(14alpha,17beta,20S,22R)-14,20-Epoxy-17-hydroxy-1-oxowitha-3,5,24-trienolide (CHEM027024)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-25 23:26:52 UTC
Update Date2016-11-09 01:18:22 UTC
Accession NumberCHEM027024
Identification
Common Name(14alpha,17beta,20S,22R)-14,20-Epoxy-17-hydroxy-1-oxowitha-3,5,24-trienolide
ClassSmall Molecule
DescriptionConstituent of Physalis peruviana (Cape gooseberry). (14alpha,17beta,20S,22R)-14,20-Epoxy-17-hydroxy-1-oxowitha-3,5,24-trienolide is found in fruits.
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(14a,17b,20S,22R)-14,20-Epoxy-17-hydroxy-1-oxowitha-3,5,24-trienolideGenerator
(14Α,17β,20S,22R)-14,20-epoxy-17-hydroxy-1-oxowitha-3,5,24-trienolideGenerator
Chemical FormulaC28H36O5
Average Molecular Mass452.582 g/mol
Monoisotopic Mass452.256 g/mol
CAS Registry NumberNot Available
IUPAC Name16-(4,5-dimethyl-6-oxo-3,6-dihydro-2H-pyran-2-yl)-15-hydroxy-10,14,16-trimethyl-17-oxapentacyclo[13.2.2.0¹,¹⁴.0²,¹¹.0⁵,¹⁰]nonadeca-4,6-dien-9-one
Traditional Name16-(4,5-dimethyl-6-oxo-2,3-dihydropyran-2-yl)-15-hydroxy-10,14,16-trimethyl-17-oxapentacyclo[13.2.2.0¹,¹⁴.0²,¹¹.0⁵,¹⁰]nonadeca-4,6-dien-9-one
SMILESCC1=C(C)C(=O)OC(C1)C1(C)OC23CCC1(O)C2(C)CCC1C3CC=C2C=CCC(=O)C12C
InChI IdentifierInChI=1S/C28H36O5/c1-16-15-22(32-23(30)17(16)2)26(5)28(31)14-13-27(33-26)20-10-9-18-7-6-8-21(29)25(18,4)19(20)11-12-24(27,28)3/h6-7,9,19-20,22,31H,8,10-15H2,1-5H3
InChI KeyKOYNICXFSFFIPU-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as withanolides and derivatives. These are c28 steroids structurally characterized by an ergostane skeleton usually functionalized at carbons 1, 22 and 26 to form a lactone ring.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassSteroid lactones
Direct ParentWithanolides and derivatives
Alternative ParentsNot Available
SubstituentsNot Available
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 Solubility0.0038 g/LALOGPS
logP4.32ALOGPS
logP4.16ChemAxon
logS-5.1ALOGPS
pKa (Strongest Acidic)13.19ChemAxon
pKa (Strongest Basic)-3.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area72.83 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity126.4 m³·mol⁻¹ChemAxon
Polarizability50.6 ųChemAxon
Number of Rings6ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-003i-5893600000-e53d4ccf4fcc74d2a9acSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0a4i-5509350000-b3e360222f23f8242978Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0102900000-ed52c032774b8d3cc85dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-9107400000-84e673e3ace95618e03bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0uyr-9474200000-fbfc8ef57fcafd44cb0cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0002900000-a1a519533d32bcf115c6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0zfr-1003900000-1a7c20ce888212ac3d57Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-02t9-9203000000-aff88b35db039e3664caSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0000900000-159b2996bf6fe76614e4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udr-4338900000-d38aebf7f02d6fec872bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0j4r-4928100000-1bb4260ea21842302f3eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0000900000-169e1b4194a44a788bbaSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0fb9-2109700000-4eae2bb02656d7cd3a69Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0fn9-9300100000-a8985d2a0afcf49ad95bSpectrum
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 IDHMDB0032685
FooDB IDFDB010642
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider IDNot Available
ChEBI IDNot Available
PubChem Compound ID73699089
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