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Record Information
Version2.0
Created at2022-09-03 20:02:48 UTC
Updated at2022-09-03 20:02:48 UTC
NP-MRD IDNP0181518
Secondary Accession NumbersNone
Natural Product Identification
Common Name15-[4-(acetyloxy)-5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-6-({4,5-dihydroxy-3-[(3,4,5-trihydroxyoxan-2-yl)oxy]oxan-2-yl}oxy)-9-hydroxy-7,7,12,16-tetramethylpentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecan-14-yl 2-hydroxyacetate
Description15-[4-(Acetyloxy)-5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-6-({4,5-dihydroxy-3-[(3,4,5-trihydroxyoxan-2-yl)oxy]oxan-2-yl}oxy)-9-hydroxy-7,7,12,16-tetramethylpentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]Octadecan-14-yl 2-hydroxyacetate belongs to the class of organic compounds known as cucurbitacin glycosides. These are polycyclic compounds containing a carbohydrate derivative glycosidically linked to a curcubitane nucleus. 15-[4-(acetyloxy)-5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-6-({4,5-dihydroxy-3-[(3,4,5-trihydroxyoxan-2-yl)oxy]oxan-2-yl}oxy)-9-hydroxy-7,7,12,16-tetramethylpentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecan-14-yl 2-hydroxyacetate is found in Astragalus pendulus. 15-[4-(Acetyloxy)-5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-6-({4,5-dihydroxy-3-[(3,4,5-trihydroxyoxan-2-yl)oxy]oxan-2-yl}oxy)-9-hydroxy-7,7,12,16-tetramethylpentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]Octadecan-14-yl 2-hydroxyacetate is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
Thumb
Synonyms
ValueSource
15-[4-(Acetyloxy)-5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-6-({4,5-dihydroxy-3-[(3,4,5-trihydroxyoxan-2-yl)oxy]oxan-2-yl}oxy)-9-hydroxy-7,7,12,16-tetramethylpentacyclo[9.7.0.0,.0,.0,]octadecan-14-yl 2-hydroxyacetic acidGenerator
15-[4-(Acetyloxy)-5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-6-({4,5-dihydroxy-3-[(3,4,5-trihydroxyoxan-2-yl)oxy]oxan-2-yl}oxy)-9-hydroxy-7,7,12,16-tetramethylpentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecan-14-yl 2-hydroxyacetic acidGenerator
Chemical FormulaC44H70O17
Average Mass871.0270 Da
Monoisotopic Mass870.46130 Da
IUPAC Name15-[4-(acetyloxy)-5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-6-({4,5-dihydroxy-3-[(3,4,5-trihydroxyoxan-2-yl)oxy]oxan-2-yl}oxy)-9-hydroxy-7,7,12,16-tetramethylpentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecan-14-yl 2-hydroxyacetate
Traditional Name15-[4-(acetyloxy)-5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-6-({4,5-dihydroxy-3-[(3,4,5-trihydroxyoxan-2-yl)oxy]oxan-2-yl}oxy)-9-hydroxy-7,7,12,16-tetramethylpentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecan-14-yl 2-hydroxyacetate
CAS Registry NumberNot Available
SMILES
CC(=O)OC1CC(C)(OC1C(C)(C)O)C1C(CC2(C)C3CC(O)C4C5(CC35CCC12C)CCC(OC1OCC(O)C(O)C1OC1OCC(O)C(O)C1O)C4(C)C)OC(=O)CO
InChI Identifier
InChI=1S/C44H70O17/c1-20(46)57-25-15-42(8,61-35(25)39(4,5)54)34-24(58-28(50)16-45)14-41(7)26-13-21(47)33-38(2,3)27(9-10-44(33)19-43(26,44)12-11-40(34,41)6)59-37-32(30(52)23(49)18-56-37)60-36-31(53)29(51)22(48)17-55-36/h21-27,29-37,45,47-49,51-54H,9-19H2,1-8H3
InChI KeyYLAGFDBJODXZKF-UHFFFAOYSA-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
Astragalus pendulusLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as cucurbitacin glycosides. These are polycyclic compounds containing a carbohydrate derivative glycosidically linked to a curcubitane nucleus.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassSteroidal glycosides
Direct ParentCucurbitacin glycosides
Alternative Parents
Substituents
  • Cucurbitacin glycoside skeleton
  • Triterpene saponin
  • Triterpene glycoside
  • Cycloartanol-skeleton
  • 9b,19-cyclo-lanostane-skeleton
  • Cycloartane-skeleton
  • Triterpenoid
  • Steroid ester
  • 6-hydroxysteroid
  • Hydroxysteroid
  • C-glycosyl compound
  • Disaccharide
  • Glycosyl compound
  • O-glycosyl compound
  • Dicarboxylic acid or derivatives
  • Oxane
  • Tertiary alcohol
  • Cyclic alcohol
  • Tetrahydrofuran
  • Carboxylic acid ester
  • Secondary alcohol
  • Polyol
  • Organoheterocyclic compound
  • Carboxylic acid derivative
  • Acetal
  • Oxacycle
  • Dialkyl ether
  • Ether
  • Organic oxygen compound
  • Organooxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Carbonyl group
  • Primary alcohol
  • 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
logP0.79ALOGPS
logP-0.76ChemAxon
logS-3.8ALOGPS
pKa (Strongest Acidic)12.1ChemAxon
pKa (Strongest Basic)-2.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count15ChemAxon
Hydrogen Donor Count8ChemAxon
Polar Surface Area260.59 ŲChemAxon
Rotatable Bond Count11ChemAxon
Refractivity209.94 m³·mol⁻¹ChemAxon
Polarizability93.98 ųChemAxon
Number of Rings8ChemAxon
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 CompoundNot Available
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. LOTUS database [Link]