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Record Information
Version1.0
Created at2022-09-12 17:03:44 UTC
Updated at2022-09-12 17:03:44 UTC
NP-MRD IDNP0331074
Secondary Accession NumbersNone
Natural Product Identification
Common Name5-[(1s,3as,3br,5ar,7s,9as,9bs,11ar)-7-{[(2r,3r,4r,5r,6r)-3,4-dihydroxy-6-methyl-5-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-3a-hydroxy-9a,11a-dimethyl-tetradecahydrocyclopenta[a]phenanthren-1-yl]-3h-furan-2-one
Description5-[(1S,2S,5S,7R,10R,11S,14S,15R)-5-{[(2R,3R,4R,5R,6R)-3,4-dihydroxy-6-methyl-5-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-11-hydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]Heptadecan-14-yl]-2,3-dihydrofuran-2-one 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. 5-[(1s,3as,3br,5ar,7s,9as,9bs,11ar)-7-{[(2r,3r,4r,5r,6r)-3,4-dihydroxy-6-methyl-5-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-3a-hydroxy-9a,11a-dimethyl-tetradecahydrocyclopenta[a]phenanthren-1-yl]-3h-furan-2-one is found in Digitalis lanata. Based on a literature review very few articles have been published on 5-[(1S,2S,5S,7R,10R,11S,14S,15R)-5-{[(2R,3R,4R,5R,6R)-3,4-dihydroxy-6-methyl-5-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-11-hydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]Heptadecan-14-yl]-2,3-dihydrofuran-2-one.
Structure
Thumb
SynonymsNot Available
Chemical FormulaC35H54O13
Average Mass682.8040 Da
Monoisotopic Mass682.35644 Da
IUPAC Name5-[(1S,2S,5S,7R,10R,11S,14S,15R)-5-{[(2R,3R,4R,5R,6R)-3,4-dihydroxy-6-methyl-5-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-11-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]-2,3-dihydrofuran-2-one
Traditional Name5-[(1S,2S,5S,7R,10R,11S,14S,15R)-5-{[(2R,3R,4R,5R,6R)-3,4-dihydroxy-6-methyl-5-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-11-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]-3H-furan-2-one
CAS Registry NumberNot Available
SMILES
C[C@H]1O[C@@H](O[C@H]2CC[C@@]3(C)[C@H](CC[C@@H]4[C@@H]3CC[C@]3(C)[C@H](CC[C@]43O)C3=CCC(=O)O3)C2)[C@H](O)[C@@H](O)[C@H]1O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O
InChI Identifier
InChI=1S/C35H54O13/c1-16-30(48-32-28(41)26(39)25(38)23(15-36)47-32)27(40)29(42)31(44-16)45-18-8-11-33(2)17(14-18)4-5-20-19(33)9-12-34(3)21(10-13-35(20,34)43)22-6-7-24(37)46-22/h6,16-21,23,25-32,36,38-43H,4-5,7-15H2,1-3H3/t16-,17-,18+,19+,20-,21-,23-,25-,26+,27-,28-,29-,30+,31+,32+,33+,34-,35+/m1/s1
InChI KeyHXGILYGLDFFZPW-DFJCFYETSA-N
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Digitalis lanataLOTUS 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
  • 14-hydroxysteroid
  • Hydroxysteroid
  • Disaccharide
  • Glycosyl compound
  • O-glycosyl compound
  • 2-furanone
  • Oxane
  • Cyclic alcohol
  • Dihydrofuran
  • Tertiary alcohol
  • Enol ester
  • Carboxylic acid ester
  • Secondary alcohol
  • Lactone
  • Polyol
  • Organoheterocyclic compound
  • Oxacycle
  • Acetal
  • Carboxylic acid derivative
  • Monocarboxylic acid or derivatives
  • Primary alcohol
  • Alcohol
  • Hydrocarbon derivative
  • Carbonyl group
  • Organic oxide
  • Organic oxygen compound
  • Organooxygen compound
  • 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
logP0.18ChemAxon
pKa (Strongest Acidic)11.94ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count12ChemAxon
Hydrogen Donor Count7ChemAxon
Polar Surface Area204.83 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity167.46 m³·mol⁻¹ChemAxon
Polarizability73.13 ųChemAxon
Number of Rings7ChemAxon
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 Compound163024049
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. LOTUS database [Link]