9-hydroxy-6-methoxy-8-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxymethyl]oxan-2-yl]oxy-3H-benzo[f][2]benzofuran-1-one

Details

• Internal ID: 7cef5456-fe60-4526-8758-dde948b683ba
• Taxonomy: Organic oxygen compounds > Organooxygen compounds > Carbohydrates and carbohydrate conjugates > Glycosyl compounds > Phenolic glycosides
• IUPAC Name: 9-hydroxy-6-methoxy-8-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxymethyl]oxan-2-yl]oxy-3H-benzo[f][2]benzofuran-1-one
• SMILES (Canonical): COC1=CC(=C2C(=C1)C=C3COC(=O)C3=C2O)OC4C(C(C(C(O4)COC5C(C(C(CO5)O)O)O)O)O)O
• SMILES (Isomeric): COC1=CC(=C2C(=C1)C=C3COC(=O)C3=C2O)O[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO[C@H]5[C@@H]([C@H]([C@@H](CO5)O)O)O)O)O)O
• InChI: InChI=1S/C24H28O14/c1-33-10-3-8-2-9-5-34-22(32)15(9)18(28)14(8)12(4-10)37-24-21(31)19(29)17(27)13(38-24)7-36-23-20(30)16(26)11(25)6-35-23/h2-4,11,13,16-17,19-21,23-31H,5-7H2,1H3/t11-,13-,16+,17-,19+,20-,21-,23+,24-/m1/s1
• InChI Key: OCGVUJOAGGZNKK-HEDOZFJWSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₄H₂₈O₁₄
• Molecular Weight: 540.50 g/mol
• Exact Mass: 540.14790556 g/mol
• Topological Polar Surface Area (TPSA): 214.00 Ų
• XlogP: -1.50
• Atomic LogP (AlogP): -2.13
• H-Bond Acceptor: 14
• H-Bond Donor: 7
• Rotatable Bonds: 6

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.6569	65.69%
Caco-2	-	0.8746	87.46%
Blood Brain Barrier	-	0.6750	67.50%
Human oral bioavailability	-	0.7286	72.86%
Subcellular localzation	Mitochondria	0.6640	66.40%
OATP2B1 inhibitior	-	0.8542	85.42%
OATP1B1 inhibitior	+	0.8536	85.36%
OATP1B3 inhibitior	+	0.9586	95.86%
MATE1 inhibitior	-	0.7800	78.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	-	0.5225	52.25%
P-glycoprotein inhibitior	-	0.7486	74.86%
P-glycoprotein substrate	-	0.5679	56.79%
CYP3A4 substrate	+	0.6433	64.33%
CYP2C9 substrate	-	0.8148	81.48%
CYP2D6 substrate	-	0.8575	85.75%
CYP3A4 inhibition	-	0.8514	85.14%
CYP2C9 inhibition	-	0.9053	90.53%
CYP2C19 inhibition	-	0.7823	78.23%
CYP2D6 inhibition	-	0.8489	84.89%
CYP1A2 inhibition	-	0.8328	83.28%
CYP2C8 inhibition	-	0.5637	56.37%
CYP inhibitory promiscuity	-	0.8036	80.36%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.5675	56.75%
Eye corrosion	-	0.9916	99.16%
Eye irritation	-	0.9311	93.11%
Skin irritation	-	0.8281	82.81%
Skin corrosion	-	0.9579	95.79%
Ames mutagenesis	+	0.5700	57.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7254	72.54%
Micronuclear	+	0.5774	57.74%
Hepatotoxicity	-	0.6698	66.98%
skin sensitisation	-	0.8496	84.96%
Respiratory toxicity	+	0.5556	55.56%
Reproductive toxicity	+	0.9111	91.11%
Mitochondrial toxicity	+	0.6625	66.25%
Nephrotoxicity	-	0.8406	84.06%
Acute Oral Toxicity (c)	III	0.7133	71.33%
Estrogen receptor binding	+	0.8453	84.53%
Androgen receptor binding	+	0.5257	52.57%
Thyroid receptor binding	-	0.5264	52.64%
Glucocorticoid receptor binding	-	0.4686	46.86%
Aromatase binding	+	0.6137	61.37%
PPAR gamma	+	0.7245	72.45%
Honey bee toxicity	-	0.8116	81.16%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.7349	73.49%
Fish aquatic toxicity	+	0.8301	83.01%

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	99.76%	91.11%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	96.95%	85.14%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.61%	96.09%
CHEMBL2581	P07339	Cathepsin D	94.77%	98.95%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	94.59%	94.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	93.30%	86.33%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.30%	95.56%
CHEMBL3714130	P46095	G-protein coupled receptor 6	90.73%	97.36%
CHEMBL3137262	O60341	LSD1/CoREST complex	89.14%	97.09%
CHEMBL3401	O75469	Pregnane X receptor	88.18%	94.73%
CHEMBL4208	P20618	Proteasome component C5	87.14%	90.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	86.92%	94.45%
CHEMBL2002	P12268	Inosine-5'-monophosphate dehydrogenase 2	86.60%	98.21%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	85.98%	92.62%
CHEMBL5608	Q16288	NT-3 growth factor receptor	85.56%	95.89%
CHEMBL3060	Q9Y345	Glycine transporter 2	85.49%	99.17%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	85.35%	96.21%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	85.24%	99.15%
CHEMBL1806	P11388	DNA topoisomerase II alpha	84.86%	89.00%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	83.17%	95.50%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	82.32%	95.83%
CHEMBL2535	P11166	Glucose transporter	82.17%	98.75%
CHEMBL4581	P52732	Kinesin-like protein 1	80.67%	93.18%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	80.59%	95.89%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	80.51%	99.23%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	80.50%	96.00%

Plants that contains it

• Cirsium oligophyllum
• Dalbergia hupeana
• Rhamnus pallasii

Cross-Links

• PubChem: 16216015
• NPASS: NPC250796
• LOTUS: LTS0158928
• wikiData: Q105189354