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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-12 02:37:53 UTC
Update Date2022-03-07 02:56:50 UTC
HMDB IDHMDB0040999
Secondary Accession Numbers
  • HMDB40999
Metabolite Identification
Common NameSecasterone
DescriptionSecasterone belongs to the class of organic compounds known as ergostane steroids. These are steroids with a structure based on the ergostane skeleton, which arises from the methylation of cholestane at the 24-position. Secasterone is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
Data?1563863613
Synonyms
ValueSource
SecasteroneMeSH
(22R,23R,24S)-22,23-Dihydroxy-2alpha,3alpha-epoxy-24-methyl-5alpha-cholest-6-oneMeSH
2,3-DiepisecasteroneMeSH
Chemical FormulaC28H46O4
Average Molecular Weight446.6624
Monoisotopic Molecular Weight446.33960996
IUPAC Name15-(3,4-dihydroxy-5,6-dimethylheptan-2-yl)-2,16-dimethyl-5-oxapentacyclo[9.7.0.0²,⁸.0⁴,⁶.0¹²,¹⁶]octadecan-9-one
Traditional Name15-(3,4-dihydroxy-5,6-dimethylheptan-2-yl)-2,16-dimethyl-5-oxapentacyclo[9.7.0.0²,⁸.0⁴,⁶.0¹²,¹⁶]octadecan-9-one
CAS Registry Number164321-81-7
SMILES
CC(C)C(C)C(O)C(O)C(C)C1CCC2C3CC(=O)C4CC5OC5CC4(C)C3CCC12C
InChI Identifier
InChI=1S/C28H46O4/c1-14(2)15(3)25(30)26(31)16(4)18-7-8-19-17-11-22(29)21-12-23-24(32-23)13-28(21,6)20(17)9-10-27(18,19)5/h14-21,23-26,30-31H,7-13H2,1-6H3
InChI KeyWDGGOKUICSKRHH-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as ergostane steroids. These are steroids with a structure based on the ergostane skeleton, which arises from the methylation of cholestane at the 24-position.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassErgostane steroids
Direct ParentErgostane steroids
Alternative ParentsNot Available
SubstituentsNot Available
Molecular FrameworkAliphatic heteropolycyclic 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 SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.0069 g/LALOGPS
logP3.38ALOGPS
logP4.66ChemAxon
logS-4.8ALOGPS
pKa (Strongest Acidic)13.66ChemAxon
pKa (Strongest Basic)-3.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area70.06 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity125.71 m³·mol⁻¹ChemAxon
Polarizability51.91 ųChemAxon
Number of Rings5ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+204.88731661259
DarkChem[M-H]-200.72931661259
DeepCCS[M-2H]-237.88630932474
DeepCCS[M+Na]+213.09830932474
AllCCS[M+H]+212.232859911
AllCCS[M+H-H2O]+210.432859911
AllCCS[M+NH4]+213.932859911
AllCCS[M+Na]+214.332859911
AllCCS[M-H]-210.232859911
AllCCS[M+Na-2H]-212.332859911
AllCCS[M+HCOO]-214.732859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
SecasteroneCC(C)C(C)C(O)C(O)C(C)C1CCC2C3CC(=O)C4CC5OC5CC4(C)C3CCC12C3322.3Standard polar33892256
SecasteroneCC(C)C(C)C(O)C(O)C(C)C1CCC2C3CC(=O)C4CC5OC5CC4(C)C3CCC12C3266.0Standard non polar33892256
SecasteroneCC(C)C(C)C(O)C(O)C(C)C1CCC2C3CC(=O)C4CC5OC5CC4(C)C3CCC12C3688.2Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Secasterone,1TMS,isomer #1CC(C)C(C)C(O[Si](C)(C)C)C(O)C(C)C1CCC2C3CC(=O)C4CC5OC5CC4(C)C3CCC12C3662.3Semi standard non polar33892256
