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Solasonine (FDB002456)

Record Information
Version1.0
Creation date2010-04-08 22:05:23 UTC
Update date2019-11-26 02:57:28 UTC
Primary IDFDB002456
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameSolasonine
DescriptionSolasonine, also known as alpha-solamargine or alpha-solamarine, (3beta,22alpha,25r)-isomer, is a member of the class of compounds known as steroidal saponins. Steroidal saponins are saponins in which the aglycone moiety is a steroid. The steroidal aglycone is usually a spirostane, furostane, spirosolane, solanidane, or curcubitacin derivative. Solasonine is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Solasonine can be found in eggplant, which makes solasonine a potential biomarker for the consumption of this food product. Solasonine is a poisonous chemical compound. It is a glycoside of solasodine. Solasonine occurs in plants of the Solanaceae family. Solasonine was one component of the unsuccessful experimental cancer drug candidate Coramsine .
CAS Number19121-58-5
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
Not AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.41 g/LALOGPS
logP0.9ALOGPS
logP0.34ChemAxon
logS-3.3ALOGPS
pKa (Strongest Acidic)11.89ChemAxon
pKa (Strongest Basic)9.54ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count17ChemAxon
Hydrogen Donor Count10ChemAxon
Polar Surface Area258.71 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity217.64 m³·mol⁻¹ChemAxon
Polarizability97.61 ųChemAxon
Number of Rings9ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC45H73NO16
IUPAC name2-{[3-hydroxy-2-(hydroxymethyl)-6-{5',7,9,13-tetramethyl-5-oxaspiro[pentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosane-6,2'-piperidin]-18-eneoxy}-5-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]oxan-4-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol
InChI IdentifierInChI=1S/C45H73NO16/c1-19-8-13-45(46-16-19)20(2)30-27(62-45)15-26-24-7-6-22-14-23(9-11-43(22,4)25(24)10-12-44(26,30)5)57-42-39(61-40-36(54)34(52)31(49)21(3)56-40)38(33(51)29(18-48)59-42)60-41-37(55)35(53)32(50)28(17-47)58-41/h6,19-21,23-42,46-55H,7-18H2,1-5H3
InChI KeyQCTMYNGDIBTNSK-UHFFFAOYSA-N
Isomeric SMILESCC1C2C(CC3C4CC=C5CC(CCC5(C)C4CCC23C)OC2OC(CO)C(O)C(OC3OC(CO)C(O)C(O)C3O)C2OC2OC(C)C(O)C(O)C2O)OC11CCC(C)CN1
Average Molecular Weight884.0582
Monoisotopic Molecular Weight883.492935293
Classification
Description Belongs to the class of organic compounds known as steroidal saponins. These are saponins in which the aglycone moiety is a steroid. The steroidal aglycone is usually a spirostane, furostane, spirosolane, solanidane, or curcubitacin derivative.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassSteroidal glycosides
Direct ParentSteroidal saponins
Alternative Parents
Substituents
  • Steroidal saponin
  • Diterpene glycoside
  • Spirosolane skeleton
  • Oligosaccharide
  • Diterpenoid
  • Steroidal alkaloid
  • Azasteroid
  • Delta-5-steroid
  • Terpene glycoside
  • O-glycosyl compound
  • Glycosyl compound
  • Azaspirodecane
  • Alkaloid or derivatives
  • Piperidine
  • Oxane
  • Tetrahydrofuran
  • Secondary alcohol
  • Hemiaminal
  • Azacycle
  • Oxacycle
  • Organoheterocyclic compound
  • Secondary amine
  • Polyol
  • Acetal
  • Secondary aliphatic amine
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Organic nitrogen compound
  • Organopnictogen compound
  • Alcohol
  • Organonitrogen compound
  • Organooxygen compound
  • Amine
  • Primary alcohol
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
OntologyNo ontology term
Physico-Chemical Properties
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 61.14%; H 8.32%; N 1.58%; O 28.96%DFC
Melting PointMp 300-301°DFC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]D -74 (MeOH)DFC
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MSNot Available
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-001i-0000000090-9bf170876f32817e5dbc2021-09-20View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-02mj-0104430950-70e341ab59aa217fd2cd2016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0229-0215790700-ba76bbf58c8707bd0f0a2016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-074i-1407490210-d03157537604793e007e2016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-3602512970-eac797891a6d1b1b96052016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-2902811620-3e91c250f47e5cbe7aeb2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-03di-6902511000-813a20c1027fb1fa80762016-08-03View Spectrum
NMRNot Available
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDC10824
Pubchem Compound ID73410
Pubchem Substance IDNot Available
ChEBI ID469447
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDHKH07-E:CLW97-G
EAFUS IDNot Available
Dr. Duke IDSOLASONINE
BIGG IDNot Available
KNApSAcK IDC00002265
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDSolasonine
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
antitumor35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
cardiodepressant38070 A drug used for the treatment or prevention of cardiac arrhythmias. Anti-arrhythmia drugs may affect the polarisation-repolarisation phase of the action potential, its excitability or refractoriness, or impulse conduction or membrane responsiveness within cardiac fibres.DUKE
cardiotonic38070 A drug used for the treatment or prevention of cardiac arrhythmias. Anti-arrhythmia drugs may affect the polarisation-repolarisation phase of the action potential, its excitability or refractoriness, or impulse conduction or membrane responsiveness within cardiac fibres.DUKE
erythrocytolyticDUKE
hemolyticDUKE
hepatoprotective62868 Any compound that is able to prevent damage to the liver.DUKE
insecticide24852 Strictly, a substance intended to kill members of the class Insecta. In common usage, any substance used for preventing, destroying, repelling or controlling insects.DUKE
memranolyticDUKE
molluscicide33904 A substance used to destroy pests of the phylum Mollusca.DUKE
myostimulantDUKE
pesticide25944 Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests.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).
— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.