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Record Information
Version2.0
Created at2022-09-06 22:42:48 UTC
Updated at2022-09-06 22:42:48 UTC
NP-MRD IDNP0239180
Secondary Accession NumbersNone
Natural Product Identification
Common Name(4s,4ar,5r,6s,8as)-3,4a,5-trimethyl-4-(2-methylpropoxy)-9-oxo-4h,5h,6h,7h,8h,8ah-naphtho[2,3-b]furan-6-yl 2-methylprop-2-enoate
Description(4S,4aR,5R,6S,8aS)-3,4a,5-trimethyl-4-(2-methylpropoxy)-9-oxo-4H,4aH,5H,6H,7H,8H,8aH,9H-naphtho[2,3-b]furan-6-yl 2-methylprop-2-enoate belongs to the class of organic compounds known as eremophilane, 8,9-secoeremophilane and furoeremophilane sesquiterpenoids. These are sesquiterpenoids with a structure based either on the eremophilane skeleton, its 8,9-seco derivative, or the furoeremophilane skeleton. Eremophilanes have been shown to be derived from eudesmanes by migration of the methyl group at C-10 to C-5. Based on a literature review very few articles have been published on (4S,4aR,5R,6S,8aS)-3,4a,5-trimethyl-4-(2-methylpropoxy)-9-oxo-4H,4aH,5H,6H,7H,8H,8aH,9H-naphtho[2,3-b]furan-6-yl 2-methylprop-2-enoate.
Structure
Thumb
Synonyms
ValueSource
(4S,4AR,5R,6S,8as)-3,4a,5-trimethyl-4-(2-methylpropoxy)-9-oxo-4H,4ah,5H,6H,7H,8H,8ah,9H-naphtho[2,3-b]furan-6-yl 2-methylprop-2-enoic acidGenerator
Chemical FormulaC23H32O5
Average Mass388.5040 Da
Monoisotopic Mass388.22497 Da
IUPAC Name(4S,4aR,5R,6S,8aS)-3,4a,5-trimethyl-4-(2-methylpropoxy)-9-oxo-4H,4aH,5H,6H,7H,8H,8aH,9H-naphtho[2,3-b]furan-6-yl 2-methylprop-2-enoate
Traditional Name(4S,4aR,5R,6S,8aS)-3,4a,5-trimethyl-4-(2-methylpropoxy)-9-oxo-4H,5H,6H,7H,8H,8aH-naphtho[2,3-b]furan-6-yl 2-methylprop-2-enoate
CAS Registry NumberNot Available
SMILES
CC(C)CO[C@@H]1C2=C(OC=C2C)C(=O)[C@H]2CC[C@H](OC(=O)C(C)=C)[C@H](C)[C@@]12C
InChI Identifier
InChI=1S/C23H32O5/c1-12(2)10-27-21-18-14(5)11-26-20(18)19(24)16-8-9-17(15(6)23(16,21)7)28-22(25)13(3)4/h11-12,15-17,21H,3,8-10H2,1-2,4-7H3/t15-,16+,17-,21+,23+/m0/s1
InChI KeySRCJXKXKNAJRTJ-BISBRFNCSA-N
Experimental Spectra
Not Available
Predicted Spectra
Chemical Shift Submissions
Not Available
Species
Species of OriginNot Available
Chemical Taxonomy
Description Belongs to the class of organic compounds known as eremophilane, 8,9-secoeremophilane and furoeremophilane sesquiterpenoids. These are sesquiterpenoids with a structure based either on the eremophilane skeleton, its 8,9-seco derivative, or the furoeremophilane skeleton. Eremophilanes have been shown to be derived from eudesmanes by migration of the methyl group at C-10 to C-5.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassSesquiterpenoids
Direct ParentEremophilane, 8,9-secoeremophilane and furoeremophilane sesquiterpenoids
Alternative Parents
Substituents
  • Furoeremophilane sesquiterpenoid
  • Naphthofuran
  • Benzofuran
  • Aryl alkyl ketone
  • Aryl ketone
  • Furan
  • Heteroaromatic compound
  • Alpha,beta-unsaturated carboxylic ester
  • Enoate ester
  • Carboxylic acid ester
  • Ketone
  • Carboxylic acid derivative
  • Dialkyl ether
  • Ether
  • Oxacycle
  • Monocarboxylic acid or derivatives
  • Organoheterocyclic compound
  • Carbonyl group
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic 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
logP5.03ChemAxon
pKa (Strongest Acidic)14.04ChemAxon
pKa (Strongest Basic)-2.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area65.74 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity106.91 m³·mol⁻¹ChemAxon
Polarizability43.63 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
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 Compound162878607
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. LOTUS database [Link]