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Record Information
Version2.0
Created at2022-09-12 14:17:14 UTC
Updated at2022-09-12 14:17:14 UTC
NP-MRD IDNP0329680
Secondary Accession NumbersNone
Natural Product Identification
Common Name[(1r,2s,3s,4r,7r,8r)-4-(acetyloxy)-3,7,9-trimethyl-11-oxotricyclo[5.4.0.0²,⁸]undec-9-en-3-yl]methyl (2z)-2-methylbut-2-enoate
Description[(1R,2S,3S,4R,7R,8R)-4-(acetyloxy)-3,7,9-trimethyl-11-oxotricyclo[5.4.0.0²,⁸]Undec-9-en-3-yl]methyl (2Z)-2-methylbut-2-enoate belongs to the class of organic compounds known as bicyclic monoterpenoids. These are monoterpenoids containing exactly 2 rings, which are fused to each other. [(1r,2s,3s,4r,7r,8r)-4-(acetyloxy)-3,7,9-trimethyl-11-oxotricyclo[5.4.0.0²,⁸]undec-9-en-3-yl]methyl (2z)-2-methylbut-2-enoate is found in Stevia origanoides. Based on a literature review very few articles have been published on [(1R,2S,3S,4R,7R,8R)-4-(acetyloxy)-3,7,9-trimethyl-11-oxotricyclo[5.4.0.0²,⁸]Undec-9-en-3-yl]methyl (2Z)-2-methylbut-2-enoate.
Structure
Thumb
Synonyms
ValueSource
[(1R,2S,3S,4R,7R,8R)-4-(Acetyloxy)-3,7,9-trimethyl-11-oxotricyclo[5.4.0.0,]undec-9-en-3-yl]methyl (2Z)-2-methylbut-2-enoic acidGenerator
Chemical FormulaC22H30O5
Average Mass374.4770 Da
Monoisotopic Mass374.20932 Da
IUPAC Name[(1R,2S,3S,4R,7R,8R)-4-(acetyloxy)-3,7,9-trimethyl-11-oxotricyclo[5.4.0.0^{2,8}]undec-9-en-3-yl]methyl (2Z)-2-methylbut-2-enoate
Traditional Name[(1R,2S,3S,4R,7R,8R)-4-(acetyloxy)-3,7,9-trimethyl-11-oxotricyclo[5.4.0.0^{2,8}]undec-9-en-3-yl]methyl (2Z)-2-methylbut-2-enoate
CAS Registry NumberNot Available
SMILES
C\C=C(\C)C(=O)OC[C@]1(C)[C@H]2[C@@H]3C(C)=CC(=O)[C@H]2[C@]3(C)CC[C@H]1OC(C)=O
InChI Identifier
InChI=1S/C22H30O5/c1-7-12(2)20(25)26-11-22(6)16(27-14(4)23)8-9-21(5)17-13(3)10-15(24)18(21)19(17)22/h7,10,16-19H,8-9,11H2,1-6H3/b12-7-/t16-,17+,18-,19+,21-,22+/m1/s1
InChI KeyDXXNRRAYPLARAY-SHAZKNBMSA-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
Stevia origanoidesLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as bicyclic monoterpenoids. These are monoterpenoids containing exactly 2 rings, which are fused to each other.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassMonoterpenoids
Direct ParentBicyclic monoterpenoids
Alternative Parents
Substituents
  • Pinane monoterpenoid
  • Cyclohexenone
  • Fatty acid ester
  • Fatty acyl
  • Dicarboxylic acid or derivatives
  • Alpha,beta-unsaturated carboxylic ester
  • Enoate ester
  • Carboxylic acid ester
  • Ketone
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • 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
logP3.68ChemAxon
pKa (Strongest Acidic)18.93ChemAxon
pKa (Strongest Basic)-4.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area69.67 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity102.61 m³·mol⁻¹ChemAxon
Polarizability40.99 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
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 Compound163075110
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. LOTUS database [Link]