alpha-Tomatine (CED0009639)

Record Information
Version1.0
Creation Date2016-05-22 04:27:13 UTC
Update Date2026-04-03 15:58:43 UTC
Accession NumberCHEM017543
Identification
Common Namealpha-Tomatine
ClassSmall Molecule
Description
alpha-Tomatine is a compound with the chemical formula C50H83NO21. alpha-Tomatine belongs to the steroidal glycosides, a subclass of steroids and steroid derivatives within the organic compounds. With an average molecular weight of 1,034 g/mol, alpha-Tomatine is a heavy molecule. This substance is found in or released from 18 recorded sources across several diverse sectors. Within the realm of electrical and electronic equipment, it is associated with batteries, capacitors, printed circuit boards, wires and cables, and cell phones, among two other sources. In the food, food processing and cookware sector, it is linked to food packaging and the preparation of vinegar, wine, or sparkling wine. It is also found in the textiles, leather and furnishings sector, specifically in carpets, rugs, and synthetic textiles. Other recorded sources include lubricants from the energy, oil and gas sector, medical devices from the healthcare, pharmaceuticals and veterinary products sector, and tobacco smoke filters and cigar cigarettes from the household cleaning and consumer products sector. Additionally, it is present in two other unnamed sectors. Recorded exposure routes for alpha-Tomatine include oral, inhalation, and touch.
Contaminant Type
  • PFAS
  • Phytotoxin
Chemical Structure
Synonyms
ValueSource
(3beta,5alpha,22beta,25S)-Spirosolan-3-yl O-beta-D-glucopyranosyl-(1->2)-O-(beta-D-xylopyranosyl)-(1->3)-O-beta-D-glucopyranosyl-(1->4)-beta-D-galactopyranosideChEBI
A''-tomatidineChEBI
alpha-TomatineChEBI
LycopersicinChEBI
TomatinChEBI
(3b,5a,22b,25S)-Spirosolan-3-yl O-b-D-glucopyranosyl-(1->2)-O-(b-D-xylopyranosyl)-(1->3)-O-b-D-glucopyranosyl-(1->4)-b-D-galactopyranosideGenerator
(3Β,5α,22β,25S)-spirosolan-3-yl O-β-D-glucopyranosyl-(1->2)-O-(β-D-xylopyranosyl)-(1->3)-O-β-D-glucopyranosyl-(1->4)-β-D-galactopyranosideGenerator
a-TomatineGenerator
Α-tomatineGenerator
Chemical FormulaC50H83NO21
Average Molecular Mass1034.188 g/mol
Monoisotopic Mass1033.546 g/mol
CAS Registry Number17406-45-0
IUPAC Name(2S,3R,4S,5S,6R)-2-{[(2S,3R,4S,5R,6R)-2-{[(2R,3R,4R,5R,6R)-4,5-dihydroxy-2-(hydroxymethyl)-6-[(1R,2S,4S,5'S,6S,7S,8R,9S,12S,13S,16S,18S)-5',7,9,13-tetramethyl-5-oxaspiro[pentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosane-6,2'-piperidine]oxy]oxan-3-yl]oxy}-5-hydroxy-6-(hydroxymethyl)-4-{[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxy}oxan-3-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol
Traditional Nametomatin
SMILESC[C@H]1[C@H]2[C@H](C[C@H]3[C@@H]4CC[C@H]5C[C@H](CC[C@]5(C)[C@H]4CC[C@]23C)O[C@@H]2O[C@H](CO)[C@H](O[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O[C@@H]4OC[C@@H](O)[C@H](O)[C@H]4O)[C@H]3O[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)[C@H](O)[C@H]2O)O[C@@]11CC[C@H](C)CN1
InChI IdentifierInChI=1S/C50H83NO21/c1-20-7-12-50(51-15-20)21(2)32-28(72-50)14-26-24-6-5-22-13-23(8-10-48(22,3)25(24)9-11-49(26,32)4)65-45-40(63)37(60)41(31(18-54)68-45)69-47-43(71-46-39(62)36(59)34(57)29(16-52)66-46)42(35(58)30(17-53)67-47)70-44-38(61)33(56)27(55)19-64-44/h20-47,51-63H,5-19H2,1-4H3/t20-,21-,22-,23-,24+,25-,26-,27+,28-,29+,30+,31+,32-,33-,34+,35+,36-,37+,38+,39+,40+,41-,42-,43+,44-,45+,46-,47-,48-,49-,50-/m0/s1
InChI KeyREJLGAUYTKNVJM-SGXCCWNXSA-N
Chemical Taxonomy
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.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassSteroidal glycosides
