Record Information
Version1.0
Creation date2010-04-08 22:04:56 UTC
Update date2019-11-26 02:56:21 UTC
Primary IDFDB001354
Secondary Accession NumbersNot Available
Chemical Information
FooDB 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.
CAS Number126-18-1
Structure
Thumb
Synonyms
SynonymSource
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
5β-Spirostan-3β-ol, (25R)-biospider
5beta-Spirostan-3beta-ol, (25R)- (8CI)biospider
Spirostan-3-ol, (3beta,5beta,25R)- (9CI)biospider
Predicted 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
Chemical FormulaC27H44O3
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
InChI IdentifierInChI=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
Isomeric 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
Average Molecular Weight416.6365
Monoisotopic Molecular Weight416.329045274
Classification
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

Route of exposure:

Biological location:

Source:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 77.84%; H 10.64%; O 11.52%DFC
Melting PointMp 185°DFC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]25D -69 (c, 0.5 in CHCl3)DFC
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSSmilagenin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0pbi-2129100000-ce00917c9402bf19f2cbSpectrum
Predicted GC-MSSmilagenin, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-05fr-5206900000-6994401f8cd0564b077aSpectrum
Predicted GC-MSSmilagenin, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSSmilagenin, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014j-5039500000-2dc535b5234668294429Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0avi-5094100000-73cb8de52ed2c81a6008Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0pvi-9055000000-cd920b055b8c4a5478c0Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-5003900000-c46f2a81526a3824ec01Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014j-2019200000-3a3da9fcf5a22a3b2993Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0gb9-9025000000-662616db765aefc27d75Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0000900000-67ea14fb7a26b9b2d929Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-0001900000-ff4f5d155a47a38a5c07Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-02ta-0229700000-519f15705a81d147ae88Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0043900000-2b302fdea4f63c5306c1Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0ar0-1193300000-17ee1df0d3203669d2c3Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00b9-2590000000-9a82cac1ff37947e3a4aSpectrum
NMRNot Available
ChemSpider ID82568
ChEMBL IDNot Available
KEGG Compound IDC08913
Pubchem Compound ID91439
Pubchem Substance IDNot Available
ChEBI ID28933
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB30048
CRC / DFC (Dictionary of Food Compounds) IDHJR73-M:BZQ17-N
EAFUS IDNot Available
Dr. Duke IDSMILAGENIN
BIGG IDNot Available
KNApSAcK IDC00003592
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
anti Alzheimeran52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti dementia52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
cerebrotonicDUKE
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).