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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 18:26:28 UTC
Update Date2022-03-07 02:53:49 UTC
HMDB IDHMDB0033686
Secondary Accession Numbers
  • HMDB33686
Metabolite Identification
Common Name(3beta,4alpha,5alpha,24(28)Z)-4,14-Dimethylstigmasta-8,24(28)-dien-3-ol
Description(3beta,4alpha,5alpha,24(28)Z)-4,14-Dimethylstigmasta-8,24(28)-dien-3-ol belongs to the class of organic compounds known as stigmastanes and derivatives. These are sterol lipids with a structure based on the stigmastane skeleton, which consists of a cholestane moiety bearing an ethyl group at the carbon atom C24 (3beta,4alpha,5alpha,24(28)Z)-4,14-Dimethylstigmasta-8,24(28)-dien-3-ol is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
Data?1563862445
Synonyms
ValueSource
(3b,4a,5a,24(28)Z)-4,14-Dimethylstigmasta-8,24(28)-dien-3-olGenerator
(3Β,4α,5α,24(28)Z)-4,14-dimethylstigmasta-8,24(28)-dien-3-olGenerator
Chemical FormulaC31H52O
Average Molecular Weight440.744
Monoisotopic Molecular Weight440.401816286
IUPAC Name2,6,11,15-tetramethyl-14-[(5Z)-5-(propan-2-yl)hept-5-en-2-yl]tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-1(10)-en-5-ol
Traditional Name14-[(5Z)-5-isopropylhept-5-en-2-yl]-2,6,11,15-tetramethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-1(10)-en-5-ol
CAS Registry Number73148-03-5
SMILES
C\C=C(\CCC(C)C1CCC2(C)C3=C(CCC12C)C1(C)CCC(O)C(C)C1CC3)C(C)C
InChI Identifier
InChI=1S/C31H52O/c1-9-23(20(2)3)11-10-21(4)24-14-18-31(8)27-13-12-25-22(5)28(32)16-17-29(25,6)26(27)15-19-30(24,31)7/h9,20-22,24-25,28,32H,10-19H2,1-8H3/b23-9-
InChI KeyWJNCLXFJDFOIKU-AQHIEDMUSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as stigmastanes and derivatives. These are sterol lipids with a structure based on the stigmastane skeleton, which consists of a cholestane moiety bearing an ethyl group at the carbon atom C24.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassStigmastanes and derivatives
Direct ParentStigmastanes and derivatives
Alternative Parents
Substituents
  • Triterpenoid
  • Stigmastane-skeleton
  • Hydroxysteroid
  • 3-hydroxysteroid
  • Cyclic alcohol
  • Secondary alcohol
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Alcohol
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point42.35 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP-1.436Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.0003 g/LALOGPS
logP7.95ALOGPS
logP8.06ChemAxon
logS-6.2ALOGPS
pKa (Strongest Acidic)18.96ChemAxon
pKa (Strongest Basic)-1.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity139.3 m³·mol⁻¹ChemAxon
Polarizability57.3 ųChemAxon
Number of Rings4ChemAxon
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]+205.59531661259
DarkChem[M-H]-202.50631661259
DeepCCS[M-2H]-247.2330932474
DeepCCS[M+Na]+222.45830932474
AllCCS[M+H]+216.632859911
AllCCS[M+H-H2O]+214.932859911
AllCCS[M+NH4]+218.332859911
AllCCS[M+Na]+218.732859911
AllCCS[M-H]-212.332859911
AllCCS[M+Na-2H]-214.832859911
AllCCS[M+HCOO]-217.732859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
(3beta,4alpha,5alpha,24(28)Z)-4,14-Dimethylstigmasta-8,24(28)-dien-3-olC\C=C(\CCC(C)C1CCC2(C)C3=C(CCC12C)C1(C)CCC(O)C(C)C1CC3)C(C)C3044.5Standard polar33892256
(3beta,4alpha,5alpha,24(28)Z)-4,14-Dimethylstigmasta-8,24(28)-dien-3-olC\C=C(\CCC(C)C1CCC2(C)C3=C(CCC12C)C1(C)CCC(O)C(C)C1CC3)C(C)C3448.2Standard non polar33892256
(3beta,4alpha,5alpha,24(28)Z)-4,14-Dimethylstigmasta-8,24(28)-dien-3-olC\C=C(\CCC(C)C1CCC2(C)C3=C(CCC12C)C1(C)CCC(O)C(C)C1CC3)C(C)C3435.1Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
