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Record Information
Version2.0
Created at2022-09-06 22:49:36 UTC
Updated at2022-09-06 22:49:36 UTC
NP-MRD IDNP0239264
Secondary Accession NumbersNone
Natural Product Identification
Common Name(1s,2s,3ar,4r,5r,10r,11s,13r,13ar)-4,10,11,13-tetrakis(acetyloxy)-3a-hydroxy-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)-4,6,7,13-tetraacetoxy-5-methylene-13aalpha-hydroxy-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)-4,10,11,13-tetrakis(acetyloxy)-3a-hydroxy-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)-4,6,7,13-tetraacetoxy-5-methylene-13aalpha-hydroxy-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)-4,6,7,13-tetraacetoxy-5-methylene-13aalpha-hydroxy-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)-4,6,7,13-tetraacetoxy-5-methylene-13aalpha-hydroxy-8H-cyclopentacyclododecen-8-oneGenerator
Chemical FormulaC35H44O12
Average Mass656.7250 Da
Monoisotopic Mass656.28328 Da
IUPAC Name(1S,2S,3aR,4R,5R,10R,11S,13R,13aR)-4,10,11,13-tetrakis(acetyloxy)-3a-hydroxy-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)-4,10,11,13-tetrakis(acetyloxy)-3a-hydroxy-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](OC(C)=O)C(=O)C(C)(C)\C=C\[C@@H](C)[C@H]2OC(C)=O
InChI Identifier
InChI=1S/C35H44O12/c1-18-15-16-34(8,9)31(40)30(45-23(6)38)29(44-22(5)37)20(3)28(43-21(4)36)26-27(47-33(41)25-13-11-10-12-14-25)19(2)17-35(26,42)32(18)46-24(7)39/h10-16,18-19,26-30,32,42H,3,17H2,1-2,4-9H3/b16-15+/t18-,19+,26-,27+,28+,29+,30-,32-,35-/m1/s1
InChI KeyRWCCSDWQXFKGJW-LDHUFNJZSA-N
Experimental Spectra
Not Available
Predicted Spectra
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
  • Pentacarboxylic acid or derivatives
  • Benzoate ester
  • Benzoic acid or derivatives
  • Benzoyl
  • Alpha-acyloxy ketone
  • Monocyclic benzene moiety
  • Benzenoid
  • Tertiary alcohol
  • Cyclic alcohol
  • Cyclic ketone
  • Ketone
  • Carboxylic acid ester
  • Carboxylic acid derivative
  • Organooxygen compound
  • Hydrocarbon derivative
  • Carbonyl group
  • Alcohol
  • Organic oxide
  • Organic oxygen compound
  • 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
logP3.96ChemAxon
pKa (Strongest Acidic)13.39ChemAxon
pKa (Strongest Basic)-3.5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area168.8 ŲChemAxon
Rotatable Bond Count11ChemAxon
Refractivity166.03 m³·mol⁻¹ChemAxon
Polarizability66.49 ųChemAxon
Number of Rings3ChemAxon
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 ID8993380
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound10818076
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. LOTUS database [Link]