Hmdb loader
You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:34:25 UTC
Update Date2022-03-07 02:52:24 UTC
HMDB IDHMDB0030048
Secondary Accession Numbers
  • HMDB30048
Metabolite Identification
Common NameSmilagenin
DescriptionSmilagenin, also known as isosarsapogenin or tigogenin, belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units. Thus, smilagenin is considered to be a sterol. Based on a literature review a significant number of articles have been published on Smilagenin.
Structure
Data?1563861929
Synonyms
ValueSource
IsosarsapogeninChEBI
(25R)-5beta-Spirostan-3beta-olKegg
(25R)-5b-Spirostan-3b-olGenerator
(25R)-5Β-spirostan-3β-olGenerator
Epi-sarsasapogeninMeSH
EpismilageninMeSH
SarsaponinMeSH
SarsasapogeninMeSH
Sarsasapogenin, (3beta,5alpha,25R)-isomerMeSH
Sarsasapogenin, (3beta,5alpha,25S)-isomerMeSH
Sarsasapogenin, (3beta,5beta)-isomerMeSH
Sarsasapogenin, (3beta,5beta,25R)-isomerMeSH
Sarsasapogenin, (3beta,5beta,25S)-isomerMeSH
TigogeninMeSH
(25R)-Spirostan-3beta-olHMDB
5beta -Spirostan-3beta (25R)--olHMDB
5beta-Spirostan-3beta-ol, (25R)- (8ci)HMDB
IsosarsasapogeninHMDB
Spirostan-3-ol, (3beta,5beta,25R)- (9ci)HMDB
SmilageninChEBI
Chemical FormulaC27H44O3
Average Molecular Weight416.6365
Monoisotopic Molecular Weight416.329045274
IUPAC Name(1'R,2R,2'S,4'S,5R,7'S,8'R,9'S,12'S,13'S,16'S,18'R)-5,7',9',13'-tetramethyl-5'-oxaspiro[oxane-2,6'-pentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosane]-16'-ol
Traditional Namesmilagenin
CAS Registry Number126-18-1
SMILES
[H][C@]12C[C@@]3([H])[C@]4([H])CC[C@]5([H])C[C@@H](O)CC[C@]5(C)[C@@]4([H])CC[C@]3(C)[C@@]1([H])[C@H](C)[C@@]1(CC[C@@H](C)CO1)O2
InChI Identifier
InChI=1S/C27H44O3/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/h16-24,28H,5-15H2,1-4H3/t16-,17+,18-,19+,20-,21+,22+,23+,24+,25+,26+,27-/m1/s1
InChI KeyGMBQZIIUCVWOCD-UQHLGXRBSA-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-hydroxysteroid
  • Hydroxysteroid
  • 3-beta-hydroxysteroid
  • Steroid
  • Ketal
  • Oxane
  • Tetrahydrofuran
  • Cyclic alcohol
  • Secondary alcohol
  • Acetal
  • Organoheterocyclic compound
  • Oxacycle
  • Alcohol
  • Organic oxygen compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Biological location

Source

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point185 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility3.3e-05 g/LALOGPS
logP4.52ALOGPS
logP5.33ChemAxon
logS-7.1ALOGPS
pKa (Strongest Acidic)18.3ChemAxon
pKa (Strongest Basic)-1.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area38.69 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity119.42 m³·mol⁻¹ChemAxon
Polarizability51.37 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
DeepCCS[M-2H]-221.4730932474
DeepCCS[M+Na]+195.93630932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Smilagenin[H][C@]12C[C@@]3([H])[C@]4([H])CC[C@]5([H])C[C@@H](O)CC[C@]5(C)[C@@]4([H])CC[C@]3(C)[C@@]1([H])[C@H](C)[C@@]1(CC[C@@H](C)CO1)O22681.0Standard polar33892256
Smilagenin[H][C@]12C[C@@]3([H])[C@]4([H])CC[C@]5([H])C[C@@H](O)CC[C@]5(C)[C@@]4([H])CC[C@]3(C)[C@@]1([H])[C@H](C)[C@@]1(CC[C@@H](C)CO1)O23236.6Standard non polar33892256
Smilagenin[H][C@]12C[C@@]3([H])[C@]4([H])CC[C@]5([H])C[C@@H](O)CC[C@]5(C)[C@@]4([H])CC[C@]3(C)[C@@]1([H])[C@H](C)[C@@]1(CC[C@@H](C)CO1)O23397.5Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Smilagenin,1TMS,isomer #1C[C@H]1[C@H]2[C@H](C[C@H]3[C@@H]4CC[C@@H]5C[C@@H](O[Si](C)(C)C)CC[C@]5(C)[C@H]4CC[C@@]32C)O[C@]12CC[C@@H](C)CO23297.8Semi standard non polar33892256
Smilagenin,1TBDMS,isomer #1C[C@H]1[C@H]2[C@H](C[C@H]3[C@@H]4CC[C@@H]5C[C@@H](O[Si](C)(C)C(C)(C)C)CC[C@]5(C)[C@H]4CC[C@@]32C)O[C@]12CC[C@@H](C)CO23586.2Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Smilagenin GC-MS (Non-derivatized) - 70eV, Positivesplash10-0pbi-2129100000-ce00917c9402bf19f2cb2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Smilagenin GC-MS (1 TMS) - 70eV, Positivesplash10-05fr-5206900000-6994401f8cd0564b077a2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Smilagenin GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Smilagenin 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 - Smilagenin 10V, Positive-QTOFsplash10-014j-5039500000-2dc535b52346682944292016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Smilagenin 20V, Positive-QTOFsplash10-0avi-5094100000-73cb8de52ed2c81a60082016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Smilagenin 40V, Positive-QTOFsplash10-0pvi-9055000000-cd920b055b8c4a5478c02016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Smilagenin 10V, Negative-QTOFsplash10-014i-5003900000-c46f2a81526a3824ec012016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Smilagenin 20V, Negative-QTOFsplash10-014j-2019200000-3a3da9fcf5a22a3b29932016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Smilagenin 40V, Negative-QTOFsplash10-0gb9-9025000000-662616db765aefc27d752016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Smilagenin 10V, Negative-QTOFsplash10-014i-0000900000-67ea14fb7a26b9b2d9292021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Smilagenin 20V, Negative-QTOFsplash10-014i-0001900000-ff4f5d155a47a38a5c072021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Smilagenin 40V, Negative-QTOFsplash10-02ta-0229700000-519f15705a81d147ae882021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Smilagenin 10V, Positive-QTOFsplash10-014i-0043900000-2b302fdea4f63c5306c12021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Smilagenin 20V, Positive-QTOFsplash10-0ar0-1193300000-17ee1df0d3203669d2c32021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Smilagenin 40V, Positive-QTOFsplash10-00b9-2590000000-9a82cac1ff37947e3a4a2021-09-22Wishart 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 IDFDB001354
KNApSAcK IDC00003592
Chemspider ID82568
KEGG Compound IDC08913
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound91439
PDB IDNot Available
ChEBI ID28933
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.