(3beta,4alpha,5alpha,24(28)Z)-4,14-Dimethylstigmasta-8,24(28)-dien-3-ol,1TMS,isomer #1C/C=C(/CCC(C)C1CCC2(C)C3=C(CCC12C)C1(C)CCC(O[Si](C)(C)C)C(C)C1CC3)C(C)C3484.3Semi standard non polar33892256
(3beta,4alpha,5alpha,24(28)Z)-4,14-Dimethylstigmasta-8,24(28)-dien-3-ol,1TBDMS,isomer #1C/C=C(/CCC(C)C1CCC2(C)C3=C(CCC12C)C1(C)CCC(O[Si](C)(C)C(C)(C)C)C(C)C1CC3)C(C)C3714.9Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - (3beta,4alpha,5alpha,24(28)Z)-4,14-Dimethylstigmasta-8,24(28)-dien-3-ol GC-MS (Non-derivatized) - 70eV, Positivesplash10-0imi-1005900000-5dad0418f8c4569fab302017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (3beta,4alpha,5alpha,24(28)Z)-4,14-Dimethylstigmasta-8,24(28)-dien-3-ol GC-MS (1 TMS) - 70eV, Positivesplash10-000t-2002900000-e6997957a10ba4fbaa402017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (3beta,4alpha,5alpha,24(28)Z)-4,14-Dimethylstigmasta-8,24(28)-dien-3-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 - (3beta,4alpha,5alpha,24(28)Z)-4,14-Dimethylstigmasta-8,24(28)-dien-3-ol 10V, Positive-QTOFsplash10-00dl-0002900000-b21e05b126cfdd8c3b122016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (3beta,4alpha,5alpha,24(28)Z)-4,14-Dimethylstigmasta-8,24(28)-dien-3-ol 20V, Positive-QTOFsplash10-0095-5219400000-52dc967899aa43fd29102016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (3beta,4alpha,5alpha,24(28)Z)-4,14-Dimethylstigmasta-8,24(28)-dien-3-ol 40V, Positive-QTOFsplash10-0frt-9257300000-e1b08018ab4163d342e22016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (3beta,4alpha,5alpha,24(28)Z)-4,14-Dimethylstigmasta-8,24(28)-dien-3-ol 10V, Negative-QTOFsplash10-000i-0000900000-5c1026a388dce4952bd32016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (3beta,4alpha,5alpha,24(28)Z)-4,14-Dimethylstigmasta-8,24(28)-dien-3-ol 20V, Negative-QTOFsplash10-000i-0000900000-16ce7a50e905be085d692016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (3beta,4alpha,5alpha,24(28)Z)-4,14-Dimethylstigmasta-8,24(28)-dien-3-ol 40V, Negative-QTOFsplash10-00di-3003900000-262e4d571710aac7bd782016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (3beta,4alpha,5alpha,24(28)Z)-4,14-Dimethylstigmasta-8,24(28)-dien-3-ol 10V, Positive-QTOFsplash10-03di-2918600000-f4ed00ec378de4bfce032021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (3beta,4alpha,5alpha,24(28)Z)-4,14-Dimethylstigmasta-8,24(28)-dien-3-ol 20V, Positive-QTOFsplash10-001j-9211100000-e00ad2a04cfcadd328382021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (3beta,4alpha,5alpha,24(28)Z)-4,14-Dimethylstigmasta-8,24(28)-dien-3-ol 40V, Positive-QTOFsplash10-01pp-9522000000-514c53b9fe076617b8d32021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (3beta,4alpha,5alpha,24(28)Z)-4,14-Dimethylstigmasta-8,24(28)-dien-3-ol 10V, Negative-QTOFsplash10-000i-0000900000-6abf4200d93b5ca719d02021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (3beta,4alpha,5alpha,24(28)Z)-4,14-Dimethylstigmasta-8,24(28)-dien-3-ol 20V, Negative-QTOFsplash10-000i-0000900000-a5a94faf463880fe9cdb2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (3beta,4alpha,5alpha,24(28)Z)-4,14-Dimethylstigmasta-8,24(28)-dien-3-ol 40V, Negative-QTOFsplash10-0079-0001900000-1b3c293c3dd6a8bef8382021-09-24Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • 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 IDFDB011793
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound131751478
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
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.