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Record Information
Version1.0
Created at2021-06-19 21:28:42 UTC
Updated at2021-06-29 23:57:43 UTC
NP-MRD IDNP0030007
Secondary Accession NumbersNone
Natural Product Identification
Common Name3beta-chlorodehydrocostuslactone
Provided ByJEOL DatabaseJEOL Logo
Description3Beta-Chlorodehydrocostuslactone 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. 3beta-chlorodehydrocostuslactone is found in Laurus nobilis. It was first documented in 2006 (PMID: 16880666). Based on a literature review very few articles have been published on 3beta-Chlorodehydrocostuslactone.
Structure
Thumb
Synonyms
ValueSource
3b-ChlorodehydrocostuslactoneGenerator
3Β-chlorodehydrocostuslactoneGenerator
Chemical FormulaC15H17ClO2
Average Mass264.7470 Da
Monoisotopic Mass264.09171 Da
IUPAC Name(3aS,6aR,8S,9aR,9bS)-8-chloro-3,6,9-trimethylidene-dodecahydroazuleno[4,5-b]furan-2-one
Traditional Name(3aS,6aR,8S,9aR,9bS)-8-chloro-3,6,9-trimethylidene-octahydroazuleno[4,5-b]furan-2-one
CAS Registry NumberNot Available
SMILES
[H]C([H])=C1C(=O)O[C@@]2([H])[C@@]1([H])C([H])([H])C([H])([H])C(=C([H])[H])[C@]1([H])C([H])([H])[C@]([H])(Cl)C(=C([H])[H])[C@]21[H]
InChI Identifier
InChI=1S/C15H17ClO2/c1-7-4-5-10-8(2)15(17)18-14(10)13-9(3)12(16)6-11(7)13/h10-14H,1-6H2/t10-,11-,12-,13-,14-/m0/s1
InChI KeyXVGIEOUYQLZGPH-PEDHHIEDSA-N
Spectra
Spectrum TypeDescriptionDepositor IDDeposition DateView
1D NMR13C NMR Spectrum (1D, 300 MHz, CD3OD, simulated)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, CD3OD, simulated)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 100 MHz, CD3OD, simulated)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, CD3OD, simulated)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, CD3OD, simulated)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, CD3OD, simulated)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, CD3OD, simulated)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, CD3OD, simulated)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, CD3OD, simulated)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, CD3OD, simulated)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 600 MHz, CD3OD, simulated)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, CD3OD, simulated)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 700 MHz, CD3OD, simulated)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, CD3OD, simulated)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 800 MHz, CD3OD, simulated)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, CD3OD, simulated)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 900 MHz, CD3OD, simulated)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, CD3OD, simulated)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 1000 MHz, CD3OD, simulated)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, CD3OD, simulated)Wishart Lab2021-06-20View Spectrum
Species
Species of Origin
Species NameSourceReference
Laurus nobilisKNApSAcK Database
Laurus nobilis L.
    • Dall'Acqua, S., et al, Chem. Pharm. Bull. 54, 1187 (2006)
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 ParentsNot Available
SubstituentsNot Available
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
logP3.14ALOGPS
logP3.2ChemAxon
logS-3.5ALOGPS
pKa (Strongest Basic)-6.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area26.3 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity70.54 m³·mol⁻¹ChemAxon
Polarizability28.08 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
External Links
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB001782
KNApSAcK IDC00029488
Chemspider ID8834671
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound10659317
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Dall'Acqua S, Viola G, Giorgetti M, Loi MC, Innocenti G: Two new sesquiterpene lactones from the leaves of Laurus nobilis. Chem Pharm Bull (Tokyo). 2006 Aug;54(8):1187-9. doi: 10.1248/cpb.54.1187. [PubMed:16880666 ]
  2. Dall'Acqua, S., et al. (2006). Dall'Acqua, S., et al, Chem. Pharm. Bull. 54, 1187 (2006). Chem. Pharm. Bull..