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Record Information
Version2.0
Created at2022-09-04 10:19:17 UTC
Updated at2022-09-04 10:19:18 UTC
NP-MRD IDNP0192987
Secondary Accession NumbersNone
Natural Product Identification
Common Name3a-hydroxy-7-({3-hydroxy-4-methoxy-6-methyl-5-[(3,4,5-trihydroxy-6-{[(3,4,5,6-tetrahydroxyoxan-2-yl)methoxy]methyl}oxan-2-yl)oxy]oxan-2-yl}oxy)-9a,11a-dimethyl-1-(5-oxo-2h-furan-3-yl)-tetradecahydrocyclopenta[a]phenanthren-2-yl acetate
Description11-Hydroxy-5-({3-hydroxy-4-methoxy-6-methyl-5-[(3,4,5-trihydroxy-6-{[(3,4,5,6-tetrahydroxyoxan-2-yl)methoxy]methyl}oxan-2-yl)oxy]oxan-2-yl}oxy)-2,15-dimethyl-14-(5-oxo-2,5-dihydrofuran-3-yl)tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]Heptadecan-13-yl acetate belongs to the class of organic compounds known as cardenolide glycosides and derivatives. Cardenolide glycosides and derivatives are compounds containing a carbohydrate glycosidically bound to the cardenolide moiety. 3a-hydroxy-7-({3-hydroxy-4-methoxy-6-methyl-5-[(3,4,5-trihydroxy-6-{[(3,4,5,6-tetrahydroxyoxan-2-yl)methoxy]methyl}oxan-2-yl)oxy]oxan-2-yl}oxy)-9a,11a-dimethyl-1-(5-oxo-2h-furan-3-yl)-tetradecahydrocyclopenta[a]phenanthren-2-yl acetate is found in Adenium obesum. 11-Hydroxy-5-({3-hydroxy-4-methoxy-6-methyl-5-[(3,4,5-trihydroxy-6-{[(3,4,5,6-tetrahydroxyoxan-2-yl)methoxy]methyl}oxan-2-yl)oxy]oxan-2-yl}oxy)-2,15-dimethyl-14-(5-oxo-2,5-dihydrofuran-3-yl)tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]Heptadecan-13-yl acetate is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
Thumb
Synonyms
ValueSource
11-Hydroxy-5-({3-hydroxy-4-methoxy-6-methyl-5-[(3,4,5-trihydroxy-6-{[(3,4,5,6-tetrahydroxyoxan-2-yl)methoxy]methyl}oxan-2-yl)oxy]oxan-2-yl}oxy)-2,15-dimethyl-14-(5-oxo-2,5-dihydrofuran-3-yl)tetracyclo[8.7.0.0,.0,]heptadecan-13-yl acetic acidGenerator
11-Hydroxy-5-({3-hydroxy-4-methoxy-6-methyl-5-[(3,4,5-trihydroxy-6-{[(3,4,5,6-tetrahydroxyoxan-2-yl)methoxy]methyl}oxan-2-yl)oxy]oxan-2-yl}oxy)-2,15-dimethyl-14-(5-oxo-2,5-dihydrofuran-3-yl)tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-13-yl acetic acidGenerator
Chemical FormulaC44H68O20
Average Mass917.0080 Da
Monoisotopic Mass916.43039 Da
IUPAC Name11-hydroxy-5-({3-hydroxy-4-methoxy-6-methyl-5-[(3,4,5-trihydroxy-6-{[(3,4,5,6-tetrahydroxyoxan-2-yl)methoxy]methyl}oxan-2-yl)oxy]oxan-2-yl}oxy)-2,15-dimethyl-14-(5-oxo-2,5-dihydrofuran-3-yl)tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-13-yl acetate
Traditional Name11-hydroxy-5-({3-hydroxy-4-methoxy-6-methyl-5-[(3,4,5-trihydroxy-6-{[(3,4,5,6-tetrahydroxyoxan-2-yl)methoxy]methyl}oxan-2-yl)oxy]oxan-2-yl}oxy)-2,15-dimethyl-14-(5-oxo-2H-furan-3-yl)tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-13-yl acetate
CAS Registry NumberNot Available
SMILES
COC1C(O)C(OC2CCC3(C)C(CCC4C3CCC3(C)C(C(CC43O)OC(C)=O)C3=CC(=O)OC3)C2)OC(C)C1OC1OC(COCC2OC(O)C(O)C(O)C2O)C(O)C(O)C1O
InChI Identifier
InChI=1S/C44H68O20/c1-18-37(64-40-35(52)33(50)31(48)27(63-40)17-57-16-26-30(47)32(49)34(51)39(54)62-26)38(56-5)36(53)41(59-18)61-22-8-10-42(3)21(13-22)6-7-24-23(42)9-11-43(4)29(20-12-28(46)58-15-20)25(60-19(2)45)14-44(24,43)55/h12,18,21-27,29-41,47-55H,6-11,13-17H2,1-5H3
InChI KeyOGMCNHRGUJNQOE-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Adenium obesumLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as cardenolide glycosides and derivatives. Cardenolide glycosides and derivatives are compounds containing a carbohydrate glycosidically bound to the cardenolide moiety.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassSteroid lactones
Direct ParentCardenolide glycosides and derivatives
Alternative Parents
Substituents
  • Cardanolide-glycoside
  • Steroidal glycoside
  • Steroid ester
  • 14-hydroxysteroid
  • Hydroxysteroid
  • Disaccharide
  • Glycosyl compound
  • O-glycosyl compound
  • 2-furanone
  • Dicarboxylic acid or derivatives
  • Oxane
  • Cyclic alcohol
  • Tertiary alcohol
  • Dihydrofuran
  • Alpha,beta-unsaturated carboxylic ester
  • Enoate ester
  • Secondary alcohol
  • Carboxylic acid ester
  • Lactone
  • Hemiacetal
  • Polyol
  • Oxacycle
  • Carboxylic acid derivative
  • Dialkyl ether
  • Organoheterocyclic compound
  • Acetal
  • Ether
  • Organic oxygen compound
  • Organooxygen compound
  • Organic oxide
  • Carbonyl group
  • Alcohol
  • Hydrocarbon derivative
  • 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
logP-0.57ALOGPS
logP-1.5ChemAxon
logS-3.1ALOGPS
pKa (Strongest Acidic)6.82ChemAxon
pKa (Strongest Basic)-3.6ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count18ChemAxon
Hydrogen Donor Count9ChemAxon
Polar Surface Area299.28 ŲChemAxon
Rotatable Bond Count12ChemAxon
Refractivity214.79 m³·mol⁻¹ChemAxon
Polarizability95.05 ųChemAxon
Number of Rings8ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. LOTUS database [Link]