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Record Information
Version2.0
Created at2022-09-10 03:33:18 UTC
Updated at2022-09-10 03:33:18 UTC
NP-MRD IDNP0294836
Secondary Accession NumbersNone
Natural Product Identification
Common Name6-(hydroxymethyl)-10,14-dimethyl-3-methylidene-3ah,4h,7h,8h,11h,12h,15h,15ah-cyclotetradeca[b]furan-2-one
Description6-(Hydroxymethyl)-10,14-dimethyl-3-methylidene-2H,3H,3aH,4H,7H,8H,11H,12H,15H,15aH-cyclotetradeca[b]furan-2-one belongs to the class of organic compounds known as cembranolides. These are diterpenoids with a structure based on a cembrane skeleton fused to a lactone ring (5- or 6-membered). 6-(hydroxymethyl)-10,14-dimethyl-3-methylidene-3ah,4h,7h,8h,11h,12h,15h,15ah-cyclotetradeca[b]furan-2-one is found in Lobophytum crassum. 6-(Hydroxymethyl)-10,14-dimethyl-3-methylidene-2H,3H,3aH,4H,7H,8H,11H,12H,15H,15aH-cyclotetradeca[b]furan-2-one is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
Thumb
SynonymsNot Available
Chemical FormulaC20H28O3
Average Mass316.4410 Da
Monoisotopic Mass316.20384 Da
IUPAC Name6-(hydroxymethyl)-10,14-dimethyl-3-methylidene-2H,3H,3aH,4H,7H,8H,11H,12H,15H,15aH-cyclotetradeca[b]furan-2-one
Traditional Name6-(hydroxymethyl)-10,14-dimethyl-3-methylidene-3aH,4H,7H,8H,11H,12H,15H,15aH-cyclotetradeca[b]furan-2-one
CAS Registry NumberNot Available
SMILES
CC1=CCCC(CO)=CCC2C(CC(C)=CCC1)OC(=O)C2=C
InChI Identifier
InChI=1S/C20H28O3/c1-14-6-4-8-15(2)12-19-18(16(3)20(22)23-19)11-10-17(13-21)9-5-7-14/h7-8,10,18-19,21H,3-6,9,11-13H2,1-2H3
InChI KeyKXVIJXIRUBWYDB-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
Lobophytum crassumLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as cembranolides. These are diterpenoids with a structure based on a cembrane skeleton fused to a lactone ring (5- or 6-membered).
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassTerpene lactones
Direct ParentCembranolides
Alternative Parents
Substituents
  • Cembranolide-skeleton
  • Cembrane diterpenoid
  • Diterpenoid
  • Gamma butyrolactone
  • Oxolane
  • Enoate ester
  • Alpha,beta-unsaturated carboxylic ester
  • Lactone
  • Carboxylic acid ester
  • Monocarboxylic acid or derivatives
  • Oxacycle
  • Carboxylic acid derivative
  • Organoheterocyclic compound
  • Primary alcohol
  • Alcohol
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • 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
logP4.4ALOGPS
logP4.04ChemAxon
logS-3.9ALOGPS
pKa (Strongest Acidic)16.95ChemAxon
pKa (Strongest Basic)-1.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area46.53 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity95.68 m³·mol⁻¹ChemAxon
Polarizability36.22 ųChemAxon
Number of Rings2ChemAxon
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 Compound73830894
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. LOTUS database [Link]