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Record Information
Version2.0
Created at2022-09-06 13:32:25 UTC
Updated at2022-09-06 13:32:25 UTC
NP-MRD IDNP0232334
Secondary Accession NumbersNone
Natural Product Identification
Common Name(1r,2s,3as,3br,7s,9ar,9bs,11ar)-3a-hydroxy-9a,11a-dimethyl-1-(6-oxopyran-3-yl)-7-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,2h,3h,3bh,4h,5h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-2-yl acetate
Description16Beta-Acetoxyscillarenin 3-glucoside belongs to the class of organic compounds known as bufanolides and derivatives. These are steroid lactones containing a pyran-2-one moiety linked to the C17 atom of a cyclopenta[a]phenanthrene derivative. (1r,2s,3as,3br,7s,9ar,9bs,11ar)-3a-hydroxy-9a,11a-dimethyl-1-(6-oxopyran-3-yl)-7-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,2h,3h,3bh,4h,5h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-2-yl acetate is found in Drimia maritima. Based on a literature review very few articles have been published on 16beta-Acetoxyscillarenin 3-glucoside.
Structure
Thumb
Synonyms
ValueSource
16b-Acetoxyscillarenin 3-glucosideGenerator
16Β-acetoxyscillarenin 3-glucosideGenerator
Chemical FormulaC32H44O11
Average Mass604.6930 Da
Monoisotopic Mass604.28836 Da
IUPAC Name(1S,2R,5S,10R,11S,13S,14S,15R)-11-hydroxy-2,15-dimethyl-14-(2-oxo-2H-pyran-5-yl)-5-{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-13-yl acetate
Traditional Name(1S,2R,5S,10R,11S,13S,14S,15R)-11-hydroxy-2,15-dimethyl-14-(6-oxopyran-3-yl)-5-{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-13-yl acetate
CAS Registry NumberNot Available
SMILES
CC(=O)O[C@H]1C[C@]2(O)[C@@H]3CCC4=C[C@H](CC[C@]4(C)[C@H]3CC[C@]2(C)[C@H]1C1=COC(=O)C=C1)O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O
InChI Identifier
InChI=1S/C32H44O11/c1-16(34)41-22-13-32(39)21-6-5-18-12-19(42-29-28(38)27(37)26(36)23(14-33)43-29)8-10-30(18,2)20(21)9-11-31(32,3)25(22)17-4-7-24(35)40-15-17/h4,7,12,15,19-23,25-29,33,36-39H,5-6,8-11,13-14H2,1-3H3/t19-,20-,21+,22-,23+,25-,26+,27-,28+,29+,30-,31+,32-/m0/s1
InChI KeyYNJFTCNGKDLURQ-VMOLNVSSSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Drimia maritimaLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as bufanolides and derivatives. These are steroid lactones containing a pyran-2-one moiety linked to the C17 atom of a cyclopenta[a]phenanthrene derivative.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassSteroid lactones
Direct ParentBufanolides and derivatives
Alternative Parents
Substituents
  • Bufanolide-skeleton
  • Steroidal glycoside
  • Steroid ester
  • 14-hydroxysteroid
  • Hydroxysteroid
  • Delta-4-steroid
  • Hexose monosaccharide
  • Glycosyl compound
  • O-glycosyl compound
  • Pyranone
  • Pyran
  • Monosaccharide
  • Oxane
  • Tertiary alcohol
  • Cyclic alcohol
  • Heteroaromatic compound
  • Carboxylic acid ester
  • Secondary alcohol
  • Lactone
  • Acetal
  • Oxacycle
  • Organoheterocyclic compound
  • Carboxylic acid derivative
  • Monocarboxylic acid or derivatives
  • Polyol
  • Hydrocarbon derivative
  • Organic oxide
  • Primary alcohol
  • Alcohol
  • Carbonyl group
  • Organic oxygen compound
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic 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
logP0.32ChemAxon
pKa (Strongest Acidic)12.2ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count9ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area172.21 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity152.3 m³·mol⁻¹ChemAxon
Polarizability64.49 ųChemAxon
Number of Rings6ChemAxon
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 Compound101985989
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. LOTUS database [Link]