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Record Information
Version2.0
Created at2022-03-17 20:29:30 UTC
Updated at2022-03-17 20:29:30 UTC
NP-MRD IDNP0046784
Secondary Accession NumbersNone
Natural Product Identification
Common NameZaluzanin D
DescriptionZaluzanin D belongs to the class of organic compounds known as guaianolides and derivatives. These are diterpene lactones with a structure characterized by the presence of a gamma-lactone fused to a guaiane, forming 3,6,9-trimethyl-azuleno[4,5-b]furan-2-one or a derivative. Zaluzanin D is found in Conocephalum conicum, Laurus nobilis, Vernonia arborea, Vernonia leopoldi, Zaluzania angusta and Zaluzania triloba. Zaluzanin D is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
Thumb
SynonymsNot Available
Chemical FormulaC17H20O4
Average Mass288.3383 Da
Monoisotopic Mass288.13616 Da
IUPAC Name(3aS,6aS,8S,9aR,9bS)-3,6,9-trimethylidene-2-oxo-dodecahydroazuleno[4,5-b]furan-8-yl acetate
Traditional Name(3aS,6aS,8S,9aR,9bS)-3,6,9-trimethylidene-2-oxo-octahydroazuleno[4,5-b]furan-8-yl acetate
CAS Registry NumberNot Available
SMILES
CC(=O)O[C@H]1C[C@H]2[C@@H]([C@H]3OC(=O)C(=C)[C@@H]3CCC2=C)C1=C
InChI Identifier
InChI=1S/C17H20O4/c1-8-5-6-12-9(2)17(19)21-16(12)15-10(3)14(7-13(8)15)20-11(4)18/h12-16H,1-3,5-7H2,4H3/t12-,13+,14-,15-,16-/m0/s1
InChI KeyGKMFOEIZCLMZDE-QRJUGERDSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Conocephalum conicumPlant
Laurus nobilisLOTUS Database
Laurus nobilis L.FooDB
Strobocalyx arboreaLOTUS Database
Vernonia leopoldiLOTUS Database
Zaluzania angustaPlant
Zaluzania trilobaLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as guaianolides and derivatives. These are diterpene lactones with a structure characterized by the presence of a gamma-lactone fused to a guaiane, forming 3,6,9-trimethyl-azuleno[4,5-b]furan-2-one or a derivative.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassTerpene lactones
Direct ParentGuaianolides and derivatives
Alternative Parents
Substituents
  • Guaianolide-skeleton
  • Guaiane sesquiterpenoid
  • Sesquiterpenoid
  • Dicarboxylic acid or derivatives
  • Gamma butyrolactone
  • Tetrahydrofuran
  • Enoate ester
  • Alpha,beta-unsaturated carboxylic ester
  • Lactone
  • Carboxylic acid ester
  • Organoheterocyclic compound
  • Oxacycle
  • Carboxylic acid derivative
  • 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
logP2.12ALOGPS
logP2.29ChemAxon
logS-3ALOGPS
pKa (Strongest Basic)-6.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area52.6 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity76.64 m³·mol⁻¹ChemAxon
Polarizability31.24 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 IDFDB005904
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound637305
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General ReferencesNot Available