Secasterone,1TMS,isomer #2CC(C)C(C)C(O)C(O[Si](C)(C)C)C(C)C1CCC2C3CC(=O)C4CC5OC5CC4(C)C3CCC12C3639.5Semi standard non polar33892256
Secasterone,1TMS,isomer #3CC(C)C(C)C(O)C(O)C(C)C1CCC2C3CC(O[Si](C)(C)C)=C4CC5OC5CC4(C)C3CCC12C3616.8Semi standard non polar33892256
Secasterone,1TMS,isomer #4CC(C)C(C)C(O)C(O)C(C)C1CCC2C3C=C(O[Si](C)(C)C)C4CC5OC5CC4(C)C3CCC12C3658.1Semi standard non polar33892256
Secasterone,2TMS,isomer #1CC(C)C(C)C(O[Si](C)(C)C)C(O[Si](C)(C)C)C(C)C1CCC2C3CC(=O)C4CC5OC5CC4(C)C3CCC12C3546.8Semi standard non polar33892256
Secasterone,2TMS,isomer #2CC(C)C(C)C(O[Si](C)(C)C)C(O)C(C)C1CCC2C3CC(O[Si](C)(C)C)=C4CC5OC5CC4(C)C3CCC12C3544.2Semi standard non polar33892256
Secasterone,2TMS,isomer #3CC(C)C(C)C(O[Si](C)(C)C)C(O)C(C)C1CCC2C3C=C(O[Si](C)(C)C)C4CC5OC5CC4(C)C3CCC12C3540.8Semi standard non polar33892256
Secasterone,2TMS,isomer #4CC(C)C(C)C(O)C(O[Si](C)(C)C)C(C)C1CCC2C3CC(O[Si](C)(C)C)=C4CC5OC5CC4(C)C3CCC12C3520.6Semi standard non polar33892256
Secasterone,2TMS,isomer #5CC(C)C(C)C(O)C(O[Si](C)(C)C)C(C)C1CCC2C3C=C(O[Si](C)(C)C)C4CC5OC5CC4(C)C3CCC12C3512.9Semi standard non polar33892256
Secasterone,3TMS,isomer #1CC(C)C(C)C(O[Si](C)(C)C)C(O[Si](C)(C)C)C(C)C1CCC2C3CC(O[Si](C)(C)C)=C4CC5OC5CC4(C)C3CCC12C3448.2Semi standard non polar33892256
Secasterone,3TMS,isomer #1CC(C)C(C)C(O[Si](C)(C)C)C(O[Si](C)(C)C)C(C)C1CCC2C3CC(O[Si](C)(C)C)=C4CC5OC5CC4(C)C3CCC12C3529.4Standard non polar33892256
Secasterone,3TMS,isomer #2CC(C)C(C)C(O[Si](C)(C)C)C(O[Si](C)(C)C)C(C)C1CCC2C3C=C(O[Si](C)(C)C)C4CC5OC5CC4(C)C3CCC12C3429.4Semi standard non polar33892256
Secasterone,3TMS,isomer #2CC(C)C(C)C(O[Si](C)(C)C)C(O[Si](C)(C)C)C(C)C1CCC2C3C=C(O[Si](C)(C)C)C4CC5OC5CC4(C)C3CCC12C3377.2Standard non polar33892256
Secasterone,1TBDMS,isomer #1CC(C)C(C)C(O[Si](C)(C)C(C)(C)C)C(O)C(C)C1CCC2C3CC(=O)C4CC5OC5CC4(C)C3CCC12C3895.9Semi standard non polar33892256
Secasterone,1TBDMS,isomer #2CC(C)C(C)C(O)C(O[Si](C)(C)C(C)(C)C)C(C)C1CCC2C3CC(=O)C4CC5OC5CC4(C)C3CCC12C3879.3Semi standard non polar33892256
Secasterone,1TBDMS,isomer #3CC(C)C(C)C(O)C(O)C(C)C1CCC2C3CC(O[Si](C)(C)C(C)(C)C)=C4CC5OC5CC4(C)C3CCC12C3873.0Semi standard non polar33892256
Secasterone,1TBDMS,isomer #4CC(C)C(C)C(O)C(O)C(C)C1CCC2C3C=C(O[Si](C)(C)C(C)(C)C)C4CC5OC5CC4(C)C3CCC12C3893.4Semi standard non polar33892256
Secasterone,2TBDMS,isomer #1CC(C)C(C)C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C(C)C1CCC2C3CC(=O)C4CC5OC5CC4(C)C3CCC12C4032.4Semi standard non polar33892256
Secasterone,2TBDMS,isomer #2CC(C)C(C)C(O[Si](C)(C)C(C)(C)C)C(O)C(C)C1CCC2C3CC(O[Si](C)(C)C(C)(C)C)=C4CC5OC5CC4(C)C3CCC12C4011.6Semi standard non polar33892256
Secasterone,2TBDMS,isomer #3CC(C)C(C)C(O[Si](C)(C)C(C)(C)C)C(O)C(C)C1CCC2C3C=C(O[Si](C)(C)C(C)(C)C)C4CC5OC5CC4(C)C3CCC12C4010.9Semi standard non polar33892256
Secasterone,2TBDMS,isomer #4CC(C)C(C)C(O)C(O[Si](C)(C)C(C)(C)C)C(C)C1CCC2C3CC(O[Si](C)(C)C(C)(C)C)=C4CC5OC5CC4(C)C3CCC12C3989.8Semi standard non polar33892256
