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Record Information
Version2.0
Created at2022-09-12 02:06:28 UTC
Updated at2022-09-12 02:06:28 UTC
NP-MRD IDNP0322981
Secondary Accession NumbersNone
Natural Product Identification
Common Name[(1r,3ar,5as,7s,9ar,9br,11ar)-3a-hydroxy-11a-methyl-1-(5-oxo-2h-furan-3-yl)-7-{[(2s,3s,5s)-2,3,4,5-tetrahydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,2h,3h,5h,5ah,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-9a-yl]methyl acetate
Description[(1R,2R,5S,7S,11R,14R,15R)-11-hydroxy-15-methyl-14-(5-oxo-2,5-dihydrofuran-3-yl)-5-{[(2S,3S,5S)-2,3,4,5-tetrahydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]Heptadec-9-en-2-yl]methyl acetate belongs to the class of organic compounds known as steroidal glycosides. These are sterol lipids containing a carbohydrate moiety glycosidically linked to the steroid skeleton. [(1r,3ar,5as,7s,9ar,9br,11ar)-3a-hydroxy-11a-methyl-1-(5-oxo-2h-furan-3-yl)-7-{[(2s,3s,5s)-2,3,4,5-tetrahydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,2h,3h,5h,5ah,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-9a-yl]methyl acetate is found in Gomphocarpus sinaicus. Based on a literature review very few articles have been published on [(1R,2R,5S,7S,11R,14R,15R)-11-hydroxy-15-methyl-14-(5-oxo-2,5-dihydrofuran-3-yl)-5-{[(2S,3S,5S)-2,3,4,5-tetrahydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]Heptadec-9-en-2-yl]methyl acetate.
Structure
Thumb
Synonyms
ValueSource
[(1R,2R,5S,7S,11R,14R,15R)-11-Hydroxy-15-methyl-14-(5-oxo-2,5-dihydrofuran-3-yl)-5-{[(2S,3S,5S)-2,3,4,5-tetrahydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}tetracyclo[8.7.0.0,.0,]heptadec-9-en-2-yl]methyl acetic acidGenerator
Chemical FormulaC31H44O12
Average Mass608.6810 Da
Monoisotopic Mass608.28328 Da
IUPAC Name[(1R,2R,5S,7S,11R,14R,15R)-11-hydroxy-15-methyl-14-(5-oxo-2,5-dihydrofuran-3-yl)-5-{[(2S,3S,5S)-2,3,4,5-tetrahydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-9-en-2-yl]methyl acetate
Traditional Name[(1R,2R,5S,7S,11R,14R,15R)-11-hydroxy-15-methyl-14-(5-oxo-2H-furan-3-yl)-5-{[(2S,3S,5S)-2,3,4,5-tetrahydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-9-en-2-yl]methyl acetate
CAS Registry NumberNot Available
SMILES
CC(=O)OC[C@]12CC[C@@H](C[C@@H]1CC=C1[C@@H]2CC[C@]2(C)[C@H](CC[C@]12O)C1=CC(=O)OC1)O[C@]1(O)OC(CO)[C@@H](O)C(O)[C@@H]1O
InChI Identifier
InChI=1S/C31H44O12/c1-16(33)41-15-29-9-5-19(42-31(39)27(37)26(36)25(35)23(13-32)43-31)12-18(29)3-4-22-21(29)6-8-28(2)20(7-10-30(22,28)38)17-11-24(34)40-14-17/h4,11,18-21,23,25-27,32,35-39H,3,5-10,12-15H2,1-2H3/t18-,19-,20+,21-,23?,25+,26?,27-,28+,29+,30-,31-/m0/s1
InChI KeyZYRPJCLYYOJFPF-LCAZPICKSA-N
Experimental Spectra
Not Available
Predicted Spectra
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Gomphocarpus sinaicusLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as steroidal glycosides. These are sterol lipids containing a carbohydrate moiety glycosidically linked to the steroid skeleton.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassSteroidal glycosides
Direct ParentSteroidal glycosides
Alternative Parents
Substituents
  • Steroidal glycoside
  • Steroid lactone
  • Androstane-skeleton
  • Hydroxysteroid
  • 14-hydroxysteroid
  • Delta-7-steroid
  • Hexose monosaccharide
  • Oxane
  • Monosaccharide
  • Dicarboxylic acid or derivatives
  • 2-furanone
  • Alpha,beta-unsaturated carboxylic ester
  • Enoate ester
  • Tertiary alcohol
  • Dihydrofuran
  • Cyclic alcohol
  • Secondary alcohol
  • Orthocarboxylic acid derivative
  • Lactone
  • Carboxylic acid ester
  • Oxacycle
  • Organoheterocyclic compound
  • Polyol
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Primary alcohol
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • 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-0.25ChemAxon
pKa (Strongest Acidic)7.18ChemAxon
pKa (Strongest Basic)-0.11ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count10ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area192.44 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity150.1 m³·mol⁻¹ChemAxon
Polarizability62.97 ųChemAxon
Number of Rings6ChemAxon
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 Compound162817529
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. LOTUS database [Link]