Np mrd loader

You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on NP-MRD.
Record Information
Version1.0
Created at2021-06-19 17:36:50 UTC
Updated at2021-06-29 23:50:31 UTC
NP-MRD IDNP0025505
Secondary Accession NumbersNone
Natural Product Identification
Common Name21beta-O-benzoylsitakisogenin 3-O-beta-D-glucopyranosyl(1-3)-beta-D-glucu+
Provided ByJEOL DatabaseJEOL Logo
Description 21beta-O-benzoylsitakisogenin 3-O-beta-D-glucopyranosyl(1-3)-beta-D-glucu+ is found in Gymnema sylvestre. It was first documented in 2001 (Ye, W., et al.).
Structure
Thumb
SynonymsNot Available
Chemical FormulaC49H72O16
Average Mass917.0990 Da
Monoisotopic Mass916.48204 Da
IUPAC Name(2R,3R,4R,5S,6S)-6-{[(3S,4aS,6aR,6bS,8S,8aS,10S,12aS,14aR,14bR)-10-(benzoyloxy)-8-hydroxy-8a-(hydroxymethyl)-4,4,6a,6b,11,11,14b-heptamethyl-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,14,14a,14b-icosahydropicen-3-yl]oxy}-3,5-dihydroxy-4-{[(2R,3S,4R,5R,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxane-2-carboxylic acid
Traditional Name(2R,3R,4R,5S,6S)-6-{[(3S,4aS,6aR,6bS,8S,8aS,10S,12aS,14aR,14bR)-10-(benzoyloxy)-8-hydroxy-8a-(hydroxymethyl)-4,4,6a,6b,11,11,14b-heptamethyl-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicen-3-yl]oxy}-3,5-dihydroxy-4-{[(2R,3S,4R,5R,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxane-2-carboxylic acid
CAS Registry NumberNot Available
SMILES
[H]OC(=O)[C@]1([H])O[C@]([H])(O[C@@]2([H])C([H])([H])C([H])([H])[C@@]3(C([H])([H])[H])[C@]([H])(C([H])([H])C([H])([H])[C@]4(C([H])([H])[H])[C@]3([H])C([H])([H])C([H])=C3[C@]5([H])C([H])([H])C(C([H])([H])[H])(C([H])([H])[H])[C@@]([H])(OC(=O)C6=C([H])C([H])=C([H])C([H])=C6[H])C([H])([H])[C@]5(C([H])([H])O[H])[C@@]([H])(O[H])C([H])([H])[C@@]43C([H])([H])[H])C2(C([H])([H])[H])C([H])([H])[H])[C@@]([H])(O[H])[C@]([H])(O[C@@]2([H])O[C@@]([H])(C([H])([H])O[H])[C@]([H])(O[H])[C@@]([H])(O[H])[C@]2([H])O[H])[C@@]1([H])O[H]
InChI Identifier
InChI=1S/C49H72O16/c1-44(2)19-26-25-13-14-29-46(5)17-16-31(63-43-37(57)38(36(56)39(65-43)40(58)59)64-42-35(55)34(54)33(53)27(22-50)61-42)45(3,4)28(46)15-18-47(29,6)48(25,7)20-30(52)49(26,23-51)21-32(44)62-41(60)24-11-9-8-10-12-24/h8-13,26-39,42-43,50-57H,14-23H2,1-7H3,(H,58,59)/t26-,27-,28+,29+,30-,31-,32-,33-,34+,35-,36+,37-,38+,39+,42+,43-,46-,47+,48+,49+/m0/s1
InChI KeyBCXIIRGZVLQKIH-SUZGMMLNSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 500 MHz, C5D5N, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, C5D5N, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 100 MHz, C5D5N, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, C5D5N, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, C5D5N, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, C5D5N, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 300 MHz, C5D5N, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, C5D5N, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, C5D5N, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, C5D5N, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 600 MHz, C5D5N, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, C5D5N, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 700 MHz, C5D5N, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, C5D5N, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 800 MHz, C5D5N, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, C5D5N, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 900 MHz, C5D5N, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, C5D5N, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 1000 MHz, C5D5N, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, C5D5N, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Gymnema sylvestreJEOL database
    • Ye, W., et al, J. Nat. prod. 64, 243 (2001)
Chemical Taxonomy
ClassificationNot classified
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
logP3.26ALOGPS
logP2.93ChemAxon
logS-4.4ALOGPS
pKa (Strongest Acidic)3.44ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count15ChemAxon
Hydrogen Donor Count9ChemAxon
Polar Surface Area262.36 ŲChemAxon
Rotatable Bond Count10ChemAxon
Refractivity231.23 m³·mol⁻¹ChemAxon
Polarizability98.62 ųChemAxon
Number of Rings8ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
External LinksNot Available
References
General References
  1. Ye, W., et al. (2001). Ye, W., et al, J. Nat. prod. 64, 243 (2001). J. Nat. Prod..