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CHEBI:9112 - sennoside A

ChEBI IDCHEBI:9112
ChEBI Namesennoside A
Stars
DefinitionA member of the class of sennosides that is rel-(9R,9'R)-9,9',10,10'-tetrahydro-9,9'-bianthracene-2,2'-dicarboxylic acid which is substituted by hydroxy groups at positions 4 and 4', by β-D-glucopyranosyloxy groups at positions 5 and 5', and by oxo groups at positions 10 and 10'. The exact stereochemisty at positions 9 and 9' is not known - it may be R,R (as shown) or S,S.
Last Modified7 January 2015
DownloadsMolfile
FormulaC42H38O20
Net Charge0
Average Mass862.746
Monoisotopic Mass862.19564
SMILES[H][C@]1([C@@]2([H])c3cc(C(=O)O)cc(O)c3C(=O)c3c(O[C@@H]4O[C@H](CO)[C@@H](O)[C@H](O)[C@H]4O)cccc32)c2cc(C(=O)O)cc(O)c2C(=O)c2c(O[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)cccc21
InChIInChI=1S/C42H38O20/c43-11-23-31(47)35(51)37(53)41(61-23)59-21-5-1-3-15-25(17-7-13(39(55)56)9-19(45)27(17)33(49)29(15)21)26-16-4-2-6-22(60-42-38(54)36(52)32(48)24(12-44)62-42)30(16)34(50)28-18(26)8-14(40(57)58)10-20(28)46/h1-10,23-26,31-32,35-38,41-48,51-54H,11-12H2,(H,55,56)(H,57,58)/t23-,24-,25-,26-,31-,32-,35+,36+,37-,38-,41-,42-/m1/s1
InChIKeyIPQVTOJGNYVQEO-KGFNBKMBSA-N
Species of MetaboliteComponentSourceComments
Rheum rhabarbarum (ncbitaxon:333310) - Article (Chem. Pharm. Bull., 1974, v22(4), 823-831.)
Roles Classification
Chemical Role:
Bronsted acid  A molecular entity capable of donating a hydron to an acceptor (Brønsted base).
Biological Roles:
cathartic  Any substance that accelerates defecation. Compare with laxatives, which are substances that ease defecation (usually by softening faeces). A substance can be both a laxative and a cathartic.
plant metabolite  Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
Application:
laxative  An agent that produces a soft formed stool, and relaxes and loosens the bowels, typically used over a protracted period, to relieve constipation. Compare with cathartic, which is a substance that accelerates defecation. A substances can be both a laxative and a cathartic.
ChEBI Ontology
Outgoing Relation(s)
sennoside A (CHEBI:9112) is a oxo dicarboxylic acid (CHEBI:36145)
sennoside A (CHEBI:9112) is a sennosides (CHEBI:84154)
Incoming Relation(s)
sennoside (CHEBI:34974) has part sennoside A (CHEBI:9112)
IUPAC Name 
(9R*,9'R*)-5,5'-bis(β-D-glucopyranosyloxy)-4,4'-dihydroxy-10,10'-dioxo-9,9',10,10'-tetrahydro-9,9'-bianthracene-2,2'-dicarboxylic acid
Synonym  Source
(−)-(9R*,9'R*)-5,5'-bis(β-D-glucopyranosyloxy)-4,4'-dihydroxy-10,10'-dioxo-9,9',10,10'-tetrahydro-9,9'-bianthracene-2,2'-dicarboxylic acidChEBI
Manual XrefsDatabases
C10404KEGG COMPOUND
C00002863KNApSAcK
HMDB0034317HMDB
LMPK13040016LIPID MAPS
Registry NumbersSources
Reaxys:5723747Reaxys
CAS:81-27-6KEGG COMPOUND
CAS:81-27-6ChemIDplus
Citations