CHEBI:9112 - sennoside A

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ChEBI Name sennoside A
ChEBI ID CHEBI:9112
Definition A 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.
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C42H38O20
Net Charge 0
Average Mass 862.73910
Monoisotopic Mass 862.19564
InChI InChI=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
InChIKey IPQVTOJGNYVQEO-KGFNBKMBSA-N
SMILES OC[C@H]1O[C@@H](Oc2cccc3[C@@H]([C@@H]4c5cccc(O[C@@H]6O[C@H](CO)[C@@H](O)[C@H](O)[C@H]6O)c5C(=O)c5c(O)cc(cc45)C(O)=O)c4cc(cc(O)c4C(=O)c23)C(O)=O)[C@H](O)[C@@H](O)[C@@H]1O
Metabolite of Species Details
Rheum rhabarbarum (NCBI:txid333310) See: Chem. Pharm. Bull., 1974, v22(4), 823-831.
Roles Classification
Chemical Role(s): Bronsted acid
A molecular entity capable of donating a hydron to an acceptor (Bronsted base).
(via oxoacid )
Biological Role(s): plant metabolite
Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
(via sennosides )
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.
(via sennosides )
Application(s): 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.
(via sennosides )
View more via ChEBI Ontology
ChEBI Ontology
Outgoing sennoside A (CHEBI:9112) is a oxo dicarboxylic acid (CHEBI:36145)
sennoside A (CHEBI:9112) is a sennosides (CHEBI:84154)
Incoming 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 acid ChEBI
Manual Xrefs Databases
C00002863 KNApSAcK
C10404 KEGG COMPOUND
HMDB0034317 HMDB
LMPK13040016 LIPID MAPS
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Registry Numbers Types Sources
5723747 Reaxys Registry Number Reaxys
81-27-6 CAS Registry Number KEGG COMPOUND
81-27-6 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
15497761 PubMed citation Europe PMC
15807252 PubMed citation Europe PMC
20091132 PubMed citation Europe PMC
21695913 PubMed citation Europe PMC
21881230 PubMed citation Europe PMC
21881253 PubMed citation Europe PMC
23207772 PubMed citation Europe PMC
24412547 PubMed citation Europe PMC
538110 PubMed citation Europe PMC
Last Modified
07 January 2015