Sennoside C

Details

• Internal ID: 037bacee-a2bc-44f1-bdce-8a41813b8172
• Taxonomy: Benzenoids > Anthracenes > Anthracenecarboxylic acids and derivatives > Anthracenecarboxylic acids
• IUPAC Name: (9R)-4-hydroxy-9-[(9R)-4-hydroxy-2-(hydroxymethyl)-10-oxo-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-9H-anthracen-9-yl]-10-oxo-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-9H-anthracene-2-carboxylic acid
• SMILES (Canonical): C1=CC2=C(C(=C1)OC3C(C(C(C(O3)CO)O)O)O)C(=O)C4=C(C2C5C6=C(C(=CC=C6)OC7C(C(C(C(O7)CO)O)O)O)C(=O)C8=C5C=C(C=C8O)C(=O)O)C=C(C=C4O)CO
• SMILES (Isomeric): C1=CC2=C(C(=C1)O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O)C(=O)C4=C([C@@H]2[C@@H]5C6=C(C(=CC=C6)O[C@H]7[C@@H]([C@H]([C@@H]([C@H](O7)CO)O)O)O)C(=O)C8=C5C=C(C=C8O)C(=O)O)C=C(C=C4O)CO
• InChI: InChI=1S/C42H40O19/c43-11-14-7-18-26(16-3-1-5-22(30(16)34(50)28(18)20(46)8-14)58-41-38(54)36(52)32(48)24(12-44)60-41)27-17-4-2-6-23(59-42-39(55)37(53)33(49)25(13-45)61-42)31(17)35(51)29-19(27)9-15(40(56)57)10-21(29)47/h1-10,24-27,32-33,36-39,41-49,52-55H,11-13H2,(H,56,57)/t24-,25-,26-,27-,32-,33-,36+,37+,38-,39-,41-,42-/m1/s1
• InChI Key: ZFWOUNNKSHIAFK-RDAFFBQNSA-N
• Popularity: 4 references in papers

Physical and Chemical Properties

• Molecular Formula: C₄₂H₄₀O₁₉
• Molecular Weight: 848.80 g/mol
• Exact Mass: 848.21637904 g/mol
• Topological Polar Surface Area (TPSA): 331.00 Ų
• XlogP: 0.80
• Atomic LogP (AlogP): -1.30
• H-Bond Acceptor: 18
• H-Bond Donor: 12
• Rotatable Bonds: 9

Synonyms

• 37271-16-2
• UNII-UQ166P8802
• UQ166P8802
• (9R)-4-hydroxy-9-[(9R)-4-hydroxy-2-(hydroxymethyl)-10-oxo-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-9H-anthracen-9-yl]-10-oxo-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-9H-anthracene-2-carboxylic acid
• Sennosid C
• 26403-11-2
• Sennoside-C
• C42H40O19
• CHEBI:80734
• AKOS025287037
• C42-H40-O19
• C16797
• Q-100439
• Q27149784
• SENNOSIDE C (CONSTITUENT OF SENNA LEAF AND PODS) [DSC]
• (9,9'-BIANTHRACENE)-2-CARBOXYLIC ACID, 5,5'-BIS(.BETA.-D-GLUCOPYRANOSYLOXY)-9,9',10,10'-TETRAHYDRO-4,4'-DIHYDROXY-2'-(HYDROXYMETHYL)-10,10'-DIOXO-, (9R,9'R)-REL-
• (9,9'-Bianthracene)-2-carboxylic acid, 5,5'-bis(beta-D-glucopyranosyloxy)-9,9',10,10'-tetrahydro-4,4'-dihydroxy-2'-(hydroxymethyl)-10,10'-dioxo-, (R*,R*)-
• (9R,9'R)-5,5'-Bis(beta-D-glucopyranosyloxy)-9,9',10,10'-tetrahydro-4,4'-dihydroxy-2'-(hydroxymethyl)-10,10'-dioxo-9,9'-bianthracene-2-carboxylic acid

