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Tomatine

CAT: 0931-T3786-01Size: 2 mgDry Ice: NoHazardous: No
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CAT#:0931-T3786-01Size:2 mg
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CAS Number
17406-45-0
Target
Apoptosis, Proteasome
Related Pathways
Ubiquitination, Proteases/Proteasome, Apoptosis
Purity
0.9994
Bioactivity
Tomatine (lycopersicin) is an antiproliferatve agent of breast adenocarcinoma cells.
Smiles
C[C@@]12[C@@]3([C@](C[C@]1([C@]4([C@](CC2)([C@]5(C)[C@@](CC4)(C[C@@H](O[C@@H]6O[C@H](CO)[C@H](O[C@H]7[C@H](O[C@@H]8O[C@H](CO)[C@@H](O)[C@H](O)[C@H]8O)[C@@H](O[C@H]9[C@H](O)[C@@H](O)[C@H](O)CO9)[C@H](O)[C@@H](CO)O7)[C@H](O)[C@H]6O)CC5)[H])[H])[H])[H])(O[C@]%10([C@H]3C)CC[C@H](C)CN%10)[H])[H]
Molecular Formula
C50H83NO21
Molecular Weight
1034.19
Shipping Conditions
Ice Packs
Storage Temperature
-20°C

Chemical Information

Tomatine

Tomatine is a 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. It has a role as an antifungal agent, a phytotoxin and an immunological adjuvant. It is a glycoalkaloid, a glycoside, a steroid alkaloid, a tetrasaccharide derivative and an alkaloid antibiotic. It is functionally related to a tomatidine.

CAS Number17406-45-0
PubChem CID28523
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-tetramethylspiro[5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icosane-6,2'-piperidine]-16-yl]oxyoxan-3-yl]oxy-5-hydroxy-6-(hydroxymethyl)-4-[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxyoxan-3-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol
Molecular FormulaC50H83NO21
Molecular Weight1034.2
XLogP-0.7
Topological Polar Surface Area338
Hydrogen Bond Donor Count13
Hydrogen Bond Acceptor Count22
Rotatable Bond Count11
Heavy Atom Count72
Formal Charge0
Complexity1840
SMILES
C[C@H]1CC[C@]2([C@H]([C@H]3[C@@H](O2)C[C@@H]4[C@@]3(CC[C@H]5[C@H]4CC[C@@H]6[C@@]5(CC[C@@H](C6)O[C@H]7[C@@H]([C@H]([C@H]([C@H](O7)CO)O[C@H]8[C@@H]([C@H]([C@@H]([C@H](O8)CO)O)O[C@H]9[C@@H]([C@H]([C@@H](CO9)O)O)O)O[C@H]2[C@@H]([C@H]([C@@H]([C@H](O2)CO)O)O)O)O)O)C)C)C)NC1
InChI
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
InChIKey
REJLGAUYTKNVJM-SGXCCWNXSA-N
Chemical Structure
2D Structure
2D structure of Tomatine
CAS: 17406-45-0
CID: 28523
Formula: C50H83NO21
MW: 1034.2
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight1034.2
XLogP3-0.7
Hydrogen Bond Donor Count13
Hydrogen Bond Acceptor Count22
Rotatable Bond Count11
Exact Mass1033.54575866
Monoisotopic Mass1033.54575866
Topological Polar Surface Area338 Ų
Heavy Atom Count72
Formal Charge0
Complexity1840
Isotope Atom Count0
Defined Atom Stereocenter Count31
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count1
Compound Is CanonicalizedYes

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