Sennoside A (CHEM016870)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-22 03:46:01 UTC
Update Date2016-11-09 01:15:29 UTC
Accession NumberCHEM016870
Identification
Common NameSennoside A
ClassSmall Molecule
DescriptionA member of the class of sennosides that is rel-(9R,9'R)-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'. The exact stereochemisty at positions 9 and 9' is not known - it may be R,R (as shown) or S,S.
Contaminant Sources
  • FooDB Chemicals
  • STOFF IDENT Compounds
  • ToxCast & Tox21 Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
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
PursennidMeSH
Sennoside a calciumMeSH
SennosidesMeSH
Senna glycosideMeSH
Sennoside a and b, calcium saltMeSH
Sennoside a calcium and sennoside b calciumMeSH
Sennoside b, calcium saltMeSH
Sennoside b calciumMeSH
Sennosides a and bMeSH
Sennosides a and b acidsMeSH
SenokotMeSH
Sennoside a+b calciumMeSH
Sennoside a, calcium saltMeSH
SennosideMeSH
Sennoside a and bMeSH
Sennoside a, calcium salt (1:1)MeSH
AmyranHMDB
ExprepHMDB
GlaxennaHMDB
MoivatHMDB
SenanHMDB
Tisasen aHMDB
Sennoside bMeSH, HMDB
ND 10MeSH, HMDB
ND-10MeSH, 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
(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
(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
(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
Sennosides sennoside bMeSH
Sennosides sennoside aMeSH
(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
Chemical FormulaC42H38O20
Average Molecular Mass862.739 g/mol
Monoisotopic Mass862.196 g/mol
CAS Registry Number81-27-6
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
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-KGFNBKMBSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as alpha amino acids. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon).
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentAlpha amino acids
Alternative Parents
Substituents
  • Alpha-amino acid
  • Short-chain hydroxy acid
  • Fatty acid
  • 1,3-aminoalcohol
  • Guanidine
  • Secondary alcohol
  • Amino acid
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Carboximidamide
  • Propargyl-type 1,3-dipolar organic compound
  • Organic 1,3-dipolar compound
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Alcohol
  • Primary aliphatic amine
  • Organopnictogen compound
  • Organic nitrogen compound
  • Carbonyl group
  • Organic oxide
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Amine
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic 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
Polarizability82.14 ųChemAxon
Number of Rings8ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
LC-MS/MSLC-MS/MS Spectrum - , negativesplash10-002r-0196402020-ff8b37f085408f0257b2Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITTOF , positivesplash10-00dr-0090080000-b00304ad8c3e233399cbSpectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-00di-0090000000-c2be1e87625e3835dfbbSpectrum
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, 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
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
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 IDHMDB0034317
FooDB IDFDB012669
Phenol Explorer IDNot Available
KNApSAcK IDC00002863
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID65892
ChEBI ID9112
PubChem Compound ID73111
Kegg Compound IDC10404
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=15497761
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=15807252
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=20091132
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=21695913
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=21881230
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=21881253
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=23207772
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=24412547
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=538110
10. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.