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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 22:07:51 UTC
Update Date2022-03-07 02:55:07 UTC
HMDB IDHMDB0036941
Secondary Accession Numbers
  • HMDB36941
Metabolite Identification
Common NameSmilagenone
DescriptionSmilagenone, also known as sarsasapogenone or spirostan-3-one, belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units. Smilagenone is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
Data?1563862953
Synonyms
ValueSource
(5beta,25R)-Spirostan-3-oneHMDB
25-EpisarsasapogenoneHMDB
SarsasapogenoneHMDB
Spirostan-3-oneHMDB
Sarsasapogenone, (5alpha-25R)-isomerMeSH
Chemical FormulaC27H42O3
Average Molecular Weight414.6206
Monoisotopic Molecular Weight414.31339521
IUPAC Name5,7',9',13'-tetramethyl-5'-oxaspiro[oxane-2,6'-pentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosane]-16'-one
Traditional Name5,7',9',13'-tetramethyl-5'-oxaspiro[oxane-2,6'-pentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosane]-16'-one
CAS Registry Number512-07-2
SMILES
CC1C2C(CC3C4CCC5CC(=O)CCC5(C)C4CCC23C)OC11CCC(C)CO1
InChI Identifier
InChI=1S/C27H42O3/c1-16-7-12-27(29-15-16)17(2)24-23(30-27)14-22-20-6-5-18-13-19(28)8-10-25(18,3)21(20)9-11-26(22,24)4/h16-18,20-24H,5-15H2,1-4H3
InChI KeyCIBAPVLFORANSS-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassTriterpenoids
Direct ParentTriterpenoids
Alternative Parents
Substituents
  • Triterpenoid
  • Spirostane skeleton
  • 3-oxosteroid
  • Oxosteroid
  • Steroid
  • Ketal
  • Oxane
  • Tetrahydrofuran
  • Ketone
  • Cyclic ketone
  • Oxacycle
  • Organoheterocyclic compound
  • Acetal
  • Hydrocarbon derivative
  • Organic oxide
  • Organooxygen compound
  • Organic oxygen compound
  • Carbonyl group
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
Process
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point188 - 189 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility2.9e-05 g/LALOGPS
logP4.14ALOGPS
logP5.54ChemAxon
logS-7.2ALOGPS
pKa (Strongest Basic)-4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area35.53 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity118.39 m³·mol⁻¹ChemAxon
Polarizability49.65 ųChemAxon
Number of Rings6ChemAxon
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]+196.60131661259
DarkChem[M-H]-191.15531661259
DeepCCS[M-2H]-236.52330932474
DeepCCS[M+Na]+212.10330932474
AllCCS[M+H]+207.732859911
AllCCS[M+H-H2O]+205.632859911
AllCCS[M+NH4]+209.732859911
AllCCS[M+Na]+210.232859911
AllCCS[M-H]-206.232859911
AllCCS[M+Na-2H]-207.832859911
AllCCS[M+HCOO]-209.632859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
SmilagenoneCC1C2C(CC3C4CCC5CC(=O)CCC5(C)C4CCC23C)OC11CCC(C)CO13536.8Standard polar33892256
SmilagenoneCC1C2C(CC3C4CCC5CC(=O)CCC5(C)C4CCC23C)OC11CCC(C)CO13127.6Standard non polar33892256
SmilagenoneCC1C2C(CC3C4CCC5CC(=O)CCC5(C)C4CCC23C)OC11CCC(C)CO13405.3Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Smilagenone,1TMS,isomer #1CC1CCC2(OC1)OC1CC3C4CCC5CC(O[Si](C)(C)C)=CCC5(C)C4CCC3(C)C1C2C3330.2Semi standard non polar33892256
Smilagenone,1TMS,isomer #1CC1CCC2(OC1)OC1CC3C4CCC5CC(O[Si](C)(C)C)=CCC5(C)C4CCC3(C)C1C2C3159.7Standard non polar33892256
Smilagenone,1TMS,isomer #2CC1CCC2(OC1)OC1CC3C4CCC5C=C(O[Si](C)(C)C)CCC5(C)C4CCC3(C)C1C2C3357.5Semi standard non polar33892256
Smilagenone,1TMS,isomer #2CC1CCC2(OC1)OC1CC3C4CCC5C=C(O[Si](C)(C)C)CCC5(C)C4CCC3(C)C1C2C3216.7Standard non polar33892256
