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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 23:20:52 UTC
Update Date2022-03-07 02:55:37 UTC
HMDB IDHMDB0038063
Secondary Accession Numbers
  • HMDB38063
Metabolite Identification
Common NameStigmast-4-ene-3,6-dione
DescriptionStigmast-4-ene-3,6-dione 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. Thus, stigmast-4-ene-3,6-dione is considered to be a sterol lipid molecule. Stigmast-4-ene-3,6-dione is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.
Structure
Data?1563863134
Synonyms
ValueSource
(-)-Stigmast-4-en-3,6-dioneHMDB
24-Ethylcholest-4-ene-3,6-dioneHMDB
Stigmast-4-en-3,6-dioneHMDB
Chemical FormulaC29H46O2
Average Molecular Weight426.6743
Monoisotopic Molecular Weight426.349780716
IUPAC Name(2R,15R)-14-[(2R,5R)-5-ethyl-6-methylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-6-ene-5,8-dione
Traditional Name(2R,15R)-14-[(2R,5R)-5-ethyl-6-methylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-6-ene-5,8-dione
CAS Registry Number57458-57-8
SMILES
CC[C@H](CC[C@@H](C)C1CCC2C3CC(=O)C4=CC(=O)CC[C@]4(C)C3CC[C@]12C)C(C)C
InChI Identifier
InChI=1S/C29H46O2/c1-7-20(18(2)3)9-8-19(4)23-10-11-24-22-17-27(31)26-16-21(30)12-14-29(26,6)25(22)13-15-28(23,24)5/h16,18-20,22-25H,7-15,17H2,1-6H3/t19-,20-,22?,23?,24?,25?,28-,29-/m1/s1
InChI KeyUVFOCYGYACXLAY-UQYXHCMHSA-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
  • Stigmastane-skeleton
  • Triterpenoid
  • 3-oxo-delta-4-steroid
  • 3-oxosteroid
  • Oxosteroid
  • 6-oxosteroid
  • Delta-4-steroid
  • Cyclohexenone
  • Ketone
  • Cyclic ketone
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organic oxygen compound
  • Carbonyl group
  • Organic oxide
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
Process
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point170 - 172 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility3.2e-05 g/LALOGPS
logP6.2ALOGPS
logP7.74ChemAxon
logS-7.1ALOGPS
pKa (Strongest Acidic)19.65ChemAxon
pKa (Strongest Basic)-6.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area34.14 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity129.41 m³·mol⁻¹ChemAxon
Polarizability53.05 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+199.64131661259
DarkChem[M-H]-200.88931661259
DeepCCS[M-2H]-233.96130932474
DeepCCS[M+Na]+209.38630932474
AllCCS[M+H]+209.132859911
AllCCS[M+H-H2O]+207.132859911
AllCCS[M+NH4]+210.932859911
AllCCS[M+Na]+211.432859911
AllCCS[M-H]-208.232859911
AllCCS[M+Na-2H]-210.332859911
AllCCS[M+HCOO]-212.832859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Stigmast-4-ene-3,6-dioneCC[C@H](CC[C@@H](C)C1CCC2C3CC(=O)C4=CC(=O)CC[C@]4(C)C3CC[C@]12C)C(C)C4021.6Standard polar33892256
Stigmast-4-ene-3,6-dioneCC[C@H](CC[C@@H](C)C1CCC2C3CC(=O)C4=CC(=O)CC[C@]4(C)C3CC[C@]12C)C(C)C3379.0Standard non polar33892256
Stigmast-4-ene-3,6-dioneCC[C@H](CC[C@@H](C)C1CCC2C3CC(=O)C4=CC(=O)CC[C@]4(C)C3CC[C@]12C)C(C)C3645.8Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Stigmast-4-ene-3,6-dione,1TMS,isomer #1CC[C@H](CC[C@@H](C)C1CCC2C3C=C(O[Si](C)(C)C)C4=CC(=O)CC[C@]4(C)C3CC[C@@]21C)C(C)C3563.9Semi standard non polar33892256
Stigmast-4-ene-3,6-dione,1TMS,isomer #1CC[C@H](CC[C@@H](C)C1CCC2C3C=C(O[Si](C)(C)C)C4=CC(=O)CC[C@]4(C)C3CC[C@@]21C)C(C)C3374.4Standard non polar33892256
Stigmast-4-ene-3,6-dione,1TMS,isomer #2CC[C@H](CC[C@@H](C)C1CCC2C3CC(=O)C4=CC(O[Si](C)(C)C)=CC[C@]4(C)C3CC[C@@]21C)C(C)C3562.8Semi standard non polar33892256
Stigmast-4-ene-3,6-dione,1TMS,isomer #2CC[C@H](CC[C@@H](C)C1CCC2C3CC(=O)C4=CC(O[Si](C)(C)C)=CC[C@]4(C)C3CC[C@@]21C)C(C)C3438.3Standard non polar33892256
