This website is for informational and educational purposes only. Please do not self-medicate; contact a medical professional for advice before administration. This website is for informational and educational purposes only. Please do not self-medicate; contact a medical professional for advice before administration.

Sennoside B

PubChem CID: 91440

Connections displayed (default: 10).
Loading graph...

ℹ️ Click here to know more about the properties
Compound Synonyms Sennoside B, 128-57-4, EINECS 204-895-0, NSC 112930, CHEBI:34975, MFCD00151528, F887D1637W, SENNOSIDE B [USP-RS], SENNOSIDE B [WHO-DD], MLS002473001, DTXSID6051433, (9R,9'S)-4,4'-dihydroxy-10,10'-dioxo-5,5'-bis(((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)-9,9',10,10'-tetrahydro-[9,9'-bianthracene]-2,2'-dicarboxylic acid, [9,9'-Bianthracene]-2,2'-dicarboxylic acid, 5,5'-bis(beta-D-glucopyranosyloxy)-9,9',10,10'-tetrahydro-4,4'-dihydroxy-10,10'-dioxo-, (9R,9'S)-, SMR001397106, SennosideB, (9S)-9-[(9R)-2-carboxy-4-hydroxy-10-oxo-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-9H-anthracen-9-yl]-4-hydroxy-10-oxo-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-9H-anthracene-2-carboxylic acid, SENNOSIDE B (USP-RS), SENNOSIDE B (CONSTITUENT OF SENNA LEAF AND PODS) [DSC], (-)-(9R,9'S)-5,5'-bis(beta-D-glucopyranosyloxy)-4,4'-dihydroxy-10,10'-dioxo-9,9',10,10'-tetrahydro-9,9'-bianthracene-2,2'-dicarboxylic acid, (9R,9'S)-5,5'-BIS(.BETA.-D-GLUCOPYRANOSYLOXY)-9,9',10,10'-TETRAHYDRO-4,4'-DIHYDROXY-10,10'-DIOXO(9,9'-BIANTHRACENE)-2,2'-DICARBOXYLIC ACID, (9R,9'S)-5,5'-bis(beta-D-glucopyranosyloxy)-4,4'-dihydroxy-10,10'-dioxo-9,9',10,10'-tetrahydro-9,9'-bianthracene-2,2'-dicarboxylic acid, NSC112930, Sennoside-B, UNII-F887D1637W, NSC-112930, Sennoside B CRS, (9S)-9-((9R)-2-carboxy-4-hydroxy-10-oxo-5-((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl)oxy-9H-anthracen-9-yl)-4-hydroxy-10-oxo-5-((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl)oxy-9H-anthracene-2-carboxylic acid, Sennoside B (Standard), cid_91440, SCHEMBL441194, CHEMBL445268, DTXCID5030034, BDBM80739, HY-N0366R, Sennoside B (6CI,7CI,8CI), IPQVTOJGNYVQEO-AIFLABODSA-N, HMS2226P04, C42H38O2, EX-A4953, SENNOSIDES SENNOSIDE B [MI], LMPK13040017, s4018, AKOS016034289, CCG-270539, MS08137, 1ST40351, NS00079121, Q27116344, SENNOSIDE B (CONSTITUENT OF SENNA LEAF AND PODS), (9R)-9-[(9S)-2-carboxy-4-hydroxy-10-oxo-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxy-9H-anthracen-9-yl]-4-hydroxy-10-oxo-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxy-9H-anthracene-2-carboxylic acid, (9R,9'S)-4,4'-dihydroxy-10,10'-dioxo-5,5'-bis((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yloxy)-9,9',10,10'-tetrahydro-9,9'-bianthracene-2,2'-dicarboxylic