(4beta,5beta,6beta,14beta,15alpha,20S,22R)-5,6-Epoxy-4,14,15-trihydroxy-1-oxowitha-2,24-dienolide (CHEM027439)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-25 23:44:23 UTC
Update Date2016-11-09 01:18:27 UTC
Accession NumberCHEM027439
Identification
Common Name(4beta,5beta,6beta,14beta,15alpha,20S,22R)-5,6-Epoxy-4,14,15-trihydroxy-1-oxowitha-2,24-dienolide
ClassSmall Molecule
DescriptionConstituent of Physalis peruviana (Cape gooseberry). (4beta,5beta,6beta,14beta,15alpha,20S,22R)-5,6-Epoxy-4,14,15-trihydroxy-1-oxowitha-2,24-dienolide is found in fruits.
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(4b,5b,6b,14b,15a,20S,22R)-5,6-Epoxy-4,14,15-trihydroxy-1-oxowitha-2,24-dienolideGenerator
(4Β,5β,6β,14β,15α,20S,22R)-5,6-epoxy-4,14,15-trihydroxy-1-oxowitha-2,24-dienolideGenerator
Chemical FormulaC28H38O7
Average Molecular Mass486.597 g/mol
Monoisotopic Mass486.262 g/mol
CAS Registry Number222609-98-5
IUPAC Name15-[1-(4,5-dimethyl-6-oxo-3,6-dihydro-2H-pyran-2-yl)ethyl]-6,12,13-trihydroxy-2,16-dimethyl-8-oxapentacyclo[9.7.0.0²,⁷.0⁷,⁹.0¹²,¹⁶]octadec-4-en-3-one
Traditional Name15-[1-(4,5-dimethyl-6-oxo-2,3-dihydropyran-2-yl)ethyl]-6,12,13-trihydroxy-2,16-dimethyl-8-oxapentacyclo[9.7.0.0²,⁷.0⁷,⁹.0¹²,¹⁶]octadec-4-en-3-one
SMILESCC(C1CC(O)C2(O)C3CC4OC44C(O)C=CC(=O)C4(C)C3CCC12C)C1CC(C)=C(C)C(=O)O1
InChI IdentifierInChI=1S/C28H38O7/c1-13-10-19(34-24(32)14(13)2)15(3)17-11-22(31)27(33)18-12-23-28(35-23)21(30)7-6-20(29)26(28,5)16(18)8-9-25(17,27)4/h6-7,15-19,21-23,30-31,33H,8-12H2,1-5H3
InChI KeyTUSMTCBTWSKFRH-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 Solubility0.12 g/LALOGPS
logP1.4ALOGPS
logP2.71ChemAxon
logS-3.6ALOGPS
pKa (Strongest Acidic)13.02ChemAxon
pKa (Strongest Basic)-3.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area116.59 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity128.23 m³·mol⁻¹ChemAxon
Polarizability53.19 ųChemAxon
Number of Rings6ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0aou-4263900000-38cf9c7012660bb1f9e9Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-016r-7300749000-4e7ba32977dee5b64ad5Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00kr-0001900000-69a116c484807d687d2dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0gi0-3208900000-1995a2e3dca31c74edd2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0uxr-9408400000-2f02cbacb00bdae20c56Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0000900000-1aa2597f3d278d1b5fb5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00ku-0001900000-95a43aa6a06319ba2084Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014i-9104300000-d22b35a1b0db6a22c37cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0000900000-95a4713a20806de36744Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0007900000-b3954081d52544adb10dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-008d-2109500000-df36d0f8c80fc1bcaefcSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0502900000-626bf87810b62ac3a3d9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-02wm-5309500000-cc39fd4776675b1926ffSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-017i-5927000000-c99425d66e6168c3f096Spectrum
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 IDHMDB0033199
FooDB IDFDB011211
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 ID78384890
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