(3S,3'S,5R,5'R,6R)-3,6-Epoxy-5,6-dihydro-3',5,8'-trihydroxy-beta,kappa-caroten-6'-one (CHEM031241)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 02:30:15 UTC
Update Date2016-11-09 01:19:13 UTC
Accession NumberCHEM031241
Identification
Common Name(3S,3'S,5R,5'R,6R)-3,6-Epoxy-5,6-dihydro-3',5,8'-trihydroxy-beta,kappa-caroten-6'-one
ClassSmall Molecule
Description(3S,3'S,5R,5'R,6R)-3,6-Epoxy-5,6-dihydro-3',5,8'-trihydroxy-beta,kappa-caroten-6'-one is found in mollusks. (3S,3'S,5R,5'R,6R)-3,6-Epoxy-5,6-dihydro-3',5,8'-trihydroxy-beta,kappa-caroten-6'-one is a constituent of the oyster Crassostrea gigas.
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(3S,3's,5R,5'r,6R)-3,6-Epoxy-5,6-dihydro-3',5,8'-trihydroxy-b,kappa-caroten-6'-oneGenerator
(3S,3's,5R,5'r,6R)-3,6-Epoxy-5,6-dihydro-3',5,8'-trihydroxy-β,kappa-caroten-6'-oneGenerator
Chemical FormulaC40H56O5
Average Molecular Mass616.870 g/mol
Monoisotopic Mass616.413 g/mol
CAS Registry Number256505-53-0
IUPAC Name(2Z,4E,6E,8E,10E,12E,14E,16E,18E)-3-hydroxy-1-(3-hydroxy-1,2,2-trimethylcyclopentyl)-19-{2-hydroxy-2,6,6-trimethyl-7-oxabicyclo[2.2.1]heptan-1-yl}-4,8,13,17-tetramethylnonadeca-2,4,6,8,10,12,14,16,18-nonaen-1-one
Traditional Name(2Z,4E,6E,8E,10E,12E,14E,16E,18E)-3-hydroxy-1-(3-hydroxy-1,2,2-trimethylcyclopentyl)-19-{2-hydroxy-2,6,6-trimethyl-7-oxabicyclo[2.2.1]heptan-1-yl}-4,8,13,17-tetramethylnonadeca-2,4,6,8,10,12,14,16,18-nonaen-1-one
SMILESC\C(\C=C\C=C(/C)\C=C\C12OC(CC1(C)C)CC2(C)O)=C/C=C/C=C(\C)/C=C/C=C(\C)/C(/O)=C/C(=O)C1(C)CCC(O)C1(C)C
InChI IdentifierInChI=1S/C40H56O5/c1-28(17-13-18-30(3)21-24-40-36(5,6)26-32(45-40)27-39(40,10)44)15-11-12-16-29(2)19-14-20-31(4)33(41)25-35(43)38(9)23-22-34(42)37(38,7)8/h11-21,24-25,32,34,41-42,44H,22-23,26-27H2,1-10H3/b12-11+,17-13+,19-14+,24-21+,28-15+,29-16+,30-18+,31-20+,33-25-
InChI KeyJBFAUTAUPAPLMY-UQDXBYLISA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as xanthophylls. These are carotenoids containing an oxygenated carotene backbone. Carotenes are characterized by the presence of two end-groups (mostly cyclohexene rings, but also cyclopentene rings or acyclic groups) linked by a long branched alkyl chain. Carotenes belonging form a subgroup of the carotenoids family. Xanthophylls arise by oxygenation of the carotene backbone.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassTetraterpenoids
Direct ParentXanthophylls
Alternative Parents
Substituents
  • Xanthophyll
  • Cyclopentanol
  • Monosaccharide
  • Acryloyl-group
  • Cyclic alcohol
  • Enone
  • Vinylogous acid
  • Alpha,beta-unsaturated ketone
  • Tetrahydrofuran
  • Tertiary alcohol
  • Ketone
  • Secondary alcohol
  • Dialkyl ether
  • Enol
  • Oxacycle
  • Ether
  • Organoheterocyclic compound
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Alcohol
  • Carbonyl group
  • Organic oxide
  • Organooxygen compound
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic 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 Solubility0.00076 g/LALOGPS
logP7.38ALOGPS
logP7.44ChemAxon
logS-5.9ALOGPS
pKa (Strongest Acidic)8.88ChemAxon
pKa (Strongest Basic)-2.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area86.99 ŲChemAxon
Rotatable Bond Count11ChemAxon
Refractivity195.39 m³·mol⁻¹ChemAxon
Polarizability75.43 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, Positivesplash10-0pb9-7100294000-70b2c68b664763cace64Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00di-7100049000-2c6595df0e1bea6c74dcSpectrum
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 (TMS_3_1) - 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,3'S,5R,5'R,6R)-3,6-Epoxy-5,6-dihydro-3',5,8'-trihydroxy-beta,kappa-caroten-6'-one,1TMS,#1" TMS) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0521942000-06a440d53a07f0e8f10aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-052b-3642930000-1c1db9100109609353deSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-056r-3960100000-cb602f77717137c9f4d8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0500539000-decbf06136b865825d5cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014j-0800933000-f439dc3a0f87fd1efc0eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-1009-1900240000-02c218983e61abc2d7f1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0710009000-284ccdd7f575875a4713Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014j-0605934000-29bbc3bcd234348c9ca8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-6539551000-dded066ce27a07be07aeSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-1204097000-3a885104aa0f8a621557Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a6r-3329220000-e25d6418a9339959f363Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00p0-5497300000-430f0c5c73b566084176Spectrum
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 IDHMDB0037795
FooDB IDFDB016939
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID35014472
ChEBI ID176237
PubChem Compound ID131752236
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