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Record Information
Version2.0
Creation Date2014-08-29 04:55:32 UTC
Update Date2014-12-24 20:26:36 UTC
Accession NumberT3D4042
Identification
Common Namealpha-Solanine
ClassSmall Molecule
Descriptionalpha-Solanine is found in alcoholic beverages. alpha-Solanine is an alkaloid from potato (Solanum tuberosum) and very many other Solanum species (Solanaceae). Responsible for the teratogenicity of sprouting potatoes.
Compound Type
  • Amine
  • Food Toxin
  • Metabolite
  • Natural Compound
  • Organic Compound
  • Plant Toxin
Chemical Structure
Thumb
Synonyms
Synonym
a-Solanine
Solanine
α-Solanine
Chemical FormulaC45H73NO15
Average Molecular Mass868.059 g/mol
Monoisotopic Mass867.498 g/mol
CAS Registry Number20562-02-1
IUPAC Name2-{[3-hydroxy-2-(hydroxymethyl)-6-({10,14,16,20-tetramethyl-22-azahexacyclo[12.10.0.0²,¹¹.0⁵,¹⁰.0¹⁵,²³.0¹⁷,²²]tetracos-4-en-7-yl}oxy)-5-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]oxan-4-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol
Traditional Nameα-solanine
SMILESCC1C2CCC(C)CN2C2CC3C4CC=C5CC(CCC5(C)C4CCC3(C)C12)OC1OC(CO)C(O)C(OC2OC(CO)C(O)C(O)C2O)C1OC1OC(C)C(O)C(O)C1O
InChI IdentifierInChI=1/C45H73NO15/c1-19-6-9-27-20(2)31-28(46(27)16-19)15-26-24-8-7-22-14-23(10-12-44(22,4)25(24)11-13-45(26,31)5)57-43-40(61-41-37(54)35(52)32(49)21(3)56-41)39(34(51)30(18-48)59-43)60-42-38(55)36(53)33(50)29(17-47)58-42/h7,19-21,23-43,47-55H,6,8-18H2,1-5H3
InChI KeyInChIKey=ZGVSETXHNHBTRK-UHFFFAOYNA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as depsides and depsidones. These are polycyclic compounds that is either a polyphenolic compound composed of two or more monocyclic aromatic units linked by an ester bond (depside), or a compound containing the depsidone structure (depsidone).
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassDepsides and depsidones
Sub ClassNot Available
Direct ParentDepsides and depsidones
Alternative Parents
Substituents
  • Depsidone
  • Diaryl ether
  • Anisole
  • Aryl ketone
  • 1-hydroxy-2-unsubstituted benzenoid
  • 1,4-dioxepine
  • Alkyl aryl ether
  • Aryl-aldehyde
  • Dioxepine
  • Benzenoid
  • Acryloyl-group
  • Vinylogous acid
  • Alpha,beta-unsaturated ketone
  • Enone
  • Carboxylic acid ester
  • Lactone
  • Ketone
  • Monocarboxylic acid or derivatives
  • Organoheterocyclic compound
  • Carboxylic acid derivative
  • Oxacycle
  • Ether
  • Organooxygen compound
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Aldehyde
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
Applications
Biological Roles
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting Point286°C
Boiling PointNot Available
SolubilityNot Available
LogPNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.62 g/LALOGPS
logP1.29ALOGPS
logP-0.43ChemAxon
logS-3.2ALOGPS
pKa (Strongest Acidic)12.22ChemAxon
pKa (Strongest Basic)11.78ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count16ChemAxon
Hydrogen Donor Count9ChemAxon
Polar Surface Area240.69 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity216.55 m³·mol⁻¹ChemAxon
Polarizability96.68 ųChemAxon
Number of Rings9ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
LC-MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-014i-0100000490-26fbd1e8e7c4fb54358cJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-0wt9-2910000000-1486688b2530f7ae2c63JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-0gb9-0100000790-3982d4df09db1854e9efJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-0ldi-1000000960-8f2b5f58a8b2e8157883JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-014i-0000000190-20779a3b109d59adb5c1JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-014i-2200000490-b704282b2763f43b5aabJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-03du-3900000000-e46a672317512c3c2d81JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-014i-0000000090-86cc287ae5feda4b6d27JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-014i-0000000090-66a874259102babaa4caJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - 6V, Negativesplash10-014i-0100000490-16fffc999b9c8ac3c1c5JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-014i-0000000090-62318979f4a819fe9381JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-0gi0-0400000910-63bd04f091ae211d5348JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-0udi-0100000900-6d995d3d546c5f395ba7JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-014i-0000000090-83ec62b58c22dd982bcaJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-0gb9-3900000000-e638309eff0463450fa1JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-0udi-0300000900-8f061acf9db073174a49JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-0zfr-0100000900-bdb62b7c4f901d862f22JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-0udi-2910000000-16ff2d37d80e30891d42JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-014i-0020000490-ecc1692c1d846a42fcb0JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0k9t-0209031640-e83f7005c90396a5118bJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-052b-0109040200-1a96e39178d96af0cf1bJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4j-1209050100-afe02a8bd2ff9f579566JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0fr2-2709122770-f083f6af091813806360JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-1709012310-7dc0b53017f950d2d69dJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0002-8809010000-a2432091c3eede4b8230JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicitySolanum glycoalkaloids can inhibit cholinesterase, disrupt cell membranes, and be teratogenic (cause birth defects). One study suggests that the toxic mechanism of solanine is caused by the chemical's interaction with mitochondrial membranes. Experiments show that solanine exposure opens the potassium channels of mitochondria, decreasing their membrane potential. This in turn leads to Ca2+ being transported from the mitochondria into the cytoplasm, and it is this increased concentration of Ca2+ in the cytoplasm that triggers cell damage and apoptosis. (Wikipedia)
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/Sourcesalpha-Solanine is found in alcoholic beverages.
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB34202
PubChem Compound ID262500
ChEMBL IDNot Available
ChemSpider ID230519
KEGG IDC10820
UniProt IDNot Available
OMIM ID
ChEBI IDNot Available
BioCyc IDNot Available
CTD IDNot Available
Stitch IDNot Available
PDB IDNot Available
ACToR IDNot Available
Wikipedia LinkNot Available
References
Synthesis ReferenceNot Available
MSDST3D4042.pdf
General References
  1. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.
Gene Regulation
Up-Regulated GenesNot Available
Down-Regulated GenesNot Available