acid, (9R,9'S)-5,5'-BIS(BETA-D-GLUCOPYRANOSYLOXY)-9,9',10,10'-TETRAHYDRO-4,4'-DIHYDROXY-10,10'-DIOXO(9,9'-BIANTHRACENE)-2,2'-DICARBOXYLIC ACID, (9S)-9-[(9R)-2-carboxy-4-hydroxy-10-oxo-5-[(2S,3R,4S,5S,6R)-3,4 ,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-9H-anthracen-9-yl]-4-hyd roxy-10-oxo-5-[(2S,3R,4S,5S,6R)-3,4 ,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-9H-anthracene-2-carboxylic acid, [9,9'-Bianthracene]-2,2'-dicarboxylic acid, 5,5'-bis(, A-D-glucopyranosyloxy)-9,9',10,10'-tetrahydro-4,4'-dihydroxy-10,10'-dioxo-, (9R,9'S)-, 204-895-0, 5,5'-bis(b-D-glucopyranosyloxy)-9,9',10,10'-tetrahydro-4,4'-dihydroxy-10,10'-dioxo-[9,9'-Bianthracene]-2,2'-dicarboxylic acid, 5,5'-bis(b-delta-glucopyranosyloxy)-9,9',10,10'-tetrahydro-4,4'-dihydroxy-10,10'-dioxo-[9,9'-Bianthracene]-2,2'-dicarboxylic acid, 5,5'-bis(beta-D-glucopyranosyloxy)-9,9',10,10'-tetrahydro-4,4'-dihydroxy-10,10'-dioxo-[9,9'-Bianthracene]-2,2'-dicarboxylic acid, 5,5'-bis(beta-delta-glucopyranosyloxy)-9,9',10,10'-tetrahydro-4,4'-dihydroxy-10,10'-dioxo-[9,9'-Bianthracene]-2,2'-dicarboxylic acid, 9,9'-Bianthracene]-2,2'-dicarboxylic acid, 5,5'-bis(hexopyranosyloxy)-9,9',10,10'-tetrahydro-4,4'-dihydroxy-10,10'-dioxo-, (9R,9'S)-
Ghose Rule False
Classyfire Kingdom Organic compounds
Topological Polar Surface Area 348.0
Hydrogen Bond Donor Count 12.0
Pfizer 3 75 Rule True
Scaffold Graph Level CC1C2CCCCC2C(C2C3CCCCC3C(C)C3C(CC4CCCCC4)CCCC32)C2CCCC(CC3CCCCC3)C12
Np Classifier Class Anthraquinones and anthrones
Deep Smiles OC[C@H]O[C@@H]Occcccc6C=O)cc[C@@H]6[C@@H]cccccc6C=O)cc%10cccc6O[C@@H]O[C@H]CO))[C@H][C@@H][C@H]6O))O))O))))))))))))))O)))C=O)O)))))))cccc6O)))C=O)O))))))))))))))[C@@H][C@H][C@@H]6O))O))O
Heavy Atom Count 62.0
Classyfire Class Anthracenes
Description Sennoside B is an anthranoid. Anthranoid derivatives are used all over the world as a treatment for constipation. These compounds are present in several drugs of plant origin, especially as O- or C-glycosides. Besides featuring different substituents, the aglycone might consist of an anthraquinone, an anthrone or a dianthrone. So far, detailed information concerning their metabolism and pharmacokinetic characteristics is available only in a few cases. The best characterized compounds are sennoside, a dianthrone O-glycoside present in senna leaves and senna pods, and its aglycone (rhein anthrone). After oral administration, sennoside is degraded only in the lower parts of the gastrointestinal tract, releasing its active metabolite rhein anthrone. (PMID: 8234447). Sennoside B is found in garden rhubarb.