Direct ParentSteroidal 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 FrameworkAliphatic heteropolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Organoleptic EffectsNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility1.71 g/LALOGPS
logP-0.14ALOGPS
logP-1.4ChemAxon
logS-2.8ALOGPS
pKa (Strongest Acidic)11.78ChemAxon
pKa (Strongest Basic)9.54ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count22ChemAxon
Hydrogen Donor Count13ChemAxon
Polar Surface Area337.86 ŲChemAxon
Rotatable Bond Count11ChemAxon
Refractivity244.79 m³·mol⁻¹ChemAxon
Polarizability111.29 ųChemAxon
Number of Rings10ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0gb9-5204670292-72459f4273420a0738b3Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-014i-0214950450-6f668fd9129c02200681Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-014r-2307930620-ab4a5e84ca62aaea6a8bNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0imi-9501430051-9e65298ae4af3bb3275cNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-03fr-5901730221-46b75404e473456c21e3Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-03fr-4902610100-086630745326817fce4cNot AvailableView Spectrum
Toxicity Profile
Mechanism of ToxicityNot Available
Carcinogenicity (IARC Classification)Not Available
Minimum Risk LevelNot Available
SymptomsNot Available
TreatmentNot Available
Toxicity ValuesNot Available
Health Effects
Health EffectRelationshipDirectionReference
Exposure Sources
Source IDSourceSectorReference
7PesticidesAgriculture & land managementNot Available
120Wires and cablesElectrical & Electronic EquipmentNot Available
121Printed circuit boardsElectrical & Electronic EquipmentNot Available
125BatteriesElectrical & Electronic EquipmentNot Available
130SemiconductorsElectrical & Electronic EquipmentNot Available
138LubricantsEnergy, oil & gasNot Available
147Food packagingFood, food processing & cookwareNot Available
174LubricantsIndustrial manufacturing & chemical processingNot Available
234Medical devicesHealthcare, pharmaceuticals & veterinary productsNot Available
451Carpets and RugsTextiles, leather & furnishingsNot Available
454Synthetic textilesTextiles, leather & furnishingsNot Available
490Personal care & cosmeticsNot Available
492Cell phonesElectrical & Electronic EquipmentNot Available
493CapacitorsElectrical & Electronic EquipmentNot Available
539Video GamesElectrical & Electronic EquipmentNot Available
548Preparation Of VinegarFood, food processing & cookwareNot Available
549Preparation Of Wine Or Sparkling WineFood, food processing & cookwareNot Available
556Cigar CigarettesHousehold cleaning & consumer productsNot Available
569Tobacco Smoke FiltersHousehold cleaning & consumer productsNot Available
578Making CigarsIndustrial manufacturing & chemical processingNot Available
597ChemosterilantsAgriculture & land managementNot Available
602MolluscicidesAgriculture & land managementNot Available
603NematocidesAgriculture & land managementNot Available
604Pest AttractantsAgriculture & land managementNot Available
605Pest RepellantsAgriculture & land managementNot Available
607Rodenticides(1)Agriculture & land managementNot Available
608RodenticidesAgriculture & land managementNot Available
Pathways
0 pathways

No pathways found

No metabolic pathways have been associated with this synthetic chemical

Targets
StructureProteinUniProt IDOrganismRelationshipDetails
Heparanase structureClick to view 3D structureHeparanaseQ9Y251HumansPredicted (SEA)1.08989
Click to view 3D structureEndo-beta-N-acetylglucosaminidaseQ9ZB22Arthrobacter protophormiaePredicted (SEA)1.63483
