alpha-Solasonine
Basic information
- CAS
19121-58-5- Standard SMILES
CC1CCC2(NC1)OC1CC3C4CC=C5CC(OC6OC(CO)C(O)C(OC7OC(CO)C(O)C(O)C7O)C6OC6OC(C)C(O)C(O)C6O)CCC5(C)C4CCC3(C)C1C2C- InChIKey
QCTMYNGDIBTNSK-UHFFFAOYSA-N- Molecular formula
- C45H73NO16
- Average molar mass
- 884.1 g/mol
- Monoisotopic mass
- 883.49293524
Overview
alpha-Solasonine has been reported in Solanum kieseritzkii, Solanum aviculare, and other organisms with data available.
Names & identifiers
- Preferred name
- alpha-Solasonine
- IUPAC
- 2-[5-hydroxy-6-(hydroxymethyl)-2-(5',7,9,13-tetramethylspiro[5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icos-18-ene-6,2'-piperidine]-16-yl)oxy-4-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-3-yl]oxy-6-methyloxane-3,4,5-triol
- English name
- SOLASONINE
- Molecular formula
- C45H73NO16
- Molecular weight
- 884.07
Names & synonyms
alpha-Solasonine2-(5-hydroxy-6-(hydroxymethyl)-2-(5',7,9,13-tetramethylspiro(5-oxapentacyclo(10.8.0.02,9.04,8.013,18)icos-18-ene-6,2'-piperidine)-16-yl)oxy-4-(3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl)oxyoxan-3-yl)oxy-6-methyloxane-3,4,5-triol2-[5-hydroxy-6-(hydroxymethyl)-2-(5',7,9,13-tetramethylspiro[5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icos-18-ene-6,2'-piperidine]-16-yl)oxy-4-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-3-yl]oxy-6-methyloxane-3,4,5-triolRefChem:1076565.alpha.-SolasonineSolasonine [M+H]+SCHEMBL29460311QCTMYNGDIBTNSK-UHFFFAOYSA-NS9144Spirosol-5-en-3-yl 2-O-(6-deoxyhexopyranosyl)-3-O-hexopyranosylhexopyranoside #.beta.-D-Galactopyranoside, (3.beta.,22.alpha.,25R)-spirosol-5-en-3-yl O-6-deoxy-.alpha.-L-mannopyranosyl-(12)-O-[.beta.-D-glucopyranosyl-(13)]-SOLASONIN
Show more names
PURAPURINNSC 82149SOLANINE SPURAPURINESOLASONINESOLANCARPIN
Properties
Computed structural properties
- XLogP
- 1.1
- Topological polar surface area
- 259 Ų
- Hydrogen bond donors
- 10
- Hydrogen bond acceptors
- 17
- Rotatable bonds
- 8
- Heavy atoms
- 62
- Formal charge
- 0
- Complexity
- 1,630
Physicochemical properties
- Melting point
- 301 · 301-303℃
- alpha
- 23 · D23 -88° (c = 1.01 in pyridine); D22 -74.5° (c = 0.51 in methanol)
- Density
- 1.42 · 1.42
- solubility
- 100 mg/mL · DMSO : 100 mg/mL (113.11 mM; Need ultrasonic)
- form
- powder
- pka
- 12.78 · 12.78±0.70(Predicted)
- color
- White-beige
- InChIKey
- QCTMYNGDIBTNSK-YQBIRKIONA-N
- LogP
- 4.35 · 4.350 (est)
- EWG's Food Scores
- 1 · 1
- FDA UNII
- 60638 HXL · TR60638HXL
- Symbol(GHS)
- 7 · GHS07
- Signal word
- Warning
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Safety data
- Signal word
- Warning
- Symbol(GHS)
- GHS07
Chemistry & industry
Applications
DescriptionThis gly25D - 68° (EtOH) and yields the following salts: hydrochloride, m.p. 265°C; picrate, m.p. 199-201 °C; picrolonate, m.p. 230-loC and the acetyl derivative, m.p. l35-8°C. On alkaline hydrolysis, the alkaloid gives solasodine and one mole each of galactose, glucose and rhamnose. The solution in concentrated H2S04 eventually gives a crimson colour with a brown fluorescence.
Usesα-Solasonine is a natural glycoalkaloid compound which has been shown to inhibit Gli-mediated transcritional activity.
Additional notes
DefinitionChEBI: Solasonine is an azaspiro compound, an oxaspiro compound and a steroid.
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