[(2S,3R,4R,5S,6S)-3-acetyloxy-2-(4,5-dihydroxy-7-methyl-9,10-dioxoanthracen-2-yl)oxy-5-hydroxy-6-methyloxan-4-yl] acetate

Details

• Internal ID: 35b937ef-18d7-47fb-aa0f-fe1a9558a775
• Taxonomy: Benzenoids > Anthracenes > Anthraquinones
• IUPAC Name: [(2S,3R,4R,5S,6S)-3-acetyloxy-2-(4,5-dihydroxy-7-methyl-9,10-dioxoanthracen-2-yl)oxy-5-hydroxy-6-methyloxan-4-yl] acetate
• SMILES (Canonical): CC1C(C(C(C(O1)OC2=CC3=C(C(=C2)O)C(=O)C4=C(C3=O)C=C(C=C4O)C)OC(=O)C)OC(=O)C)O
• SMILES (Isomeric): C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)OC2=CC3=C(C(=C2)O)C(=O)C4=C(C3=O)C=C(C=C4O)C)OC(=O)C)OC(=O)C)O
• InChI: InChI=1S/C25H24O11/c1-9-5-14-18(16(28)6-9)22(32)19-15(21(14)31)7-13(8-17(19)29)36-25-24(35-12(4)27)23(34-11(3)26)20(30)10(2)33-25/h5-8,10,20,23-25,28-30H,1-4H3/t10-,20-,23+,24+,25-/m0/s1
• InChI Key: KCNQHDPLSQKCFV-QXXCCVGTSA-N
• Popularity: 3 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₅H₂₄O₁₁
• Molecular Weight: 500.40 g/mol
• Exact Mass: 500.13186158 g/mol
• Topological Polar Surface Area (TPSA): 166.00 Ų
• XlogP: 2.60
• Atomic LogP (AlogP): 1.53
• H-Bond Acceptor: 11
• H-Bond Donor: 3
• Rotatable Bonds: 4

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9073	90.73%
Caco-2	-	0.7552	75.52%
Blood Brain Barrier	-	0.8750	87.50%
Human oral bioavailability	-	0.6286	62.86%
Subcellular localzation	Mitochondria	0.7342	73.42%
OATP2B1 inhibitior	-	0.8519	85.19%
OATP1B1 inhibitior	+	0.8950	89.50%
OATP1B3 inhibitior	+	0.8421	84.21%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	+	0.7391	73.91%
P-glycoprotein inhibitior	+	0.7106	71.06%
P-glycoprotein substrate	-	0.8485	84.85%
CYP3A4 substrate	+	0.6088	60.88%
CYP2C9 substrate	-	0.8177	81.77%
CYP2D6 substrate	-	0.8814	88.14%
CYP3A4 inhibition	-	0.9579	95.79%
CYP2C9 inhibition	-	0.8971	89.71%
CYP2C19 inhibition	-	0.9545	95.45%
CYP2D6 inhibition	-	0.9564	95.64%
CYP1A2 inhibition	+	0.6649	66.49%
CYP2C8 inhibition	-	0.6608	66.08%
CYP inhibitory promiscuity	-	0.8076	80.76%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.6027	60.27%
Eye corrosion	-	0.9877	98.77%
Eye irritation	-	0.8888	88.88%
Skin irritation	-	0.7413	74.13%
Skin corrosion	-	0.9726	97.26%
Ames mutagenesis	+	0.7400	74.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5673	56.73%
Micronuclear	+	0.8800	88.00%
Hepatotoxicity	-	0.5072	50.72%
skin sensitisation	-	0.9378	93.78%
Respiratory toxicity	+	0.5444	54.44%
Reproductive toxicity	+	0.7778	77.78%
Mitochondrial toxicity	+	0.5375	53.75%
Nephrotoxicity	+	0.6372	63.72%
Acute Oral Toxicity (c)	III	0.4710	47.10%
Estrogen receptor binding	+	0.7310	73.10%
Androgen receptor binding	-	0.4888	48.88%
Thyroid receptor binding	-	0.5242	52.42%
Glucocorticoid receptor binding	+	0.7416	74.16%
Aromatase binding	-	0.5334	53.34%
PPAR gamma	+	0.6328	63.28%
Honey bee toxicity	-	0.7734	77.34%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	-	0.5350	53.50%
Fish aquatic toxicity	+	0.9734	97.34%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL1951	P21397	Monoamine oxidase A	99.61%	91.49%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.70%	91.11%
CHEMBL1806	P11388	DNA topoisomerase II alpha	97.31%	89.00%
CHEMBL2581	P07339	Cathepsin D	96.88%	98.95%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	93.94%	99.23%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.85%	95.56%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	92.33%	94.00%
CHEMBL3401	O75469	Pregnane X receptor	92.16%	94.73%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	91.90%	99.15%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	91.20%	96.09%
CHEMBL4208	P20618	Proteasome component C5	90.57%	90.00%
CHEMBL340	P08684	Cytochrome P450 3A4	90.35%	91.19%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	89.51%	94.80%
CHEMBL3714130	P46095	G-protein coupled receptor 6	87.89%	97.36%
CHEMBL1293249	Q13887	Kruppel-like factor 5	87.08%	86.33%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	83.92%	95.89%
CHEMBL1293277	O15118	Niemann-Pick C1 protein	83.39%	81.11%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	82.79%	91.07%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	81.86%	96.21%
CHEMBL5852	Q96P65	Pyroglutamylated RFamide peptide receptor	81.43%	85.00%
CHEMBL226	P30542	Adenosine A1 receptor	81.38%	95.93%
CHEMBL3060	Q9Y345	Glycine transporter 2	80.32%	99.17%

Plants that contains it

• Rhamnus prinoides

Cross-Links

• PubChem: 25107460
• LOTUS: LTS0046830
• wikiData: Q105138853