Withaperuvin D (CHEM024141)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-25 21:31:25 UTC
Update Date2016-11-09 01:17:50 UTC
Accession NumberCHEM024141
Identification
Common NameWithaperuvin D
ClassSmall Molecule
DescriptionConstituent of leaves of Physalis peruviana (Cape gooseberry). Withaperuvin D is found in fruits.
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
4b,5a,14a,17b,20S-Pentahydroxy-3a,6a-oxido-1-oxo-24-ergosten-26,22R-olideHMDB
Chemical FormulaC28H40O9
Average Molecular Mass520.612 g/mol
Monoisotopic Mass520.267 g/mol
CAS Registry Number87749-17-5
IUPAC Name7-[1-(4,5-dimethyl-6-oxo-3,6-dihydro-2H-pyran-2-yl)-1-hydroxyethyl]-4,7,16,17-tetrahydroxy-8,12-dimethyl-18-oxapentacyclo[13.2.1.0³,¹¹.0⁴,⁸.0¹²,¹⁷]octadecan-13-one
Traditional Name7-[1-(4,5-dimethyl-6-oxo-2,3-dihydropyran-2-yl)-1-hydroxyethyl]-4,7,16,17-tetrahydroxy-8,12-dimethyl-18-oxapentacyclo[13.2.1.0³,¹¹.0⁴,⁸.0¹²,¹⁷]octadecan-13-one
SMILESCC1=C(C)C(=O)OC(C1)C(C)(O)C1(O)CCC2(O)C3CC4OC5CC(=O)C(C)(C3CCC12C)C4(O)C5O
InChI IdentifierInChI=1S/C28H40O9/c1-13-10-19(37-22(31)14(13)2)25(5,32)27(34)9-8-26(33)16-11-20-28(35)21(30)17(36-20)12-18(29)24(28,4)15(16)6-7-23(26,27)3/h15-17,19-21,30,32-35H,6-12H2,1-5H3
InChI KeyDMAZCUJZFYKTRY-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
  • 5-hydroxysteroid
  • Hydroxysteroid
  • Naphthofuran
  • Dihydropyranone
  • Oxepane
  • Pyran
  • Monosaccharide
  • Enoate ester
  • Alpha,beta-unsaturated carboxylic ester
  • Tetrahydrofuran
  • Tertiary alcohol
  • Cyclic alcohol
  • Secondary alcohol
  • Carboxylic acid ester
  • Ketone
  • Lactone
  • Organoheterocyclic compound
  • Oxacycle
  • Carboxylic acid derivative
  • Polyol
  • Dialkyl ether
  • Ether
  • Monocarboxylic acid or derivatives
  • Alcohol
  • Organic oxygen compound
  • Organic oxide
  • Organooxygen compound
  • Hydrocarbon derivative
  • Carbonyl group
  • 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 Solubility1.35 g/LALOGPS
logP0.62ALOGPS
logP0.7ChemAxon
logS-2.6ALOGPS
pKa (Strongest Acidic)12.12ChemAxon
pKa (Strongest Basic)-3.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area153.75 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity129.89 m³·mol⁻¹ChemAxon
Polarizability54.94 ųChemAxon
Number of Rings6ChemAxon
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, Positivesplash10-0zfv-4279130000-aa7bfd361599ba23dc1bSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-0f7d-6140629000-55bb8423303c12a0ac15Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0uk9-0003390000-31b34b905d9d29c831c9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-9224540000-7b9d408036a102b7d3a7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0uy0-6069100000-7c4b896e06f4c92be4a4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-016r-0103590000-f80f26b2f869dda95007Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0gb9-1906120000-f6877ea6c94139ee6da9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014i-9404000000-f2cee4f61b39c3ba53d1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0000290000-da0a7f19c69082fea3d4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00c0-7009450000-f42d9d4b0119736e95faSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00b9-5439000000-f033b3872b97504a992cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0002190000-06511588915f6f24691cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-016r-2109040000-a2b7bf519fbdcf2dcdc9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0gdl-9402000000-f2cf24fe86542434e36eSpectrum
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 IDHMDB0030116
FooDB IDFDB001917
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 ID131750960
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