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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-11 19:10:25 UTC
Update Date2019-07-23 06:15:50 UTC
HMDB IDHMDB0034353
Secondary Accession Numbers
  • HMDB34353
Metabolite Identification
Common NamePhysalin D
DescriptionPhysalin D belongs to the class of organic compounds known as physalins and derivatives. These are steroidal constituents of Physalis plants which possess an unusual 13,14-seco-16,24-cyclo-steroidal ring skeleton (where the bond that is normally present between the 13 and 14 positions in other steroids is broken while a new bond between positions 16 and 24 is formed). Physalin D is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
Data?1563862550
Synonyms
ValueSource
Physalin DMeSH
Chemical FormulaC28H32O11
Average Molecular Weight544.5471
Monoisotopic Molecular Weight544.194461866
IUPAC Name5,14,15-trihydroxy-2,9,26-trimethyl-3,19,23,28-tetraoxaoctacyclo[16.9.1.1¹⁸,²⁷.0¹,⁵.0²,²⁴.0⁸,¹⁷.0⁹,¹⁴.0²¹,²⁶]nonacos-11-ene-4,10,22,29-tetrone
Traditional Name5,14,15-trihydroxy-2,9,26-trimethyl-3,19,23,28-tetraoxaoctacyclo[16.9.1.1¹⁸,²⁷.0¹,⁵.0²,²⁴.0⁸,¹⁷.0⁹,¹⁴.0²¹,²⁶]nonacos-11-ene-4,10,22,29-tetrone
CAS Registry Number54980-22-2
SMILES
CC12OC(=O)C3(O)CCC4C(CC(O)C5(O)CC=CC(=O)C45C)C45OC13C(C4=O)C1(C)CC2OC(=O)C1CO5
InChI Identifier
InChI=1S/C28H32O11/c1-22-10-17-24(3)28-18(22)19(31)27(39-28,36-11-14(22)20(32)37-17)13-9-16(30)25(34)7-4-5-15(29)23(25,2)12(13)6-8-26(28,35)21(33)38-24/h4-5,12-14,16-18,30,34-35H,6-11H2,1-3H3
InChI KeyDUGJJSWZRHBJJK-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as physalins and derivatives. These are steroidal constituents of Physalis plants which possess an unusual 13,14-seco-16,24-cyclo-steroidal ring skeleton (where the bond that is normally present between the 13 and 14 positions in other steroids is broken while a new bond between positions 16 and 24 is formed).
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassPhysalins and derivatives
Direct ParentPhysalins and derivatives
Alternative Parents
Substituents
  • Physalin skeleton
  • Delta valerolactone
  • Ketal
  • Cyclohexenone
  • Delta_valerolactone
  • Oxepane
  • Dicarboxylic acid or derivatives
  • 3-furanone
  • Gamma butyrolactone
  • Oxane
  • Cyclic alcohol
  • Tetrahydrofuran
  • Tertiary alcohol
  • Lactone
  • Ketone
  • Carboxylic acid ester
  • Secondary alcohol
  • Organoheterocyclic compound
  • Oxacycle
  • Acetal
  • Carboxylic acid derivative
  • Polyol
  • Alcohol
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Carbonyl group
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Biological location:

Source:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point286 - 287 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility3.72 g/LALOGPS
logP0.48ALOGPS
logP0.76ChemAxon
logS-2.2ALOGPS
pKa (Strongest Acidic)9.68ChemAxon
pKa (Strongest Basic)-3.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count9ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area165.89 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity127.74 m³·mol⁻¹ChemAxon
Polarizability52.76 ųChemAxon
Number of Rings8ChemAxon
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, Positivesplash10-0a4i-2290220000-dceaaec5dd10266c6f2fSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-00xr-4160119000-10acd363604d5392f38cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-002b-0000090000-e5d3d8d8767be169be56Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-056s-0100090000-8afd5b1247d6edbe4970Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9301130000-6513dab55db981e13316Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0000290000-9d2b0676b30013a1fbb9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-002g-0000490000-9cb4b27f439019701925Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0avr-4290700000-d776335c2e5a4c0a4b5aSpectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
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 IDFDB012715
KNApSAcK IDNot Available
Chemspider ID381234
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound431071
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.