ContaminantDB: alpha-Solanine

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2014-08-29 04:55:32 UTC

Update Date

2026-04-06 02:23:35 UTC

Accession Number

CHEM003002

Identification

Common Name

alpha-Solanine

Class

Small Molecule

Description

alpha-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.

Contaminant Sources

FooDB Chemicals
T3DB toxins
ToxCast & Tox21 Chemicals

Contaminant Type

Amine
Food Toxin
Metabolite
Natural Compound
Organic Compound
Plant Toxin

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
a-Solanine	Generator
Α-solanine	Generator
Solanine	HMDB, MeSH
alpha-Solanin	ChEBI
a-Solanin	Generator
Α-solanin	Generator

Chemical Formula

C₄₅H₇₃NO₁₅

Average Molecular Mass

868.059 g/mol

Monoisotopic Mass

867.498 g/mol

CAS Registry Number

20562-02-1

IUPAC Name

2-{[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 Name

α-solanine

SMILES

CC1C2CCC(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 Identifier

InChI=1S/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 Key

ZGVSETXHNHBTRK-UHFFFAOYSA-N

Chemical Taxonomy

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.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Steroidal glycosides

Direct Parent

Steroidal saponins

Alternative Parents

Substituents

Steroidal saponin
Diterpene glycoside
Solanidane skeleton
Oligosaccharide
Diterpenoid
Steroidal alkaloid
Azasteroid
Delta-5-steroid
Terpene glycoside
Glycosyl compound
O-glycosyl compound
Alkaloid or derivatives
Indolizidine
Piperidine
Oxane
N-alkylpyrrolidine
Pyrrolidine
Tertiary aliphatic amine
Tertiary amine
Secondary alcohol
Acetal
Organoheterocyclic compound
Azacycle
Oxacycle
Polyol
Alcohol
Organooxygen compound
Organonitrogen compound
Hydrocarbon derivative
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Amine
Primary alcohol
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Cytoplasm
Extracellular
Membrane

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

antineoplastic agent

Biological Roles

Chemical Roles

Not Available

Physical Properties

State

Solid

Appearance

White powder.

Experimental Properties

Property	Value
Melting Point	286°C
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.62 g/L	ALOGPS
logP	1.29	ALOGPS
logP	-0.43	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Acidic)	12.22	ChemAxon
pKa (Strongest Basic)	11.78	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	16	ChemAxon
Hydrogen Donor Count	9	ChemAxon
Polar Surface Area	240.69 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	216.55 m³·mol⁻¹	ChemAxon
Polarizability	96.68 Å³	ChemAxon
Number of Rings	9	ChemAxon
Bioavailability	0	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
LC-MS/MS	LC-MS/MS Spectrum - 6V, Positive	splash10-014i-0100000490-26fbd1e8e7c4fb54358c	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 6V, Positive	splash10-0wt9-2910000000-1486688b2530f7ae2c63	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 6V, Positive	splash10-0gb9-0100000790-3982d4df09db1854e9ef	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 6V, Positive	splash10-0ldi-1000000960-8f2b5f58a8b2e8157883	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 6V, Positive	splash10-014i-0000000190-20779a3b109d59adb5c1	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 6V, Positive	splash10-014i-2200000490-b704282b2763f43b5aab	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 6V, Positive	splash10-03du-3900000000-e46a672317512c3c2d81	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 6V, Positive	splash10-014i-0000000090-86cc287ae5feda4b6d27	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 6V, Positive	splash10-014i-0000000090-66a874259102babaa4ca	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 6V, Negative	splash10-014i-0100000490-16fffc999b9c8ac3c1c5	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 6V, Positive	splash10-014i-0000000090-62318979f4a819fe9381	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 6V, Positive	splash10-0gi0-0400000910-63bd04f091ae211d5348	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 6V, Positive	splash10-0udi-0100000900-6d995d3d546c5f395ba7	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 6V, Positive	splash10-014i-0000000090-83ec62b58c22dd982bca	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 6V, Positive	splash10-0gb9-3900000000-e638309eff0463450fa1	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 6V, Positive	splash10-0udi-0300000900-8f061acf9db073174a49	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 6V, Positive	splash10-0zfr-0100000900-bdb62b7c4f901d862f22	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 6V, Positive	splash10-0udi-2910000000-16ff2d37d80e30891d42	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 6V, Positive	splash10-014i-0020000490-ecc1692c1d846a42fcb0	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0k9t-0209031640-e83f7005c90396a5118b	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-052b-0109040200-1a96e39178d96af0cf1b	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4j-1209050100-afe02a8bd2ff9f579566	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0fr2-2709122770-f083f6af091813806360	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0002-1709012310-7dc0b53017f950d2d69d	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0002-8809010000-a2432091c3eede4b8230	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum

Toxicity Profile

Route of Exposure

Not Available

Mechanism of Toxicity

Solanum 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)

Metabolism

Not Available

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

No indication of carcinogenicity to humans (not listed by IARC).

Uses/Sources

alpha-Solanine is found in alcoholic beverages.

Minimum Risk Level

Not Available