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Record Information
Version2.0
Created at2022-09-06 22:46:44 UTC
Updated at2022-09-06 22:46:44 UTC
NP-MRD IDNP0239231
Secondary Accession NumbersNone
Natural Product Identification
Common Name(3as,5as,6s,9ar,9br)-6-hydroxy-5a,9-dimethyl-3-methylidene-3ah,4h,5h,6h,7h,9ah,9bh-naphtho[1,2-b]furan-2-one
Description(1R)-alpha-Methylene-1alpha,5beta-dihydroxy-4abeta,8-dimethyl-1,2,3,4,4a,5,6,8aalpha-octahydronaphthalene-2alpha-acetic acid 2,1-lactone 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,5as,6s,9ar,9br)-6-hydroxy-5a,9-dimethyl-3-methylidene-3ah,4h,5h,6h,7h,9ah,9bh-naphtho[1,2-b]furan-2-one is found in Eria mucronata. Based on a literature review very few articles have been published on (1R)-alpha-Methylene-1alpha,5beta-dihydroxy-4abeta,8-dimethyl-1,2,3,4,4a,5,6,8aalpha-octahydronaphthalene-2alpha-acetic acid 2,1-lactone.
Structure
Thumb
Synonyms
ValueSource
(1R)-a-Methylene-1a,5b-dihydroxy-4abeta,8-dimethyl-1,2,3,4,4a,5,6,8aalpha-octahydronaphthalene-2a-acetate 2,1-lactoneGenerator
(1R)-a-Methylene-1a,5b-dihydroxy-4abeta,8-dimethyl-1,2,3,4,4a,5,6,8aalpha-octahydronaphthalene-2a-acetic acid 2,1-lactoneGenerator
(1R)-alpha-Methylene-1alpha,5beta-dihydroxy-4abeta,8-dimethyl-1,2,3,4,4a,5,6,8aalpha-octahydronaphthalene-2alpha-acetate 2,1-lactoneGenerator
(1R)-Α-methylene-1α,5β-dihydroxy-4abeta,8-dimethyl-1,2,3,4,4a,5,6,8aalpha-octahydronaphthalene-2α-acetate 2,1-lactoneGenerator
(1R)-Α-methylene-1α,5β-dihydroxy-4abeta,8-dimethyl-1,2,3,4,4a,5,6,8aalpha-octahydronaphthalene-2α-acetic acid 2,1-lactoneGenerator
Chemical FormulaC15H20O3
Average Mass248.3220 Da
Monoisotopic Mass248.14124 Da
IUPAC Name(3aS,5aS,6S,9aR,9bR)-6-hydroxy-5a,9-dimethyl-3-methylidene-2H,3H,3aH,4H,5H,5aH,6H,7H,9aH,9bH-naphtho[1,2-b]furan-2-one
Traditional Name(3aS,5aS,6S,9aR,9bR)-6-hydroxy-5a,9-dimethyl-3-methylidene-3aH,4H,5H,6H,7H,9aH,9bH-naphtho[1,2-b]furan-2-one
CAS Registry NumberNot Available
SMILES
CC1=CC[C@H](O)[C@@]2(C)CC[C@@H]3[C@@H](OC(=O)C3=C)[C@H]12
InChI Identifier
InChI=1S/C15H20O3/c1-8-4-5-11(16)15(3)7-6-10-9(2)14(17)18-13(10)12(8)15/h4,10-13,16H,2,5-7H2,1,3H3/t10-,11-,12-,13+,15+/m0/s1
InChI KeyPLSSEPIRACGCBO-XOBFJNJYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Eria mucronataLOTUS Database
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
  • Oxolane
  • Enoate ester
  • Alpha,beta-unsaturated carboxylic ester
  • Secondary alcohol
  • Lactone
  • Carboxylic acid ester
  • Oxacycle
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Organoheterocyclic compound
  • 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
logP2.15ChemAxon
pKa (Strongest Acidic)14.63ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area46.53 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity68.71 m³·mol⁻¹ChemAxon
Polarizability27.1 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 Compound12309331
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. LOTUS database [Link]