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.6788	67.88%
Caco-2	-	0.9052	90.52%
Blood Brain Barrier	-	0.7500	75.00%
Human oral bioavailability	-	0.6857	68.57%
Subcellular localzation	Mitochondria	0.5329	53.29%
OATP2B1 inhibitior	-	0.7069	70.69%
OATP1B1 inhibitior	+	0.8669	86.69%
OATP1B3 inhibitior	+	0.9724	97.24%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.7500	75.00%
BSEP inhibitior	+	0.8140	81.40%
P-glycoprotein inhibitior	+	0.6691	66.91%
P-glycoprotein substrate	-	0.7739	77.39%
CYP3A4 substrate	+	0.6284	62.84%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8793	87.93%
CYP3A4 inhibition	-	0.9365	93.65%
CYP2C9 inhibition	-	0.9171	91.71%
CYP2C19 inhibition	-	0.9032	90.32%
CYP2D6 inhibition	-	0.9596	95.96%
CYP1A2 inhibition	-	0.9320	93.20%
CYP2C8 inhibition	+	0.7145	71.45%
CYP inhibitory promiscuity	-	0.8607	86.07%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.6966	69.66%
Eye corrosion	-	0.9927	99.27%
Eye irritation	-	0.8943	89.43%
Skin irritation	-	0.8466	84.66%
Skin corrosion	-	0.9636	96.36%
Ames mutagenesis	+	0.6131	61.31%
Human Ether-a-go-go-Related Gene inhibition	+	0.7908	79.08%
Micronuclear	+	0.6533	65.33%
Hepatotoxicity	+	0.5875	58.75%
skin sensitisation	-	0.9177	91.77%
Respiratory toxicity	+	0.5444	54.44%
Reproductive toxicity	+	0.7556	75.56%
Mitochondrial toxicity	+	0.7000	70.00%
Nephrotoxicity	+	0.5117	51.17%
Acute Oral Toxicity (c)	IV	0.5235	52.35%
Estrogen receptor binding	+	0.8072	80.72%
Androgen receptor binding	-	0.7719	77.19%
Thyroid receptor binding	-	0.5190	51.90%
Glucocorticoid receptor binding	-	0.8452	84.52%
Aromatase binding	-	0.5000	50.00%
PPAR gamma	+	0.7148	71.48%
Honey bee toxicity	-	0.7766	77.66%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.7650	76.50%
Fish aquatic toxicity	+	0.8498	84.98%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.06%	91.11%
CHEMBL220	P22303	Acetylcholinesterase	97.34%	94.45%
CHEMBL2581	P07339	Cathepsin D	96.45%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.05%	95.56%
CHEMBL1293249	Q13887	Kruppel-like factor 5	91.12%	86.33%
CHEMBL1806	P11388	DNA topoisomerase II alpha	90.90%	89.00%
CHEMBL3194	P02766	Transthyretin	90.56%	90.71%
CHEMBL3060	Q9Y345	Glycine transporter 2	89.83%	99.17%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	85.94%	96.09%
CHEMBL2563	Q9UQL6	Histone deacetylase 5	85.44%	89.67%
CHEMBL5608	Q16288	NT-3 growth factor receptor	85.23%	95.89%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	85.04%	96.21%
CHEMBL1255126	O15151	Protein Mdm4	84.78%	90.20%
CHEMBL3401	O75469	Pregnane X receptor	83.80%	94.73%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	82.34%	96.95%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	81.24%	99.23%
CHEMBL2535	P11166	Glucose transporter	80.67%	98.75%

Plants that contains it

• Albizia myriophylla
• Amphorogyne spicata
• Anaphalis lactea
• Anchusa azurea
• Balanophora laxiflora
• Benincasa hispida
• Carduus tenuiflorus
• Chaiturus marrubiastrum
• Cryptochilus strictus
• Degenia velebitica
• Delphinium nuttallianum
• Delphinium virgatum
• Dillenia indica
• Dipsacus dipsacoides
• Erythrophleum ivorense
• Grangea maderaspatana
• Helichrysum chionosphaerum
• Jacquemontia paniculata
• Leptocereus quadricostatus
• Lespedeza tomentosa
• Lupinus argenteus subsp. argenteus
• Mandragora officinarum
• Metrodorea nigra
• Nepeta granatensis
• Onobrychis arenaria
• Petunia inflata
• Phedimus selskanianus
• Photinia serratifolia
• Pittocaulon praecox
• Quercus rubra
• Rheum officinale
• Rheum palmatum
• Rheum tanguticum
• Rosa villosa
• Salvia greggii
• Senecio behnii
• Senna alexandrina
• Sticherus quadripartitus
• Tagetes filifolia
• Tanacetum coccineum
• Terminalia chebula
• Verbascum densiflorum

Cross-Links

• PubChem: 46173829
• NPASS: NPC205570
• LOTUS: LTS0082504
• wikiData: Q27149784