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Record Information
Version2.0
Created at2022-09-12 00:14:33 UTC
Updated at2022-09-12 00:14:34 UTC
NP-MRD IDNP0321825
Secondary Accession NumbersNone
Natural Product Identification
Common Name(4s,4ar,5r,6r,8ar)-6-(acetyloxy)-3,4a,5-trimethyl-9-oxo-4h,5h,6h,7h,8h,8ah-naphtho[2,3-b]furan-4-yl (2z)-2-methylbut-2-enoate
Description(4S,4aR,5R,6R,8aR)-6-(acetyloxy)-3,4a,5-trimethyl-9-oxo-4H,4aH,5H,6H,7H,8H,8aH,9H-naphtho[2,3-b]furan-4-yl (2Z)-2-methylbut-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. (4s,4ar,5r,6r,8ar)-6-(acetyloxy)-3,4a,5-trimethyl-9-oxo-4h,5h,6h,7h,8h,8ah-naphtho[2,3-b]furan-4-yl (2z)-2-methylbut-2-enoate is found in Telanthophora grandifolia. Based on a literature review very few articles have been published on (4S,4aR,5R,6R,8aR)-6-(acetyloxy)-3,4a,5-trimethyl-9-oxo-4H,4aH,5H,6H,7H,8H,8aH,9H-naphtho[2,3-b]furan-4-yl (2Z)-2-methylbut-2-enoate.
Structure
Thumb
Synonyms
ValueSource
(4S,4AR,5R,6R,8ar)-6-(acetyloxy)-3,4a,5-trimethyl-9-oxo-4H,4ah,5H,6H,7H,8H,8ah,9H-naphtho[2,3-b]furan-4-yl (2Z)-2-methylbut-2-enoic acidGenerator
Chemical FormulaC22H28O6
Average Mass388.4600 Da
Monoisotopic Mass388.18859 Da
IUPAC Name(4S,4aR,5R,6R,8aR)-6-(acetyloxy)-3,4a,5-trimethyl-9-oxo-4H,4aH,5H,6H,7H,8H,8aH,9H-naphtho[2,3-b]furan-4-yl (2Z)-2-methylbut-2-enoate
Traditional Name(4S,4aR,5R,6R,8aR)-6-(acetyloxy)-3,4a,5-trimethyl-9-oxo-4H,5H,6H,7H,8H,8aH-naphtho[2,3-b]furan-4-yl (2Z)-2-methylbut-2-enoate
CAS Registry NumberNot Available
SMILES
C\C=C(\C)C(=O)O[C@@H]1C2=C(OC=C2C)C(=O)[C@@H]2CC[C@@H](OC(C)=O)[C@H](C)[C@@]12C
InChI Identifier
InChI=1S/C22H28O6/c1-7-11(2)21(25)28-20-17-12(3)10-26-19(17)18(24)15-8-9-16(27-14(5)23)13(4)22(15,20)6/h7,10,13,15-16,20H,8-9H2,1-6H3/b11-7-/t13-,15-,16+,20+,22+/m0/s1
InChI KeyZBEIDAHTEHJVBJ-HMAFTSSZSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Telanthophora grandifoliaLOTUS Database
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 ketone
  • Aryl alkyl ketone
  • Fatty acid ester
  • Dicarboxylic acid or derivatives
  • Fatty acyl
  • Furan
  • Heteroaromatic compound
  • Enoate ester
  • Alpha,beta-unsaturated carboxylic ester
  • Ketone
  • Carboxylic acid ester
  • Carboxylic acid derivative
  • Oxacycle
  • Organoheterocyclic compound
  • Organooxygen compound
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Carbonyl group
  • 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
logP3.97ChemAxon
pKa (Strongest Acidic)13.91ChemAxon
pKa (Strongest Basic)-2.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area82.81 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity103.24 m³·mol⁻¹ChemAxon
Polarizability41.68 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 Compound163191376
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. LOTUS database [Link]