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Record Information
Version1.0
Created at2022-09-07 08:25:41 UTC
Updated at2022-09-07 08:25:41 UTC
NP-MRD IDNP0246836
Secondary Accession NumbersNone
Natural Product Identification
Common Name2,11-dimethyl-7-methylidene-6,12-dioxo-5,14-dioxatricyclo[9.2.1.0⁴,⁸]tetradeca-1(13),2-dien-9-yl 2-[(acetyloxy)methyl]but-2-enoate
Description2,11-Dimethyl-7-methylidene-6,12-dioxo-5,14-dioxatricyclo[9.2.1.0⁴,⁸]Tetradeca-1(13),2-dien-9-yl 2-[(acetyloxy)methyl]but-2-enoate belongs to the class of organic compounds known as terpene lactones. These are prenol lipids containing a lactone ring. 2,11-dimethyl-7-methylidene-6,12-dioxo-5,14-dioxatricyclo[9.2.1.0⁴,⁸]tetradeca-1(13),2-dien-9-yl 2-[(acetyloxy)methyl]but-2-enoate is found in Bejaranoa semistriata. 2,11-Dimethyl-7-methylidene-6,12-dioxo-5,14-dioxatricyclo[9.2.1.0⁴,⁸]Tetradeca-1(13),2-dien-9-yl 2-[(acetyloxy)methyl]but-2-enoate is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
Thumb
Synonyms
ValueSource
2,11-Dimethyl-7-methylidene-6,12-dioxo-5,14-dioxatricyclo[9.2.1.0,]tetradeca-1(13),2-dien-9-yl 2-[(acetyloxy)methyl]but-2-enoic acidGenerator
2,11-Dimethyl-7-methylidene-6,12-dioxo-5,14-dioxatricyclo[9.2.1.0⁴,⁸]tetradeca-1(13),2-dien-9-yl 2-[(acetyloxy)methyl]but-2-enoic acidGenerator
Chemical FormulaC22H24O8
Average Mass416.4260 Da
Monoisotopic Mass416.14712 Da
IUPAC Name2,11-dimethyl-7-methylidene-6,12-dioxo-5,14-dioxatricyclo[9.2.1.0⁴,⁸]tetradeca-1(13),2-dien-9-yl 2-[(acetyloxy)methyl]but-2-enoate
Traditional Name2,11-dimethyl-7-methylidene-6,12-dioxo-5,14-dioxatricyclo[9.2.1.0⁴,⁸]tetradeca-1(13),2-dien-9-yl 2-[(acetyloxy)methyl]but-2-enoate
CAS Registry NumberNot Available
SMILES
CC=C(COC(C)=O)C(=O)OC1CC2(C)OC(=CC2=O)C(C)=CC2OC(=O)C(=C)C12
InChI Identifier
InChI=1S/C22H24O8/c1-6-14(10-27-13(4)23)21(26)29-17-9-22(5)18(24)8-15(30-22)11(2)7-16-19(17)12(3)20(25)28-16/h6-8,16-17,19H,3,9-10H2,1-2,4-5H3
InChI KeyJPDNQRSOPZNKHO-UHFFFAOYSA-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
Bejaranoa semistriataLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as terpene lactones. These are prenol lipids containing a lactone ring.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassTerpene lactones
Direct ParentTerpene lactones
Alternative Parents
Substituents
  • Terpene lactone
  • Sesquiterpenoid
  • Tricarboxylic acid or derivatives
  • Fatty acid ester
  • 3-furanone
  • Gamma butyrolactone
  • Fatty acyl
  • Alpha,beta-unsaturated carboxylic ester
  • Enoate ester
  • Vinylogous ester
  • Tetrahydrofuran
  • Dihydrofuran
  • Carboxylic acid ester
  • Ketone
  • Lactone
  • Organoheterocyclic compound
  • Carboxylic acid derivative
  • Oxacycle
  • Carbonyl group
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organic oxide
  • 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
logP1.91ALOGPS
logP2.23ChemAxon
logS-3.9ALOGPS
pKa (Strongest Acidic)19.56ChemAxon
pKa (Strongest Basic)-4.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area105.2 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity107.15 m³·mol⁻¹ChemAxon
Polarizability41.45 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 Compound74191805
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. LOTUS database [Link]