beta-Citraurin epoxide (CHEM032416)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 03:22:13 UTC
Update Date2016-11-09 01:19:27 UTC
Accession NumberCHEM032416
Identification
Common Namebeta-Citraurin epoxide
ClassSmall Molecule
Descriptionbeta-Citraurin epoxide is found in citrus. beta-Citraurin epoxide is isolated from orange peel.
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
b-Citraurin epoxideGenerator
Β-citraurin epoxideGenerator
5,6-Epoxy-3-hydroxy-8'-apo-b-caroten-8'-alHMDB
apo-8'-ViolaxanthalHMDB
Chemical FormulaC30H40O3
Average Molecular Mass448.637 g/mol
Monoisotopic Mass448.298 g/mol
CAS Registry Number71869-83-5
IUPAC Name(2E,4E,6E,8E,10E,12E,14Z,16E)-17-{4-hydroxy-2,2,6-trimethyl-7-oxabicyclo[4.1.0]heptan-1-yl}-2,6,11,15-tetramethylheptadeca-2,4,6,8,10,12,14,16-octaenal
Traditional Name(2E,4E,6E,8E,10E,12E,14Z,16E)-17-{4-hydroxy-2,2,6-trimethyl-7-oxabicyclo[4.1.0]heptan-1-yl}-2,6,11,15-tetramethylheptadeca-2,4,6,8,10,12,14,16-octaenal
SMILESC\C(C=O)=C/C=C/C(/C)=C/C=C/C=C(\C)/C=C/C=C(/C)\C=C\C12OC1(C)CC(O)CC2(C)C
InChI IdentifierInChI=1S/C30H40O3/c1-23(12-8-9-13-24(2)15-11-17-26(4)22-31)14-10-16-25(3)18-19-30-28(5,6)20-27(32)21-29(30,7)33-30/h8-19,22,27,32H,20-21H2,1-7H3/b9-8+,14-10+,15-11+,19-18+,23-12+,24-13+,25-16-,26-17+
InChI KeyTUSQPOXZYYVVMH-STNACPSUSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassTriterpenoids
Direct ParentTriterpenoids
Alternative Parents
Substituents
  • Triterpenoid
  • Oxepane
  • Alpha,beta-unsaturated aldehyde
  • Cyclic alcohol
  • Enal
  • Secondary alcohol
  • Dialkyl ether
  • Oxirane
  • Ether
  • Oxacycle
  • Organoheterocyclic compound
  • Hydrocarbon derivative
  • Alcohol
  • Organic oxide
  • Aldehyde
  • Organooxygen compound
  • Organic oxygen compound
  • Carbonyl group
  • 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 Solubility0.0014 g/LALOGPS
logP6.86ALOGPS
logP5.67ChemAxon
logS-5.5ALOGPS
pKa (Strongest Acidic)15.14ChemAxon
pKa (Strongest Basic)-2.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area49.83 ŲChemAxon
Rotatable Bond Count9ChemAxon
Refractivity147.14 m³·mol⁻¹ChemAxon
Polarizability55.68 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-001i-6003900000-7c594c3f7b3a1bef2dcfSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0a4i-8721290000-b3e4876fc544d36d7b8cSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001j-1140900000-88f076c6a57440132035Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-040r-1691300000-a36f214471ffcb76b512Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-066s-8970000000-6ef31e43775fd8ba5679Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0000900000-c9489c9ee886c1b1ab83Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-002b-0000900000-276acfb0100781dc25d0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0f6t-7918600000-ebec514ebcdaf4301785Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0000900000-d14279dd5da3938e72c2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-0205900000-09530ba537d1451c4639Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0ufv-1019100000-0de7d90f49e61f45b03bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0037900000-a9383096ba3191e41d33Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00lr-3537900000-49b81232f1c3420307c2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ar4-3910100000-4ba665d585a66cba6f95Spectrum
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 IDHMDB0039079
FooDB IDFDB018579
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID35014740
ChEBI IDNot Available
PubChem Compound ID131752538
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