Hmdb loader
Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 20:46:29 UTC
Update Date2023-02-21 17:24:53 UTC
HMDB IDHMDB0035753
Secondary Accession Numbers
  • HMDB35753
Metabolite Identification
Common Name(R)-(E)-4,7-Megastigmadien-9-one
Description(R)-(E)-4,7-Megastigmadien-9-one belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. Based on a literature review a small amount of articles have been published on (R)-(E)-4,7-Megastigmadien-9-one.
Structure
Data?1677000293
Synonyms
ValueSource
(+)-(6R)-alpha-IononeHMDB
(+)-alpha-IononeHMDB
(R)-(+)-alpha-IononeHMDB
(R)-alpha-IononeHMDB
(R-(e))-4-(2,6,6-Trimethyl-2-cyclohexen-1-yl)-3-buten-2-oneHMDB
3-Buten-2-one, 4-(2,6,6-trimethyl-2-cyclohexen-1-yl)-, (R)-(+)- (8ci)HMDB
4-[(1R)-2,6,6-Trimethyl-2-cyclohexen-1-yl]-(3E)-3-buten-2-oneHMDB
ParmoneHMDB
Chemical FormulaC13H20O
Average Molecular Weight192.2973
Monoisotopic Molecular Weight192.151415262
IUPAC Name(3E)-4-[(1R)-2,6,6-trimethylcyclohex-2-en-1-yl]but-3-en-2-one
Traditional Name(3E)-4-[(1R)-2,6,6-trimethylcyclohex-2-en-1-yl]but-3-en-2-one
CAS Registry Number24190-29-2
SMILES
CC(=O)\C=C\[C@H]1C(C)=CCCC1(C)C
InChI Identifier
InChI=1S/C13H20O/c1-10-6-5-9-13(3,4)12(10)8-7-11(2)14/h6-8,12H,5,9H2,1-4H3/b8-7+/t12-/m0/s1
InChI KeyUZFLPKAIBPNNCA-GUOLPTJISA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassSesquiterpenoids
Direct ParentSesquiterpenoids
Alternative Parents
Substituents
  • Cyclofarsesane sesquiterpenoid
  • Megastigmane sesquiterpenoid
  • Sesquiterpenoid
  • Ionone derivative
  • Alpha,beta-unsaturated ketone
  • Enone
  • Acryloyl-group
  • Ketone
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
Process
Role
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility24.67 mg/L @ 25 °C (est)The Good Scents Company Information System
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.05 g/LALOGPS
logP4.14ALOGPS
logP3.32ChemAxon
logS-3.6ALOGPS
pKa (Strongest Acidic)19.83ChemAxon
pKa (Strongest Basic)-4.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area17.07 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity62.09 m³·mol⁻¹ChemAxon
Polarizability23.08 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+151.03830932474
DeepCCS[M-H]-148.64230932474
DeepCCS[M-2H]-181.73530932474
DeepCCS[M+Na]+156.9530932474
AllCCS[M+H]+143.032859911
AllCCS[M+H-H2O]+138.932859911
AllCCS[M+NH4]+146.832859911
AllCCS[M+Na]+147.932859911
AllCCS[M-H]-149.732859911
AllCCS[M+Na-2H]-150.732859911
AllCCS[M+HCOO]-151.832859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
(R)-(E)-4,7-Megastigmadien-9-oneCC(=O)\C=C\[C@H]1C(C)=CCCC1(C)C1813.0Standard polar33892256
(R)-(E)-4,7-Megastigmadien-9-oneCC(=O)\C=C\[C@H]1C(C)=CCCC1(C)C1419.6Standard non polar33892256
(R)-(E)-4,7-Megastigmadien-9-oneCC(=O)\C=C\[C@H]1C(C)=CCCC1(C)C1424.4Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
(R)-(E)-4,7-Megastigmadien-9-one,1TMS,isomer #1C=C(/C=C/[C@H]1C(C)=CCCC1(C)C)O[Si](C)(C)C1602.3Semi standard non polar33892256
(R)-(E)-4,7-Megastigmadien-9-one,1TMS,isomer #1C=C(/C=C/[C@H]1C(C)=CCCC1(C)C)O[Si](C)(C)C1632.0Standard non polar33892256
(R)-(E)-4,7-Megastigmadien-9-one,1TBDMS,isomer #1C=C(/C=C/[C@H]1C(C)=CCCC1(C)C)O[Si](C)(C)C(C)(C)C1839.8Semi standard non polar33892256
(R)-(E)-4,7-Megastigmadien-9-one,1TBDMS,isomer #1C=C(/C=C/[C@H]1C(C)=CCCC1(C)C)O[Si](C)(C)C(C)(C)C1867.1Standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - (R)-(E)-4,7-Megastigmadien-9-one EI-B (Non-derivatized)splash10-0006-9600000000-f52514927b7c7e5bd79a2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - (R)-(E)-4,7-Megastigmadien-9-one EI-B (Non-derivatized)splash10-0006-9600000000-93c21f85616fb52a67632017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - (R)-(E)-4,7-Megastigmadien-9-one EI-B (Non-derivatized)splash10-0076-6900000000-0d604eb8b564376365162017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - (R)-(E)-4,7-Megastigmadien-9-one EI-B (Non-derivatized)splash10-0006-9600000000-f52514927b7c7e5bd79a2018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - (R)-(E)-4,7-Megastigmadien-9-one EI-B (Non-derivatized)splash10-0006-9600000000-93c21f85616fb52a67632018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - (R)-(E)-4,7-Megastigmadien-9-one EI-B (Non-derivatized)splash10-0076-6900000000-0d604eb8b564376365162018-05-18HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (R)-(E)-4,7-Megastigmadien-9-one GC-MS (Non-derivatized) - 70eV, Positivesplash10-0fia-4900000000-9e9a8dc88676517f40552017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (R)-(E)-4,7-Megastigmadien-9-one 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 - (R)-(E)-4,7-Megastigmadien-9-one 10V, Positive-QTOFsplash10-002f-0900000000-0d1ee7a07c25e0eb379a2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (R)-(E)-4,7-Megastigmadien-9-one 20V, Positive-QTOFsplash10-004u-3900000000-122599cd5a3606da38582016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (R)-(E)-4,7-Megastigmadien-9-one 40V, Positive-QTOFsplash10-014i-9400000000-5525adff7c75947a38302016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (R)-(E)-4,7-Megastigmadien-9-one 10V, Negative-QTOFsplash10-0006-0900000000-86ad4191ecec06d667eb2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (R)-(E)-4,7-Megastigmadien-9-one 20V, Negative-QTOFsplash10-0006-0900000000-81ca79f706995e1f23132016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (R)-(E)-4,7-Megastigmadien-9-one 40V, Negative-QTOFsplash10-0aed-2900000000-e754146e5b21f942f91e2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (R)-(E)-4,7-Megastigmadien-9-one 10V, Negative-QTOFsplash10-0006-0900000000-14436e4d9ff8d032db542021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (R)-(E)-4,7-Megastigmadien-9-one 20V, Negative-QTOFsplash10-00di-0900000000-7cd7cf4235cb00fbc0b52021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (R)-(E)-4,7-Megastigmadien-9-one 40V, Negative-QTOFsplash10-0kmj-3900000000-b5da866d6db21994e86c2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (R)-(E)-4,7-Megastigmadien-9-one 10V, Positive-QTOFsplash10-006x-0900000000-dca766c12d151f3d74b12021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (R)-(E)-4,7-Megastigmadien-9-one 20V, Positive-QTOFsplash10-05fu-8900000000-26ead371c8e940e8859e2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (R)-(E)-4,7-Megastigmadien-9-one 40V, Positive-QTOFsplash10-05mo-9600000000-ad142c26c199a3741a022021-09-24Wishart LabView Spectrum

IR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)2023-02-04FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)2023-02-04FELIX 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 IDFDB014487
KNApSAcK IDNot Available
Chemspider ID4594306
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5498521
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1445651
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.