Record Information
Version1.0
Creation date2010-04-08 22:10:59 UTC
Update date2018-01-23 19:31:47 UTC
Primary IDFDB013944
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameSolasodine
DescriptionSolasodine is a poisonous glycoalkaloid chemical compound that occurs in plants of the Solanaceae family. Solasodine is found in many foods, some of which are peppermint, chinese cinnamon, alaska blueberry, and sweet rowanberry.
CAS Number126-17-0
Structure
Thumb
Synonyms
SynonymSource
PurapuridineHMDB
SalasdineHMDB
SalasodineHMDB
SolancarpidineHMDB
SolancarpineHMDB
Solanidine SHMDB
Solanidine-SHMDB
Solasod-5-en-3 beta-olHMDB
Solasod-5-en-3beta -olHMDB
SolasodinHMDB
Solasodine hydrochloride baseHMDB
SosasodineHMDB
Spirosol-5-en-3-olHMDB
TomatidenolHMDB
SolasodineMeSH
Solasodine, (3beta,22beta,25S)-isomerMeSH
Solasodine citrate, (3alpha,22alpha,25R)-isomerMeSH
Solanidine-sbiospider
Solasod-5-en-3α,25R)-biospider
Solasod-5-en-3β-olbiospider
Spirosol-5-en-3-ol, (3β,22α,25R)-biospider
Predicted Properties
PropertyValueSource
Water Solubility0.00084 g/LALOGPS
logP4.45ALOGPS
logP4.61ChemAxon
logS-5.7ALOGPS
pKa (Strongest Acidic)18.2ChemAxon
pKa (Strongest Basic)9.54ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area41.49 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity121.95 m³·mol⁻¹ChemAxon
Polarizability50.31 ųChemAxon
Number of Rings6ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC27H43NO2
IUPAC name5',7,9,13-tetramethyl-5-oxaspiro[pentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosane-6,2'-piperidin]-18-en-16-ol
InChI IdentifierInChI=1S/C27H43NO2/c1-16-7-12-27(28-15-16)17(2)24-23(30-27)14-22-20-6-5-18-13-19(29)8-10-25(18,3)21(20)9-11-26(22,24)4/h5,16-17,19-24,28-29H,6-15H2,1-4H3
InChI KeyKWVISVAMQJWJSZ-UHFFFAOYSA-N
Isomeric SMILESCC1C2C(CC3C4CC=C5CC(O)CCC5(C)C4CCC23C)OC11CCC(C)CN1
Average Molecular Weight413.6358
Monoisotopic Molecular Weight413.329379625
Classification
Description belongs to the class of organic compounds known as spirosolanes and derivatives. These are steroidal alkaloids with a structure containing a spirosolane skeleton. Siporosolane is a polycyclic compound that is characterized by a 1-oxa-6-azaspiro[4.5]decane moiety where the oxolane ring is fused to a docosahydronaphth[2,1:4',5']indene ring system. Spirosolane arises from the conversion of a cholestane side-chain into a bicyclic system containing a piperidine and a tetrahydrofuran ring.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassSteroidal alkaloids
Direct ParentSpirosolanes and derivatives
Alternative Parents
Substituents
  • Spirosolane skeleton
  • 3-hydroxy-delta-5-steroid
  • 3-hydroxysteroid
  • Hydroxysteroid
  • Azasteroid
  • Delta-5-steroid
  • Azaspirodecane
  • Alkaloid or derivatives
  • Piperidine
  • Cyclic alcohol
  • Tetrahydrofuran
  • Hemiaminal
  • Secondary alcohol
  • Oxacycle
  • Azacycle
  • Secondary aliphatic amine
  • Organoheterocyclic compound
  • Secondary amine
  • Organic oxygen compound
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Alcohol
  • Amine
  • Organonitrogen compound
  • Organooxygen compound
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
OntologyShould have ontology for this compound
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 78.40%; H 10.48%; N 3.39%; O 7.74%DFC
Melting PointMp 200-201°DFC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]D -98 (MeOH)DFC
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-000w-0129000000-c0f006faa45f6504b94aView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00di-2116900000-ffdb43be61543b5cdf31View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-03di-0000900000-e0308c250bfeb4a8e3f0View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-03di-0100900000-885f5ba1460df2a81f9dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0a4j-0910000000-83c702d144b914031b01View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01ot-0009500000-894bee60ed0946470ec4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0w91-0198200000-bd353c3bcebbb6b18195View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0mpp-4298000000-ff41d9eaa787776766c6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0002900000-556f3f408a422b05cd8cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03dl-0009600000-00a27d38d42e4d209801View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-3119000000-6c61de8babead29f83fbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01ot-0009500000-894bee60ed0946470ec4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0w91-0198200000-bd353c3bcebbb6b18195View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0mpp-4298000000-ff41d9eaa787776766c6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0002900000-556f3f408a422b05cd8cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03dl-0009600000-00a27d38d42e4d209801View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-3119000000-6c61de8babead29f83fbView in MoNA
ChemSpider ID5060
ChEMBL IDCHEMBL1964743
KEGG Compound IDC10822
Pubchem Compound ID5250
Pubchem Substance IDNot Available
ChEBI ID565242
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB35282
CRC / DFC (Dictionary of Food Compounds) IDHKH07-E:JKY38-R
EAFUS IDNot Available
Dr. Duke IDSOLASODINE
BIGG IDNot Available
KNApSAcK IDC00002264
HET IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDSolasodine
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 androgenic35497 A compound which inhibits or antagonises the biosynthesis or actions of androgens.DUKE
anti cancer35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
anti carcinomic35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
anti cholinesterase37733 An EC 3.1.1.* (carboxylic ester hydrolase) inhibitor that interferes with the action of cholinesterase (EC 3.1.1.8).DUKE
anti fertilityDUKE
anti inflammatory35472 A substance that reduces or suppresses inflammation.DUKE
anti melanomic35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
anti spermatogenicDUKE
anti tachycardic38070 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
antitumor35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
contraceptive52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
cytotoxic52209 A role played by the molecular entity or part thereof which causes the development of a pathological process.DUKE
embryotoxic52209 A role played by the molecular entity or part thereof which causes the development of a pathological process.DUKE
fungicide24127 A substance used to destroy fungal pests.DUKE
hepatomegalic52209 A role played by the molecular entity or part thereof which causes the development of a pathological process.DUKE
hepatoprotective62868 Any compound that is able to prevent damage to the liver.DUKE
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
teratogenic50905 A role played by a chemical compound in biological systems with adverse consequences in embryo developments, leading to birth defects, embryo death or altered development, growth retardation and functional defect.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).