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Record Information
Version2.0
Created at2022-09-04 11:24:05 UTC
Updated at2022-09-04 11:24:05 UTC
NP-MRD IDNP0193844
Secondary Accession NumbersNone
Natural Product Identification
Common Name[(3as,4as,8r,8as,10r)-4a,8,10-trihydroxy-1-isopropyl-3a-methyl-5-methylidene-2-oxo-3h,4h,6h,7h,8h,9h,10h-cyclohexa[f]azulen-8a-yl]methyl acetate
Description[(3AS,4aS,8R,8aS,10R)-4a,8,10-trihydroxy-3a-methyl-5-methylidene-2-oxo-1-(propan-2-yl)-2H,3H,3aH,4H,4aH,5H,6H,7H,8H,8aH,9H,10H-cyclohexa[f]azulen-8a-yl]methyl acetate belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units. [(3as,4as,8r,8as,10r)-4a,8,10-trihydroxy-1-isopropyl-3a-methyl-5-methylidene-2-oxo-3h,4h,6h,7h,8h,9h,10h-cyclohexa[f]azulen-8a-yl]methyl acetate is found in Dictyota dichotoma. Based on a literature review very few articles have been published on [(3aS,4aS,8R,8aS,10R)-4a,8,10-trihydroxy-3a-methyl-5-methylidene-2-oxo-1-(propan-2-yl)-2H,3H,3aH,4H,4aH,5H,6H,7H,8H,8aH,9H,10H-cyclohexa[f]azulen-8a-yl]methyl acetate.
Structure
Thumb
Synonyms
ValueSource
[(3AS,4as,8R,8as,10R)-4a,8,10-trihydroxy-3a-methyl-5-methylidene-2-oxo-1-(propan-2-yl)-2H,3H,3ah,4H,4ah,5H,6H,7H,8H,8ah,9H,10H-cyclohexa[F]azulen-8a-yl]methyl acetic acidGenerator
Chemical FormulaC22H32O6
Average Mass392.4920 Da
Monoisotopic Mass392.21989 Da
IUPAC Name[(3aS,4aS,8R,8aS,10R)-4a,8,10-trihydroxy-3a-methyl-5-methylidene-2-oxo-1-(propan-2-yl)-2H,3H,3aH,4H,4aH,5H,6H,7H,8H,8aH,9H,10H-cyclohexa[f]azulen-8a-yl]methyl acetate
Traditional Name[(3aS,4aS,8R,8aS,10R)-4a,8,10-trihydroxy-1-isopropyl-3a-methyl-5-methylidene-2-oxo-3H,4H,6H,7H,8H,9H,10H-cyclohexa[f]azulen-8a-yl]methyl acetate
CAS Registry NumberNot Available
SMILES
CC(C)C1=C2[C@H](O)C[C@]3(COC(C)=O)[C@H](O)CCC(=C)[C@@]3(O)C[C@@]2(C)CC1=O
InChI Identifier
InChI=1S/C22H32O6/c1-12(2)18-15(24)8-20(5)10-22(27)13(3)6-7-17(26)21(22,11-28-14(4)23)9-16(25)19(18)20/h12,16-17,25-27H,3,6-11H2,1-2,4-5H3/t16-,17-,20-,21+,22+/m1/s1
InChI KeyWEVXQFIRFPWFGR-SRBMLKMVSA-N
Experimental Spectra
Not Available
Predicted Spectra
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Dictyota dichotomaLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassDiterpenoids
Direct ParentDiterpenoids
Alternative Parents
Substituents
  • Diterpenoid
  • Dolastane diterpenoid
  • Cyclic alcohol
  • Tertiary alcohol
  • Carboxylic acid ester
  • Ketone
  • Secondary alcohol
  • Cyclic ketone
  • Monocarboxylic acid or derivatives
  • Polyol
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Alcohol
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic 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
logP0.8ChemAxon
pKa (Strongest Acidic)13.56ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area104.06 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity104.18 m³·mol⁻¹ChemAxon
Polarizability42.36 ųChemAxon
Number of Rings3ChemAxon
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 ID29213295
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound162809563
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. LOTUS database [Link]