Cassiaside B

Details

• Internal ID: d8dd1c29-e529-4317-87aa-641375c8710f
• Taxonomy: Organoheterocyclic compounds > Naphthopyrans > Naphthopyranones > Naphthopyranone glycosides
• IUPAC Name: 6-[(2S,3R,4S,5S,6R)-6-[[(2R,3R,4R)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxymethyl]-3,4,5-trihydroxyoxan-2-yl]oxy-5-hydroxy-8-methoxy-2-methylbenzo[g]chromen-4-one
• SMILES (Canonical): CC1=CC(=O)C2=C(C3=C(C=C(C=C3C=C2O1)OC)OC4C(C(C(C(O4)COC5C(C(CO5)(CO)O)O)O)O)O)O
• SMILES (Isomeric): CC1=CC(=O)C2=C(C3=C(C=C(C=C3C=C2O1)OC)O[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO[C@H]5[C@@H]([C@](CO5)(CO)O)O)O)O)O)O
• InChI: InChI=1S/C26H30O14/c1-10-3-13(28)18-14(38-10)5-11-4-12(35-2)6-15(17(11)20(18)30)39-24-22(32)21(31)19(29)16(40-24)7-36-25-23(33)26(34,8-27)9-37-25/h3-6,16,19,21-25,27,29-34H,7-9H2,1-2H3/t16-,19-,21+,22-,23+,24-,25-,26-/m1/s1
• InChI Key: NIVCJAYDAMQSJO-PAMAHNMISA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₆H₃₀O₁₄
• Molecular Weight: 566.50 g/mol
• Exact Mass: 566.16355563 g/mol
• Topological Polar Surface Area (TPSA): 214.00 Ų
• XlogP: -0.60
• Atomic LogP (AlogP): -1.39
• H-Bond Acceptor: 14
• H-Bond Donor: 7
• Rotatable Bonds: 7

Synonyms

• CassiasideB
• 119170-51-3
• CHEBI:197161
• DTXSID101108365
• HY-N8148
• AKOS040760312
• CS-0140206
• 6-[(2S,3R,4S,5S,6R)-6-[[(2R,3R,4R)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxymethyl]-3,4,5-trihydroxyoxan-2-yl]oxy-5-hydroxy-8-methoxy-2-methylbenzo[g]chromen-4-one
• 6-[(6-O-D-APio-|A-D-furanosyl-|A-D-glucopyranosyl)oxy]-5-hydroxy-8-methoxy-2-methyl-4H-naphtho[2,3-b]pyran-4-one
• 6-[(6-O-D-Apio-beta-D-furanosyl-beta-D-glucopyranosyl)oxy]-5-hydroxy-8-methoxy-2-methyl-4H-naphtho[2,3-b]pyran-4-one

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.5599	55.99%
Caco-2	-	0.8685	86.85%
Blood Brain Barrier	-	0.6000	60.00%
Human oral bioavailability	-	0.6286	62.86%
Subcellular localzation	Mitochondria	0.6282	62.82%
OATP2B1 inhibitior	-	0.7183	71.83%
OATP1B1 inhibitior	+	0.8625	86.25%
OATP1B3 inhibitior	+	0.9541	95.41%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	+	0.6612	66.12%
P-glycoprotein inhibitior	-	0.5114	51.14%
P-glycoprotein substrate	+	0.5192	51.92%
CYP3A4 substrate	+	0.6758	67.58%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8586	85.86%
CYP3A4 inhibition	-	0.8939	89.39%
CYP2C9 inhibition	-	0.9438	94.38%
CYP2C19 inhibition	-	0.8834	88.34%
CYP2D6 inhibition	-	0.8993	89.93%
CYP1A2 inhibition	-	0.9098	90.98%
CYP2C8 inhibition	+	0.5360	53.60%
CYP inhibitory promiscuity	-	0.8780	87.80%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.5816	58.16%
Eye corrosion	-	0.9915	99.15%
Eye irritation	-	0.9327	93.27%
Skin irritation	-	0.8171	81.71%
Skin corrosion	-	0.9552	95.52%
Ames mutagenesis	+	0.5400	54.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6974	69.74%
Micronuclear	-	0.5026	50.26%
Hepatotoxicity	-	0.7698	76.98%
skin sensitisation	-	0.8615	86.15%
Respiratory toxicity	+	0.5889	58.89%
Reproductive toxicity	+	0.8667	86.67%
Mitochondrial toxicity	+	0.6000	60.00%
Nephrotoxicity	-	0.7440	74.40%
Acute Oral Toxicity (c)	III	0.6019	60.19%
Estrogen receptor binding	+	0.8102	81.02%
Androgen receptor binding	+	0.6188	61.88%
Thyroid receptor binding	+	0.5753	57.53%
Glucocorticoid receptor binding	+	0.6739	67.39%
Aromatase binding	+	0.7204	72.04%
PPAR gamma	+	0.7623	76.23%
Honey bee toxicity	-	0.7846	78.46%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.7700	77.00%
Fish aquatic toxicity	+	0.7139	71.39%

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	99.65%	91.11%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	97.81%	94.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	95.34%	95.56%
CHEMBL3714130	P46095	G-protein coupled receptor 6	92.72%	97.36%
CHEMBL3401	O75469	Pregnane X receptor	91.73%	94.73%
CHEMBL4581	P52732	Kinesin-like protein 1	91.56%	93.18%
CHEMBL1806	P11388	DNA topoisomerase II alpha	91.49%	89.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	91.15%	99.23%
CHEMBL1293249	Q13887	Kruppel-like factor 5	90.58%	86.33%
CHEMBL3137262	O60341	LSD1/CoREST complex	90.52%	97.09%
CHEMBL241	Q14432	Phosphodiesterase 3A	89.08%	92.94%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	88.60%	86.92%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	87.95%	96.95%
CHEMBL2581	P07339	Cathepsin D	87.58%	98.95%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	87.58%	99.15%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	86.64%	85.14%
CHEMBL3864	Q06124	Protein-tyrosine phosphatase 2C	86.11%	94.42%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	85.49%	96.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	83.49%	95.89%
CHEMBL1937	Q92769	Histone deacetylase 2	81.98%	94.75%
CHEMBL4208	P20618	Proteasome component C5	81.08%	90.00%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	81.06%	95.89%
CHEMBL3060	Q9Y345	Glycine transporter 2	80.50%	99.17%
CHEMBL1873	P00750	Tissue-type plasminogen activator	80.12%	93.33%

Plants that contains it

• Senna obtusifolia

Cross-Links

• PubChem: 14189967
• LOTUS: LTS0019206
• wikiData: Q105180005