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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-12 02:38:00 UTC
Update Date2022-03-07 02:56:50 UTC
HMDB IDHMDB0041001
Secondary Accession Numbers
  • HMDB41001
Metabolite Identification
Common NameVolemolide
DescriptionVolemolide belongs to the class of organic compounds known as terpene lactones. These are prenol lipids containing a lactone ring. Based on a literature review a small amount of articles have been published on Volemolide.
Structure
Data?1563863613
Synonyms
ValueSource
17R-MethylincisterolHMDB
Chemical FormulaC22H34O3
Average Molecular Weight346.5036
Monoisotopic Molecular Weight346.250794954
IUPAC Name6-[(3E)-5,6-dimethylhept-3-en-2-yl]-3a-methoxy-5a-methyl-2H,3aH,4H,5H,5aH,6H,7H,8H,8aH-indeno[5,4-b]furan-2-one
Traditional Name6-[(3E)-5,6-dimethylhept-3-en-2-yl]-3a-methoxy-5a-methyl-4H,5H,6H,7H,8H,8aH-indeno[5,4-b]furan-2-one
CAS Registry Number125974-96-1
SMILES
COC12CCC3(C)C(CCC3C1=CC(=O)O2)C(C)\C=C\C(C)C(C)C
InChI Identifier
InChI=1S/C22H34O3/c1-14(2)15(3)7-8-16(4)17-9-10-18-19-13-20(23)25-22(19,24-6)12-11-21(17,18)5/h7-8,13-18H,9-12H2,1-6H3/b8-7+
InChI KeyFCFUSYHGZLEMJM-BQYQJAHWSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as terpene lactones. These are prenol lipids containing a lactone ring.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassTerpene lactones
Direct ParentTerpene lactones
Alternative Parents
Substituents
  • Terpene lactone
  • Sesquiterpenoid
  • Ketal
  • 2-furanone
  • Dihydrofuran
  • Enoate ester
  • Alpha,beta-unsaturated carboxylic ester
  • Carboxylic acid ester
  • Lactone
  • Monocarboxylic acid or derivatives
  • Acetal
  • Carboxylic acid derivative
  • Oxacycle
  • Organoheterocyclic compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organic oxide
  • Carbonyl group
  • Organic oxygen compound
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Not AvailableNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point61 - 62 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.0073 mg/L @ 25 °C (est)The Good Scents Company Information System
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.0002 g/LALOGPS
logP5.5ALOGPS
logP5.79ChemAxon
logS-6.2ALOGPS
pKa (Strongest Acidic)17.45ChemAxon
pKa (Strongest Basic)-4.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area35.53 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity102.29 m³·mol⁻¹ChemAxon
Polarizability40.56 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+184.70531661259
DarkChem[M-H]-183.73531661259
DeepCCS[M-2H]-219.99930932474
DeepCCS[M+Na]+195.22730932474
AllCCS[M+H]+187.332859911
AllCCS[M+H-H2O]+184.532859911
AllCCS[M+NH4]+189.932859911
AllCCS[M+Na]+190.632859911
AllCCS[M-H]-194.332859911
AllCCS[M+Na-2H]-195.232859911
AllCCS[M+HCOO]-196.432859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
VolemolideCOC12CCC3(C)C(CCC3C1=CC(=O)O2)C(C)\C=C\C(C)C(C)C3442.8Standard polar33892256
VolemolideCOC12CCC3(C)C(CCC3C1=CC(=O)O2)C(C)\C=C\C(C)C(C)C2434.0Standard non polar33892256
VolemolideCOC12CCC3(C)C(CCC3C1=CC(=O)O2)C(C)\C=C\C(C)C(C)C2574.1Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Volemolide GC-MS (Non-derivatized) - 70eV, Positivesplash10-000x-6379000000-aef756745a74a25acf0b2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Volemolide 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 - Volemolide 10V, Positive-QTOFsplash10-0002-3039000000-e03d74d0197b4a47cafd2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Volemolide 20V, Positive-QTOFsplash10-001i-9043000000-3192052f07a8e1413bda2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Volemolide 40V, Positive-QTOFsplash10-001i-9501000000-43fd4273a96b18015fc32017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Volemolide 10V, Negative-QTOFsplash10-0002-0009000000-50ebda94bcbd8d3cb9fd2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Volemolide 20V, Negative-QTOFsplash10-0002-0009000000-6afc1773e7cc5334adf82017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Volemolide 40V, Negative-QTOFsplash10-00dv-4091000000-7c18d1893cc18edead292017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Volemolide 10V, Positive-QTOFsplash10-0002-0049000000-5f420644c086d022b1b62021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Volemolide 20V, Positive-QTOFsplash10-05o9-9451000000-7f271cdc97f0b2ff0c3d2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Volemolide 40V, Positive-QTOFsplash10-001l-9220000000-5216e9c8bbe19bc7de0d2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Volemolide 10V, Negative-QTOFsplash10-0002-0009000000-2c896c0e1ded8ee379552021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Volemolide 20V, Negative-QTOFsplash10-03di-0019000000-3b13aaaa3b5ce5582bbe2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Volemolide 40V, Negative-QTOFsplash10-01ow-1196000000-72f6031b73a46b54ca762021-09-24Wishart 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 IDFDB020861
KNApSAcK IDC00056757
Chemspider ID35015073
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound14584690
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1888611
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.