CHEBI:34975 - sennoside B

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ChEBI Name sennoside B
ChEBI ID CHEBI:34975
Definition A member of the class of sennosides that is (9R,9'S)-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'.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
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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-AIFLABODSA-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 B (CHEBI:34975) is a oxo dicarboxylic acid (CHEBI:36145)
sennoside B (CHEBI:34975) is a sennosides (CHEBI:84154)
Incoming sennoside (CHEBI:34974) has part sennoside B (CHEBI:34975)
IUPAC Name
(9R,9'S)-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'S)-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
C13526 KEGG COMPOUND
HMDB0002783 HMDB
LMPK13040017 LIPID MAPS
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Registry Numbers Types Sources
128-57-4 CAS Registry Number ChemIDplus
79604 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
11534608 PubMed citation Europe PMC
13487413 PubMed citation Europe PMC
13495995 PubMed citation Europe PMC
17401811 PubMed citation Europe PMC
18926890 PubMed citation Europe PMC
19142851 PubMed citation Europe PMC
19393247 PubMed citation Europe PMC
20091132 PubMed citation Europe PMC
21695913 PubMed citation Europe PMC
3368512 PubMed citation Europe PMC
5910268 PubMed citation Europe PMC
9922712 PubMed citation Europe PMC
Last Modified
07 January 2015
General Comment
2015-01-06 Hydrolysis of sennoside B affords an optically inactive (meso) aglycone, sennidine B. Hence the optical activity of sennoside B ([α]D = −100° in aqueous acetone at 20°C) is entirely due to the glucose moieties. In contrast, sennosides A and C yield optically active aglycones.