Smilagenone,1TBDMS,isomer #1CC1CCC2(OC1)OC1CC3C4CCC5CC(O[Si](C)(C)C(C)(C)C)=CCC5(C)C4CCC3(C)C1C2C3574.5Semi standard non polar33892256
Smilagenone,1TBDMS,isomer #1CC1CCC2(OC1)OC1CC3C4CCC5CC(O[Si](C)(C)C(C)(C)C)=CCC5(C)C4CCC3(C)C1C2C3367.5Standard non polar33892256
Smilagenone,1TBDMS,isomer #2CC1CCC2(OC1)OC1CC3C4CCC5C=C(O[Si](C)(C)C(C)(C)C)CCC5(C)C4CCC3(C)C1C2C3598.1Semi standard non polar33892256
Smilagenone,1TBDMS,isomer #2CC1CCC2(OC1)OC1CC3C4CCC5C=C(O[Si](C)(C)C(C)(C)C)CCC5(C)C4CCC3(C)C1C2C3437.0Standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Smilagenone GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4s-3159000000-542e7dc675517bf4ce052017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Smilagenone 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 - Smilagenone 10V, Positive-QTOFsplash10-014i-8048900000-9b13f9aa3b594130cff72015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Smilagenone 20V, Positive-QTOFsplash10-00xr-8198200000-f32c85cf75f50873a5ab2015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Smilagenone 40V, Positive-QTOFsplash10-066r-9054000000-b9d4208da6e48c4ee19a2015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Smilagenone 10V, Positive-QTOFsplash10-014i-8048900000-9b13f9aa3b594130cff72015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Smilagenone 20V, Positive-QTOFsplash10-00xr-8198200000-f32c85cf75f50873a5ab2015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Smilagenone 40V, Positive-QTOFsplash10-066r-9054000000-b9d4208da6e48c4ee19a2015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Smilagenone 10V, Negative-QTOFsplash10-03di-4011900000-2473bea931f335f7cac62015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Smilagenone 20V, Negative-QTOFsplash10-03dj-2039300000-5c3b29791cfa45af139f2015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Smilagenone 40V, Negative-QTOFsplash10-014j-9033000000-b05e67e3a7880c576f3a2015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Smilagenone 10V, Negative-QTOFsplash10-03di-4011900000-2473bea931f335f7cac62015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Smilagenone 20V, Negative-QTOFsplash10-03dj-2039300000-5c3b29791cfa45af139f2015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Smilagenone 40V, Negative-QTOFsplash10-014j-9033000000-b05e67e3a7880c576f3a2015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Smilagenone 10V, Positive-QTOFsplash10-014i-0013900000-8600851e1b5173533f012021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Smilagenone 20V, Positive-QTOFsplash10-00mk-1159300000-c0eba19fafc68510a6f72021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Smilagenone 40V, Positive-QTOFsplash10-0036-3952000000-27be854367b89fd29eec2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Smilagenone 10V, Negative-QTOFsplash10-03di-0000900000-382bbcadd43c6789b8322021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Smilagenone 20V, Negative-QTOFsplash10-03di-0000900000-af0d9054cd738c556ebf2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Smilagenone 40V, Negative-QTOFsplash10-03di-0009500000-341b22116ef35ac10e8b2021-09-24Wishart 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 IDFDB015910
KNApSAcK IDNot Available
Chemspider ID277091
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound313275
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.