(5alpha,6beta,14alpha,20R,22R)-5,6,14,20,27-Pentahydroxy-1-oxowith-24-enolide (CHEM027438)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-25 23:44:21 UTC
Update Date2016-11-09 01:18:27 UTC
Accession NumberCHEM027438
Identification
Common Name(5alpha,6beta,14alpha,20R,22R)-5,6,14,20,27-Pentahydroxy-1-oxowith-24-enolide
ClassSmall Molecule
DescriptionConstituent of Physalis peruviana (Cape gooseberry). (5alpha,6beta,14alpha,20R,22R)-5,6,14,20,27-Pentahydroxy-1-oxowith-24-enolide is found in fruits.
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(5a,6b,14a,20R,22R)-5,6,14,20,27-Pentahydroxy-1-oxowith-24-enolideGenerator
(5Α,6β,14α,20R,22R)-5,6,14,20,27-pentahydroxy-1-oxowith-24-enolideGenerator
Chemical FormulaC28H42O8
Average Molecular Mass506.628 g/mol
Monoisotopic Mass506.288 g/mol
CAS Registry Number222609-97-4
IUPAC Name6-(1-hydroxy-1-{7,8,11-trihydroxy-2,15-dimethyl-3-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl}ethyl)-3-(hydroxymethyl)-4-methyl-5,6-dihydro-2H-pyran-2-one
Traditional Name6-(1-hydroxy-1-{7,8,11-trihydroxy-2,15-dimethyl-3-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl}ethyl)-3-(hydroxymethyl)-4-methyl-5,6-dihydropyran-2-one
SMILESCC1=C(CO)C(=O)OC(C1)C(C)(O)C1CCC2(O)C3CC(O)C4(O)CCCC(=O)C4(C)C3CCC12C
InChI IdentifierInChI=1S/C28H42O8/c1-15-12-22(36-23(32)16(15)14-29)26(4,33)19-8-11-27(34)18-13-21(31)28(35)9-5-6-20(30)25(28,3)17(18)7-10-24(19,27)2/h17-19,21-22,29,31,33-35H,5-14H2,1-4H3
InChI KeyAYSGOPOJGPEGSU-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 Solubility0.44 g/LALOGPS
logP1.4ALOGPS
logP1.18ChemAxon
logS-3.1ALOGPS
pKa (Strongest Acidic)13.07ChemAxon
pKa (Strongest Basic)-2.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area144.52 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity131.31 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, Positivesplash10-002r-1246900000-9b83d706ba13049f34e7Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-0079-2243419000-56842deecb780fba4f2dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0079-0001920000-a97e8a0ae06c93eb9086Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-05fr-2124900000-e53bd18dae7d0bd7c684Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-007p-9137500000-29936e31d1747660a44aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0002970000-35ce10a76bc9045f0551Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0zor-0608910000-127a8851953f382b7752Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001r-9302000000-c80b1af715f919ea3d81Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0000390000-1f00086190caef706c1cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a6u-1203910000-abc9a4684b146453ca01Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014i-9700810000-49785d57e2a489ae9504Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4r-0000970000-8de23dbacd6b265cfb77Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00kb-8905000000-9a55c16b4438fbcaca8aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0095-7924000000-5937c4a4c056d0b539d1Spectrum
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 IDHMDB0033198
FooDB IDFDB011210
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 ID78385401
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