Showing Compound Solasonine (FDB002456)

Record Information

Version

1.0

Creation date

2010-04-08 22:05:23 UTC

Update date

2019-11-26 02:57:28 UTC

Primary ID

FDB002456

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Solasonine

Description

Solasonine, 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 Number

19121-58-5

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
alpha-Solamarine	MeSH
alpha-Solamarine, (3beta,22alpha,25R)-isomer	MeSH
alpha-Solamargine	MeSH
alpha-Solasonine	MeSH
alpha-solamarine, (3beta,22alpha,25R)-isomer	biospider
Alpha-solasonine	biospider
Solasodamine	db_source
Solasonin	biospider
Solasonine	db_source
Solasonine;tomatine solaradixine	biospider
Tomatine solaradixine	biospider

Predicted Properties

Property	Value	Source
Water Solubility	0.41 g/L	ALOGPS
logP	0.9	ALOGPS
logP	0.34	ChemAxon
logS	-3.3	ALOGPS
pKa (Strongest Acidic)	11.89	ChemAxon
pKa (Strongest Basic)	9.54	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	17	ChemAxon
Hydrogen Donor Count	10	ChemAxon
Polar Surface Area	258.71 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	217.64 m³·mol⁻¹	ChemAxon
Polarizability	97.61 Å³	ChemAxon
Number of Rings	9	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Chemical Formula

C45H73NO16

IUPAC name

2-{[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 Identifier

InChI=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 Key

QCTMYNGDIBTNSK-UHFFFAOYSA-N

Isomeric SMILES

CC1C2C(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 Weight

884.0582

Monoisotopic Molecular Weight

883.492935293

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.

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
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 Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

No ontology term

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Not Available
Physical Description	Not Available
Mass Composition	C 61.14%; H 8.32%; N 1.58%; O 28.96%	DFC
Melting Point	Mp 300-301°	DFC
Boiling Point	Not Available
Experimental Water Solubility	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Isoelectric point	Not Available
Charge	Not Available
Optical Rotation	[a]D -74 (MeOH)	DFC
Spectroscopic UV Data	Not Available
Density	Not Available
Refractive Index	Not Available

Spectra

EI-MS/GC-MS

Not Available

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - 6V, Positive	splash10-001i-0000000090-9bf170876f32817e5dbc	2021-09-20	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-02mj-0104430950-70e341ab59aa217fd2cd	2016-08-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0229-0215790700-ba76bbf58c8707bd0f0a	2016-08-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-074i-1407490210-d03157537604793e007e	2016-08-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03di-3602512970-eac797891a6d1b1b9605	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-03di-2902811620-3e91c250f47e5cbe7aeb	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-03di-6902511000-813a20c1027fb1fa8076	2016-08-03	View Spectrum

NMR

Not Available

External Links

ChemSpider ID

Not Available

ChEMBL ID

Not Available

KEGG Compound ID

C10824

Pubchem Compound ID

73410

Pubchem Substance ID

Not Available

ChEBI ID

469447

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

Not Available

CRC / DFC (Dictionary of Food Compounds) ID

HKH07-E:CLW97-G

EAFUS ID

Not Available

Dr. Duke ID

SOLASONINE

BIGG ID

Not Available

KNApSAcK ID

C00002265

HET ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

Not Available

SuperScent ID

Not Available

Wikipedia ID

Solasonine

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

Food	Content Range	Average	Reference
Food			Reference

Biological Effects and Interactions

Health Effects / Bioactivities

Descriptor	ID	Definition	Reference
Antitumor	35610	An agent that inhibits tumor growth and proliferation, playing a crucial role in cancer treatment. Therapeutically, antitumors are used to manage various types of cancer, including chemotherapy, targeted therapy, and immunotherapy, helping to reduce tumor size, prevent metastasis, and improve patient outcomes.	DUKE
Cardiodepressant	38070	An agent that slows heart rate and reduces cardiac contractility, used to manage conditions like hypertension, angina, and arrhythmias, reducing the heart's workload and oxygen demand.	DUKE
Cardiotonic	38070	An agent that strengthens heart muscle contractions, enhancing cardiac output. It plays a biological role in regulating heart function and is therapeutically used to treat heart failure, improving symptoms and exercise tolerance. Key medical uses include managing cardiomyopathy, atrial fibrillation, and congestive heart failure.	DUKE
Erythrocytolytic		An agent that destroys red blood cells through hemolysin activity, playing a role in immune responses and therapeutic applications, such as treating polycythemia and certain blood disorders, and aiding in blood transfusion compatibility testing.	DUKE
Hemolytic		An agent that ruptures red blood cells, playing a biological role in breaking down outdated or damaged cells. Therapeutically, it is used to treat conditions like malaria and certain blood disorders. Key medical uses include managing paroxysmal nocturnal hemoglobinuria and other hemolytic diseases, often requiring careful administration to avoid adverse effects.	DUKE
Hepatoprotective	62868	An agent that protects the liver from damage, promoting liver health and function. It plays a biological role in reducing oxidative stress and inflammation, and has therapeutic applications in managing liver diseases, such as hepatitis and cirrhosis, and key medical uses in treating drug-induced liver injury and toxicities.	DUKE
Insecticide	24852	An agent that kills or repels insects, used to control pests and prevent disease transmission. Therapeutically, insecticides have applications in public health and veterinary medicine, key medical uses include controlling insect-borne diseases such as malaria, typhus, and Lyme disease.	DUKE
Memranolytic		An agent that breaks down or disrupts cell membranes, used to lyse cells, particularly in cancer treatment, and as an antimicrobial agent to combat bacterial or fungal infections.	DUKE
Molluscicide	33904	An agent that kills mollusks, particularly snails and slugs, playing a key role in controlling vectors of parasitic diseases. Therapeutically, it is used to prevent the spread of schistosomiasis and other snail-borne diseases, with medical applications in public health and epidemiology.	DUKE
Myostimulant		An agent that stimulates an increase in the rhythm and amplitude of smooth muscle movement, playing a biological role in enhancing muscle contraction. Therapeutically, it is used to treat gastrointestinal disorders, such as constipation, and other conditions characterized by reduced muscle activity, like urinary retention.	DUKE
Pesticide	25944	An agent that kills or repels pests, playing a biological role in controlling insect, weed, and fungal populations. Therapeutically, pesticides have limited applications, but some are used to treat ectoparasitic infestations, such as lice and scabies. Key medical uses include topical treatments for head lice and scabies, highlighting their role in managing parasitic infections.	DUKE