5,8-Epoxy-5,8-dihydro-10'-apo-b,y-carotene-3,10'-diol (CHEM032357)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 03:19:56 UTC
Update Date2016-11-09 01:19:27 UTC
Accession NumberCHEM032357
Identification
Common Name5,8-Epoxy-5,8-dihydro-10'-apo-b,y-carotene-3,10'-diol
ClassSmall Molecule
Description5,8-Epoxy-5,8-dihydro-10'-apo-b,y-carotene-3,10'-diol is found in citrus. 5,8-Epoxy-5,8-dihydro-10'-apo-b,y-carotene-3,10'-diol is isolated from Persea americana (avocado) and from Valencia orange juice.
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
SynonymsNot Available
Chemical FormulaC27H38O3
Average Molecular Mass410.589 g/mol
Monoisotopic Mass410.282 g/mol
CAS Registry Number53905-15-0
IUPAC Name2-[(2Z,4E,6E,8E,10E,12E)-14-hydroxy-6,11-dimethyltetradeca-2,4,6,8,10,12-hexaen-2-yl]-4,4,7a-trimethyl-2,4,5,6,7,7a-hexahydro-1-benzofuran-6-ol
Traditional Name2-[(2Z,4E,6E,8E,10E,12E)-14-hydroxy-6,11-dimethyltetradeca-2,4,6,8,10,12-hexaen-2-yl]-4,4,7a-trimethyl-2,5,6,7-tetrahydro-1-benzofuran-6-ol
SMILESC\C(\C=C\CO)=C/C=C/C=C(\C)/C=C/C=C(/C)C1OC2(C)CC(O)CC(C)(C)C2=C1
InChI IdentifierInChI=1S/C27H38O3/c1-20(11-7-8-12-21(2)14-10-16-28)13-9-15-22(3)24-17-25-26(4,5)18-23(29)19-27(25,6)30-24/h7-15,17,23-24,28-29H,16,18-19H2,1-6H3/b8-7+,13-9+,14-10+,20-11+,21-12+,22-15-
InChI KeyOOJOUQLXWXASLN-TVICGMDOSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as sesterterpenoids. These are terpenes composed of five consecutive isoprene units.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassSesterterpenoids
Direct ParentSesterterpenoids
Alternative Parents
Substituents
  • Sesterterpenoid
  • Long chain fatty alcohol
  • Benzofuran
  • Fatty alcohol
  • Fatty acyl
  • Cyclic alcohol
  • Dihydrofuran
  • Secondary alcohol
  • Dialkyl ether
  • Oxacycle
  • Ether
  • Organoheterocyclic compound
  • Alcohol
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Primary alcohol
  • 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 Solubility0.0044 g/LALOGPS
logP6.12ALOGPS
logP4.31ChemAxon
logS-5ALOGPS
pKa (Strongest Acidic)15.09ChemAxon
pKa (Strongest Basic)-2.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area49.69 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity133.39 m³·mol⁻¹ChemAxon
Polarizability49.6 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0udv-1409000000-eb429ad7cfc59d1f012bSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-000l-2141490000-7cd28af2be2d54de3f05Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01ox-0129200000-ff8d7d4f182c31961d58Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0f9x-2945000000-35fad5ed96c103c1a70bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05o0-7934000000-23a9c6723b3e64af3047Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0015900000-7c1c030a8a119325d2f9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4l-1219400000-070bdb65fa7ef1e302a1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-3649000000-5b13fd443c0189836066Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0009100000-cb3fa5ef5e5f5596324bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-066r-0009300000-fb4591a8d574b299ce01Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00ba-0039000000-a4c1d707b642f932ab80Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-02di-1209200000-a6152a27f3928816445aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4j-1937100000-5d32893ca7118f2aa190Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a5c-2900000000-e810e2854dfce1206755Spectrum
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 IDHMDB0039020
FooDB IDFDB018515
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID35014719
ChEBI ID172652
PubChem Compound ID131752516
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