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Record Information
Version2.0
Created at2022-04-28 19:03:34 UTC
Updated at2022-04-28 19:03:34 UTC
NP-MRD IDNP0073836
Secondary Accession NumbersNone
Natural Product Identification
Common Name(-)-Bacobitacin B
Description(3E,6R)-6-[(1R,2R,10S,11S,13R,14R,15R)-13-(acetyloxy)-4-hydroxy-1,6,6,11,15-pentamethyl-5,17-dioxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]Heptadeca-3,7-dien-14-yl]-6-hydroxy-2-methyl-5-oxohept-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 B is found in Bacopa monnieri . Based on a literature review very few articles have been published on (3E,6R)-6-[(1R,2R,10S,11S,13R,14R,15R)-13-(acetyloxy)-4-hydroxy-1,6,6,11,15-pentamethyl-5,17-dioxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]Heptadeca-3,7-dien-14-yl]-6-hydroxy-2-methyl-5-oxohept-3-en-2-yl acetate.
Structure
Thumb
Synonyms
ValueSource
(3E,6R)-6-[(1R,2R,10S,11S,13R,14R,15R)-13-(Acetyloxy)-4-hydroxy-1,6,6,11,15-pentamethyl-5,17-dioxotetracyclo[8.7.0.0,.0,]heptadeca-3,7-dien-14-yl]-6-hydroxy-2-methyl-5-oxohept-3-en-2-yl acetic acidGenerator
Chemical FormulaC34H46O9
Average Mass598.7330 Da
Monoisotopic Mass598.31418 Da
IUPAC Name(3E,6R)-6-[(1R,2R,10S,11S,13R,14R,15R)-13-(acetyloxy)-4-hydroxy-1,6,6,11,15-pentamethyl-5,17-dioxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-3,7-dien-14-yl]-6-hydroxy-2-methyl-5-oxohept-3-en-2-yl acetate
Traditional Name(3E,6R)-6-[(1R,2R,10S,11S,13R,14R,15R)-13-(acetyloxy)-4-hydroxy-1,6,6,11,15-pentamethyl-5,17-dioxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-3,7-dien-14-yl]-6-hydroxy-2-methyl-5-oxohept-3-en-2-yl acetate
CAS Registry NumberNot Available
SMILES
CC(=O)O[C@@H]1C[C@@]2(C)[C@@H]3CC=C4[C@@H](C=C(O)C(=O)C4(C)C)[C@]3(C)C(=O)C[C@]2(C)[C@H]1[C@@](C)(O)C(=O)\C=C\C(C)(C)OC(C)=O
InChI Identifier
InChI=1S/C34H46O9/c1-18(35)42-23-16-31(7)24-12-11-20-21(15-22(37)28(40)30(20,5)6)33(24,9)26(39)17-32(31,8)27(23)34(10,41)25(38)13-14-29(3,4)43-19(2)36/h11,13-15,21,23-24,27,37,41H,12,16-17H2,1-10H3/b14-13+/t21-,23-,24+,27+,31+,32-,33+,34+/m1/s1
InChI KeyMJBVHNXBYFMUNE-GDJGQKLVSA-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
  • Cucurbitacin skeleton
  • Triterpenoid
  • 22-oxosteroid
  • 21-oxosteroid
  • Steroid ester
  • 20-hydroxysteroid
  • 3-oxo-delta-1-steroid
  • 3-oxosteroid
  • 14-alpha-methylsteroid
  • Hydroxysteroid
  • 2-hydroxysteroid
  • Oxosteroid
  • 11-oxosteroid
  • Delta-1-steroid
  • Cyclohexenone
  • Dicarboxylic acid or derivatives
  • Acyloin
  • Acryloyl-group
  • Alpha-hydroxy ketone
  • Alpha,beta-unsaturated ketone
  • Tertiary alcohol
  • Enone
  • Cyclic ketone
  • Carboxylic acid ester
  • Ketone
  • Carboxylic acid derivative
  • Enol
  • Organic oxygen compound
  • Carbonyl group
  • Organic oxide
  • Hydrocarbon derivative
  • Alcohol
  • Organooxygen compound
  • 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
logP3.87ALOGPS
logP3.92ChemAxon
logS-5.6ALOGPS
pKa (Strongest Acidic)9.05ChemAxon
pKa (Strongest Basic)-3.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area144.27 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity161.76 m³·mol⁻¹ChemAxon
Polarizability65.04 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 Compound162959463
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General ReferencesNot Available