Scaffold Graph Node Level OC1C2CCCCC2C(C2C3CCCCC3C(O)C3C(OC4CCCCO4)CCCC32)C2CCCC(OC3CCCCO3)C12
Classyfire Subclass Anthracenecarboxylic acids and derivatives
Isotope Atom Count 0.0
Molecular Complexity 1550.0
Database Name cmaup_ingredients;fooddb_chem_all;hmdb_chem_all;imppat_phytochem;npass_chem_all;pubchem
Defined Atom Stereocenter Count 12.0
Uniprot Id P35354, O75604, Q9NUW8, Q9Y468, O75164, Q2TB90, Q92830, O15648, O00167, Q96QE3, O95149, P83916, O89049, P39748, Q9Y253, Q9UBT6, P84022, P07378, O94925, Q14191, Q13526, Q77YF9, O94782, Q8WZA2, Q03431, P53350, P27695, O95398
Iupac Name (9S)-9-[(9R)-2-carboxy-4-hydroxy-10-oxo-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-9H-anthracen-9-yl]-4-hydroxy-10-oxo-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-9H-anthracene-2-carboxylic acid
Prediction Hob 0.0
Class Anthracenes
Veber Rule False
Classyfire Superclass Benzenoids
Target Id NPT45, NPT50, NPT864, NPT4034, NPT532
Xlogp 1.2
Superclass Benzenoids
Subclass Anthracenecarboxylic acids and derivatives
Gsk 4 400 Rule False
Molecular Formula C42H38O20
Scaffold Graph Node Bond Level O=C1c2ccccc2C(C2c3ccccc3C(=O)c3c(OC4CCCCO4)cccc32)c2cccc(OC3CCCCO3)c21
Prediction Swissadme 0.0
Inchi Key IPQVTOJGNYVQEO-AIFLABODSA-N
Silicos It Class Soluble
Fcsp3 0.3333333333333333
Logs -4.638
Rotatable Bond Count 9.0
State Solid
Logd 1.025
Synonyms (-)-(9R,9'S)-5,5'-bis(b-D-glucopyranosyloxy)-4,4'-dihydroxy-10,10'-dioxo-9,9',10,10'-tetrahydro-9,9'-bianthracene-2,2'-dicarboxylate, (-)-(9R,9'S)-5,5'-bis(b-D-glucopyranosyloxy)-4,4'-dihydroxy-10,10'-dioxo-9,9',10,10'-tetrahydro-9,9'-bianthracene-2,2'-dicarboxylic acid, (-)-(9R,9'S)-5,5'-bis(beta-D-glucopyranosyloxy)-4,4'-dihydroxy-10,10'-dioxo-9,9',10,10'-tetrahydro-9,9'-bianthracene-2,2'-dicarboxylate, (-)-(9R,9'S)-5,5'-bis(beta-D-glucopyranosyloxy)-4,4'-dihydroxy-10,10'-dioxo-9,9',10,10'-tetrahydro-9,9'-bianthracene-2,2'-dicarboxylic acid, (-)-(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'-dicarboxylate, (-)-(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, 5,5'-Bis(b-D-glucopyranosyloxy)-9,9',10,10'-tetrahydro-4,4'-dihydroxy-10,10'-dioxo-[9,9'-bianthracene]-2,2'-dicarboxylic acid, 5,5'-Bis(b-delta-glucopyranosyloxy)-9,9',10,10'-tetrahydro-4,4'-dihydroxy-10,10'-dioxo-[9,9'-bianthracene]-2,2'-dicarboxylic acid, 5,5'-Bis(beta-D-glucopyranosyloxy)-9,9',10,10'-tetrahydro-4,4'-dihydroxy-10,10'-dioxo-[9,9'-bianthracene]-2,2'-dicarboxylic acid, 5,5'-Bis(beta-delta-glucopyranosyloxy)-9,9',10,10'-tetrahydro-4,4'-dihydroxy-10,10'-dioxo-[9,9'-bianthracene]-2,2'-dicarboxylic acid, Sennoside B, Sennoside b (6ci,7ci,8ci), Tisasen B, (-)-(9R,9's)-5,5'-Bis(beta-D-glucopyranosyloxy)-4,4'-dihydroxy-10,10'-dioxo-9,9',10,10'-tetrahydro-9,9'-bianthracene-2,2'-dicarboxylic acid, (-)-(9R,9's)-5,5'-Bis(b-D-glucopyranosyloxy)-4,4'-dihydroxy-10,10'-dioxo-9,9',10,10'-tetrahydro-9,9'-bianthracene-2,2'-dicarboxylate, (-)-(9R,9's)-5,5'-Bis(b-D-glucopyranosyloxy)-4,4'-dihydroxy-10,10'-dioxo-9,9',10,10'-tetrahydro-9,9'-bianthracene-2,2'-dicarboxylic