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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 19:07:40 UTC
Update Date2021-10-13 06:40:18 UTC
HMDB IDHMDB0034317
Secondary Accession Numbers
  • HMDB34317
Metabolite Identification
Common NameSennoside A
DescriptionSennoside A, also known as pursennid or senna glycoside, 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). Thus, sennoside a is considered to be an aromatic polyketide. Sennoside A has been detected, but not quantified in, garden rhubarbs (Rheum rhabarbarum) and green vegetables. This could make sennoside a a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on Sennoside A.
Structure
Data?1563862544
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 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
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
Ontology
Disposition

Biological location

Source

Route of exposure

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point220 - 243 °CNot Available
Boiling Point1144.80 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility0.041 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP1.880 (est)The Good Scents Company Information System
Experimental Spectral PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.75 g/LALOGPS
logP10(0.94) g/LALOGPS
logP10(1.19) g/LChemAxon
logS10(-3.1) g/LALOGPS
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
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted Spectral Properties

Predicted Kovats Retention Indices

Not Available
Spectra

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Sennoside A , negative-QTOFsplash10-002r-0196402020-ff8b37f085408f0257b22017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Sennoside A LC-ESI-ITTOF , positive-QTOFsplash10-00dr-0090080000-b00304ad8c3e233399cb2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Sennoside A , positive-QTOFsplash10-00di-0090000000-c2be1e87625e3835dfbb2017-09-14HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sennoside A 10V, Positive-QTOFsplash10-0il1-0100016390-ffd89cff08870550be992016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sennoside A 20V, Positive-QTOFsplash10-0f80-0110069220-c490eb043c6b21c709852016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sennoside A 40V, Positive-QTOFsplash10-000i-2310096210-083f5093912cdaf42f362016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sennoside A 10V, Negative-QTOFsplash10-03di-0100004290-85efa2f58c44068dc93e2016-08-04Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sennoside A 20V, Negative-QTOFsplash10-0002-1200019130-c2fa3c58f6f5a1d0f7fc2016-08-04Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sennoside A 40V, Negative-QTOFsplash10-000i-4200095000-65baf0c0ecdf9aaaeddf2016-08-04Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sennoside A 10V, Negative-QTOFsplash10-0nms-0100019130-1917d5eb0501884f19fe2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sennoside A 20V, Negative-QTOFsplash10-052s-1100019250-539ba733d355e99c6fe92021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sennoside A 40V, Negative-QTOFsplash10-0pbj-4000049130-95cab0e3d611e122f04a2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sennoside A 10V, Positive-QTOFsplash10-001i-0000019200-0fa42c1b6bdfd78a37ff2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sennoside A 20V, Positive-QTOFsplash10-0f8a-1410107980-715df72c71640f2cb5132021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sennoside A 40V, Positive-QTOFsplash10-114l-2100000910-772d01d66baa7f2cc39b2021-09-25Wishart LabView Spectrum
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
FooDB 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
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1698791
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.. .