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Showing Compound Sarsasapogenin (FDB001320)

Record Information
Version1.0
Creation date2010-04-08 22:04:55 UTC
Update date2019-11-26 02:56:18 UTC
Primary IDFDB001320
Secondary Accession NumbersNot Available
Chemical Information
FooDB 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.
CAS Number126-19-2
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
(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
(25S)-5beta-spirostan-3beta-olbiospider
(3beta,5beta,25S)-spirostan-3-olbiospider
Spirostan-3-ol, (3beta,5beta,25S)- (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
Polarizability51.1 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,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
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+/m0/s1
InChI KeyGMBQZIIUCVWOCD-WWASVFFGSA-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 Weight416.646
Monoisotopic Molecular Weight416.329045277
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

Biological role:

Industrial application:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 77.84%; H 10.64%; O 11.52%DFC
Melting PointMp 200-201.5°DFC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]25D -75 (CHCl3)DFC
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSSarsasapogenin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0pbi-2129100000-ce00917c9402bf19f2cbSpectrum
Predicted GC-MSSarsasapogenin, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-05fr-4217900000-31efb237b024e3b8920aSpectrum
Predicted GC-MSSarsasapogenin, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSSarsasapogenin, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014j-5039500000-2dc535b52346682944292016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0avi-5094100000-73cb8de52ed2c81a60082016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0pvi-9055000000-cd920b055b8c4a5478c02016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-5003900000-c46f2a81526a3824ec012016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014j-2019200000-3a3da9fcf5a22a3b29932016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0gb9-9025000000-662616db765aefc27d752016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0043900000-2b302fdea4f63c5306c12021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0ar0-1193300000-17ee1df0d3203669d2c32021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00b9-2590000000-9a82cac1ff37947e3a4a2021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0000900000-67ea14fb7a26b9b2d9292021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-0001900000-ff4f5d155a47a38a5c072021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-02ta-0229700000-519f15705a81d147ae882021-09-24View Spectrum
NMRNot Available
ChemSpider ID83145
ChEMBL IDNot Available
KEGG Compound IDC03963
Pubchem Compound ID92095
Pubchem Substance IDNot Available
ChEBI ID15578
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB30024
CRC / DFC (Dictionary of Food Compounds) IDHJR73-M:BZL38-V
EAFUS IDNot Available
Dr. Duke IDSARSASAPOGENIN|SARSAPOGENIN
BIGG IDNot Available
KNApSAcK IDC00003590
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDSarsasapogenin
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-psoriac52217 An agent that reduces psoriasis symptoms, commonly used in managing plaque psoriasis, scalp psoriasis, and other inflammatory skin conditions, by inhibiting cell growth, reducing inflammation, and modulating the immune system.DUKE
Anti pyretic35493 An agent that reduces fever, commonly used to relieve headache, pain, and discomfort associated with elevated body temperature, and to manage fever in various medical conditions, such as infections and inflammatory diseases.DUKE
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).