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Record Information
Version2.0
Created at2022-04-28 19:03:30 UTC
Updated at2022-04-28 19:03:30 UTC
NP-MRD IDNP0073835
Secondary Accession NumbersNone
Natural Product Identification
Common Name(-)-Bacobitacin A
Description(3E,6R)-6-hydroxy-2-methyl-5-oxo-6-[(1S,2R,9R,10S,11S,13R,14R,15R)-4,9,13-trihydroxy-1,6,6,11,15-pentamethyl-5,17-dioxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]Heptadeca-3,7-dien-14-yl]hept-3-en-2-yl acetate belongs to the class of organic compounds known as cucurbitacins. These are polycyclic compounds containing the tetracyclic cucurbitane nucleus skeleton, 19-(10->9b)-abeo-10alanost-5-ene (also known as 9b-methyl-19-nor lanosta-5-ene), with a variety of oxygenation functionalities at different positions. (-)-Bacobitacin A is found in Bacopa monnieri . Based on a literature review very few articles have been published on (3E,6R)-6-hydroxy-2-methyl-5-oxo-6-[(1S,2R,9R,10S,11S,13R,14R,15R)-4,9,13-trihydroxy-1,6,6,11,15-pentamethyl-5,17-dioxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]Heptadeca-3,7-dien-14-yl]hept-3-en-2-yl acetate.
Structure
Thumb
Synonyms
ValueSource
(3E,6R)-6-Hydroxy-2-methyl-5-oxo-6-[(1S,2R,9R,10S,11S,13R,14R,15R)-4,9,13-trihydroxy-1,6,6,11,15-pentamethyl-5,17-dioxotetracyclo[8.7.0.0,.0,]heptadeca-3,7-dien-14-yl]hept-3-en-2-yl acetic acidGenerator
Chemical FormulaC32H44O9
Average Mass572.6950 Da
Monoisotopic Mass572.29853 Da
IUPAC Name(3E,6R)-6-hydroxy-2-methyl-5-oxo-6-[(1S,2R,9R,10S,11S,13R,14R,15R)-4,9,13-trihydroxy-1,6,6,11,15-pentamethyl-5,17-dioxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-3,7-dien-14-yl]hept-3-en-2-yl acetate
Traditional Name(3E,6R)-6-hydroxy-2-methyl-5-oxo-6-[(1S,2R,9R,10S,11S,13R,14R,15R)-4,9,13-trihydroxy-1,6,6,11,15-pentamethyl-5,17-dioxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-3,7-dien-14-yl]hept-3-en-2-yl acetate
CAS Registry NumberNot Available
SMILES
CC(=O)OC(C)(C)\C=C\C(=O)[C@](C)(O)[C@H]1[C@H](O)C[C@@]2(C)[C@@H]3[C@H](O)C=C4[C@@H](C=C(O)C(=O)C4(C)C)[C@]3(C)C(=O)C[C@]12C
InChI Identifier
InChI=1S/C32H44O9/c1-16(33)41-27(2,3)11-10-22(37)32(9,40)25-21(36)14-29(6)24-19(34)12-17-18(13-20(35)26(39)28(17,4)5)31(24,8)23(38)15-30(25,29)7/h10-13,18-19,21,24-25,34-36,40H,14-15H2,1-9H3/b11-10+/t18-,19-,21-,24+,25+,29+,30-,31-,32+/m1/s1
InChI KeySGUCHYFOTGXDTG-DOFUNFASSA-N
Experimental Spectra
Not Available
Predicted Spectra
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Bacopa monnieriPlant
Chemical Taxonomy
Description Belongs to the class of organic compounds known as cucurbitacins. These are polycyclic compounds containing the tetracyclic cucurbitane nucleus skeleton, 19-(10->9b)-abeo-10alanost-5-ene (also known as 9b-methyl-19-nor lanosta-5-ene), with a variety of oxygenation functionalities at different positions.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassCucurbitacins
Direct ParentCucurbitacins
Alternative Parents
Substituents
  • Triterpenoid
  • Cucurbitacin skeleton
  • 22-oxosteroid
  • 21-oxosteroid
  • Steroid ester
  • 20-hydroxysteroid
  • 14-alpha-methylsteroid
  • 7-hydroxysteroid
  • 16-hydroxysteroid
  • 16-alpha-hydroxysteroid
  • Oxosteroid
  • 11-oxosteroid
  • Hydroxysteroid
  • 2-hydroxysteroid
  • 3-oxosteroid
  • 3-oxo-delta-1-steroid
  • Delta-1-steroid
  • Cyclohexenone
  • Acyloin
  • Alpha,beta-unsaturated ketone
  • Tertiary alcohol
  • Enone
  • Cyclic alcohol
  • Alpha-hydroxy ketone
  • Acryloyl-group
  • Cyclic ketone
  • Secondary alcohol
  • Ketone
  • Carboxylic acid ester
  • Polyol
  • Monocarboxylic acid or derivatives
  • Enol
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic 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
logP2.77ALOGPS
logP2.33ChemAxon
logS-4.6ALOGPS
pKa (Strongest Acidic)9.02ChemAxon
pKa (Strongest Basic)-2.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area158.43 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity154.05 m³·mol⁻¹ChemAxon
Polarizability61.15 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
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 Compound162982404
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References