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Record Information
Version1.0
Created at2021-06-20 23:24:04 UTC
Updated at2021-06-30 00:16:03 UTC
NP-MRD IDNP0041500
Secondary Accession NumbersNone
Natural Product Identification
Common Name(3aS,5aR,6R,9S,9aS,9bS)-6,9-dihydroxy-5a,9-dimethyl-3-methylidene-6,3a,4,+
Provided ByJEOL DatabaseJEOL Logo
Description(+)-1Beta-Hydroxyarbusculin A belongs to the class of organic compounds known as eudesmanolides, secoeudesmanolides, and derivatives. These are terpenoids with a structure based on the eudesmanolide (a 3,5a,9-trimethyl-naphtho[1,2-b]furan-2-one derivative) or secoeudesmanolide (a 3,6-dimethyl-5-(pentan-2-yl)-1-benzofuran-2-one derivative) skeleton. (3aS,5aR,6R,9S,9aS,9bS)-6,9-dihydroxy-5a,9-dimethyl-3-methylidene-6,3a,4,+ is found in Laurus nobilis L. It was first documented in 2012 (Julianti, E., et al.). Based on a literature review very few articles have been published on (+)-1beta-Hydroxyarbusculin A.
Structure
Thumb
Synonyms
ValueSource
(+)-1b-Hydroxyarbusculin aGenerator
(+)-1Β-hydroxyarbusculin aGenerator
Chemical FormulaC15H22O4
Average Mass266.3370 Da
Monoisotopic Mass266.15181 Da
IUPAC Name(3aS,5aR,6R,9S,9aS,9bS)-6,9-dihydroxy-5a,9-dimethyl-3-methylidene-dodecahydronaphtho[1,2-b]furan-2-one
Traditional Name(3aS,5aR,6R,9S,9aS,9bS)-6,9-dihydroxy-5a,9-dimethyl-3-methylidene-octahydronaphtho[1,2-b]furan-2-one
CAS Registry NumberNot Available
SMILES
[H]O[C@]1([H])C([H])([H])C([H])([H])[C@@](O[H])(C([H])([H])[H])[C@]2([H])[C@@]3([H])OC(=O)C(=C([H])[H])[C@]3([H])C([H])([H])C([H])([H])[C@@]12C([H])([H])[H]
InChI Identifier
InChI=1S/C15H22O4/c1-8-9-4-6-14(2)10(16)5-7-15(3,18)12(14)11(9)19-13(8)17/h9-12,16,18H,1,4-7H2,2-3H3/t9-,10+,11-,12+,14-,15-/m0/s1
InChI KeyLVABKRFKENTQBT-JWAKXMNJSA-N
Spectra
Spectrum TypeDescriptionDepositor IDDeposition DateView
1D NMR13C NMR Spectrum (1D, 500 MHz, CDCl3, simulated)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, CDCl3, simulated)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 100 MHz, CDCl3, simulated)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, CDCl3, simulated)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, CDCl3, simulated)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, CDCl3, simulated)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 300 MHz, CDCl3, simulated)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, CDCl3, simulated)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, CDCl3, simulated)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, CDCl3, simulated)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 600 MHz, CDCl3, simulated)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, CDCl3, simulated)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 700 MHz, CDCl3, simulated)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, CDCl3, simulated)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 800 MHz, CDCl3, simulated)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, CDCl3, simulated)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 900 MHz, CDCl3, simulated)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, CDCl3, simulated)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 1000 MHz, CDCl3, simulated)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, CDCl3, simulated)Wishart Lab2021-06-20View Spectrum
Species
Species of Origin
Species NameSourceReference
Laurus nobilis L.
    • Julianti, E., et al, Phytochem. 80, 70 (2012)
Chemical Taxonomy
Description Belongs to the class of organic compounds known as eudesmanolides, secoeudesmanolides, and derivatives. These are terpenoids with a structure based on the eudesmanolide (a 3,5a,9-trimethyl-naphtho[1,2-b]furan-2-one derivative) or secoeudesmanolide (a 3,6-dimethyl-5-(pentan-2-yl)-1-benzofuran-2-one derivative) skeleton.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassTerpene lactones
Direct ParentEudesmanolides, secoeudesmanolides, and derivatives
Alternative Parents
Substituents
  • Eudesmanolide
  • Sesquiterpenoid
  • Naphthofuran
  • Gamma butyrolactone
  • Alpha,beta-unsaturated carboxylic ester
  • Enoate ester
  • Tetrahydrofuran
  • Tertiary alcohol
  • Cyclic alcohol
  • Secondary alcohol
  • Lactone
  • Carboxylic acid ester
  • Oxacycle
  • Organoheterocyclic compound
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • 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
logP0.98ALOGPS
logP1.2ChemAxon
logS-1.6ALOGPS
pKa (Strongest Acidic)14.38ChemAxon
pKa (Strongest Basic)-2.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area66.76 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity69.52 m³·mol⁻¹ChemAxon
Polarizability28.63 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
External Links
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 Compound60199554
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Julianti, E., et al. (2012). Julianti, E., et al, Phytochem. 80, 70 (2012). Phytochem..