Cassiaside C

Details

• Internal ID: d4bd77b9-f19a-41fe-85e0-a26413aa3d98
• Taxonomy: Organoheterocyclic compounds > Naphthopyrans > Naphthopyranones > Naphthopyranone glycosides
• IUPAC Name: 10-hydroxy-7-methoxy-3-methyl-9-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]oxan-2-yl]oxybenzo[g]isochromen-1-one
• SMILES (Canonical): CC1=CC2=CC3=CC(=CC(=C3C(=C2C(=O)O1)O)OC4C(C(C(C(O4)COC5C(C(C(C(O5)CO)O)O)O)O)O)O)OC
• SMILES (Isomeric): CC1=CC2=CC3=CC(=CC(=C3C(=C2C(=O)O1)O)O[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO[C@H]5[C@@H]([C@H]([C@@H]([C@H](O5)CO)O)O)O)O)O)O)OC
• InChI: InChI=1S/C27H32O15/c1-9-3-10-4-11-5-12(37-2)6-13(16(11)20(31)17(10)25(36)39-9)40-27-24(35)22(33)19(30)15(42-27)8-38-26-23(34)21(32)18(29)14(7-28)41-26/h3-6,14-15,18-19,21-24,26-35H,7-8H2,1-2H3/t14-,15-,18-,19-,21+,22+,23-,24-,26-,27-/m1/s1
• InChI Key: GBGJNKYTLIUCMX-YUMVGKRXSA-N
• Popularity: 3 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₇H₃₂O₁₅
• Molecular Weight: 596.50 g/mol
• Exact Mass: 596.17412031 g/mol
• Topological Polar Surface Area (TPSA): 234.00 Ų
• XlogP: -0.60
• Atomic LogP (AlogP): -2.03
• H-Bond Acceptor: 15
• H-Bond Donor: 8
• Rotatable Bonds: 7

Synonyms

• 119170-52-4
• CHEMBL3634701
• 9-[(6-O-beta-D-Glucopyranosyl-beta-D-glucopyranosyl)oxy]-10-hydroxy-3-methyl-1H-naphtho[2,3-c]pyran-1-one
• 10-hydroxy-7-methoxy-3-methyl-9-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]oxan-2-yl]oxybenzo[g]isochromen-1-one
• CHEBI:191460
• DTXSID201317838
• Toralactone 9-O-b-D-gentiobioside
• HY-N7628
• BDBM50133155
• AKOS040760314
• MS-30579
• CS-0134826
• Toralatone 9-O-(6-D-glucosyl-D-glucoside)

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.6956	69.56%
Caco-2	-	0.8866	88.66%
Blood Brain Barrier	-	0.7750	77.50%
Human oral bioavailability	-	0.6000	60.00%
Subcellular localzation	Mitochondria	0.5635	56.35%
OATP2B1 inhibitior	-	0.7187	71.87%
OATP1B1 inhibitior	+	0.8376	83.76%
OATP1B3 inhibitior	+	0.9723	97.23%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	+	0.6828	68.28%
P-glycoprotein inhibitior	-	0.6324	63.24%
P-glycoprotein substrate	-	0.6391	63.91%
CYP3A4 substrate	+	0.6181	61.81%
CYP2C9 substrate	-	0.6582	65.82%
CYP2D6 substrate	-	0.8681	86.81%
CYP3A4 inhibition	-	0.9364	93.64%
CYP2C9 inhibition	-	0.9521	95.21%
CYP2C19 inhibition	-	0.9234	92.34%
CYP2D6 inhibition	-	0.9259	92.59%
CYP1A2 inhibition	-	0.9313	93.13%
CYP2C8 inhibition	-	0.5931	59.31%
CYP inhibitory promiscuity	-	0.8225	82.25%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.6598	65.98%
Eye corrosion	-	0.9893	98.93%
Eye irritation	-	0.9355	93.55%
Skin irritation	-	0.8449	84.49%
Skin corrosion	-	0.9681	96.81%
Ames mutagenesis	-	0.5100	51.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7241	72.41%
Micronuclear	+	0.5733	57.33%
Hepatotoxicity	-	0.6875	68.75%
skin sensitisation	-	0.9231	92.31%
Respiratory toxicity	-	0.5444	54.44%
Reproductive toxicity	+	0.6556	65.56%
Mitochondrial toxicity	-	0.5625	56.25%
Nephrotoxicity	-	0.7345	73.45%
Acute Oral Toxicity (c)	III	0.7432	74.32%
Estrogen receptor binding	+	0.8417	84.17%
Androgen receptor binding	-	0.4932	49.32%
Thyroid receptor binding	+	0.5429	54.29%
Glucocorticoid receptor binding	+	0.6129	61.29%
Aromatase binding	+	0.6797	67.97%
PPAR gamma	+	0.6957	69.57%
Honey bee toxicity	-	0.8201	82.01%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	-	0.7300	73.00%
Fish aquatic toxicity	-	0.4096	40.96%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL2409	P34913	Epoxide hydratase	20000 nM	IC50	PMID: 25052206

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.99%	91.11%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	96.13%	94.00%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	91.59%	96.00%
CHEMBL3401	O75469	Pregnane X receptor	91.24%	94.73%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.19%	95.56%
CHEMBL3714130	P46095	G-protein coupled receptor 6	90.51%	97.36%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	90.31%	85.14%
CHEMBL1293249	Q13887	Kruppel-like factor 5	90.10%	86.33%
CHEMBL2581	P07339	Cathepsin D	89.67%	98.95%
CHEMBL3060	Q9Y345	Glycine transporter 2	89.44%	99.17%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	87.89%	99.15%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	85.98%	96.95%
CHEMBL4581	P52732	Kinesin-like protein 1	83.11%	93.18%
CHEMBL3137262	O60341	LSD1/CoREST complex	82.39%	97.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	82.10%	89.00%
CHEMBL4208	P20618	Proteasome component C5	81.62%	90.00%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	80.62%	86.92%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	80.44%	96.21%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	80.24%	99.23%

Plants that contains it

• Senna obtusifolia
• Senna tora

Cross-Links

• PubChem: 5317701
• NPASS: NPC63105
• ChEMBL: CHEMBL3634701
• LOTUS: LTS0196150
• wikiData: Q105005848