Np mrd loader

Record Information
Version2.0
Created at2022-09-05 17:07:57 UTC
Updated at2022-09-05 17:07:57 UTC
NP-MRD IDNP0216960
Secondary Accession NumbersNone
Natural Product Identification
Common Name(1s,2s,3ar,4r,5r,10r,11s,13r,13ar)-11,13-bis(acetyloxy)-3a,4,10-trihydroxy-2,5,8,8-tetramethyl-12-methylidene-9-oxo-1h,2h,3h,4h,5h,10h,11h,13h,13ah-cyclopenta[12]annulen-1-yl benzoate
Description(2S,4R,6S,7R,10E,12R,13R)-1,2,3,3abeta,4,5,6,7,9,12,13,13a-Dodecahydro-2alpha,9,9,12-tetramethyl-3alpha-(benzoyloxy)-4,6-diacetoxy-5-methylene-7,13,13aalpha-trihydroxy-8H-cyclopentacyclododecen-8-one belongs to the class of organic compounds known as jatrophane and cyclojatrophane diterpenoids. These are diterpenoids with a structure based on the jatrophane or the 9,13-jatrophane skeleton. Jatrophane can be derived from casbane by 6,10-cyclization and opening of the cyclopropane. Cyclojatrophane diterpenoids are based on the 9,13-cyclization of the jatrophane skeleton yields the 9,13-cyclojatrophane skeleton. (1s,2s,3ar,4r,5r,10r,11s,13r,13ar)-11,13-bis(acetyloxy)-3a,4,10-trihydroxy-2,5,8,8-tetramethyl-12-methylidene-9-oxo-1h,2h,3h,4h,5h,10h,11h,13h,13ah-cyclopenta[12]annulen-1-yl benzoate is found in Euphorbia hyberna. Based on a literature review very few articles have been published on (2S,4R,6S,7R,10E,12R,13R)-1,2,3,3abeta,4,5,6,7,9,12,13,13a-Dodecahydro-2alpha,9,9,12-tetramethyl-3alpha-(benzoyloxy)-4,6-diacetoxy-5-methylene-7,13,13aalpha-trihydroxy-8H-cyclopentacyclododecen-8-one.
Structure
Thumb
Synonyms
ValueSource
(2S,4R,6S,7R,10E,12R,13R)-1,2,3,3Abeta,4,5,6,7,9,12,13,13a-dodecahydro-2a,9,9,12-tetramethyl-3a-(benzoyloxy)-4,6-diacetoxy-5-methylene-7,13,13aalpha-trihydroxy-8H-cyclopentacyclododecen-8-oneGenerator
(2S,4R,6S,7R,10E,12R,13R)-1,2,3,3Abeta,4,5,6,7,9,12,13,13a-dodecahydro-2α,9,9,12-tetramethyl-3α-(benzoyloxy)-4,6-diacetoxy-5-methylene-7,13,13aalpha-trihydroxy-8H-cyclopentacyclododecen-8-oneGenerator
Chemical FormulaC31H40O10
Average Mass572.6510 Da
Monoisotopic Mass572.26215 Da
IUPAC Name(1S,2S,3aR,4R,5R,10R,11S,13R,13aR)-11,13-bis(acetyloxy)-3a,4,10-trihydroxy-2,5,8,8-tetramethyl-12-methylidene-9-oxo-1H,2H,3H,3aH,4H,5H,8H,9H,10H,11H,12H,13H,13aH-cyclopenta[12]annulen-1-yl benzoate
Traditional Name(1S,2S,3aR,4R,5R,10R,11S,13R,13aR)-11,13-bis(acetyloxy)-3a,4,10-trihydroxy-2,5,8,8-tetramethyl-12-methylidene-9-oxo-1H,2H,3H,4H,5H,10H,11H,13H,13aH-cyclopenta[12]annulen-1-yl benzoate
CAS Registry NumberNot Available
SMILES
C[C@H]1C[C@@]2(O)[C@H]([C@H]1OC(=O)C1=CC=CC=C1)[C@@H](OC(C)=O)C(=C)[C@H](OC(C)=O)[C@@H](O)C(=O)C(C)(C)\C=C\[C@@H](C)[C@H]2O
InChI Identifier
InChI=1S/C31H40O10/c1-16-13-14-30(6,7)28(36)23(34)26(40-20(5)33)18(3)25(39-19(4)32)22-24(17(2)15-31(22,38)27(16)35)41-29(37)21-11-9-8-10-12-21/h8-14,16-17,22-27,34-35,38H,3,15H2,1-2,4-7H3/b14-13+/t16-,17+,22-,23-,24+,25+,26+,27-,31-/m1/s1
InChI KeyRCIQJDCADVYGLY-MFHFMUCMSA-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
Euphorbia hybernaLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as jatrophane and cyclojatrophane diterpenoids. These are diterpenoids with a structure based on the jatrophane or the 9,13-jatrophane skeleton. Jatrophane can be derived from casbane by 6,10-cyclization and opening of the cyclopropane. Cyclojatrophane diterpenoids are based on the 9,13-cyclization of the jatrophane skeleton yields the 9,13-cyclojatrophane skeleton.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassDiterpenoids
Direct ParentJatrophane and cyclojatrophane diterpenoids
Alternative Parents
Substituents
  • Jatrophane diterpenoid
  • Benzoate ester
  • Benzoic acid or derivatives
  • Tricarboxylic acid or derivatives
  • Benzoyl
  • Benzenoid
  • Monocyclic benzene moiety
  • Tertiary alcohol
  • Cyclic alcohol
  • Secondary alcohol
  • Cyclic ketone
  • Ketone
  • Carboxylic acid ester
  • Polyol
  • Carboxylic acid derivative
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Organic oxide
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Aromatic homopolycyclic compound
Molecular FrameworkAromatic homopolycyclic 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
logP3.08ChemAxon
pKa (Strongest Acidic)12.26ChemAxon
pKa (Strongest Basic)-3.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area156.66 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity147.73 m³·mol⁻¹ChemAxon
Polarizability58.7 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
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 ID8778549
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound10603181
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. LOTUS database [Link]