9-hydroxy-6-methoxy-3-[(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: 6c3782fb-33dd-48b3-bb5f-e3ae8d260ac9
• Taxonomy: Organoheterocyclic compounds > Naphthofurans
• IUPAC Name: 9-hydroxy-6-methoxy-3-[(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=CC2=CC3=C(C(=C2C=C1)O)C(=O)OC3OC4C(C(C(C(O4)COC5C(C(C(CO5)O)O)O)O)O)O
• SMILES (Isomeric): COC1=CC2=CC3=C(C(=C2C=C1)O)C(=O)OC3O[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/c1-33-9-2-3-10-8(4-9)5-11-14(15(10)26)21(32)37-22(11)38-24-20(31)18(29)17(28)13(36-24)7-35-23-19(30)16(27)12(25)6-34-23/h2-5,12-13,16-20,22-31H,6-7H2,1H3/t12-,13-,16+,17-,18+,19-,20-,22?,23+,24+/m1/s1
• InChI Key: YRZKMFIXCGHDMH-PQNBYTGHSA-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): -2.00
• 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	-	0.8947	89.47%
Blood Brain Barrier	-	0.6750	67.50%
Human oral bioavailability	-	0.8286	82.86%
Subcellular localzation	Mitochondria	0.6640	66.40%
OATP2B1 inhibitior	-	0.8509	85.09%
OATP1B1 inhibitior	+	0.8547	85.47%
OATP1B3 inhibitior	+	0.9586	95.86%
MATE1 inhibitior	-	0.7400	74.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	-	0.6232	62.32%
P-glycoprotein inhibitior	-	0.7308	73.08%
P-glycoprotein substrate	-	0.5463	54.63%
CYP3A4 substrate	+	0.6788	67.88%
CYP2C9 substrate	-	0.8115	81.15%
CYP2D6 substrate	-	0.8567	85.67%
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	+	0.6291	62.91%
CYP inhibitory promiscuity	-	0.8036	80.36%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.5675	56.75%
Eye corrosion	-	0.9916	99.16%
Eye irritation	-	0.9264	92.64%
Skin irritation	-	0.8281	82.81%
Skin corrosion	-	0.9579	95.79%
Ames mutagenesis	+	0.5800	58.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6871	68.71%
Micronuclear	+	0.5774	57.74%
Hepatotoxicity	-	0.5976	59.76%
skin sensitisation	-	0.8496	84.96%
Respiratory toxicity	+	0.6222	62.22%
Reproductive toxicity	+	0.9111	91.11%
Mitochondrial toxicity	+	0.6625	66.25%
Nephrotoxicity	-	0.9146	91.46%
Acute Oral Toxicity (c)	III	0.7133	71.33%
Estrogen receptor binding	+	0.7945	79.45%
Androgen receptor binding	+	0.5560	55.60%
Thyroid receptor binding	+	0.5535	55.35%
Glucocorticoid receptor binding	+	0.5649	56.49%
Aromatase binding	+	0.5887	58.87%
PPAR gamma	+	0.7459	74.59%
Honey bee toxicity	-	0.8166	81.66%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.5600	56.00%
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	99.87%	91.11%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	98.08%	85.14%
CHEMBL2581	P07339	Cathepsin D	95.37%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.71%	95.56%
CHEMBL1293249	Q13887	Kruppel-like factor 5	93.68%	86.33%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	92.94%	96.09%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	92.62%	94.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	92.31%	97.09%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	92.28%	99.15%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	90.79%	92.62%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	90.66%	86.92%
CHEMBL1806	P11388	DNA topoisomerase II alpha	86.66%	89.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	85.76%	99.23%
CHEMBL1951	P21397	Monoamine oxidase A	85.06%	91.49%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	84.69%	94.45%
CHEMBL3401	O75469	Pregnane X receptor	84.43%	94.73%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	84.40%	96.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	84.26%	95.89%
CHEMBL4208	P20618	Proteasome component C5	83.37%	90.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	81.49%	99.17%
CHEMBL3192	Q9BY41	Histone deacetylase 8	80.85%	93.99%
CHEMBL2345	P51812	Ribosomal protein S6 kinase alpha 3	80.58%	95.64%

Plants that contains it

• Rhamnus japonica

Cross-Links

• PubChem: 101293583
• LOTUS: LTS0060332
• wikiData: Q104248994