Showing Compound 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
Solasodine citrate, (3alpha,22alpha,25R)-isomer	MeSH
Solasodine, (3beta,22beta,25S)-isomer	MeSH
Tomatidenol	MeSH
Purapuridine	HMDB
Salasdine	HMDB
Salasodine	HMDB
Solancarpidine	HMDB
Solancarpine	HMDB
Solanidine S	HMDB
Solanidine-S	HMDB
Solasod-5-en-3 beta-ol	HMDB
Solasod-5-en-3beta -ol	HMDB
Solasodin	HMDB
Solasodine hydrochloride base	HMDB
Sosasodine	HMDB
Spirosol-5-en-3-ol	HMDB
Solasodine	MeSH
Solanidine-s	biospider
Solasod-5-en-3α,25R)-	biospider
Solasod-5-en-3β-ol	biospider
Spirosol-5-en-3-ol, (3β,22α,25R)-	biospider

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

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	An agent that blocks the activity of male sex hormones (androgens), reducing their effects on the body. Therapeutically, it's used to treat conditions like prostate cancer, acne, and hirsutism, as well as manage symptoms of androgen-sensitive disorders, such as benign prostatic hyperplasia.	DUKE
Anti-cancer	35610	An agent that inhibits the growth and proliferation of cancer cells, used to treat and manage various types of cancer, including chemotherapy, targeted therapy, and immunotherapy, to reduce tumor size, prevent metastasis, and improve patient survival.	DUKE
Anti carcinomic	35610	An agent that inhibits the growth and proliferation of cancer cells, playing a crucial role in cancer prevention and treatment. Therapeutically, it is used to manage and treat various types of cancer, reducing tumor size and slowing disease progression, with key medical uses in oncology and chemotherapy.	DUKE
Anti cholinesterase	37733	An agent that inhibits acetylcholinesterase, increasing acetylcholine levels, and enhancing cholinergic transmission. Therapeutically, it's used to treat myasthenia gravis, glaucoma, and Alzheimer's disease, improving muscle strength, reducing eye pressure, and enhancing cognitive function.	DUKE
Anti-fertility		An agent that inhibits reproduction, playing a biological role in population control. Therapeutically, it's used as a contraceptive, with key medical applications in family planning and birth control, preventing unwanted pregnancies and managing reproductive health.	DUKE
Anti-inflammatory	35472	An agent that reduces inflammation, playing a biological role in suppressing immune responses and therapeutic applications in managing pain, swelling, and redness. Key medical uses include treating arthritis, allergies, and autoimmune disorders, as well as relieving symptoms of conditions such as asthma and dermatitis.	DUKE
Anti-melanomic	35610	An agent that inhibits melanin production, reducing melanoma cell growth. It has therapeutic applications in treating skin cancers, particularly melanoma, and key medical uses include preventing tumor progression and metastasis, as well as managing pigmentation disorders.	DUKE
Anti-spermatogenic		An agent that blocks spermatogenesis, inhibiting male fertility. Its biological role is to suppress sperm production. Therapeutically, it has applications in male contraception and treating conditions like benign prostatic hyperplasia and prostate cancer. Key medical uses include regulating hormonal imbalances and managing fertility-related issues.	DUKE
Anti-tachycardic	38070	An agent that slows the heart rate, reducing tachycardia (rapid heartbeat). It plays a biological role in regulating cardiac function. Therapeutically, it is used to manage arrhythmias, hypertension, and cardiac conditions. Key medical uses include treating supraventricular tachycardia, atrial fibrillation, and ventricular tachycardia.	DUKE
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
Contraceptive	52217	An agent that prevents pregnancy by inhibiting ovulation, fertilization, or implantation, used to control birth rates, manage menstrual disorders, and reduce the risk of sexually transmitted infections, commonly applied in various forms such as pills, injections, and barrier methods.	DUKE
Cytotoxic	52209	An agent that kills or damages cells, playing a biological role in immune responses and therapeutic applications in cancer treatment. Key medical uses include chemotherapy, targeting and destroying cancer cells, and treating certain autoimmune diseases by eliminating harmful cells.	DUKE
Embryotoxic	52209	An agent that is toxic to embryos, causing harm or malformation during fetal development. Its biological role is to induce teratogenic effects, and it has no therapeutic applications. Key medical uses include serving as a warning for substances that pose risks during pregnancy, guiding prenatal care and medication management to prevent birth defects.	DUKE
Fungicide	24127	An agent that kills or inhibits the growth of fungi, playing a biological role in preventing fungal infections. Therapeutically, it is used to treat fungal diseases, with key medical applications including athlete's foot, ringworm, and candidiasis, as well as agricultural uses to protect crops from fungal damage.	DUKE
Hepatomegalic	52209	A condition characterized by an enlarged liver, often associated with various diseases. Its biological role is to indicate liver dysfunction or disease. Therapeutic applications involve treating underlying causes, such as hepatitis or cancer. Key medical uses include diagnostic marker for liver disease, guiding treatment and management of related conditions.	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
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
Teratogenic	50905	An agent that causes abnormal fetal development, disrupting embryonic growth and leading to birth defects. Its biological role is associated with developmental toxicity, and it has no therapeutic applications. Key medical uses include serving as a warning for substances that pose risks during pregnancy, guiding prenatal care and medication management to prevent birth defects.	DUKE