Secasterone,2TBDMS,isomer #5CC(C)C(C)C(O)C(O[Si](C)(C)C(C)(C)C)C(C)C1CCC2C3C=C(O[Si](C)(C)C(C)(C)C)C4CC5OC5CC4(C)C3CCC12C3989.1Semi standard non polar33892256
Secasterone,3TBDMS,isomer #1CC(C)C(C)C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C(C)C1CCC2C3CC(O[Si](C)(C)C(C)(C)C)=C4CC5OC5CC4(C)C3CCC12C4142.0Semi standard non polar33892256
Secasterone,3TBDMS,isomer #1CC(C)C(C)C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C(C)C1CCC2C3CC(O[Si](C)(C)C(C)(C)C)=C4CC5OC5CC4(C)C3CCC12C4231.9Standard non polar33892256
Secasterone,3TBDMS,isomer #2CC(C)C(C)C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C(C)C1CCC2C3C=C(O[Si](C)(C)C(C)(C)C)C4CC5OC5CC4(C)C3CCC12C4141.5Semi standard non polar33892256
Secasterone,3TBDMS,isomer #2CC(C)C(C)C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C(C)C1CCC2C3C=C(O[Si](C)(C)C(C)(C)C)C4CC5OC5CC4(C)C3CCC12C3957.2Standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Secasterone GC-MS (Non-derivatized) - 70eV, Positivesplash10-002f-8547900000-da6ec891e5c15c253d5b2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Secasterone GC-MS (2 TMS) - 70eV, Positivesplash10-004i-3221190000-d5ead7fbe172d2061b492017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Secasterone 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 - Secasterone 10V, Positive-QTOFsplash10-002b-1101900000-c115dd23a7668ec641cd2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Secasterone 20V, Positive-QTOFsplash10-0g29-9318600000-ae9f9d45da0c135da8392017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Secasterone 40V, Positive-QTOFsplash10-0zn9-9422200000-cf2a93d8019204cc308c2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Secasterone 10V, Negative-QTOFsplash10-0002-0000900000-a6ea2f258516e78e31be2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Secasterone 20V, Negative-QTOFsplash10-00tb-7308900000-52e17b227d5e13f84d072017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Secasterone 40V, Negative-QTOFsplash10-00xs-9105100000-bb6cd929828aeac2f16f2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Secasterone 10V, Negative-QTOFsplash10-0002-0000900000-e535a0246aadde0c6cd42021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Secasterone 20V, Negative-QTOFsplash10-0002-0102900000-ed5f7a04a2d9482da2ee2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Secasterone 40V, Negative-QTOFsplash10-05mk-3019700000-af75aef03cc3af0dc10a2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Secasterone 10V, Positive-QTOFsplash10-00kb-0037900000-30fcecc72fc8722febeb2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Secasterone 20V, Positive-QTOFsplash10-014j-3359200000-964aa7287c335157479d2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Secasterone 40V, Positive-QTOFsplash10-059i-5920000000-69a4e98f2a9ea489f3772021-09-24Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
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 IDFDB020859
KNApSAcK IDC00037797
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound76031895
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.