Fibroblast growth factor 2 structureClick to view 3D structureFibroblast growth factor 2P09038HumansPredicted (SEA)2.10193
Fibroblast growth factor 1 structureClick to view 3D structureFibroblast growth factor 1P05230HumansPredicted (SEA)1.08989
Click to view 3D structureCMP-N-acetylneuraminate-beta-galactosamide-alpha-2,3-sialyltransferase 1P54751Mus musculusPredicted (SEA)4.43741
Click to view 3D structureSodium/potassium-transporting ATPase subunit alpha-1P50997Canis lupus familiarisPredicted (SEA)0.622794
Click to view 3D structureEukaryotic initiation factor 4A-IP60843Mus musculusPredicted (SEA)0.856341
Click to view 3D structureAlpha-amylaseQ7M328Sus scrofa domesticusPredicted (SEA)2.49118
G-protein coupled bile acid receptor 1 structureClick to view 3D structureG-protein coupled bile acid receptor 1Q8TDU6HumansPredicted (SEA)226.853
CD44 antigen structureClick to view 3D structureCD44 antigenP16070HumansPredicted (SEA)6.30579
Click to view 3D structureCD44 antigenP15379Mus musculusPredicted (SEA)6.30579
Click to view 3D structureE-selectinP98105Rattus norvegicusPredicted (SEA)3.11397
Click to view 3D structureN-acetyllactosaminide alpha-1,3-galactosyltransferaseP50127Sus scrofaPredicted (SEA)15.1806
Click to view 3D structureNeurogenic locus notch homolog protein 1Q01705Mus musculusPredicted (SEA)4.28171
Click to view 3D structureCycloartenol-C-24-methyltransferaseQ9LM02Arabidopsis thalianaPredicted (SEA)9.809
Sex hormone-binding globulin structureClick to view 3D structureSex hormone-binding globulinP04278HumansPredicted (SEA)54.8837
Sialic acid-binding Ig-like lectin 7 structureClick to view 3D structureSialic acid-binding Ig-like lectin 7Q9Y286HumansPredicted (SEA)2.33548
Gap junction beta-2 protein structureClick to view 3D structureGap junction beta-2 proteinP29033HumansPredicted (SEA)6.61718
Click to view 3D structureSolute carrier organic anion transporter family member 1B2Q9QZX8Rattus norvegicusPredicted (SEA)7.23998
Sigma non-opioid intracellular receptor 1 structureClick to view 3D structureSigma non-opioid intracellular receptor 1Q99720HumansPredicted (SEA)5828.42
Click to view 3D structureC-8 sterol isomerase ERG2P32352Baker's yeastPredicted (SEA)240.943
Click to view 3D structureKiller cell lectin-like receptor subfamily B member 1AP27471Rattus norvegicusPredicted (SEA)20.7079
Galectin-3 structureClick to view 3D structureGalectin-3P17931HumansPredicted (SEA)104.941
Corticosteroid-binding globulin structureClick to view 3D structureCorticosteroid-binding globulinP08185HumansPredicted (SEA)56.1293
Signal transducer and activator of transcription 3 structureClick to view 3D structureSignal transducer and activator of transcription 3P40763HumansPredicted (SEA)3411.2
Concentrations
Not Available
External Links
DrugBank IDNot Available
HMDB IDNot Available
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDC00002268
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkTomatine
Chemspider IDNot Available
ChEBI ID9630
PubChem Compound ID28523
Kegg Compound IDC10827
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=17585910
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=17979099
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=19457446
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=19514731
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=20300588
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=21264526
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=21541327
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=23448507
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=25772114