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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:34:15 UTC
Update Date2021-10-13 06:05:00 UTC
HMDB IDHMDB0030024
Secondary Accession Numbers
  • HMDB30024
Metabolite Identification
Common NameSarsasapogenin
DescriptionSarsasapogenin, also known as parigenin, belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units. Thus, sarsasapogenin is considered to be a sterol. Based on a literature review a significant number of articles have been published on Sarsasapogenin.
Structure
Data?1563861926
Synonyms
ValueSource
(3beta,5beta,25S)-Spirostan-3-olChEBI
ParigeninChEBI
(25S)-5beta-Spirostan-3beta-olKegg
(3b,5b,25S)-Spirostan-3-olGenerator
(3Β,5β,25S)-spirostan-3-olGenerator
(25S)-5b-Spirostan-3b-olGenerator
(25S)-5Β-spirostan-3β-olGenerator
SarsasapogenineHMDB
Spirostan-3-ol, (3beta,5beta,25S)- (9ci)HMDB
SarsasapogeninChEBI
Epi-sarsasapogeninMeSH
TigogeninMeSH
SarsaponinMeSH
Sarsasapogenin, (3beta,5alpha,25S)-isomerMeSH
SmilageninMeSH
EpismilageninMeSH
Sarsasapogenin, (3beta,5alpha,25R)-isomerMeSH
Sarsasapogenin, (3beta,5beta)-isomerMeSH
Sarsasapogenin, (3beta,5beta,25R)-isomerMeSH
Sarsasapogenin, (3beta,5beta,25S)-isomerMeSH
Chemical FormulaC27H44O3
Average Molecular Weight416.646
Monoisotopic Molecular Weight416.329045277
IUPAC Name(1'R,2R,2'S,4'S,5S,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 Namesarsasapogenin
CAS Registry Number126-19-2
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+/m0/s1
InChI KeyGMBQZIIUCVWOCD-WWASVFFGSA-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

Route of exposure

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point200 - 201.5 °CNot Available
Boiling Point516.60 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility0.0066 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP6.210 (est)The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility3.3e-05 g/LALOGPS
logP10(4.52) g/LALOGPS
logP10(5.33) g/LChemAxon
logS10(-7.1) g/LALOGPS
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
Polarizability51.1 ųChemAxon
Number of Rings6ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Sarsasapogenin[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
Sarsasapogenin[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
Sarsasapogenin[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
Sarsasapogenin,1TMS,isomer #1C[C@H]1CC[C@@]2(OC1)O[C@H]1C[C@H]3[C@@H]4CC[C@@H]5C[C@@H](O[Si](C)(C)C)CC[C@]5(C)[C@H]4CC[C@]3(C)[C@H]1[C@@H]2C3297.8Semi standard non polar33892256
Sarsasapogenin,1TBDMS,isomer #1C[C@H]1CC[C@@]2(OC1)O[C@H]1C[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@]3(C)[C@H]1[C@@H]2C3586.2Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Sarsasapogenin GC-MS (Non-derivatized) - 70eV, Positivesplash10-0pbi-2129100000-ce00917c9402bf19f2cb2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Sarsasapogenin GC-MS (1 TMS) - 70eV, Positivesplash10-05fr-4217900000-31efb237b024e3b8920a2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Sarsasapogenin GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Sarsasapogenin 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 - Sarsasapogenin 10V, Positive-QTOFsplash10-014j-5039500000-2dc535b52346682944292016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sarsasapogenin 20V, Positive-QTOFsplash10-0avi-5094100000-73cb8de52ed2c81a60082016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sarsasapogenin 40V, Positive-QTOFsplash10-0pvi-9055000000-cd920b055b8c4a5478c02016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sarsasapogenin 10V, Negative-QTOFsplash10-014i-5003900000-c46f2a81526a3824ec012016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sarsasapogenin 20V, Negative-QTOFsplash10-014j-2019200000-3a3da9fcf5a22a3b29932016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sarsasapogenin 40V, Negative-QTOFsplash10-0gb9-9025000000-662616db765aefc27d752016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sarsasapogenin 10V, Positive-QTOFsplash10-014i-0043900000-2b302fdea4f63c5306c12021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sarsasapogenin 20V, Positive-QTOFsplash10-0ar0-1193300000-17ee1df0d3203669d2c32021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sarsasapogenin 40V, Positive-QTOFsplash10-00b9-2590000000-9a82cac1ff37947e3a4a2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sarsasapogenin 10V, Negative-QTOFsplash10-014i-0000900000-67ea14fb7a26b9b2d9292021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sarsasapogenin 20V, Negative-QTOFsplash10-014i-0001900000-ff4f5d155a47a38a5c072021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sarsasapogenin 40V, Negative-QTOFsplash10-02ta-0229700000-519f15705a81d147ae882021-09-24Wishart 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 IDFDB001320
KNApSAcK IDC00003590
Chemspider ID83145
KEGG Compound IDC03963
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkSarsasapogenin
METLIN IDNot Available
PubChem Compound92095
PDB IDNot Available
ChEBI ID15578
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1281751
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Ren LX, Luo YF, Li X, Zuo DY, Wu YL: Antidepressant-like effects of sarsasapogenin from Anemarrhena asphodeloides BUNGE (Liliaceae). Biol Pharm Bull. 2006 Nov;29(11):2304-6. [PubMed:17077534 ]
  2. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  3. 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 ]
  4. 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 ]
  5. 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 ]
  6. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
  7. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.