Withaperuvin C (CHEM028193)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 00:16:58 UTC
Update Date2016-11-09 01:18:38 UTC
Accession NumberCHEM028193
Identification
Common NameWithaperuvin C
ClassSmall Molecule
DescriptionConstituent of Physalis peruviana (Cape gooseberry). Withaperuvin C is found in fruits.
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(20S,22R)-6b,14,17b,20-Tetrahydroxy-1-oxowitha-2,4,24-trienolideHMDB
Chemical FormulaC28H38O7
Average Molecular Mass486.597 g/mol
Monoisotopic Mass486.262 g/mol
CAS Registry Number81644-34-0
IUPAC Name6-(1-hydroxy-1-{8,11,14-trihydroxy-2,15-dimethyl-3-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-4,6-dien-14-yl}ethyl)-3,4-dimethyl-5,6-dihydro-2H-pyran-2-one
Traditional Name6-(1-hydroxy-1-{8,11,14-trihydroxy-2,15-dimethyl-3-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-4,6-dien-14-yl}ethyl)-3,4-dimethyl-5,6-dihydropyran-2-one
SMILESCC1=C(C)C(=O)OC(C1)C(C)(O)C1(O)CCC2(O)C3CC(O)C4=CC=CC(=O)C4(C)C3CCC12C
InChI IdentifierInChI=1S/C28H38O7/c1-15-13-22(35-23(31)16(15)2)26(5,32)28(34)12-11-27(33)19-14-20(29)18-7-6-8-21(30)25(18,4)17(19)9-10-24(27,28)3/h6-8,17,19-20,22,29,32-34H,9-14H2,1-5H3
InChI KeyIBJZGHYOMSKIJB-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
  • 14-hydroxysteroid
  • 6-hydroxysteroid
  • Hydroxysteroid
  • 1-oxosteroid
  • Oxosteroid
  • 17-hydroxysteroid
  • Dihydropyranone
  • Pyran
  • Alpha,beta-unsaturated carboxylic ester
  • Tertiary alcohol
  • Enoate ester
  • Cyclic alcohol
  • Secondary alcohol
  • Carboxylic acid ester
  • Ketone
  • Lactone
  • Organoheterocyclic compound
  • Oxacycle
  • Polyol
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Carbonyl group
  • Alcohol
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organooxygen 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 Solubility0.16 g/LALOGPS
logP2.05ALOGPS
logP2.13ChemAxon
logS-3.5ALOGPS
pKa (Strongest Acidic)12.71ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area124.29 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity131.4 m³·mol⁻¹ChemAxon
Polarizability52.38 ųChemAxon
Number of Rings5ChemAxon
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, Positivesplash10-014i-1869500000-e6697ee296d52b1e5430Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-0670-3861439000-7651394e50c35034e1e8Spectrum
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, Positivesplash10-014i-0002900000-c8896799c1f73fde6f84Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0uxs-7143900000-c2244274f02e8ee8e7baSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0gi0-6192100000-f0ab2326eb5e9ed07153Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000l-0102900000-19bc2465752873f11abdSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-1934300000-d5cf35ef77882d2d730aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014i-9304000000-f93d45ebde033e9eaea0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0004900000-93cad0428936e7c16476Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0297-2029500000-c5b2e434e0ece58a6aeeSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0fr6-9400100000-c3cb9bdd02b85a6e0c79Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00kr-0000900000-cd03a1d0fe92d8f79f86Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0f9w-8209200000-270b9ca2d5a0ef3d1eb0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ug0-1923000000-fffa3514f64f0ad5412eSpectrum
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 IDHMDB0034077
FooDB IDFDB012336
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 ID14860927
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