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Record Information
Version2.0
Created at2022-04-28 23:11:33 UTC
Updated at2022-04-28 23:11:33 UTC
NP-MRD IDNP0078057
Secondary Accession NumbersNone
Natural Product Identification
Common Name(+)-Physacoztolide A
Description[(1S,2R,7R,8R,10S,11S,14S,15R)-14-[(1R)-1-[(2R)-4,5-dimethyl-6-oxo-3,6-dihydro-2H-pyran-2-yl]-1-hydroxyethyl]-7,8-dihydroxy-2-methyl-3-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]Heptadec-4-en-15-yl]methyl acetate 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. (+)-Physacoztolide A is found in Physalis coztomatl. Based on a literature review very few articles have been published on [(1S,2R,7R,8R,10S,11S,14S,15R)-14-[(1R)-1-[(2R)-4,5-dimethyl-6-oxo-3,6-dihydro-2H-pyran-2-yl]-1-hydroxyethyl]-7,8-dihydroxy-2-methyl-3-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]Heptadec-4-en-15-yl]methyl acetate.
Structure
Thumb
Synonyms
ValueSource
[(1S,2R,7R,8R,10S,11S,14S,15R)-14-[(1R)-1-[(2R)-4,5-Dimethyl-6-oxo-3,6-dihydro-2H-pyran-2-yl]-1-hydroxyethyl]-7,8-dihydroxy-2-methyl-3-oxotetracyclo[8.7.0.0,.0,]heptadec-4-en-15-yl]methyl acetic acidGenerator
Chemical FormulaC30H42O8
Average Mass530.6580 Da
Monoisotopic Mass530.28797 Da
IUPAC Name[(1S,2R,7R,8R,10S,11S,14S,15R)-14-[(1R)-1-[(2R)-4,5-dimethyl-6-oxo-3,6-dihydro-2H-pyran-2-yl]-1-hydroxyethyl]-7,8-dihydroxy-2-methyl-3-oxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-4-en-15-yl]methyl acetate
Traditional Name[(1S,2R,7R,8R,10S,11S,14S,15R)-14-[(1R)-1-[(2R)-4,5-dimethyl-6-oxo-2,3-dihydropyran-2-yl]-1-hydroxyethyl]-7,8-dihydroxy-2-methyl-3-oxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-4-en-15-yl]methyl acetate
CAS Registry NumberNot Available
SMILES
CC(=O)OC[C@]12CC[C@H]3[C@@H](C[C@@H](O)[C@@]4(O)CC=CC(=O)[C@]34C)[C@@H]1CC[C@@H]2[C@@](C)(O)[C@H]1CC(C)=C(C)C(=O)O1
InChI Identifier
InChI=1S/C30H42O8/c1-16-13-25(38-26(34)17(16)2)28(5,35)22-9-8-21-19-14-24(33)30(36)11-6-7-23(32)27(30,4)20(19)10-12-29(21,22)15-37-18(3)31/h6-7,19-22,24-25,33,35-36H,8-15H2,1-5H3/t19-,20+,21+,22-,24-,25-,27+,28-,29-,30+/m1/s1
InChI KeyHMGBZXCTALYZHS-CDIHKCCFSA-N
Experimental Spectra
Not Available
Predicted Spectra
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Physalis coztomatlPlant
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
  • 20-hydroxysteroid
  • Steroid ester
  • 6-hydroxysteroid
  • 5-hydroxysteroid
  • Hydroxysteroid
  • 1-oxosteroid
  • Oxosteroid
  • Dihydropyranone
  • Cyclohexenone
  • Pyran
  • Dicarboxylic acid or derivatives
  • Alpha,beta-unsaturated carboxylic ester
  • Enoate ester
  • Tertiary alcohol
  • Cyclic alcohol
  • Secondary alcohol
  • Carboxylic acid ester
  • Lactone
  • Ketone
  • Organoheterocyclic compound
  • Oxacycle
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Organic oxygen compound
  • Organic oxide
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External DescriptorsNot Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP2.23ALOGPS
logP2.7ChemAxon
logS-4.2ALOGPS
pKa (Strongest Acidic)13.04ChemAxon
pKa (Strongest Basic)-3.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area130.36 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity140.1 m³·mol⁻¹ChemAxon
Polarizability57.03 ųChemAxon
Number of Rings5ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID10019099
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound11844624
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General ReferencesNot Available