Showing Compound Tomatidine (FDB013270)

Record Information

Version

1.0

Creation date

2010-04-08 22:10:37 UTC

Update date

2025-11-18 23:43:00 UTC

Primary ID

FDB013270

Secondary Accession Numbers

FDB013271

Chemical Information

FooDB Name

Tomatidine

Description

Tomatidine 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 Tomatidine.

CAS Number

77-59-8

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
(22S,25S)-5alpha-Spirosolan-3beta-ol	HMDB
(3beta,5alpha,22beta,25S)-Spirosolan-3-ol	HMDB
(3beta,5alpha,25S)-Spirosolan-3-ol	HMDB
5a-Tomatidan-3b-ol, 8ci	HMDB
5alpha -Tomatidan-3beta -ol	HMDB
5alpha-Tomatidan-3beta-ol	HMDB
5alpha-Tomatidan-3beta-ol (8ci)	HMDB
Spirosolan-3-ol	HMDB
Spirosolan-3-ol, (3alpha ,22alpha -tomatidan-3beta -ol	HMDB
Spirosolan-3-ol, (3beta,5alpha,22beta,25S)- (9ci)	HMDB
Tomatidin	HMDB
Soladulcidine	MeSH
Tomatidine, (3beta,5alpha,22alpha,25R)-isomer	MeSH
5 alpha,20 beta(F),22 alpha(F),25 beta(F),27- Azaspirostan-3 beta-ol	MeSH
(22S,25S)-5alpha-spirosolan-3beta-ol	biospider
(3beta,5alpha,22beta,25S)-spirosolan-3-ol	biospider
(3beta,5alpha,25S)-spirosolan-3-ol	biospider
5α-Tomatidan-3β-ol	biospider
5a-Tomatidan-3b-ol, 8CI	db_source
5alpha-tomatidan-3beta-ol	biospider
5alpha-Tomatidan-3beta-ol (8CI)	biospider
Spirosolan-3-ol, (3α,22α-Tomatidan-3β-ol	biospider
Spirosolan-3-ol, (3β,5α,22β,25S)-	biospider
Spirosolan-3-ol, (3beta,5alpha,22beta,25S)-	biospider
Spirosolan-3-ol, (3beta,5alpha,22beta,25S)- (9CI)	biospider
Tomatidine	db_source

Predicted Properties

Property	Value	Source
Water Solubility	0.00019 g/L	ALOGPS
logP	4.72	ALOGPS
logP	5.02	ChemAxon
logS	-6.3	ALOGPS
pKa (Strongest Acidic)	18.3	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	121.1 m³·mol⁻¹	ChemAxon
Polarizability	51.09 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Chemical Formula

C27H45NO2

IUPAC name

5',7,9,13-tetramethyl-5-oxaspiro[pentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosane-6,2'-piperidine]-16-ol

InChI Identifier

InChI=1S/C27H45NO2/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/h16-24,28-29H,5-15H2,1-4H3

InChI Key

XYNPYHXGMWJBLV-UHFFFAOYSA-N

Isomeric SMILES

CC1C2C(CC3C4CCC5CC(O)CCC5(C)C4CCC23C)OC11CCC(C)CN1

Average Molecular Weight

415.6517

Monoisotopic Molecular Weight

415.345029689

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-hydroxysteroid
Hydroxysteroid
Azasteroid
Azaspirodecane
Alkaloid or derivatives
Piperidine
Tetrahydrofuran
Cyclic alcohol
Secondary alcohol
Hemiaminal
Organoheterocyclic compound
Oxacycle
Secondary amine
Azacycle
Secondary aliphatic amine
Organic nitrogen compound
Hydrocarbon derivative
Organonitrogen compound
Organooxygen compound
Organopnictogen compound
Organic oxygen compound
Amine
Alcohol
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Biological location:

Cell and elements:

Extracellular

Tissue and substructures:

Hepatic tissue

Biofluid and excreta:

Urine

Naturally occurring process:

Biological process:

Biochemical process:

Chemical reaction:

Lipid peroxidation

Biochemical pathway:

Lipid metabolism pathway

Cellular process:

Cell signaling

Role

Industrial application:

Biological role:

Molecular messenger:

Signaling molecule

Foods

Fruits and vegetables:

Vegetables:

Fruity vegetables:

Tomato

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Not Available
Physical Description	Not Available
Mass Composition	C 78.02%; H 10.91%; N 3.37%; O 7.70%	DFC
Melting Point	Mp 210-211°	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]20D +5 (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	Tomatidine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0zg0-1129200000-5d9e624514d0944e171c	Spectrum
Predicted GC-MS	Tomatidine, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-05fr-2215900000-9b8851953955b216ad28	Spectrum
Predicted GC-MS	Tomatidine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014j-0009600000-59abef74949d70a8cafc	2015-04-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0avj-0198200000-9c90978a91bba76ca55a	2015-04-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-05fr-5269000000-c49d77f03cb7c42696cd	2015-04-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014j-0009600000-59abef74949d70a8cafc	2015-04-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0avj-0198200000-9c90978a91bba76ca55a	2015-04-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-05fr-5269000000-c49d77f03cb7c42696cd	2015-04-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03di-0002900000-0177947b1b0afba7dd49	2015-04-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-03di-0009600000-594f89795c2e81f4b990	2015-04-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-052f-3119000000-96f892c1d44b480cfcca	2015-04-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03di-0002900000-0177947b1b0afba7dd49	2015-04-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-03di-0009600000-594f89795c2e81f4b990	2015-04-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-052f-3119000000-96f892c1d44b480cfcca	2015-04-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014i-0002900000-c098f83c1fc2f2160cf3	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-014j-3579800000-be21ff49c8422a55ae65	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-059y-3950000000-8454b0799a2b0fd68bfa	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03di-0000900000-713eea1f92e6cf59257a	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-03di-0001900000-a98be16fc6ee5b3252a6	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-03di-0239800000-e6773abcff13370b5fc4	2021-09-22	View Spectrum

NMR

Not Available

External Links

ChemSpider ID

276680

ChEMBL ID

Not Available

KEGG Compound ID

C10826

Pubchem Compound ID

65576

Pubchem Substance ID

Not Available

ChEBI ID

9629

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

HMDB0034731

CRC / DFC (Dictionary of Food Compounds) ID

HHM52-S:HQO35-K

EAFUS ID

Not Available

Dr. Duke ID

TOMATIDINE

BIGG ID

Not Available

KNApSAcK ID

C00002267

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

Not Available

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 feedant		A substance that inhibits normal feeding behavior, found in certain plants, deterring insects and animals from consuming them. Its therapeutic applications include pest control, while key medical uses involve managing insect-borne diseases and reducing crop damage.	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