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Record Information
Version2.0
Created at2021-06-20 00:00:51 UTC
Updated at2021-06-30 00:03:17 UTC
NP-MRD IDNP0033483
Secondary Accession NumbersNone
Natural Product Identification
Common Namecinnamodial 11alpha,12beta-dimethyl acetal
Provided ByJEOL DatabaseJEOL Logo
Description(1R,3R,5R,5aS,9aS,9bS)-9b-hydroxy-1,3-dimethoxy-6,6,9a-trimethyl-1H,3H,5H,5aH,6H,7H,8H,9H,9aH,9bH-naphtho[1,2-c]furan-5-yl acetate belongs to the class of organic compounds known as naphthofurans. Naphthofurans are compounds containing a furan ring fused to a naphthalene moiety. Furan is a 5 membered- ring aromatic ring with four carbon and one oxygen atoms. Naphthalene is a polycyclic aromatic hydrocarbon made up of two fused benzene rings. cinnamodial 11alpha,12beta-dimethyl acetal is found in Cinnamosma madagascariensis. cinnamodial 11alpha,12beta-dimethyl acetal was first documented in 2008 (Harinantenaina, L., et al.). Based on a literature review very few articles have been published on (1R,3R,5R,5aS,9aS,9bS)-9b-hydroxy-1,3-dimethoxy-6,6,9a-trimethyl-1H,3H,5H,5aH,6H,7H,8H,9H,9aH,9bH-naphtho[1,2-c]furan-5-yl acetate.
Structure
Thumb
Synonyms
ValueSource
(1R,3R,5R,5AS,9as,9BS)-9b-hydroxy-1,3-dimethoxy-6,6,9a-trimethyl-1H,3H,5H,5ah,6H,7H,8H,9H,9ah,9BH-naphtho[1,2-c]furan-5-yl acetic acidGenerator
Cinnamodial 11alpha,12beta-dimethyl acetalPhytoBank
Chemical FormulaC19H30O6
Average Mass354.4430 Da
Monoisotopic Mass354.20424 Da
IUPAC Name(1R,3R,5R,5aS,9aS,9bS)-9b-hydroxy-1,3-dimethoxy-6,6,9a-trimethyl-1H,3H,5H,5aH,6H,7H,8H,9H,9aH,9bH-naphtho[1,2-c]furan-5-yl acetate
Traditional Name(1R,3R,5R,5aS,9aS,9bS)-9b-hydroxy-1,3-dimethoxy-6,6,9a-trimethyl-1H,3H,5H,5aH,7H,8H,9H-naphtho[1,2-c]furan-5-yl acetate
CAS Registry NumberNot Available
SMILES
[H]O[C@]12C(=C([H])[C@@]([H])(OC(=O)C([H])([H])[H])[C@@]3([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])C([H])([H])C([H])([H])[C@]13C([H])([H])[H])[C@]([H])(OC([H])([H])[H])O[C@@]2([H])OC([H])([H])[H]
InChI Identifier
InChI=1S/C19H30O6/c1-11(20)24-13-10-12-15(22-5)25-16(23-6)19(12,21)18(4)9-7-8-17(2,3)14(13)18/h10,13-16,21H,7-9H2,1-6H3/t13-,14+,15-,16-,18+,19+/m1/s1
InChI KeyQWSNLCYZUAVRFO-GZXFCSGKSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 400 MHz, CDCl3, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, CDCl3, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 100 MHz, CDCl3, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, CDCl3, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, CDCl3, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, CDCl3, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 300 MHz, CDCl3, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, CDCl3, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, CDCl3, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, CDCl3, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 600 MHz, CDCl3, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, CDCl3, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 700 MHz, CDCl3, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, CDCl3, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 800 MHz, CDCl3, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, CDCl3, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 900 MHz, CDCl3, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, CDCl3, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 1000 MHz, CDCl3, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, CDCl3, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Cinnamosma madagascariensisJEOL database
    • Harinantenaina, L., et al, J. Nat. Prod. 71, 123 (2008)
Chemical Taxonomy
Description Belongs to the class of organic compounds known as naphthofurans. Naphthofurans are compounds containing a furan ring fused to a naphthalene moiety. Furan is a 5 membered- ring aromatic ring with four carbon and one oxygen atoms. Naphthalene is a polycyclic aromatic hydrocarbon made up of two fused benzene rings.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassNaphthofurans
Sub ClassNot Available
Direct ParentNaphthofurans
Alternative Parents
Substituents
  • Naphthofuran
  • Tetrahydrofuran
  • Tertiary alcohol
  • Carboxylic acid ester
  • Oxacycle
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Acetal
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • 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
logP2.55ALOGPS
logP2.32ChemAxon
logS-3.3ALOGPS
pKa (Strongest Acidic)12.06ChemAxon
pKa (Strongest Basic)-3.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area74.22 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity90.96 m³·mol⁻¹ChemAxon
Polarizability38.32 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 ID23314468
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound24770037
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Harinantenaina, L., et al. (2008). Harinantenaina, L., et al, J. Nat. Prod. 71, 123 (2008). J. Nat. Prod..