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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 20:41:49 UTC
Update Date2022-03-07 02:54:36 UTC
HMDB IDHMDB0035688
Secondary Accession Numbers
  • HMDB35688
Metabolite Identification
Common NameValencene
DescriptionValencene, also known as oxo-tremorine, belongs to the class of organic compounds known as eremophilane, 8,9-secoeremophilane and furoeremophilane sesquiterpenoids. These are sesquiterpenoids with a structure based either on the eremophilane skeleton, its 8,9-seco derivative, or the furoeremophilane skeleton. Eremophilanes have been shown to be derived from eudesmanes by migration of the methyl group at C-10 to C-5. Based on a literature review a significant number of articles have been published on Valencene.
Structure
Data?1563862755
Synonyms
ValueSource
1-(4-(1-Pyrrolidinyl)-2-butynyl)-2-pyrrolidinoneHMDB
1-(4-(Pyrrolidin-1-yl)but-2-ynyl)pyrrolidin-2-oneHMDB
1-[4-(1-Pyrrolidinyl)-2-butynyl]-2-pyrrolidinoneHMDB
2'-Oxopyrrolidino-1-pyrrolidino-4-butyneHMDB
4beta H,5alpha -Eremophila-1(10),11-dieneHMDB
oxo-TremorineHMDB
OxotremorinHMDB
OxotremorineHMDB
Oxotremorine sesquifumarate saltHMDB
OxytremorineHMDB
Valencene 85HMDB
Chemical FormulaC15H24
Average Molecular Weight204.3511
Monoisotopic Molecular Weight204.187800768
IUPAC Name4a,5-dimethyl-3-(prop-1-en-2-yl)-1,2,3,4,4a,5,6,7-octahydronaphthalene
Traditional Namevalencene
CAS Registry Number4630-07-3
SMILES
CC1CCC=C2CCC(CC12C)C(C)=C
InChI Identifier
InChI=1S/C15H24/c1-11(2)13-8-9-14-7-5-6-12(3)15(14,4)10-13/h7,12-13H,1,5-6,8-10H2,2-4H3
InChI KeyQEBNYNLSCGVZOH-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as eremophilane, 8,9-secoeremophilane and furoeremophilane sesquiterpenoids. These are sesquiterpenoids with a structure based either on the eremophilane skeleton, its 8,9-seco derivative, or the furoeremophilane skeleton. Eremophilanes have been shown to be derived from eudesmanes by migration of the methyl group at C-10 to C-5.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassSesquiterpenoids
Direct ParentEremophilane, 8,9-secoeremophilane and furoeremophilane sesquiterpenoids
Alternative Parents
Substituents
  • Eremophilane sesquiterpenoid
  • Branched unsaturated hydrocarbon
  • Polycyclic hydrocarbon
  • Cyclic olefin
  • Unsaturated aliphatic hydrocarbon
  • Unsaturated hydrocarbon
  • Olefin
  • Hydrocarbon
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling Point123.00 °C. @ 11.00 mm HgThe Good Scents Company Information System
Water Solubility0.05 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP6.494 (est)The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.0029 g/LALOGPS
logP5.86ALOGPS
logP4.52ChemAxon
logS-4.8ALOGPS
Physiological Charge0ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area0 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity67.45 m³·mol⁻¹ChemAxon
Polarizability26.05 ųChemAxon
Number of Rings2ChemAxon
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]+149.39931661259
DarkChem[M-H]-146.01931661259
DeepCCS[M-2H]-183.30630932474
DeepCCS[M+Na]+158.8730932474
AllCCS[M+H]+148.232859911
AllCCS[M+H-H2O]+144.232859911
AllCCS[M+NH4]+152.032859911
AllCCS[M+Na]+153.032859911
AllCCS[M-H]-157.332859911
AllCCS[M+Na-2H]-157.932859911
AllCCS[M+HCOO]-158.532859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
ValenceneCC1CCC=C2CCC(CC12C)C(C)=C1720.4Standard polar33892256
ValenceneCC1CCC=C2CCC(CC12C)C(C)=C1484.7Standard non polar33892256
