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Record Information
Version1.0
Created at2022-09-05 22:25:48 UTC
Updated at2022-09-05 22:25:48 UTC
NP-MRD IDNP0220975
Secondary Accession NumbersNone
Natural Product Identification
Common Name[(1r,3s,4r,6r,10s)-3-hydroxy-12,12-dimethyl-9-methylidene-5-oxatricyclo[8.2.0.0⁴,⁶]dodecan-4-yl]methyl (2z)-2-methylbut-2-enoate
Description[(1R,3S,4R,6R,10S)-3-hydroxy-12,12-dimethyl-9-methylidene-5-oxatricyclo[8.2.0.0⁴,⁶]Dodecan-4-yl]methyl (2Z)-2-methylbut-2-enoate belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. [(1r,3s,4r,6r,10s)-3-hydroxy-12,12-dimethyl-9-methylidene-5-oxatricyclo[8.2.0.0⁴,⁶]dodecan-4-yl]methyl (2z)-2-methylbut-2-enoate is found in Polyachyrus fuscus. Based on a literature review very few articles have been published on [(1R,3S,4R,6R,10S)-3-hydroxy-12,12-dimethyl-9-methylidene-5-oxatricyclo[8.2.0.0⁴,⁶]Dodecan-4-yl]methyl (2Z)-2-methylbut-2-enoate.
Structure
Thumb
Synonyms
ValueSource
[(1R,3S,4R,6R,10S)-3-Hydroxy-12,12-dimethyl-9-methylidene-5-oxatricyclo[8.2.0.0,]dodecan-4-yl]methyl (2Z)-2-methylbut-2-enoic acidGenerator
Chemical FormulaC20H30O4
Average Mass334.4560 Da
Monoisotopic Mass334.21441 Da
IUPAC Name[(1R,3S,4R,6R,10S)-3-hydroxy-12,12-dimethyl-9-methylidene-5-oxatricyclo[8.2.0.0^{4,6}]dodecan-4-yl]methyl (2Z)-2-methylbut-2-enoate
Traditional Name[(1R,3S,4R,6R,10S)-3-hydroxy-12,12-dimethyl-9-methylidene-5-oxatricyclo[8.2.0.0^{4,6}]dodecan-4-yl]methyl (2Z)-2-methylbut-2-enoate
CAS Registry NumberNot Available
SMILES
C\C=C(\C)C(=O)OC[C@]12O[C@@H]1CCC(=C)[C@H]1CC(C)(C)[C@@H]1C[C@@H]2O
InChI Identifier
InChI=1S/C20H30O4/c1-6-12(2)18(22)23-11-20-16(21)9-15-14(10-19(15,4)5)13(3)7-8-17(20)24-20/h6,14-17,21H,3,7-11H2,1-2,4-5H3/b12-6-/t14-,15-,16+,17-,20-/m1/s1
InChI KeyPLGNMEYDFUAPRS-SNIQRXAWSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Polyachyrus fuscusLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassSesquiterpenoids
Direct ParentSesquiterpenoids
Alternative Parents
Substituents
  • Sesquiterpenoid
  • Caryophyllane sesquiterpenoid
  • Fatty acid ester
  • Fatty acyl
  • Cyclic alcohol
  • Enoate ester
  • Alpha,beta-unsaturated carboxylic ester
  • Secondary alcohol
  • Carboxylic acid ester
  • Monocarboxylic acid or derivatives
  • Ether
  • Oxirane
  • Dialkyl ether
  • Carboxylic acid derivative
  • Organoheterocyclic compound
  • Oxacycle
  • Hydrocarbon derivative
  • Organic oxide
  • Organooxygen compound
  • Organic oxygen compound
  • Alcohol
  • Carbonyl group
  • 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
logP3.71ChemAxon
pKa (Strongest Acidic)13.83ChemAxon
pKa (Strongest Basic)-3.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area59.06 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity92.95 m³·mol⁻¹ChemAxon
Polarizability37.48 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 IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound162964756
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. LOTUS database [Link]