Physalolactone C (CHEM024167)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-25 21:32:20 UTC
Update Date2016-11-09 01:17:50 UTC
Accession NumberCHEM024167
Identification
Common NamePhysalolactone C
ClassSmall Molecule
DescriptionConstituent of Physalis peruviana (Cape gooseberry). Physalolactone C is found in fruits.
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
Physalis peruviana extractsHMDB
Chemical FormulaC28H37ClO7
Average Molecular Mass521.042 g/mol
Monoisotopic Mass520.223 g/mol
CAS Registry Number92594-02-0
IUPAC Name6-(1-{8-chloro-6,7,14-trihydroxy-2,15-dimethyl-3-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-4,11-dien-14-yl}-1-hydroxyethyl)-3,4-dimethyl-5,6-dihydro-2H-pyran-2-one
Traditional Name6-(1-{8-chloro-6,7,14-trihydroxy-2,15-dimethyl-3-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-4,11-dien-14-yl}-1-hydroxyethyl)-3,4-dimethyl-5,6-dihydropyran-2-one
SMILESCC1=C(C)C(=O)OC(C1)C(C)(O)C1(O)CC=C2C3CC(Cl)C4(O)C(O)C=CC(=O)C4(C)C3CCC12C
InChI IdentifierInChI=1S/C28H37ClO7/c1-14-12-22(36-23(32)15(14)2)26(5,33)27(34)11-9-17-16-13-19(29)28(35)21(31)7-6-20(30)25(28,4)18(16)8-10-24(17,27)3/h6-7,9,16,18-19,21-22,31,33-35H,8,10-13H2,1-5H3
InChI KeyBSLUVQZIEQFEOT-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 Parents
Substituents
  • Withanolide-skeleton
  • 20-hydroxysteroid
  • 6-halo-steroid
  • Halo-steroid
  • 4-hydroxysteroid
  • 5-hydroxysteroid
  • Hydroxysteroid
  • 17-hydroxysteroid
  • 1-oxosteroid
  • Oxosteroid
  • Dihydropyranone
  • Cyclohexenone
  • Pyran
  • Cyclic alcohol
  • Alpha,beta-unsaturated carboxylic ester
  • Enoate ester
  • Tertiary alcohol
  • Secondary alcohol
  • Lactone
  • Ketone
  • Carboxylic acid ester
  • Halohydrin
  • Chlorohydrin
  • Polyol
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Organoheterocyclic compound
  • Oxacycle
  • Organochloride
  • Organic oxide
  • Organic oxygen compound
  • Alcohol
  • Hydrocarbon derivative
  • Alkyl chloride
  • Carbonyl group
  • Organooxygen compound
  • Alkyl halide
  • Organohalogen compound
  • 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 Solubility0.081 g/LALOGPS
logP2.6ALOGPS
logP2.64ChemAxon
logS-3.8ALOGPS
pKa (Strongest Acidic)12.21ChemAxon
pKa (Strongest Basic)-3.5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area124.29 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity135.58 m³·mol⁻¹ChemAxon
Polarizability55.14 ųChemAxon
Number of Rings5ChemAxon
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, Positivesplash10-05mt-3819620000-1d6fd5ddc53275eeb6f9Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-0c0a-8421619000-c9c3c6da39d87bf02994Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0fk9-0003390000-2ca9454fa041a41e9e43Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0uxr-9117530000-df931d4a4ea7658e9df2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-1000-4539010000-2418823cb6ec83595663Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0104690000-fb4a50128a62d9ff1bc6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0gb9-1906120000-f893c58104637b4c3e88Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014i-9303000000-605d758316bf4edac963Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0201590000-7a8dc62ee4502864f300Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0ke9-9107430000-1e89c85732d499a0a62bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-016r-2961000000-65b9b89e07fffa0ec88eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0002190000-58faca645a002adc4a95Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00lr-8009120000-bfa84398b118240e6918Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0frx-9404000000-ed88e1eac41e3882c67cSpectrum
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 IDHMDB0030142
FooDB IDFDB001949
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID26503909
ChEBI IDNot Available
PubChem Compound ID53463094
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