Sennoside B (CHEM024583)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-25 21:47:53 UTC
Update Date2016-11-09 01:17:55 UTC
Accession NumberCHEM024583
Identification
Common NameSennoside B
ClassSmall Molecule
DescriptionA 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 beta-D-glucopyranosyloxy groups at positions 5 and 5', and by oxo groups at positions 10 and 10'.
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
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 Mass862.739 g/mol
Monoisotopic Mass862.196 g/mol
CAS Registry Number128-57-4
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
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 IdentifierInChI=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
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted 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
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0il1-0100016390-ffd89cff08870550be99Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0f80-0110069220-c490eb043c6b21c70985Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-2310096210-083f5093912cdaf42f36Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0100004290-85efa2f58c44068dc93eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-1200019130-c2fa3c58f6f5a1d0f7fcSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000i-4200095000-65baf0c0ecdf9aaaeddfSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0000019200-0fa42c1b6bdfd78a37ffSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0f8a-1410107980-715df72c71640f2cb513Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-114l-2100000910-772d01d66baa7f2cc39bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0nms-0100019130-1917d5eb0501884f19feSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-052s-1100019250-539ba733d355e99c6fe9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0pbj-4000049130-95cab0e3d611e122f04aSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0002783
FooDB IDFDB002468
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN ID2406
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID82569
ChEBI ID34975
PubChem Compound ID91440
Kegg Compound IDC13526
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=11534608
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=13487413
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=13495995
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=17401811
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=18926890
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=19142851
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=19393247
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=20091132
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=21695913
10. https://www.ncbi.nlm.nih.gov/pubmed/?term=3368512
11. https://www.ncbi.nlm.nih.gov/pubmed/?term=5910268
12. https://www.ncbi.nlm.nih.gov/pubmed/?term=9922712
13. Ogawa, Shntaro; Yoshida, Akiyoshi; Kato, Reiko. Purification of sennosides. Jpn. Kokai Tokkyo Koho (1977), 3 pp.
14. de Witte P: Metabolism and pharmacokinetics of anthranoids. Pharmacology. 1993 Oct;47 Suppl 1:86-97.