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tomatine (CHEBI:9630)

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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.
Supplier Information
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Formula Source
C50H83NO21 KEGG COMPOUND
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.
fungicide
A substance used to destroy fungal pests.
phytotoxin
Any toxin produced by a plant.
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.
fungicide
A substance used to destroy fungal pests.
View more on the ChEBI Ontology
ChEBI Ontology
Outgoing tomatine (CHEBI:9630) has functional parent tomatidine (CHEBI:9629)
tomatine (CHEBI:9630) has role fungicide (CHEBI:24127)
tomatine (CHEBI:9630) has role immunological adjuvant (CHEBI:50847)
tomatine (CHEBI:9630) has role phytotoxin (CHEBI:38231)
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
LMST01150015 LIPID MAPS
View more database links
Registry Numbers Types Sources
17406-45-0 CAS Registry Number KEGG COMPOUND
17406-45-0 CAS Registry Number ChemIDplus
78250 Reaxys Registry Number Reaxys
78250 Beilstein Registry Number Beilstein
Citations Waiting for Citations Types Sources
17585910 PubMed citation CiteXplore
19457446 PubMed citation CiteXplore
19514731 PubMed citation CiteXplore
20300588 PubMed citation CiteXplore
21264526 PubMed citation CiteXplore
21541327 PubMed citation CiteXplore
Last Modified
28 July 2014

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