Identification

PhytoHub ID
PHUB000856
Name
Tomatine
Systematic Name
Not Available
Synonyms
  • A''-Tomatidine
  • Lycopericin
  • Lycopersicin
  • Tomatine (alpha-)
CAS Number
17406-45-0
Average Mass
1034.2
Monoisotopic Mass
1033.545758697
Chemical Formula
C50H83NO21
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[10.8.0.0^{2,9}.0^{4,8}.0^{13,18}]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
InChI Key
REJLGAUYTKNVJM-SGXCCWNXSA-N
InChI Identifier
InChI=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
SMILES
C[[email protected]]1[[email protected]]2[[email protected]](C[[email protected]]3[[email protected]@H]4CC[[email protected]]5C[[email protected]](CC[[email protected]]5(C)[[email protected]]4CC[[email protected]]23C)O[[email protected]@H]2O[[email protected]](CO)[[email protected]](O[[email protected]@H]3O[[email protected]](CO)[[email protected]@H](O)[[email protected]](O[[email protected]@H]4OC[[email protected]@H](O)[[email protected]](O)[[email protected]]4O)[[email protected]]3O[[email protected]@H]3O[[email protected]](CO)[[email protected]@H](O)[[email protected]](O)[[email protected]]3O)[[email protected]](O)[[email protected]]2O)O[[email protected]@]11CC[[email protected]](C)CN1
Structure

Calculated Properties

Solubility (ALOGPS)
1.71e+00 g/l
LogS (ALOGPS)
-2.78
LogP (ALOGPS)
-0.14
Hydrogen Acceptors
22
Hydrogen Donors
13
Rotatable Bond Count
11
Polar Surface Area
337.85999999999996
Refractivity
244.7875000000001
Polarizability
111.19279698615995
Formal Charge
0
Physiological Charge
1
pKa (strongest basic)
9.539133055650797
pKa (strongest acidic)
11.779281985325845
Number of Rings
10
Rule of Five
No
Bioavailability
No
Ghose Filter
No
Veber's Rule
No
MDDR-like Rule
Yes

Taxonomy

Family
N-containing compounds
Class
Alkaloids
Sub-class
Steroid alkaloids

Classyfire Taxonomy

Kingdom Name
Organic compounds
Class
Steroids and steroid derivatives
Super-class
Lipids and lipid-like molecules
Sub-class
Steroidal glycosides
Direct Parent Name
Steroidal saponins
Alternative Parent Names
["Acetals", "Alkaloids and derivatives", "Azacyclic compounds", "Azaspirodecane derivatives", "Azasteroids and derivatives", "Dialkylamines", "Diterpene glycosides", "Diterpenoids", "Hemiaminals", "Hydrocarbon derivatives", "O-glycosyl compounds", "Oligosaccharides", "Organopnictogen compounds", "Oxacyclic compounds", "Oxanes", "Piperidines", "Polyols", "Primary alcohols", "Secondary alcohols", "Spirosolanes and derivatives", "Tetrahydrofurans"]
External Descriptor Annotations
["Solanidines and alkaloid derivatives", "Steroidal alkaloids", "alkaloid antibiotic", "glycoside", "steroid alkaloid", "tetrasaccharide derivative"]
Substituent Names
["Acetal", "Alcohol", "Aliphatic heteropolycyclic compound", "Alkaloid or derivatives", "Amine", "Azacycle", "Azaspirodecane", "Azasteroid", "Diterpene glycoside", "Diterpenoid", "Glycosyl compound", "Hemiaminal", "Hydrocarbon derivative", "O-glycosyl compound", "Oligosaccharide", "Organic nitrogen compound", "Organic oxygen compound", "Organoheterocyclic compound", "Organonitrogen compound", "Organooxygen compound", "Organopnictogen compound", "Oxacycle", "Oxane", "Piperidine", "Polyol", "Primary alcohol", "Secondary alcohol", "Secondary aliphatic amine", "Secondary amine", "Spirosolane skeleton", "Steroidal alkaloid", "Steroidal saponin", "Terpene glycoside", "Tetrahydrofuran"]

Spectra

No spectra information available

Food Sources

NameGroup
Cherry tomatoVegetables, Fruit vegetables PublicationsShow
Green tomatoVegetables, Fruit vegetables PublicationsShow
KetchupCondiments and seasonings PublicationsShow
TomatoVegetables, Fruit vegetables PublicationsShow
Tomato juiceBeverages, Non-alcoholic PublicationsShow

Metabolism

PrecursorMetaboliteSpeciesBiofluidsOriginFormulaMonoisotopic mass
Tomatine TomatidinemouseplasmaunknownC27H45NO2415.345029693 Publications
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