alpha-Tomatine (CHEM017543)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-22 04:27:13 UTC
Update Date2016-11-09 01:15:37 UTC
Accession NumberCHEM017543
Identification
Common Namealpha-Tomatine
ClassSmall Molecule
DescriptionA steroid alkaloid that is tomatidine in which the hydroxy group at position 3 is linked to lycotetraose, a tetrasaccharide composed of two units of D-glucose, one unit of D-xylose, and one unit of D-galactose.
Contaminant Sources
  • FooDB Chemicals
  • ToxCast & Tox21 Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
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
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot 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
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0imi-9501430051-9e65298ae4af3bb3275cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03fr-5901730221-46b75404e473456c21e3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-03fr-4902610100-086630745326817fce4cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0gb9-5204670292-72459f4273420a0738b3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-0214950450-6f668fd9129c02200681Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014r-2307930620-ab4a5e84ca62aaea6a8bSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
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