Apo-9-zeaxanthinone (CHEM023997)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-25 21:25:00 UTC
Update Date2016-11-09 01:17:48 UTC
Accession NumberCHEM023997
Identification
Common NameApo-9-zeaxanthinone
ClassSmall Molecule
DescriptionA beta-ionone compound having an (R)-hydroxy group at the 3-position.
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
3-Hydroxy-b-iononeGenerator
3-Hydroxy-β-iononeGenerator
(3E)-4-(4-Hydroxy-2,6,6-trimethyl-1-cyclohexen-1-yl)-3-buten-2-oneHMDB
(3E)-4-[(4R)-4-Hydroxy-2,6,6-trimethyl-1-cyclohexen-1-yl]-3-buten-2-oneHMDB
(3R)-3-Hydroxy-beta-iononeHMDB
(3R)-3-Hydroxy-β-iononeHMDB
(R)-(-)-3-Hydroxy-beta-iononeHMDB
(R)-(-)-3-Hydroxy-β-iononeHMDB
(R)-3-Hydroxy-beta-iononeHMDB
(R)-3-Hydroxy-β-iononeHMDB
3beta-Hydroxymegastigma-5,7-dien-9-oneHMDB
3Β-hydroxymegastigma-5,7-dien-9-oneHMDB
Apo-9-zeaxanthinoneHMDB
3-Hydroxy-beta-iononeHMDB
Chemical FormulaC13H20O2
Average Molecular Mass208.297 g/mol
Monoisotopic Mass208.146 g/mol
CAS Registry Number50281-38-4
IUPAC Name(3E)-4-[(4R)-4-hydroxy-2,6,6-trimethylcyclohex-1-en-1-yl]but-3-en-2-one
Traditional Name(3R)-hydroxy-β-ionone
SMILESO[C@@H]1CC(C)=C(\C=C\C(C)=O)C(C)(C)C1
InChI IdentifierInChI=1S/C13H20O2/c1-9-7-11(15)8-13(3,4)12(9)6-5-10(2)14/h5-6,11,15H,7-8H2,1-4H3/b6-5+/t11-/m1/s1
InChI KeyHFRZSVYKDDZRQY-MVIFTORASA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassSesquiterpenoids
Direct ParentSesquiterpenoids
Alternative Parents
Substituents
  • Sesquiterpenoid
  • Megastigmane sesquiterpenoid
  • Cyclofarsesane sesquiterpenoid
  • Ionone derivative
  • Acryloyl-group
  • Enone
  • Alpha,beta-unsaturated ketone
  • Secondary alcohol
  • Ketone
  • Organic oxygen compound
  • Organooxygen compound
  • Alcohol
  • Carbonyl group
  • Organic oxide
  • Hydrocarbon derivative
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External Descriptors
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 Solubility0.73 g/LALOGPS
logP2.1ALOGPS
logP1.89ChemAxon
logS-2.5ALOGPS
pKa (Strongest Acidic)18.91ChemAxon
pKa (Strongest Basic)-1.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity63.49 m³·mol⁻¹ChemAxon
Polarizability24.05 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
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, Positivesplash10-052f-0920000000-ca4bc2d8536a477454bdSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-006x-1910000000-0800f9d35f89acbe6784Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0kft-6900000000-561c8ee7b8326d943c55Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0390000000-4dfd440e0b9531f8a757Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4r-1960000000-fd1b133f482bc7573abeSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-01ox-2900000000-04eff6259412f3590dafSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0090000000-43a9bdbf7663e467c30dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4s-0940000000-e8333249a633e6a768b9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0002-1900000000-31fb706dd6e842a6860aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4r-1930000000-362c8ff12dca214674b5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0abc-4900000000-3c361104d4dd0ac028bdSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9800000000-626f2e38ffe2cc811bbeSpectrum
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 IDHMDB0036821
FooDB IDFDB001764
Phenol Explorer IDNot Available
KNApSAcK IDC00022191
BiGG IDNot Available
BioCyc IDCPD-7200
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID9302625
ChEBI ID53173
PubChem Compound ID11127505
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=12509521
2. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9.
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.
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.
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.
6. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.
7. The lipid handbook with CD-ROM