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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 21:56:45 UTC
Update Date2022-03-07 02:55:03 UTC
HMDB IDHMDB0036771
Secondary Accession Numbers
  • HMDB36771
Metabolite Identification
Common NameLaurenobiolide
DescriptionLaurenobiolide belongs to the class of organic compounds known as germacranolides and derivatives. These are sesquiterpene lactones with a structure based on the germacranolide skeleton, characterized by a gamma lactone fused to a 1,7-dimethylcyclodec-1-ene moiety. Based on a literature review a significant number of articles have been published on Laurenobiolide.
Structure
Data?1563862924
Synonyms
ValueSource
IsotulipinolideHMDB
6,10-Dimethyl-3-methylidene-2-oxo-2H,3H,3ah,4H,7H,8H,11H,11ah-cyclodeca[b]furan-4-yl acetic acidGenerator
Chemical FormulaC17H22O4
Average Molecular Weight290.3542
Monoisotopic Molecular Weight290.151809192
IUPAC Name6,10-dimethyl-3-methylidene-2-oxo-2H,3H,3aH,4H,7H,8H,11H,11aH-cyclodeca[b]furan-4-yl acetate
Traditional Name6,10-dimethyl-3-methylidene-2-oxo-3aH,4H,7H,8H,11H,11aH-cyclodeca[b]furan-4-yl acetate
CAS Registry Number35001-25-3
SMILES
CC(=O)OC1\C=C(C)/CC\C=C(C)/CC2OC(=O)C(=C)C12
InChI Identifier
InChI=1S/C17H22O4/c1-10-6-5-7-11(2)9-15-16(12(3)17(19)21-15)14(8-10)20-13(4)18/h7-8,14-16H,3,5-6,9H2,1-2,4H3/b10-8-,11-7-
InChI KeyORJVLIMAQARNOU-ACBQZUGDSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as germacranolides and derivatives. These are sesquiterpene lactones with a structure based on the germacranolide skeleton, characterized by a gamma lactone fused to a 1,7-dimethylcyclodec-1-ene moiety.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassTerpene lactones
Direct ParentGermacranolides and derivatives
Alternative Parents
Substituents
  • Germacranolide
  • Germacrane 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
Ontology
Physiological effectNot Available
Disposition
Process
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point101 - 103 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility12.63 mg/L @ 25 °C (est)The Good Scents Company Information System
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.083 g/LALOGPS
logP3.31ALOGPS
logP2.91ChemAxon
logS-3.5ALOGPS
pKa (Strongest Acidic)6.21ChemAxon
pKa (Strongest Basic)-6.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area52.6 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity80.67 m³·mol⁻¹ChemAxon
Polarizability30.89 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+168.92231661259
DarkChem[M-H]-162.86931661259
DeepCCS[M-2H]-199.58730932474
DeepCCS[M+Na]+174.81330932474
AllCCS[M+H]+169.932859911
AllCCS[M+H-H2O]+166.432859911
AllCCS[M+NH4]+173.132859911
AllCCS[M+Na]+174.032859911
AllCCS[M-H]-173.732859911
AllCCS[M+Na-2H]-173.832859911
AllCCS[M+HCOO]-174.132859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
LaurenobiolideCC(=O)OC1\C=C(C)/CC\C=C(C)/CC2OC(=O)C(=C)C122921.3Standard polar33892256
LaurenobiolideCC(=O)OC1\C=C(C)/CC\C=C(C)/CC2OC(=O)C(=C)C122142.0Standard non polar33892256
LaurenobiolideCC(=O)OC1\C=C(C)/CC\C=C(C)/CC2OC(=O)C(=C)C122241.7Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Laurenobiolide GC-MS (Non-derivatized) - 70eV, Positivesplash10-001l-7290000000-42f5680cc8ce8d9d3bbc2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Laurenobiolide 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 - Laurenobiolide 10V, Positive-QTOFsplash10-0006-0090000000-5dd05d95f16c803a48752016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Laurenobiolide 20V, Positive-QTOFsplash10-003s-1690000000-603db850d843dbf236f22016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Laurenobiolide 40V, Positive-QTOFsplash10-0ftf-9840000000-ddd7810d621ff43e35462016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Laurenobiolide 10V, Negative-QTOFsplash10-000j-0090000000-0c6ee6f48041152fa7212016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Laurenobiolide 20V, Negative-QTOFsplash10-000b-2090000000-be7ce9b54e80ed94245f2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Laurenobiolide 40V, Negative-QTOFsplash10-0kfx-8940000000-c75c9d4e3c2cbee283e22016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Laurenobiolide 10V, Negative-QTOFsplash10-0a4i-9030000000-fbea22a3cc95a5df97e12021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Laurenobiolide 20V, Negative-QTOFsplash10-0a4i-9050000000-6e0edae293cab189749e2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Laurenobiolide 40V, Negative-QTOFsplash10-0a4i-9010000000-f6230ad3cc97ec27ad712021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Laurenobiolide 10V, Positive-QTOFsplash10-000t-0090000000-50e71a036f2205e62edc2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Laurenobiolide 20V, Positive-QTOFsplash10-001i-0290000000-36acec79491d6a3126f92021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Laurenobiolide 40V, Positive-QTOFsplash10-0ae9-1590000000-98ce2e8a788e952c73c42021-09-23Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • 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 IDFDB015713
KNApSAcK IDC00003314
Chemspider ID13303669
KEGG Compound IDC09492
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound18615526
PDB IDNot Available
ChEBI ID6390
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1857081
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  2. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
  3. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
  4. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
  5. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
  6. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.