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Record Information
Version3.6
Creation Date2012-09-11 19:08:46 UTC
Update Date2016-02-11 02:26:21 UTC
HMDB IDHMDB34333
Secondary Accession NumbersNone
Metabolite Identification
Common NamePhysalolactone
DescriptionPhysalolactone is found in fruits. Physalolactone is a constituent of Physalis peruviana (Cape gooseberry). Physalolactone belongs to the family of 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.
Structure
Thumb
Synonyms
ValueSource
6a-chloro-4b,5,14,17b,20S-Pentahydroxy-1-oxo-5b,22R-witha-2,24-dienolideHMDB
Chemical FormulaC28H39ClO8
Average Molecular Weight539.057
Monoisotopic Molecular Weight538.233345931
IUPAC Name6-(1-{8-chloro-6,7,11,14-tetrahydroxy-2,15-dimethyl-3-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-4-en-14-yl}-1-hydroxyethyl)-3,4-dimethyl-5,6-dihydro-2H-pyran-2-one
Traditional Name6-(1-{8-chloro-6,7,11,14-tetrahydroxy-2,15-dimethyl-3-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-4-en-14-yl}-1-hydroxyethyl)-3,4-dimethyl-5,6-dihydropyran-2-one
CAS Registry Number71339-25-8
SMILES
CC1=C(C)C(=O)OC(C1)C(C)(O)C1(O)CCC2(O)C3CC(Cl)C4(O)C(O)C=CC(=O)C4(C)C3CCC12C
InChI Identifier
InChI=1/C28H39ClO8/c1-14-12-21(37-22(32)15(14)2)25(5,33)27(35)11-10-26(34)17-13-18(29)28(36)20(31)7-6-19(30)24(28,4)16(17)8-9-23(26,27)3/h6-7,16-18,20-21,31,33-36H,8-13H2,1-5H3
InChI KeyInChIKey=XCJUXWOCLLPHII-UHFFFAOYNA-N
Chemical Taxonomy
DescriptionThis compound 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
  • 17-hydroxysteroid
  • Oxosteroid
  • 1-oxosteroid
  • Hydroxysteroid
  • 5-hydroxysteroid
  • 4-hydroxysteroid
  • Halo-steroid
  • 6-halo-steroid
  • Dihydropyranone
  • Pyran
  • Alpha,beta-unsaturated carboxylic ester
  • Enoate ester
  • Tertiary alcohol
  • Cyclic alcohol
  • Secondary alcohol
  • Polyol
  • Lactone
  • Ketone
  • Halohydrin
  • Chlorohydrin
  • Carboxylic acid ester
  • 1,2-diol
  • Oxacycle
  • Organoheterocyclic compound
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organochloride
  • Organohalogen compound
  • Carbonyl group
  • Alkyl halide
  • Alkyl chloride
  • Alcohol
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
StatusExpected but not Quantified
Origin
  • Endogenous
  • Food
Biofunction
  • Cell signaling
  • Fuel and energy storage
  • Fuel or energy source
  • Membrane integrity/stability
  • Nutrient
Application
  • Nutrient
  • Stabilizers
  • Surfactants and Emulsifiers
Cellular locations
  • Extracellular
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting Point227 - 228 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.21 mg/mLALOGPS
logP1.53ALOGPS
logP1.97ChemAxon
logS-3.4ALOGPS
pKa (Strongest Acidic)12.21ChemAxon
pKa (Strongest Basic)-3.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area144.52 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity136.18 m3·mol-1ChemAxon
Polarizability56.2 Å3ChemAxon
Number of Rings5ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Extracellular
Biofluid LocationsNot Available
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB012692
KNApSAcK IDNot Available
Chemspider ID383693
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB34333
Metagene LinkHMDB34333
METLIN IDNot Available
PubChem Compound433866
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.