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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-11 18:59:49 UTC
Update Date2019-07-23 06:15:27 UTC
HMDB IDHMDB0034200
Secondary Accession Numbers
  • HMDB34200
Metabolite Identification
Common NamePhysalolactone B
DescriptionPhysalolactone B 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. Thus, physalolactone b is considered to be a sterol lipid molecule. Physalolactone B is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.
Structure
Data?1563862527
SynonymsNot Available
Chemical FormulaC30H44O6
Average Molecular Weight500.6668
Monoisotopic Molecular Weight500.31378914
IUPAC Name14-[1-(4,5-dimethyl-6-oxo-3,6-dihydro-2H-pyran-2-yl)-1-hydroxyethyl]-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-3-yl acetate
Traditional Name14-[1-(4,5-dimethyl-6-oxo-2,3-dihydropyran-2-yl)-1-hydroxyethyl]-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-3-yl acetate
CAS Registry Number78916-78-6
SMILES
CC(=O)OC1CC(O)CC2=CCC3C4CCC(C(C)(O)C5CC(C)=C(C)C(=O)O5)C4(C)CCC3C12C
InChI Identifier
InChI=1S/C30H44O6/c1-16-13-26(36-27(33)17(16)2)30(6,34)24-10-9-22-21-8-7-19-14-20(32)15-25(35-18(3)31)29(19,5)23(21)11-12-28(22,24)4/h7,20-26,32,34H,8-15H2,1-6H3
InChI KeyANGCIHCSPJLGME-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
  • Steroid ester
  • 20-hydroxysteroid
  • 3-hydroxy-delta-5-steroid
  • 3-hydroxysteroid
  • Hydroxysteroid
  • Delta-5-steroid
  • Dihydropyranone
  • Dicarboxylic acid or derivatives
  • Pyran
  • Cyclic alcohol
  • Alpha,beta-unsaturated carboxylic ester
  • Enoate ester
  • Tertiary alcohol
  • Carboxylic acid ester
  • Secondary alcohol
  • Lactone
  • Organoheterocyclic compound
  • Oxacycle
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Carbonyl group
  • Organic oxide
  • Organooxygen compound
  • Alcohol
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Biological location:

Route of exposure:

Source:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point252 - 254 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.004 g/LALOGPS
logP3.69ALOGPS
logP3.79ChemAxon
logS-5.1ALOGPS
pKa (Strongest Acidic)13.76ChemAxon
pKa (Strongest Basic)-2.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area93.06 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity137.64 m³·mol⁻¹ChemAxon
Polarizability56.81 ųChemAxon
Number of Rings5ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-001i-1009500000-cd9bf1a1e2af3848b0faSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-056r-4014988000-f55f18dbf76e3e76fe8aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0f89-0001920000-0e1b2c7b1ae5fafc3442Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014l-4106900000-0624d3853578cea7f745Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0gb9-3039300000-6c97017fac625aae16a7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-052b-0000900000-2879d0cc213f18a1fbe2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0ce9-3526900000-0a156a22058553728722Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-03xr-9401100000-fa76c96298839c97ffbbSpectrum
Biological Properties
Cellular Locations
  • Extracellular
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB012498
KNApSAcK IDNot Available
Chemspider ID26503394
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound53462649
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  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. [PubMed:16902246 ]
  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. [PubMed:17374880 ]
  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. [PubMed:20044567 ]
  5. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
  6. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.