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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2006-05-22 15:12:10 UTC
Update Date2022-03-07 02:49:16 UTC
HMDB IDHMDB0002783
Secondary Accession Numbers
  • HMDB02783
Metabolite Identification
Common NameSennoside B
DescriptionSennoside 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 ).
Structure
Data?1582752256
Synonyms
ValueSource
(-)-(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 acidChEBI
(-)-(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'-dicarboxylateGenerator
(-)-(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 acidGenerator
(-)-(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'-dicarboxylateGenerator
(-)-(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'-dicarboxylateGenerator
(-)-(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 acidGenerator
5,5'-Bis(b-D-glucopyranosyloxy)-9,9',10,10'-tetrahydro-4,4'-dihydroxy-10,10'-dioxo-[9,9'-bianthracene]-2,2'-dicarboxylic acidHMDB
5,5'-Bis(b-delta-glucopyranosyloxy)-9,9',10,10'-tetrahydro-4,4'-dihydroxy-10,10'-dioxo-[9,9'-bianthracene]-2,2'-dicarboxylic acidHMDB
5,5'-Bis(beta-D-glucopyranosyloxy)-9,9',10,10'-tetrahydro-4,4'-dihydroxy-10,10'-dioxo-[9,9'-bianthracene]-2,2'-dicarboxylic acidHMDB
5,5'-Bis(beta-delta-glucopyranosyloxy)-9,9',10,10'-tetrahydro-4,4'-dihydroxy-10,10'-dioxo-[9,9'-bianthracene]-2,2'-dicarboxylic acidHMDB
Sennoside b (6ci,7ci,8ci)HMDB
ND 10MeSH, HMDB
Sennoside a and bMeSH, HMDB
Sennoside a and b, calcium saltMeSH, HMDB
PursennidMeSH, HMDB
SennosideMeSH, HMDB
Sennoside aMeSH, HMDB
ND-10MeSH, HMDB
SenokotMeSH, HMDB
Sennoside a, calcium salt (1:1)MeSH, HMDB
Sennoside b, calcium saltMeSH, HMDB
Sennoside a, calcium saltMeSH, HMDB
(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)MeSH, HMDB
Sennoside a calcium and sennoside b calciumMeSH, HMDB
Sennoside b calciumMeSH, HMDB
Sennosides a and bMeSH, HMDB
Sennosides a and b acidsMeSH, HMDB
(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 saltMeSH, HMDB
Sennoside a calciumMeSH, HMDB
(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 acidMeSH, HMDB
(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 acidMeSH, HMDB
(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 acidMeSH, HMDB
Sennoside a+b calciumMeSH, HMDB
Sennosides sennoside bMeSH, HMDB
Sennosides sennoside aMeSH, HMDB
Chemical FormulaC42H38O20
Average Molecular Weight862.7391
Monoisotopic Molecular Weight862.195643656
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}-9,10-dihydroanthracen-9-yl]-4-hydroxy-10-oxo-5-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-9,10-dihydroanthracene-2-carboxylic acid
Traditional Namesennoside B
CAS Registry Number128-57-4
SMILES
[H][C@@]1(C2=C(C(O[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)=CC=C2)C(=O)C2=C1C=C(C=C2O)C(O)=O)[C@]1([H])C2=C(C(O[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)=CC=C2)C(=O)C2=C1C=C(C=C2O)C(O)=O
InChI Identifier
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
InChI KeyIPQVTOJGNYVQEO-AIFLABODSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as anthracenecarboxylic acids. These are organic compounds containing a carboxylic acid group attached to an anthracene ring system.
