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Record Information
Version1.0
Created at2022-09-12 02:24:04 UTC
Updated at2022-09-12 02:24:05 UTC
NP-MRD IDNP0323156
Secondary Accession NumbersNone
Natural Product Identification
Common Name(2r,3r,4s,5s,6r)-2-{[(1s,2r,4as,5r,8ar)-2-hydroxy-1,4a-dimethyl-5-[(3e)-3-methyl-5-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}pent-3-en-1-yl]-6-methylidene-hexahydro-2h-naphthalen-1-yl]methoxy}-6-(hydroxymethyl)oxane-3,4,5-triol
Description(2R,3R,4S,5S,6R)-2-{[(2E)-5-[(1R,4aR,5S,6R,8aS)-6-hydroxy-5,8a-dimethyl-2-methylidene-5-({[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)-decahydronaphthalen-1-yl]-3-methylpent-2-en-1-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol belongs to the class of organic compounds known as diterpene glycosides. These are diterpenoids in which an isoprene unit is glycosylated. (2r,3r,4s,5s,6r)-2-{[(1s,2r,4as,5r,8ar)-2-hydroxy-1,4a-dimethyl-5-[(3e)-3-methyl-5-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}pent-3-en-1-yl]-6-methylidene-hexahydro-2h-naphthalen-1-yl]methoxy}-6-(hydroxymethyl)oxane-3,4,5-triol is found in Rubus chingii. Based on a literature review very few articles have been published on (2R,3R,4S,5S,6R)-2-{[(2E)-5-[(1R,4aR,5S,6R,8aS)-6-hydroxy-5,8a-dimethyl-2-methylidene-5-({[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)-decahydronaphthalen-1-yl]-3-methylpent-2-en-1-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol.
Structure
Thumb
SynonymsNot Available
Chemical FormulaC32H54O13
Average Mass646.7710 Da
Monoisotopic Mass646.35644 Da
IUPAC Name(2R,3R,4S,5S,6R)-2-{[(1S,2R,4aS,5R,8aR)-2-hydroxy-1,4a-dimethyl-5-[(3E)-3-methyl-5-{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}pent-3-en-1-yl]-6-methylidene-decahydronaphthalen-1-yl]methoxy}-6-(hydroxymethyl)oxane-3,4,5-triol
Traditional Name(2R,3R,4S,5S,6R)-2-{[(1S,2R,4aS,5R,8aR)-2-hydroxy-1,4a-dimethyl-5-[(3E)-3-methyl-5-{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}pent-3-en-1-yl]-6-methylidene-hexahydro-2H-naphthalen-1-yl]methoxy}-6-(hydroxymethyl)oxane-3,4,5-triol
CAS Registry NumberNot Available
SMILES
C\C(CC[C@@H]1C(=C)CC[C@H]2[C@@](C)(CO[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)[C@H](O)CC[C@@]12C)=C/CO[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O
InChI Identifier
InChI=1S/C32H54O13/c1-16(10-12-42-29-27(40)25(38)23(36)19(13-33)44-29)5-7-18-17(2)6-8-21-31(18,3)11-9-22(35)32(21,4)15-43-30-28(41)26(39)24(37)20(14-34)45-30/h10,18-30,33-41H,2,5-9,11-15H2,1,3-4H3/b16-10+/t18-,19-,20-,21-,22-,23-,24-,25+,26+,27-,28-,29-,30-,31+,32-/m1/s1
InChI KeyQIOMMMCQFIBVKA-NARXWROJSA-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
Rubus chingiiLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as diterpene glycosides. These are diterpenoids in which an isoprene unit is glycosylated.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassTerpene glycosides
Direct ParentDiterpene glycosides
Alternative Parents
Substituents
  • Diterpene glycoside
  • Diterpenoid
  • Labdane diterpenoid
  • Fatty acyl glycoside of mono- or disaccharide
  • Fatty acyl glycoside
  • Alkyl glycoside
  • O-glycosyl compound
  • Glycosyl compound
  • Fatty acyl
  • Oxane
  • Monosaccharide
  • Cyclic alcohol
  • Secondary alcohol
  • Oxacycle
  • Organoheterocyclic compound
  • Polyol
  • Acetal
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Primary alcohol
  • Organooxygen compound
  • 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-0.89ChemAxon
pKa (Strongest Acidic)11.91ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count13ChemAxon
Hydrogen Donor Count9ChemAxon
Polar Surface Area218.99 ŲChemAxon
Rotatable Bond Count11ChemAxon
Refractivity160.17 m³·mol⁻¹ChemAxon
Polarizability68.75 ųChemAxon
Number of Rings4ChemAxon
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 Compound162970281
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. LOTUS database [Link]