/C39H48O7/c1-26(16-17-34-36(5,6)24-33(45-29(4)40)25-38(34,9)43)14-12-10-11-13-15-27(2)20-32-22-30(35(42)46-32)18-19-39(44)28(3)21-31(41)23-37(39,7)8/h10-16,18-22,33,43-44H,23-25H2,1-9H3/b12-10+,13-11+,19-18+,26-14+,27-15+,32-20-
InChI KeySXOGJBMNSIHZFB-UGBYICEJSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as terpene lactones. These are prenol lipids containing a lactone ring.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassTerpene lactones
Direct ParentTerpene lactones
Alternative Parents
Substituents
  • Terpene lactone
  • Sesquiterpenoid
  • Cyclofarsesane sesquiterpenoid
  • Cyclohexenone
  • 2-furanone
  • Dicarboxylic acid or derivatives
  • Cyclic alcohol
  • Dihydrofuran
  • Enol ester
  • Tertiary alcohol
  • Enoate ester
  • Alpha,beta-unsaturated carboxylic ester
  • Lactone
  • Ketone
  • Cyclic ketone
  • Carboxylic acid ester
  • Oxacycle
  • Organoheterocyclic compound
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organic oxygen compound
  • Organic oxide
  • Alcohol
  • Carbonyl group
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External DescriptorsNot Available
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.00061 g/LALOGPS
logP6.58ALOGPS
logP5.56ChemAxon
logS-6ALOGPS
pKa (Strongest Acidic)13.31ChemAxon
pKa (Strongest Basic)-3.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area110.13 ŲChemAxon
Rotatable Bond Count9ChemAxon
Refractivity190.45 m³·mol⁻¹ChemAxon
Polarizability73.16 ųChemAxon
Number of Rings3ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-03dl-7101295000-635226ef4a30a5ee0d60Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_1) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_2) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_3) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_3) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_2_1) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_2_2) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_2_3) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS ("(3S,5R,6R,6'S)-6,7-Didehydro-5,6-dihydro-3,5,6'-trihydroxy-13,14,20-trinor-3'-oxo-beta,epsilon-caroten-19',11'-olide 3-acetate,1TMS,#1" TMS) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03y3-0108479000-e126573036faea61ce3cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014l-0935820000-b214e35ec3d0fb19593cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-4595320000-e295ea2ae29269c0b062Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-2720179000-f8e616207d6debf1c79fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0ap0-4310294000-1b615f40aa12b784807eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052f-8430091000-d67fe88990d6e885d781Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03xu-0000094000-7852d210c722f0d52f70Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0f6w-0001391000-fc88e46314d69afc1ed3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0079-4494500000-1f3e5ac28b07c518a3f7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00kr-0000090000-9980f5e0f0c062573365Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-9210050000-e5a656768b6ccb1727efSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4m-9262101000-509b1e992ea076668a0eSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0037793
FooDB IDFDB016937
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID35014470
ChEBI ID169043
PubChem Compound ID131752234
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9.
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.
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.
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.
5. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.
6. The lipid handbook with CD-ROM