KingdomOrganic compounds
Super ClassBenzenoids
ClassAnthracenes
Sub ClassAnthracenecarboxylic acids and derivatives
Direct ParentAnthracenecarboxylic acids
Alternative Parents
Substituents
  • Anthracene carboxylic acid
  • Phenolic glycoside
  • 2-naphthalenecarboxylic acid
  • 2-naphthalenecarboxylic acid or derivatives
  • Glycosyl compound
  • O-glycosyl compound
  • Hydroxybenzoic acid
  • Aryl ketone
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Dicarboxylic acid or derivatives
  • Monosaccharide
  • Oxane
  • Vinylogous acid
  • Ketone
  • Secondary alcohol
  • Acetal
  • Carboxylic acid derivative
  • Carboxylic acid
  • Oxacycle
  • Organoheterocyclic compound
  • Polyol
  • Organic oxide
  • Hydrocarbon derivative
  • Alcohol
  • Primary alcohol
  • Organic oxygen compound
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling Point1144.80 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility1000000 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP-0.686Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.75 g/LALOGPS
logP0.94ALOGPS
logP1.19ChemAxon
logS-3.1ALOGPS
pKa (Strongest Acidic)3.23ChemAxon
pKa (Strongest Basic)-4ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count20ChemAxon
Hydrogen Donor Count12ChemAxon
Polar Surface Area347.96 ŲChemAxon
Rotatable Bond Count9ChemAxon
Refractivity205.44 m³·mol⁻¹ChemAxon
Polarizability81.89 ųChemAxon
Number of Rings8ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+257.7730932474
DeepCCS[M-H]-256.04630932474
DeepCCS[M-2H]-290.07730932474
DeepCCS[M+Na]+264.02530932474
AllCCS[M+H]+268.932859911
AllCCS[M+H-H2O]+269.132859911
AllCCS[M+NH4]+268.632859911
AllCCS[M+Na]+268.532859911
AllCCS[M-H]-251.932859911
AllCCS[M+Na-2H]-256.032859911
AllCCS[M+HCOO]-260.632859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Sennoside B[H][C@@]1(C2=C(C(O[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)=CC=C2)C(=O)C2=C1C=C(C=C2O)C(O)=O)[C@]1([H])C2=C(C(O[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)=CC=C2)C(=O)C2=C1C=C(C=C2O)C(O)=O7261.6Standard polar33892256
Sennoside B[H][C@@]1(C2=C(C(O[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)=CC=C2)C(=O)C2=C1C=C(C=C2O)C(O)=O)[C@]1([H])C2=C(C(O[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)=CC=C2)C(=O)C2=C1C=C(C=C2O)C(O)=O6105.2Standard non polar33892256
Sennoside B[H][C@@]1(C2=C(C(O[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)=CC=C2)C(=O)C2=C1C=C(C=C2O)C(O)=O)[C@]1([H])C2=C(C(O[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)=CC=C2)C(=O)C2=C1C=C(C=C2O)C(O)=O7623.4Semi standard non polar33892256
Spectra

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sennoside B 10V, Positive-QTOFsplash10-0il1-0100016390-ffd89cff08870550be992016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sennoside B 20V, Positive-QTOFsplash10-0f80-0110069220-c490eb043c6b21c709852016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sennoside B 40V, Positive-QTOFsplash10-000i-2310096210-083f5093912cdaf42f362016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sennoside B 10V, Negative-QTOFsplash10-03di-0100004290-85efa2f58c44068dc93e2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sennoside B 20V, Negative-QTOFsplash10-0002-1200019130-c2fa3c58f6f5a1d0f7fc2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sennoside B 40V, Negative-QTOFsplash10-000i-4200095000-65baf0c0ecdf9aaaeddf2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sennoside B 10V, Positive-QTOFsplash10-001i-0000019200-0fa42c1b6bdfd78a37ff2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sennoside B 20V, Positive-QTOFsplash10-0f8a-1410107980-715df72c71640f2cb5132021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sennoside B 40V, Positive-QTOFsplash10-114l-2100000910-772d01d66baa7f2cc39b2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sennoside B 10V, Negative-QTOFsplash10-0nms-0100019130-1917d5eb0501884f19fe2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sennoside B 20V, Negative-QTOFsplash10-052s-1100019250-539ba733d355e99c6fe92021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sennoside B 40V, Negative-QTOFsplash10-0pbj-4000049130-95cab0e3d611e122f04a2021-09-22Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB002468
KNApSAcK IDNot Available
Chemspider ID82569
KEGG Compound IDC13526
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID2406
PubChem Compound91440
PDB IDNot Available
ChEBI ID34975
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1698781
References
Synthesis ReferenceOgawa, Shntaro; Yoshida, Akiyoshi; Kato, Reiko. Purification of sennosides. Jpn. Kokai Tokkyo Koho (1977), 3 pp.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. de Witte P: Metabolism and pharmacokinetics of anthranoids. Pharmacology. 1993 Oct;47 Suppl 1:86-97. [PubMed:8234447 ]