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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 20:14:59 UTC
Update Date2022-03-07 02:54:27 UTC
HMDB IDHMDB0035293
Secondary Accession Numbers
  • HMDB35293
Metabolite Identification
Common NameNorambreinolide
DescriptionNorambreinolide belongs to the class of organic compounds known as naphthofurans. Naphthofurans 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. Norambreinolide is an ambergris, dry, and labdanum tasting compound. Norambreinolide has been detected, but not quantified in, herbs and spices. This could make norambreinolide a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Norambreinolide.
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
Description Belongs to the class of organic compounds known as naphthofurans. Naphthofurans 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
  • Tetrahydrofuran
  • Lactone
  • Carboxylic acid ester
  • Oxacycle
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Physiological effect
Disposition
ProcessNot Available
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point122 - 125 °CNot Available
Boiling Point320.00 to 321.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility11.99 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP4.151 (est)The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+158.22131661259
DarkChem[M-H]-155.09631661259
DeepCCS[M-2H]-194.13430932474
DeepCCS[M+Na]+169.81630932474
AllCCS[M+H]+160.532859911
AllCCS[M+H-H2O]+157.032859911
AllCCS[M+NH4]+163.732859911
AllCCS[M+Na]+164.732859911
AllCCS[M-H]-168.332859911
AllCCS[M+Na-2H]-168.632859911
AllCCS[M+HCOO]-169.032859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
NorambreinolideCC12CCC3C(C)(C)CCCC3(C)C1CC(=O)O22681.3Standard polar33892256
NorambreinolideCC12CCC3C(C)(C)CCCC3(C)C1CC(=O)O21915.6Standard non polar33892256
NorambreinolideCC12CCC3C(C)(C)CCCC3(C)C1CC(=O)O22083.9Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Norambreinolide GC-MS (Non-derivatized) - 70eV, Positivesplash10-0kg9-1970000000-9bb3c07c120cdf2870742017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Norambreinolide GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Norambreinolide GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Norambreinolide 10V, Positive-QTOFsplash10-0udi-0190000000-79e30f095ad019575c6a2015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Norambreinolide 20V, Positive-QTOFsplash10-0udi-2590000000-79b3ccd278824dce94312015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Norambreinolide 40V, Positive-QTOFsplash10-052p-9630000000-2432ca12bbc5b792f12d2015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Norambreinolide 10V, Negative-QTOFsplash10-0002-0090000000-902bb4c0ff306165a7b02015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Norambreinolide 20V, Negative-QTOFsplash10-052b-0090000000-1f61b09bb60147aa94972015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Norambreinolide 40V, Negative-QTOFsplash10-0udu-9870000000-ad9c2baccef8d25f02b12015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Norambreinolide 10V, Positive-QTOFsplash10-0udi-0190000000-3e08cef9800d1bd5a6282021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Norambreinolide 20V, Positive-QTOFsplash10-001i-9550000000-79718e042312d242ffdf2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Norambreinolide 40V, Positive-QTOFsplash10-00di-7900000000-e9f09b26ee0205d61d702021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Norambreinolide 10V, Negative-QTOFsplash10-0002-0090000000-075bfc89a138283617072021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Norambreinolide 20V, Negative-QTOFsplash10-0002-0090000000-480f6ea2fb15cfc9441f2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Norambreinolide 40V, Negative-QTOFsplash10-0002-2090000000-7c02cfeca67577f56b642021-09-25Wishart LabView Spectrum
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
FooDB IDFDB013958
KNApSAcK IDC00048497
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
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1038441
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.. .