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Record Information
Version2.0
Created at2022-09-12 00:21:49 UTC
Updated at2022-09-12 00:21:49 UTC
NP-MRD IDNP0321906
Secondary Accession NumbersNone
Natural Product Identification
Common Name5-hydroxy-4a,8-dimethyl-3-methylidene-3ah,4h,5h,8h,9h,9ah-azuleno[6,5-b]furan-2,6-dione
Description5-Hydroxy-4a,8-dimethyl-3-methylidene-2H,3H,3aH,4H,4aH,5H,6H,8H,9H,9aH-azuleno[6,5-b]furan-2,6-dione belongs to the class of organic compounds known as ambrosanolides and secoambrosanolides. These are sesquiterpene lactones from the Ambrosia family, with a backbone derivative of azuleno[6,5-b]furan-2-one (ambrosanolides) or azuleno[4,5-b]furan-2-one (secoambrosanolides). 5-Hydroxy-4a,8-dimethyl-3-methylidene-2H,3H,3aH,4H,4aH,5H,6H,8H,9H,9aH-azuleno[6,5-b]furan-2,6-dione is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
Thumb
SynonymsNot Available
Chemical FormulaC15H18O4
Average Mass262.3050 Da
Monoisotopic Mass262.12051 Da
IUPAC Name5-hydroxy-4a,8-dimethyl-3-methylidene-2H,3H,3aH,4H,4aH,5H,6H,8H,9H,9aH-azuleno[6,5-b]furan-2,6-dione
Traditional Name5-hydroxy-4a,8-dimethyl-3-methylidene-3aH,4H,5H,8H,9H,9aH-azuleno[6,5-b]furan-2,6-dione
CAS Registry NumberNot Available
SMILES
CC1CC2OC(=O)C(=C)C2CC2(C)C(O)C(=O)C=C12
InChI Identifier
InChI=1S/C15H18O4/c1-7-4-12-9(8(2)14(18)19-12)6-15(3)10(7)5-11(16)13(15)17/h5,7,9,12-13,17H,2,4,6H2,1,3H3
InChI KeyDYBGVZNCIXACSP-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 OriginNot Available
Chemical Taxonomy
Description Belongs to the class of organic compounds known as ambrosanolides and secoambrosanolides. These are sesquiterpene lactones from the Ambrosia family, with a backbone derivative of azuleno[6,5-b]furan-2-one (ambrosanolides) or azuleno[4,5-b]furan-2-one (secoambrosanolides).
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassTerpene lactones
Direct ParentAmbrosanolides and secoambrosanolides
Alternative Parents
Substituents
  • Ambrosanolide
  • Pseudoguaiane sesquiterpenoid
  • Sesquiterpenoid
  • Gamma butyrolactone
  • Tetrahydrofuran
  • Enoate ester
  • Alpha,beta-unsaturated carboxylic ester
  • Cyclic ketone
  • Secondary alcohol
  • Lactone
  • Ketone
  • Carboxylic acid ester
  • Oxacycle
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Organoheterocyclic compound
  • Alcohol
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organic oxide
  • Carbonyl group
  • Organic oxygen compound
  • 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
logP0.63ALOGPS
logP1.77ChemAxon
logS-2ALOGPS
pKa (Strongest Acidic)12.91ChemAxon
pKa (Strongest Basic)-3.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area63.6 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity69.23 m³·mol⁻¹ChemAxon
Polarizability27.41 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 CompoundNot Available
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. LOTUS database [Link]