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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-11 20:14:59 UTC
Update Date2019-07-23 06:18:15 UTC
HMDB IDHMDB0035293
Secondary Accession Numbers
  • HMDB35293
Metabolite Identification
Common NameNorambreinolide
DescriptionNorambreinolide is found in herbs and spices. Norambreinolide is used to enhance the flavour of beverages and foodstuffs. Norambreinolide is a flavouring ingredient. Norambreinolide is a constituent of labdanum oil and clary sage (Salvia sclarea).
Structure
Data?1563862695
Synonyms
ValueSource
(+)-NorambreinolideHMDB
12-NorambreinolideHMDB
3a,6,6,9a-Tetramethyl-decahydro-naphtho[2,1-b]furan-2-oneHMDB
3a,6,6,9a-tetramethyldecahydronaphtho[2,1-b]Furan-2(1H)-oneHMDB
DecahydrotetramethylnaphthofuranoneHMDB
FEMA 3794HMDB
NorambreinolidHMDB
Norambreinolide dormHMDB
SclareolideHMDB
Chemical FormulaC16H26O2
Average Molecular Weight250.3764
Monoisotopic Molecular Weight250.193280076
IUPAC Name3a,6,6,9a-tetramethyl-dodecahydronaphtho[2,1-b]furan-2-one
Traditional Namesclareolide
CAS Registry Number564-20-5
SMILES
CC12CCC3C(C)(C)CCCC3(C)C1CC(=O)O2
InChI Identifier
InChI=1S/C16H26O2/c1-14(2)7-5-8-15(3)11(14)6-9-16(4)12(15)10-13(17)18-16/h11-12H,5-10H2,1-4H3
InChI KeyIMKJGXCIJJXALX-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as naphthofurans. These are compounds containing a furan ring fused to a naphthalene moiety. Furan is a 5 membered- ring aromatic ring with four carbon and one oxygen atoms. Naphthalene is a polycyclic aromatic hydrocarbon made up of two fused benzene rings.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassNaphthofurans
Sub ClassNot Available
Direct ParentNaphthofurans
Alternative Parents
Substituents
  • Naphthofuran
  • Gamma butyrolactone
  • Oxolane
  • Lactone
  • Carboxylic acid ester
  • Oxacycle
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Biological location:

Source:

Role

Industrial application:

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point122 - 125 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.0028 g/LALOGPS
logP4.29ALOGPS
logP3.6ChemAxon
logS-4.9ALOGPS
pKa (Strongest Basic)-7.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area26.3 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity71.16 m³·mol⁻¹ChemAxon
Polarizability29.23 ųChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0kg9-1970000000-9bb3c07c120cdf287074JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0190000000-79e30f095ad019575c6aJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-2590000000-79b3ccd278824dce9431JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052p-9630000000-2432ca12bbc5b792f12dJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0090000000-902bb4c0ff306165a7b0JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-052b-0090000000-1f61b09bb60147aa9497JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0udu-9870000000-ad9c2baccef8d25f02b1JSpectraViewer | MoNA
Biological Properties
Cellular Locations
  • Membrane
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB013958
KNApSAcK IDNot Available
Chemspider ID55077
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkSclareolide
METLIN IDNot Available
PubChem Compound61129
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .