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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-12 00:04:10 UTC
Update Date2022-03-07 02:55:53 UTC
HMDB IDHMDB0038731
Secondary Accession Numbers
  • HMDB38731
Metabolite Identification
Common Name4,7-Megastigmadien-9-ol
Description4,7-Megastigmadien-9-ol 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 4,7-Megastigmadien-9-ol.
Structure
Data?1563863247
Synonyms
ValueSource
4-(2,6,6-Trimethyl-2-cyclohexen-1-yl)-3-buten-2-ol, 9ciHMDB
Chemical FormulaC13H22O
Average Molecular Weight194.3132
Monoisotopic Molecular Weight194.167065326
IUPAC Name(3E)-4-(2,6,6-trimethylcyclohex-2-en-1-yl)but-3-en-2-ol
Traditional Name(3E)-4-(2,6,6-trimethylcyclohex-2-en-1-yl)but-3-en-2-ol
CAS Registry Number25312-34-9
SMILES
CC(O)\C=C\C1C(C)=CCCC1(C)C
InChI Identifier
InChI=1S/C13H22O/c1-10-6-5-9-13(3,4)12(10)8-7-11(2)14/h6-8,11-12,14H,5,9H2,1-4H3/b8-7+
InChI KeyPWDOJWCZWKWKSE-BQYQJAHWSA-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
  • Secondary alcohol
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Alcohol
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
Not AvailableNot Available
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling Point127.00 °C. @ 15.00 mm HgThe Good Scents Company Information System
Water Solubility21.02 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP4.492 (est)The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.14 g/LALOGPS
logP4.1ALOGPS
logP3.09ChemAxon
logS-3.2ALOGPS
pKa (Strongest Acidic)16.91ChemAxon
pKa (Strongest Basic)-2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity63.09 m³·mol⁻¹ChemAxon
Polarizability23.93 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
DarkChem[M+H]+149.23431661259
DarkChem[M-H]-144.87231661259
DeepCCS[M+H]+150.57730932474
DeepCCS[M-H]-148.18230932474
DeepCCS[M-2H]-182.4530932474
DeepCCS[M+Na]+157.12730932474
AllCCS[M+H]+145.532859911
AllCCS[M+H-H2O]+141.532859911
AllCCS[M+NH4]+149.332859911
AllCCS[M+Na]+150.432859911
AllCCS[M-H]-151.132859911
AllCCS[M+Na-2H]-152.132859911
AllCCS[M+HCOO]-153.332859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
4,7-Megastigmadien-9-olCC(O)\C=C\C1C(C)=CCCC1(C)C1966.6Standard polar33892256
4,7-Megastigmadien-9-olCC(O)\C=C\C1C(C)=CCCC1(C)C1378.5Standard non polar33892256
4,7-Megastigmadien-9-olCC(O)\C=C\C1C(C)=CCCC1(C)C1387.3Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
4,7-Megastigmadien-9-ol,1TMS,isomer #1CC1=CCCC(C)(C)C1/C=C/C(C)O[Si](C)(C)C1527.7Semi standard non polar33892256
4,7-Megastigmadien-9-ol,1TBDMS,isomer #1CC1=CCCC(C)(C)C1/C=C/C(C)O[Si](C)(C)C(C)(C)C1770.1Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - 4,7-Megastigmadien-9-ol EI-B (Non-derivatized)splash10-0005-9200000000-79a43e185c1f457439762017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 4,7-Megastigmadien-9-ol EI-B (Non-derivatized)splash10-0005-9200000000-79a43e185c1f457439762018-05-18HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4,7-Megastigmadien-9-ol GC-MS (Non-derivatized) - 70eV, Positivesplash10-0fba-5900000000-c267f7a31ec9b031ae592017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4,7-Megastigmadien-9-ol GC-MS (1 TMS) - 70eV, Positivesplash10-0udi-9360000000-66d7b3229c5dd2eedca32017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4,7-Megastigmadien-9-ol 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 - 4,7-Megastigmadien-9-ol 10V, Positive-QTOFsplash10-004i-0900000000-a21cb300d61fa383daa22016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4,7-Megastigmadien-9-ol 20V, Positive-QTOFsplash10-004r-3900000000-29e9baa4c5c595eb5ba02016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4,7-Megastigmadien-9-ol 40V, Positive-QTOFsplash10-014i-9700000000-ba2237d76cc290ce2c142016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4,7-Megastigmadien-9-ol 10V, Negative-QTOFsplash10-0006-0900000000-bd8d3890ec9b5e43ef642016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4,7-Megastigmadien-9-ol 20V, Negative-QTOFsplash10-002f-0900000000-4982cb3db1855e817a392016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4,7-Megastigmadien-9-ol 40V, Negative-QTOFsplash10-0a6r-3900000000-53881c2fab6d3e4609202016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4,7-Megastigmadien-9-ol 10V, Positive-QTOFsplash10-000i-0900000000-df71ccc453498a99045b2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4,7-Megastigmadien-9-ol 20V, Positive-QTOFsplash10-05g0-5900000000-c757dd76cd7d6297457d2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4,7-Megastigmadien-9-ol 40V, Positive-QTOFsplash10-066r-9700000000-3d259c7c12b1ded9f6572021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4,7-Megastigmadien-9-ol 10V, Negative-QTOFsplash10-0006-0900000000-f4ac9f2710ef63610b812021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4,7-Megastigmadien-9-ol 20V, Negative-QTOFsplash10-00di-0900000000-a2d9b2d72bcdd63e297a2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4,7-Megastigmadien-9-ol 40V, Negative-QTOFsplash10-05fs-1900000000-6dc6312d4637bb6d53ef2021-09-25Wishart 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 IDFDB018141
KNApSAcK IDNot Available
Chemspider ID4516121
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5363817
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1015831
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.