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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-11 19:07:40 UTC
Update Date2019-01-11 19:48:16 UTC
HMDB IDHMDB0034317
Secondary Accession Numbers
  • HMDB34317
Metabolite Identification
Common NameSennoside A
DescriptionSennoside A is found in garden rhubarb. Cathartic principle from rhubar
Structure
Data?1547236096
Synonyms
ValueSource
(-)-(9R*,9'r*)-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'r*)-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'r*)-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'r*)-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'r*)-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'r*)-5,5'-bis(β-D-glucopyranosyloxy)-4,4'-dihydroxy-10,10'-dioxo-9,9',10,10'-tetrahydro-9,9'-bianthracene-2,2'-dicarboxylic acidGenerator
AmyranHMDB
ExprepHMDB
GlaxennaHMDB
MoivatHMDB
SenanHMDB
Tisasen aHMDB
Sennoside a and b, calcium saltMeSH
Sennoside a, calcium saltMeSH
Sennoside bMeSH
Sennoside b, calcium saltMeSH
ND 10MeSH
ND-10MeSH
PursennidMeSH
SennosideMeSH
Sennoside a and bMeSH
Sennoside a, calcium salt (1:1)MeSH
SenokotMeSH
Chemical FormulaC42H38O20
Average Molecular Weight862.7391
Monoisotopic Molecular Weight862.195643656
IUPAC Name(9R)-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 A
CAS Registry Number81-27-6
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-KGFNBKMBSA-N
Chemical Taxonomy
DescriptionThis compound 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
Disposition

Route of exposure:

Source:

Biological location:

Role

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point220 - 243 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot 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
Polarizability82.14 ųChemAxon
Number of Rings8ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
LC-MS/MSLC-MS/MS Spectrum - , negativesplash10-002r-0196402020-ff8b37f085408f0257b2JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITTOF , positivesplash10-00dr-0090080000-b00304ad8c3e233399cbJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-00di-0090000000-c2be1e87625e3835dfbbJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0il1-0100016390-ffd89cff08870550be99JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0f80-0110069220-c490eb043c6b21c70985JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-2310096210-083f5093912cdaf42f36JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0100004290-85efa2f58c44068dc93eJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-1200019130-c2fa3c58f6f5a1d0f7fcJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000i-4200095000-65baf0c0ecdf9aaaeddfJSpectraViewer | MoNA
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
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
FoodDB IDFDB012669
KNApSAcK IDC00002863
Chemspider ID65892
KEGG Compound IDC10404
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound73111
PDB IDNot Available
ChEBI ID9112
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .