2,6-Dihydroxy-1,3-dimethoxyanthracene-9,10-dione

Details

• Internal ID: 65829b4c-243b-4d26-aa84-afc73aea4183
• Taxonomy: Benzenoids > Anthracenes > Anthraquinones > Hydroxyanthraquinones
• IUPAC Name: 2,6-dihydroxy-1,3-dimethoxyanthracene-9,10-dione
• SMILES (Canonical): COC1=C(C(=C2C(=C1)C(=O)C3=C(C2=O)C=CC(=C3)O)OC)O
• SMILES (Isomeric): COC1=C(C(=C2C(=C1)C(=O)C3=C(C2=O)C=CC(=C3)O)OC)O
• InChI: InChI=1S/C16H12O6/c1-21-11-6-10-12(16(22-2)15(11)20)14(19)8-4-3-7(17)5-9(8)13(10)18/h3-6,17,20H,1-2H3
• InChI Key: ZOTYVTMFTQVAFY-UHFFFAOYSA-N
• Popularity: 3 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₆H₁₂O₆
• Molecular Weight: 300.26 g/mol
• Exact Mass: 300.06338810 g/mol
• Topological Polar Surface Area (TPSA): 93.10 Ų
• XlogP: 2.10
• Atomic LogP (AlogP): 1.89
• H-Bond Acceptor: 6
• H-Bond Donor: 2
• Rotatable Bonds: 2

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9867	98.67%
Caco-2	+	0.7305	73.05%
Blood Brain Barrier	-	0.7750	77.50%
Human oral bioavailability	+	0.5143	51.43%
Subcellular localzation	Mitochondria	0.8309	83.09%
OATP2B1 inhibitior	-	0.7150	71.50%
OATP1B1 inhibitior	+	0.8810	88.10%
OATP1B3 inhibitior	+	0.9329	93.29%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	1.0000	100.00%
BSEP inhibitior	-	0.8517	85.17%
P-glycoprotein inhibitior	-	0.8125	81.25%
P-glycoprotein substrate	-	0.8085	80.85%
CYP3A4 substrate	+	0.5217	52.17%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.6961	69.61%
CYP3A4 inhibition	-	0.8346	83.46%
CYP2C9 inhibition	+	0.5067	50.67%
CYP2C19 inhibition	-	0.6468	64.68%
CYP2D6 inhibition	-	0.7472	74.72%
CYP1A2 inhibition	+	0.9109	91.09%
CYP2C8 inhibition	-	0.6036	60.36%
CYP inhibitory promiscuity	-	0.6522	65.22%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.8795	87.95%
Carcinogenicity (trinary)	Non-required	0.5355	53.55%
Eye corrosion	-	0.9806	98.06%
Eye irritation	+	0.9438	94.38%
Skin irritation	-	0.5600	56.00%
Skin corrosion	-	0.9405	94.05%
Ames mutagenesis	+	0.5600	56.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7786	77.86%
Micronuclear	+	0.8300	83.00%
Hepatotoxicity	-	0.5074	50.74%
skin sensitisation	-	0.8987	89.87%
Respiratory toxicity	-	0.5444	54.44%
Reproductive toxicity	+	0.6222	62.22%
Mitochondrial toxicity	+	0.5125	51.25%
Nephrotoxicity	-	0.6620	66.20%
Acute Oral Toxicity (c)	II	0.5323	53.23%
Estrogen receptor binding	+	0.8139	81.39%
Androgen receptor binding	+	0.6530	65.30%
Thyroid receptor binding	-	0.5056	50.56%
Glucocorticoid receptor binding	+	0.8253	82.53%
Aromatase binding	+	0.6323	63.23%
PPAR gamma	+	0.5851	58.51%
Honey bee toxicity	-	0.8715	87.15%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.5949	59.49%
Fish aquatic toxicity	+	0.9767	97.67%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	96.25%	98.95%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.02%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	94.42%	95.56%
CHEMBL1951	P21397	Monoamine oxidase A	92.20%	91.49%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	90.37%	96.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	89.90%	89.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	88.74%	86.33%
CHEMBL2535	P11166	Glucose transporter	88.73%	98.75%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	86.49%	99.15%
CHEMBL4208	P20618	Proteasome component C5	85.97%	90.00%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	84.17%	94.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	83.56%	99.17%
CHEMBL1907	P15144	Aminopeptidase N	81.33%	93.31%

Plants that contains it

• Galium sinaicum
• Morinda citrifolia

Cross-Links

• PubChem: 15118826
• NPASS: NPC36817
• LOTUS: LTS0114699
• wikiData: Q105380713