acid, (-)-(9R,9's)-5,5'-Bis(beta-D-glucopyranosyloxy)-4,4'-dihydroxy-10,10'-dioxo-9,9',10,10'-tetrahydro-9,9'-bianthracene-2,2'-dicarboxylate, (-)-(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'-dicarboxylate, (-)-(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, ND 10, Sennoside a and b, Sennoside a and b, calcium salt, Pursennid, Sennoside, Sennoside a, ND-10, Senokot, Sennoside a, calcium salt (1:1), Sennoside b, calcium salt, Sennoside a, calcium salt, (9,9'-Bianthracene)-2,2'-dicarboxylic acid, 5,5'-bis(beta-D-glucopyranosyloxy)-9,9',10,10'-tetrahydro-4,4'-dihydroxy-10,10'-dioxo-, calcium salt (1:1), Sennoside a calcium and sennoside b calcium, Sennoside b calcium, Sennosides a and b, Sennosides a and b acids, (9,9'-Bianthracene)-2,2'-dicarboxylic acid, 5,5'-bis(beta-D-glucopyranosyloxy)-9,9',10,10'-tetrahydro-4,4'-dihydroxy-10,10'-dioxo-, (9R,9's)-, calcium salt, Sennoside a calcium, (9R,9's)-5,5'-Bis(beta-D-glucopyranosyloxy)-9,9',10,10'-tetrahydro-4,4'-dihydroxy-10,10'-dioxo(9,9'-bianthracene)-2,2'-dicarboxylic acid, (9R,9R)-5,5-Bis(beta-D-glucopyranosyloxy)-9,9,10,10-tetrahydro-4,4-dihydroxy-10,10-dioxo(9,9-bianthracene)-2,2-dicarboxylic acid, (R*,r*)-5,5'-bis(beta-D-glucopyranosyloxy)-9,9',10,10'-tetrahydro-4,4'-dihydroxy-10,10'-dioxo(9,9'-bianthracene)-2,2'-dicarboxylic acid, Sennoside a+b calcium, Sennosides sennoside b, Sennosides sennoside a, sennoside b
Substituent Name Anthracene carboxylic acid, 2-naphthalenecarboxylic acid or derivatives, 2-naphthalenecarboxylic acid, O-glycosyl compound, Glycosyl compound, Hydroxybenzoic acid, Aryl ketone, Benzoyl, Oxane, Monosaccharide, Dicarboxylic acid or derivatives, Saccharide, Vinylogous acid, Secondary alcohol, Polyol, Ketone, 1,2-diol, Oxacycle, Organoheterocyclic compound, Ether, Carboxylic acid, Carboxylic acid derivative, Acetal, Hydrocarbon derivative, Aromatic alcohol, Primary alcohol, Organooxygen compound, Carbonyl group, Alcohol, Aromatic heteropolycyclic compound
Esol Class Moderately soluble
Functional Groups CO, cC(=O)O, cC(c)=O, cO, cO[C@@H](C)OC
Compound Name Sennoside B
Kingdom Organic compounds
Prediction Hob Swissadme 0.0
Exact Mass 862.196
Formal Charge 0.0
Monoisotopic Mass 862.196
Hydrogen Bond Acceptor Count 20.0
Molecular Weight 862.7
Gi Absorption False
Covalent Unit Count 1.0
Total Atom Stereocenter Count 12.0
Total Bond Stereocenter Count 0.0
Molecular Framework Aromatic heteropolycyclic compounds
Lipinski Rule Of 5 False
Esol -5.637476812903228
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
Smiles C1=CC2=C(C(=C1)O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O)C(=O)C4=C([C@@H]2[C@H]5C6=C(C(=CC=C6)O[C@H]7[C@@H]([C@H]([C@@H]([C@H](O7)CO)O)O)O)C(=O)C8=C5C=C(C=C8O)C(=O)O)C=C(C=C4O)C(=O)O
Nring 8.0
Np Classifier Biosynthetic Pathway Polyketides
Defined Bond Stereocenter Count 0.0
Egan Rule False
Taxonomy Direct Parent Anthracenecarboxylic acids
Np Classifier Superclass Polycyclic aromatic polyketides

Back to Browse   Back to Home