Stigmast-4-ene-3,6-dione,2TMS,isomer #1CC[C@H](CC[C@@H](C)C1CCC2C3C=C(O[Si](C)(C)C)C4=CC(O[Si](C)(C)C)=CC[C@]4(C)C3CC[C@@]21C)C(C)C3460.9Semi standard non polar33892256
Stigmast-4-ene-3,6-dione,2TMS,isomer #1CC[C@H](CC[C@@H](C)C1CCC2C3C=C(O[Si](C)(C)C)C4=CC(O[Si](C)(C)C)=CC[C@]4(C)C3CC[C@@]21C)C(C)C3440.7Standard non polar33892256
Stigmast-4-ene-3,6-dione,1TBDMS,isomer #1CC[C@H](CC[C@@H](C)C1CCC2C3C=C(O[Si](C)(C)C(C)(C)C)C4=CC(=O)CC[C@]4(C)C3CC[C@@]21C)C(C)C3790.7Semi standard non polar33892256
Stigmast-4-ene-3,6-dione,1TBDMS,isomer #1CC[C@H](CC[C@@H](C)C1CCC2C3C=C(O[Si](C)(C)C(C)(C)C)C4=CC(=O)CC[C@]4(C)C3CC[C@@]21C)C(C)C3575.3Standard non polar33892256
Stigmast-4-ene-3,6-dione,1TBDMS,isomer #2CC[C@H](CC[C@@H](C)C1CCC2C3CC(=O)C4=CC(O[Si](C)(C)C(C)(C)C)=CC[C@]4(C)C3CC[C@@]21C)C(C)C3798.9Semi standard non polar33892256
Stigmast-4-ene-3,6-dione,1TBDMS,isomer #2CC[C@H](CC[C@@H](C)C1CCC2C3CC(=O)C4=CC(O[Si](C)(C)C(C)(C)C)=CC[C@]4(C)C3CC[C@@]21C)C(C)C3661.5Standard non polar33892256
Stigmast-4-ene-3,6-dione,2TBDMS,isomer #1CC[C@H](CC[C@@H](C)C1CCC2C3C=C(O[Si](C)(C)C(C)(C)C)C4=CC(O[Si](C)(C)C(C)(C)C)=CC[C@]4(C)C3CC[C@@]21C)C(C)C3889.8Semi standard non polar33892256
Stigmast-4-ene-3,6-dione,2TBDMS,isomer #1CC[C@H](CC[C@@H](C)C1CCC2C3C=C(O[Si](C)(C)C(C)(C)C)C4=CC(O[Si](C)(C)C(C)(C)C)=CC[C@]4(C)C3CC[C@@]21C)C(C)C3806.3Standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Stigmast-4-ene-3,6-dione GC-MS (Non-derivatized) - 70eV, Positivesplash10-01pt-4339300000-16ec2f1196dd1fe4bbf22017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Stigmast-4-ene-3,6-dione 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 - Stigmast-4-ene-3,6-dione 10V, Positive-QTOFsplash10-004i-0103900000-4fa560faacf31f1022af2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Stigmast-4-ene-3,6-dione 20V, Positive-QTOFsplash10-054k-6109300000-1c9257f9fea3fdfa3fa22016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Stigmast-4-ene-3,6-dione 40V, Positive-QTOFsplash10-000t-9226100000-09521a1ff415978b21082016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Stigmast-4-ene-3,6-dione 10V, Negative-QTOFsplash10-004i-0000900000-7ded552d075526836e772016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Stigmast-4-ene-3,6-dione 20V, Negative-QTOFsplash10-004i-0000900000-2a58019635e009d6aecf2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Stigmast-4-ene-3,6-dione 40V, Negative-QTOFsplash10-0a4i-3019700000-351baf0cd4f13953e94f2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Stigmast-4-ene-3,6-dione 10V, Negative-QTOFsplash10-004i-0000900000-e0002f0b464d749332dc2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Stigmast-4-ene-3,6-dione 20V, Negative-QTOFsplash10-004i-0000900000-d910e6a23ed8ca528dfd2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Stigmast-4-ene-3,6-dione 40V, Negative-QTOFsplash10-0ab9-1017900000-dcc1ce95b9fb9110f9d72021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Stigmast-4-ene-3,6-dione 10V, Positive-QTOFsplash10-004i-0013900000-9aa26ac5906e018ce95b2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Stigmast-4-ene-3,6-dione 20V, Positive-QTOFsplash10-004u-8449400000-f20622a6290d600a51f72021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Stigmast-4-ene-3,6-dione 40V, Positive-QTOFsplash10-0a4i-9540000000-3fd146adc7b7f410f76f2021-09-25Wishart 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 IDFDB017275
KNApSAcK IDC00031394
Chemspider ID9917933
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound11743229
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.