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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2013-05-17 01:21:12 UTC
Update Date2019-07-23 07:14:21 UTC
HMDB IDHMDB0060443
Secondary Accession Numbers
  • HMDB60443
Metabolite Identification
Common Namebeta-Carotene-15,15'-epoxide
Descriptionbeta-Carotene-15,15'-epoxide, also known as 15,15'-epoxy-b,b-carotene or 15-ebbct, 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. beta-Carotene-15,15'-epoxide is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
Data?1563866061
Synonyms
ValueSource
15,15'-Epoxy-15,15'-dihydro-beta,beta-caroteneChEBI
15,15'-Epoxy-beta,beta-caroteneChEBI
15,15'-Epoxy-beta-caroteneChEBI
15-EbbctChEBI
beta-Carotene 15,15' epoxideChEBI
15,15'-Epoxy-15,15'-dihydro-b,b-caroteneGenerator
15,15'-Epoxy-15,15'-dihydro-β,β-caroteneGenerator
15,15'-Epoxy-b,b-caroteneGenerator
15,15'-Epoxy-β,β-caroteneGenerator
15,15'-Epoxy-b-caroteneGenerator
15,15'-Epoxy-β-caroteneGenerator
b-Carotene 15,15' epoxideGenerator
Β-carotene 15,15' epoxideGenerator
b-Carotene-15,15'-epoxideGenerator
Β-carotene-15,15'-epoxideGenerator
Chemical FormulaC40H56O
Average Molecular Weight552.872
Monoisotopic Molecular Weight552.433116414
IUPAC Name2,3-bis[(1E,3E,5E,7E)-2,6-dimethyl-8-(2,6,6-trimethylcyclohex-1-en-1-yl)octa-1,3,5,7-tetraen-1-yl]oxirane
Traditional Name2,3-bis[(1E,3E,5E,7E)-2,6-dimethyl-8-(2,6,6-trimethylcyclohex-1-en-1-yl)octa-1,3,5,7-tetraen-1-yl]oxirane
CAS Registry NumberNot Available
SMILES
C\C(\C=C\C1=C(C)CCCC1(C)C)=C/C=C/C(/C)=C/C1OC1\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C
InChI Identifier
InChI=1S/C40H56O/c1-29(21-23-35-33(5)19-13-25-39(35,7)8)15-11-17-31(3)27-37-38(41-37)28-32(4)18-12-16-30(2)22-24-36-34(6)20-14-26-40(36,9)10/h11-12,15-18,21-24,27-28,37-38H,13-14,19-20,25-26H2,1-10H3/b17-11+,18-12+,23-21+,24-22+,29-15+,30-16+,31-27+,32-28+
InChI KeyAULCUSCIZQQSMU-WDJSDFAOSA-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
  • Retinoid skeleton
  • Oxacycle
  • Organoheterocyclic compound
  • Ether
  • Oxirane
  • Dialkyl ether
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Biological role:

Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.00045 g/LALOGPS
logP9.11ALOGPS
logP10.5ChemAxon
logS-6.1ALOGPS
pKa (Strongest Basic)-4.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area12.53 ŲChemAxon
Rotatable Bond Count10ChemAxon
Refractivity189.71 m³·mol⁻¹ChemAxon
Polarizability72.78 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00kr-3190180000-18fa5fe375427a90ed93Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0443390000-b86b444d8de208d46aaaSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-02aa-0984620000-2682c6f17feedeb9332dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-029i-3894710000-ef12554b6332cee19bedSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0010090000-fec996a718d809f6d4f8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-1050090000-bcba82082e0652fa9ae1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00kr-1192020000-eea6310dad0468f80d93Spectrum
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
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 IDFDB031284
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDC20331
BioCyc IDCPD-14386
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound6449945
PDB IDNot Available
ChEBI ID67227
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB ID
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Magrane M: UniProt Knowledgebase: a hub of integrated protein data. Database (Oxford). 2011 Mar 29;2011:bar009. doi: 10.1093/database/bar009. Print 2011. [PubMed:21447597 ]
  2. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  3. 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 ]
  4. 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 ]
  5. 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 ]
  6. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Enzymes

General function:
Secondary metabolites biosynthesis, transport and catabolism
Specific function:
Symmetrically cleaves beta-carotene into two molecules of retinal. The reaction proceeds in three stages, epoxidation of the 15,15'-double bond, hydration of the double bond leading to ring opening, and oxidative cleavage of the diol formed.
Gene Name:
BCMO1
Uniprot ID:
Q9HAY6
Molecular weight:
62636.69
Reactions
beta-Carotene + Oxygen + Reduced acceptor → beta-Carotene-15,15'-epoxide + Water + Acceptordetails
beta-Carotene-15,15'-epoxide + Water → 15,15'-Dihydroxy-beta-carotenedetails