AFCDB: Solasodine (FDB013944)

Record Information

Version

1.0

Creation date

2010-04-08 22:10:59 UTC

Update date

2019-11-26 03:09:20 UTC

Primary ID

FDB013944

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Solasodine

Description

Solasodine, also known as tomatidenol, 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. Based on a literature review a significant number of articles have been published on Solasodine.

CAS Number

126-17-0

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
Not Available	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.00084 g/L	ALOGPS
logP	4.45	ALOGPS
logP	4.61	ChemAxon
logS	-5.7	ALOGPS
pKa (Strongest Acidic)	18.2	ChemAxon
pKa (Strongest Basic)	9.54	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	41.49 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	121.95 m³·mol⁻¹	ChemAxon
Polarizability	50.31 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Chemical Formula

C27H43NO2

IUPAC name

5',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 Identifier

InChI=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 Key

KWVISVAMQJWJSZ-UHFFFAOYSA-N

Isomeric SMILES

CC1C2C(CC3C4CC=C5CC(O)CCC5(C)C4CCC23C)OC11CCC(C)CN1

Average Molecular Weight

413.6358

Monoisotopic Molecular Weight

413.329379625

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.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Steroidal alkaloids

Direct Parent

Spirosolanes 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 Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

No ontology term

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Not Available
Physical Description	Not Available
Mass Composition	C 78.40%; H 10.48%; N 3.39%; O 7.74%	DFC
Melting Point	Mp 200-201°	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 -98 (MeOH)	DFC
Spectroscopic UV Data	Not Available
Density	Not Available
Refractive Index	Not Available

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
Predicted GC-MS	alpha-Solanigrine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-000w-0129000000-c0f006faa45f6504b94a	Spectrum
Predicted GC-MS	alpha-Solanigrine, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-00di-2116900000-ffdb43be61543b5cdf31	Spectrum
Predicted GC-MS	alpha-Solanigrine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	alpha-Solanigrine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-03di-0000900000-e0308c250bfeb4a8e3f0	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-03di-0100900000-885f5ba1460df2a81f9d	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-0a4j-0910000000-83c702d144b914031b01	2017-09-14	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-01ot-0009500000-894bee60ed0946470ec4	2015-04-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0w91-0198200000-bd353c3bcebbb6b18195	2015-04-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0mpp-4298000000-ff41d9eaa787776766c6	2015-04-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03di-0002900000-556f3f408a422b05cd8c	2015-04-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-03dl-0009600000-00a27d38d42e4d209801	2015-04-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-3119000000-6c61de8babead29f83fb	2015-04-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-01ot-0009500000-894bee60ed0946470ec4	2015-05-26	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0w91-0198200000-bd353c3bcebbb6b18195	2015-05-26	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0mpp-4298000000-ff41d9eaa787776766c6	2015-05-26	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03di-0002900000-556f3f408a422b05cd8c	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-03dl-0009600000-00a27d38d42e4d209801	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-3119000000-6c61de8babead29f83fb	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03di-0002900000-0a90221781aebad0d4ad	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03dj-1377900000-c3848916e815c4aa8126	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-006w-2941000000-15316ff6e3dbd8eff7a1	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03di-0000900000-c711d723aed1a4c0a919	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-03di-0001900000-d4db0d16b12f8c57b0f6	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-03di-0029400000-17c2461a5822bb81c1e7	2021-09-23	View Spectrum

NMR

Not Available

External Links

ChemSpider ID

ChEMBL ID

KEGG Compound ID

Pubchem Compound ID

Pubchem Substance ID

Not Available

ChEBI ID

565242

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

HMDB35282

CRC / DFC (Dictionary of Food Compounds) ID

HKH07-E:JKY38-R

EAFUS ID

Not Available

Dr. Duke ID

SOLASODINE

BIGG ID

Not Available

KNApSAcK ID

C00002264

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

Solasodine

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
anti androgenic	35497	A compound which inhibits or antagonises the biosynthesis or actions of androgens.	DUKE
anti cancer	35610	A substance that inhibits or prevents the proliferation of neoplasms.	DUKE
anti carcinomic	35610	A substance that inhibits or prevents the proliferation of neoplasms.	DUKE
anti cholinesterase	37733	An EC 3.1.1.* (carboxylic ester hydrolase) inhibitor that interferes with the action of cholinesterase (EC 3.1.1.8).	DUKE
anti fertility			DUKE
anti inflammatory	35472	A substance that reduces or suppresses inflammation.	DUKE
anti melanomic	35610	A substance that inhibits or prevents the proliferation of neoplasms.	DUKE
anti spermatogenic			DUKE
anti tachycardic	38070	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
antitumor	35610	A substance that inhibits or prevents the proliferation of neoplasms.	DUKE
contraceptive	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
cytotoxic	52209	A role played by the molecular entity or part thereof which causes the development of a pathological process.	DUKE
embryotoxic	52209	A role played by the molecular entity or part thereof which causes the development of a pathological process.	DUKE
fungicide	24127	A substance used to destroy fungal pests.	DUKE
hepatomegalic	52209	A role played by the molecular entity or part thereof which causes the development of a pathological process.	DUKE
hepatoprotective	62868	Any compound that is able to prevent damage to the liver.	DUKE
pesticide	25944	Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests.	DUKE
teratogenic	50905	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

Enzymes

Not Available

Pathways

Not Available

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

Not Available

Files

MSDS

Not Available

References

Synthesis Reference

Not Available

General Reference

Not Available

Content Reference

— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).

Solasodine (FDB013944)

Structure for FDB013944 (Solasodine)