1,4,8-Trihydroxy-2-methoxy-6-methylanthracene-9,10-dione

Details

• Internal ID: 3d843f9a-e4ed-45c4-ad5a-8842d57e6e5f
• Taxonomy: Benzenoids > Anthracenes > Anthraquinones
• IUPAC Name: 1,4,8-trihydroxy-2-methoxy-6-methylanthracene-9,10-dione
• SMILES (Canonical): CC1=CC2=C(C(=C1)O)C(=O)C3=C(C2=O)C(=CC(=C3O)OC)O
• SMILES (Isomeric): CC1=CC2=C(C(=C1)O)C(=O)C3=C(C2=O)C(=CC(=C3O)OC)O
• InChI: InChI=1S/C16H12O6/c1-6-3-7-11(8(17)4-6)16(21)13-12(14(7)19)9(18)5-10(22-2)15(13)20/h3-5,17-18,20H,1-2H3
• InChI Key: AMASMQWBGMKOFH-UHFFFAOYSA-N
• Popularity: 1 reference 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): 104.00 Ų
• XlogP: 3.20
• Atomic LogP (AlogP): 1.90
• H-Bond Acceptor: 6
• H-Bond Donor: 3
• Rotatable Bonds: 1

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	+	0.6605	66.05%
Blood Brain Barrier	-	0.7750	77.50%
Human oral bioavailability	+	0.7286	72.86%
Subcellular localzation	Mitochondria	0.8309	83.09%
OATP2B1 inhibitior	-	0.7031	70.31%
OATP1B1 inhibitior	+	0.9182	91.82%
OATP1B3 inhibitior	+	0.9329	93.29%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	1.0000	100.00%
BSEP inhibitior	-	0.7043	70.43%
P-glycoprotein inhibitior	-	0.8407	84.07%
P-glycoprotein substrate	-	0.9404	94.04%
CYP3A4 substrate	-	0.5252	52.52%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.7976	79.76%
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	-	0.7896	78.96%
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	+	0.9077	90.77%
Skin irritation	-	0.5600	56.00%
Skin corrosion	-	0.9405	94.05%
Ames mutagenesis	+	0.6300	63.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6939	69.39%
Micronuclear	+	0.8300	83.00%
Hepatotoxicity	+	0.8180	81.80%
skin sensitisation	-	0.8987	89.87%
Respiratory toxicity	-	0.5222	52.22%
Reproductive toxicity	+	0.6222	62.22%
Mitochondrial toxicity	+	0.5125	51.25%
Nephrotoxicity	+	0.6051	60.51%
Acute Oral Toxicity (c)	II	0.5323	53.23%
Estrogen receptor binding	+	0.7707	77.07%
Androgen receptor binding	+	0.5334	53.34%
Thyroid receptor binding	-	0.6421	64.21%
Glucocorticoid receptor binding	+	0.8566	85.66%
Aromatase binding	+	0.6622	66.22%
PPAR gamma	+	0.7412	74.12%
Honey bee toxicity	-	0.8876	88.76%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.5900	59.00%
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
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	95.49%	95.56%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	95.12%	91.11%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	91.59%	85.14%
CHEMBL2581	P07339	Cathepsin D	91.52%	98.95%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	91.35%	94.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	89.69%	99.23%
CHEMBL1806	P11388	DNA topoisomerase II alpha	89.69%	89.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	88.76%	96.09%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	87.90%	99.15%
CHEMBL4208	P20618	Proteasome component C5	87.26%	90.00%
CHEMBL1951	P21397	Monoamine oxidase A	84.94%	91.49%
CHEMBL1293249	Q13887	Kruppel-like factor 5	84.55%	86.33%
CHEMBL2056	P21728	Dopamine D1 receptor	82.01%	91.00%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	81.63%	96.21%
CHEMBL3401	O75469	Pregnane X receptor	81.07%	94.73%
CHEMBL2378	P30307	Dual specificity phosphatase Cdc25C	80.82%	96.67%

Plants that contains it

• Psorospermum laurentii

Cross-Links

• PubChem: 85926407
• LOTUS: LTS0141310
• wikiData: Q104914491