ChEBI Name tomatine
ChEBI ID CHEBI:9630
Definition 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.
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C50H83NO21
Net Charge 0
Average Mass 1034.18816
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
SMILES [H][C@@]12CC[C@]3([H])[C@]([H])(CC[C@@]4(C)[C@@]3([H])C[C@]3([H])O[C@@]5(CC[C@H](C)CN5)[C@@H](C)[C@]43[H])[C@@]1(C)CC[C@@H](C2)O[C@@H]1O[C@H](CO)[C@H](O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O[C@@H]3OC[C@@H](O)[C@H](O)[C@H]3O)[C@H]2O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)[C@H](O)[C@H]1O
Roles Classification
Biological Role(s): immunological adjuvant
A substance that augments, stimulates, activates, potentiates, or modulates the immune response at either the cellular or humoral level. A classical agent (Freund's adjuvant, BCG, Corynebacterium parvum, et al.) contains bacterial antigens. It could also be endogenous (e.g., histamine, interferon, transfer factor, tuftsin, interleukin-1). Its mode of action is either non-specific, resulting in increased immune responsiveness to a wide variety of antigens, or antigen-specific, i.e., affecting a restricted type of immune response to a narrow group of antigens. The therapeutic efficacy is related to its antigen-specific immunoadjuvanticity.
phytotoxin
Any toxin produced by a plant.
antifungal agent
An antimicrobial agent that destroys fungi by suppressing their ability to grow or reproduce.
antimicrobial agent
A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.
(via alkaloid antibiotic )
metabolite
Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
(via alkaloid )
Application(s): immunological adjuvant
A substance that augments, stimulates, activates, potentiates, or modulates the immune response at either the cellular or humoral level. A classical agent (Freund's adjuvant, BCG, Corynebacterium parvum, et al.) contains bacterial antigens. It could also be endogenous (e.g., histamine, interferon, transfer factor, tuftsin, interleukin-1). Its mode of action is either non-specific, resulting in increased immune responsiveness to a wide variety of antigens, or antigen-specific, i.e., affecting a restricted type of immune response to a narrow group of antigens. The therapeutic efficacy is related to its antigen-specific immunoadjuvanticity.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing tomatine (CHEBI:9630) has functional parent tomatidine (CHEBI:9629)
tomatine (CHEBI:9630) has role antifungal agent (CHEBI:35718)
tomatine (CHEBI:9630) has role immunological adjuvant (CHEBI:50847)
tomatine (CHEBI:9630) has role phytotoxin (CHEBI:38231)
tomatine (CHEBI:9630) is a alkaloid antibiotic (CHEBI:86322)
tomatine (CHEBI:9630) is a glycoside (CHEBI:24400)
tomatine (CHEBI:9630) is a steroid alkaloid (CHEBI:26767)
tomatine (CHEBI:9630) is a tetrasaccharide derivative (CHEBI:63567)
IUPAC Name
(22S,25S)-5α-spirosolan-3β-yl β-D-glucopyranosyl-(1→2)-[β-D-xylopyranosyl-(1→3)]-β-D-glucopyranosyl-(1→4)-β-D-galactopyranoside
Synonyms Sources
(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-galactopyranoside ChemIDplus
A''-Tomatidine ChemIDplus
α-tomatine ChemIDplus
lycopersicin ChemIDplus
Tomatine KEGG COMPOUND
Database Links Databases
C00002268 KNApSAcK
C10827 KEGG COMPOUND
HMDB34103 HMDB
LMST01150015 LIPID MAPS
Tomatine Wikipedia
View more database links
Registry Numbers Types Sources
17406-45-0 CAS Registry Number KEGG COMPOUND
17406-45-0 CAS Registry Number ChemIDplus
78250 Beilstein Registry Number Beilstein
78250 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
17585910 PubMed citation CiteXplore
17979099 PubMed citation CiteXplore
19457446 PubMed citation CiteXplore
19514731 PubMed citation CiteXplore
20300588 PubMed citation CiteXplore
21264526 PubMed citation CiteXplore
21541327 PubMed citation CiteXplore
23448507 PubMed citation CiteXplore
25772114 PubMed citation CiteXplore
Last Modified
08 julio 2015