ValenceneCC1CCC=C2CCC(CC12C)C(C)=C1521.5Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Valencene GC-EI-Q (Non-derivatized)splash10-06r6-6900000000-6056307d54773f6a82a72020-07-08HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Valencene GC-MS (Non-derivatized) - 70eV, Positivesplash10-000i-1900000000-924c0ed0f560e2343f552017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Valencene 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 - Valencene 10V, Positive-QTOFsplash10-0a4i-1490000000-64b1f2c7f108e8d251ee2016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Valencene 20V, Positive-QTOFsplash10-0cdr-3920000000-6ec0f8bff5e08c3188eb2016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Valencene 40V, Positive-QTOFsplash10-000i-6900000000-de9b8430cbefd1ff8a232016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Valencene 10V, Negative-QTOFsplash10-0udi-0090000000-dceadc1eb356d16afae62016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Valencene 20V, Negative-QTOFsplash10-0udi-0190000000-2e9a22282b05ad9143292016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Valencene 40V, Negative-QTOFsplash10-000i-1910000000-25622133ba47e98f5e5d2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Valencene 10V, Positive-QTOFsplash10-0bt9-0970000000-3dce51d91747df18039b2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Valencene 20V, Positive-QTOFsplash10-0a4i-6920000000-7d73224ac3ffa81a2d3c2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Valencene 40V, Positive-QTOFsplash10-0006-9200000000-2cd94e921e3ed07cd7902021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Valencene 10V, Negative-QTOFsplash10-0udi-0090000000-7ccf03fa1149a1e9f55f2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Valencene 20V, Negative-QTOFsplash10-0udi-0090000000-7ccf03fa1149a1e9f55f2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Valencene 40V, Negative-QTOFsplash10-0udi-0290000000-6c318cb263f435b16ddb2021-09-24Wishart 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 IDFDB014408
KNApSAcK IDC00034741
Chemspider ID254202
KEGG Compound IDC17277
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkValencene
METLIN IDNot Available
PubChem Compound288227
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1006341
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
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  2. Kuroiwa M, Hamada M, Hieda E, Shuto T, Sotogaku N, Flajolet M, Snyder GL, Hendrick JP, Fienberg A, Nishi A: Muscarinic receptors acting at pre- and post-synaptic sites differentially regulate dopamine/DARPP-32 signaling in striatonigral and striatopallidal neurons. Neuropharmacology. 2012 Dec;63(7):1248-57. doi: 10.1016/j.neuropharm.2012.07.046. Epub 2012 Aug 7. [PubMed:22971543 ]
  3. Westermann KH, Oelszner W, Funk KF, Staib AH: Effects of oxotremorine after nigrostriatal lesions in rats. Pol J Pharmacol Pharm. 1975 Jul-Aug;27(4):413-7. [PubMed:1166022 ]
  4. Pavesi E, Gooch A, Lee E, Fletcher ML: Cholinergic modulation during acquisition of olfactory fear conditioning alters learning and stimulus generalization in mice. Learn Mem. 2012 Dec 14;20(1):6-10. doi: 10.1101/lm.028324.112. [PubMed:23242418 ]
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  6. Gholami M, Saboory E, Zare S, Roshan-Milani S, Hajizadeh-Moghaddam A: The effect of dorsal hippocampal administration of nicotinic and muscarinic cholinergic ligands on pentylenetetrazol-induced generalized seizures in rats. Epilepsy Behav. 2012 Oct;25(2):244-9. doi: 10.1016/j.yebeh.2012.07.004. Epub 2012 Oct 2. [PubMed:23037131 ]
  7. Daigle TL, Caron MG: Elimination of GRK2 from cholinergic neurons reduces behavioral sensitivity to muscarinic receptor activation. J Neurosci. 2012 Aug 15;32(33):11461-6. doi: 10.1523/JNEUROSCI.2234-12.2012. [PubMed:22895728 ]
  8. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  9. 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 ]
  10. 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 ]
  11. 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 ]
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