Back to Compounds

Showing Compound (5R,5'R,6S,6'S)-5,6:5',6'-Diepoxy-5,5',6,6'-tetrahydro-beta,beta-carotene (FDB001770)

Record Information
Version1.0
Creation date2010-04-08 22:05:06 UTC
Update date2019-11-26 02:56:39 UTC
Primary IDFDB001770
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name(5R,5'R,6S,6'S)-5,6:5',6'-Diepoxy-5,5',6,6'-tetrahydro-beta,beta-carotene
Description(5r,5'r,6s,6's)-5,6:5',6'-diepoxy-5,5',6,6'-tetrahydro-beta,beta-carotene is a member of the class of compounds known as xanthophylls. Xanthophylls 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 (5r,5'r,6s,6's)-5,6:5',6'-diepoxy-5,5',6,6'-tetrahydro-beta,beta-carotene is practically insoluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). (5r,5'r,6s,6's)-5,6:5',6'-diepoxy-5,5',6,6'-tetrahydro-beta,beta-carotene can be found in sweet potato, which makes (5r,5'r,6s,6's)-5,6:5',6'-diepoxy-5,5',6,6'-tetrahydro-beta,beta-carotene a potential biomarker for the consumption of this food product.
CAS Number34222-90-7
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
Predicted Properties
PropertyValueSource
Water Solubility9.8e-05 g/LALOGPS
logP9.56ALOGPS
logP10.18ChemAxon
logS-6.8ALOGPS
pKa (Strongest Basic)-4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area25.06 ŲChemAxon
Rotatable Bond Count10ChemAxon
Refractivity189.08 m³·mol⁻¹ChemAxon
Polarizability73.02 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC40H56O2
IUPAC name(1S,6R)-2,2,6-trimethyl-1-[(1E,3E,5E,7E,9E,11E,13E,15E,17E)-3,7,12,16-tetramethyl-18-[(1S,6R)-2,2,6-trimethyl-7-oxabicyclo[4.1.0]heptan-1-yl]octadeca-1,3,5,7,9,11,13,15,17-nonaen-1-yl]-7-oxabicyclo[4.1.0]heptane
InChI IdentifierInChI=1S/C40H56O2/c1-31(19-13-21-33(3)23-29-39-35(5,6)25-15-27-37(39,9)41-39)17-11-12-18-32(2)20-14-22-34(4)24-30-40-36(7,8)26-16-28-38(40,10)42-40/h11-14,17-24,29-30H,15-16,25-28H2,1-10H3/b12-11+,19-13+,20-14+,29-23+,30-24+,31-17+,32-18+,33-21+,34-22+/t37-,38-,39+,40+/m1/s1
InChI KeyJMZDCQZKLCHTFI-HPLZOGFXSA-N
Isomeric SMILESC/C(=C\C=C\C=C(/C)\C=C\C=C(/C)\C=C\[C@@]12O[C@]1(C)CCCC2(C)C)/C=C/C=C(\C)/C=C/[C@@]12O[C@]1(C)CCCC2(C)C
Average Molecular Weight568.8714
Monoisotopic Molecular Weight568.428031036
Classification
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
  • Oxepane
  • Oxacycle
  • Organoheterocyclic compound
  • Ether
  • Oxirane
  • Dialkyl ether
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
OntologyNo ontology term
Physico-Chemical Properties
Physico-Chemical Properties - Experimental
Spectra
Spectra
EI-MS/GC-MSNot Available
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0243590000-f1877b5c481de779c8cd2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-3397230000-03b577bf9b10bc5ec87d2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-07vi-9473100000-2153b281f189bc4121982016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0000090000-6f3332b747df323579962016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-0100090000-9705b77790d86ef586d02016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0080-3900250000-09699631f743c4f777d32016-08-03View Spectrum
NMRNot Available
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound IDNot Available
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDC00022952
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
Sweet potatoExpected but not quantifiedNot AvailableKNAPSACK
Showing 1 to 1 of 1 entries
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.