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Record Information
Version2.0
Created at2022-09-10 00:15:56 UTC
Updated at2022-09-10 00:15:56 UTC
NP-MRD IDNP0292642
Secondary Accession NumbersNone
Natural Product Identification
Common Name(1r,2r,5s,6s,7r,10r,11s,15r,18r)-5-acetyl-6,15,18-trihydroxy-12,12-dimethyl-9,17-dioxapentacyclo[8.5.3.0¹,¹¹.0²,⁷.0⁷,¹⁸]octadecan-8-one
Description(1R,2R,5S,6S,7R,10R,11S,15R,18R)-5-acetyl-6,15,18-trihydroxy-12,12-dimethyl-9,17-dioxapentacyclo[8.5.3.0¹,¹¹.0²,⁷.0⁷,¹⁸]Octadecan-8-one belongs to the class of organic compounds known as diterpene lactones. These are diterpenoids containing a lactone moiety. (1r,2r,5s,6s,7r,10r,11s,15r,18r)-5-acetyl-6,15,18-trihydroxy-12,12-dimethyl-9,17-dioxapentacyclo[8.5.3.0¹,¹¹.0²,⁷.0⁷,¹⁸]octadecan-8-one is found in Isodon rubescens. Based on a literature review very few articles have been published on (1R,2R,5S,6S,7R,10R,11S,15R,18R)-5-acetyl-6,15,18-trihydroxy-12,12-dimethyl-9,17-dioxapentacyclo[8.5.3.0¹,¹¹.0²,⁷.0⁷,¹⁸]Octadecan-8-one.
Structure
Thumb
SynonymsNot Available
Chemical FormulaC20H28O7
Average Mass380.4370 Da
Monoisotopic Mass380.18350 Da
IUPAC Name(1R,2R,5S,6S,7R,10R,11S,15R,18R)-5-acetyl-6,15,18-trihydroxy-12,12-dimethyl-9,17-dioxapentacyclo[8.5.3.0^{1,11}.0^{2,7}.0^{7,18}]octadecan-8-one
Traditional Name(1R,2R,5S,6S,7R,10R,11S,15R,18R)-5-acetyl-6,15,18-trihydroxy-12,12-dimethyl-9,17-dioxapentacyclo[8.5.3.0^{1,11}.0^{2,7}.0^{7,18}]octadecan-8-one
CAS Registry NumberNot Available
SMILES
CC(=O)[C@H]1CC[C@H]2[C@]3([C@H]1O)C(=O)O[C@@H]1[C@H]4C(C)(C)CC[C@@H](O)[C@]24CO[C@]31O
InChI Identifier
InChI=1S/C20H28O7/c1-9(21)10-4-5-11-18-8-26-20(25)15(27-16(24)19(11,20)14(10)23)13(18)17(2,3)7-6-12(18)22/h10-15,22-23,25H,4-8H2,1-3H3/t10-,11-,12-,13+,14+,15-,18+,19+,20+/m1/s1
InChI KeyGYOGRQYLXXCRLH-IBFSYLBISA-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
Isodon rubescensLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as diterpene lactones. These are diterpenoids containing a lactone moiety.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassTerpene lactones
Direct ParentDiterpene lactones
Alternative Parents
Substituents
  • Diterpene lactone
  • Diterpenoid
  • Kaurane diterpenoid
  • Furopyran
  • Caprolactone
  • Oxepane
  • Pyran
  • Gamma butyrolactone
  • Oxane
  • Cyclic alcohol
  • Furan
  • Tetrahydrofuran
  • Carboxylic acid ester
  • Secondary alcohol
  • Hemiacetal
  • Ketone
  • Lactone
  • Polyol
  • Organoheterocyclic compound
  • Oxacycle
  • Carboxylic acid derivative
  • Monocarboxylic acid or derivatives
  • Hydrocarbon derivative
  • Organic oxide
  • Alcohol
  • Organic oxygen compound
  • Carbonyl group
  • 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
logP0.42ChemAxon
pKa (Strongest Acidic)10.41ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area113.29 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity92 m³·mol⁻¹ChemAxon
Polarizability38.54 ųChemAxon
Number of Rings5ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
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 Compound162961532
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. LOTUS database [Link]