3,5,8-Trihydroxy-1,2-dimethoxy-6-methylanthracene-9,10-dione

Details

• Internal ID: 27a9e88c-c148-4934-af4f-3cd310f72f55
• Taxonomy: Benzenoids > Anthracenes > Anthraquinones > Hydroxyanthraquinones
• IUPAC Name: 3,5,8-trihydroxy-1,2-dimethoxy-6-methylanthracene-9,10-dione
• SMILES (Canonical): CC1=CC(=C2C(=C1O)C(=O)C3=CC(=C(C(=C3C2=O)OC)OC)O)O
• SMILES (Isomeric): CC1=CC(=C2C(=C1O)C(=O)C3=CC(=C(C(=C3C2=O)OC)OC)O)O
• InChI: InChI=1S/C17H14O7/c1-6-4-8(18)11-12(13(6)20)14(21)7-5-9(19)16(23-2)17(24-3)10(7)15(11)22/h4-5,18-20H,1-3H3
• InChI Key: UVKIYOBBRXDLLC-UHFFFAOYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₇H₁₄O₇
• Molecular Weight: 330.29 g/mol
• Exact Mass: 330.07395278 g/mol
• Topological Polar Surface Area (TPSA): 113.00 Ų
• XlogP: 3.20
• Atomic LogP (AlogP): 1.90
• H-Bond Acceptor: 7
• H-Bond Donor: 3
• Rotatable Bonds: 2

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9863	98.63%
Caco-2	+	0.6151	61.51%
Blood Brain Barrier	-	0.7750	77.50%
Human oral bioavailability	+	0.6571	65.71%
Subcellular localzation	Mitochondria	0.8104	81.04%
OATP2B1 inhibitior	-	0.7096	70.96%
OATP1B1 inhibitior	+	0.9011	90.11%
OATP1B3 inhibitior	+	0.7963	79.63%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	1.0000	100.00%
BSEP inhibitior	-	0.7877	78.77%
P-glycoprotein inhibitior	-	0.8283	82.83%
P-glycoprotein substrate	-	0.9457	94.57%
CYP3A4 substrate	-	0.5230	52.30%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.7976	79.76%
CYP3A4 inhibition	-	0.8430	84.30%
CYP2C9 inhibition	-	0.8526	85.26%
CYP2C19 inhibition	-	0.8521	85.21%
CYP2D6 inhibition	-	0.8259	82.59%
CYP1A2 inhibition	+	0.8940	89.40%
CYP2C8 inhibition	-	0.7996	79.96%
CYP inhibitory promiscuity	-	0.7081	70.81%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.8895	88.95%
Carcinogenicity (trinary)	Non-required	0.5451	54.51%
Eye corrosion	-	0.9852	98.52%
Eye irritation	+	0.8437	84.37%
Skin irritation	-	0.6817	68.17%
Skin corrosion	-	0.9632	96.32%
Ames mutagenesis	+	0.7956	79.56%
Human Ether-a-go-go-Related Gene inhibition	-	0.7161	71.61%
Micronuclear	+	0.7800	78.00%
Hepatotoxicity	+	0.5125	51.25%
skin sensitisation	-	0.9215	92.15%
Respiratory toxicity	-	0.5111	51.11%
Reproductive toxicity	+	0.6000	60.00%
Mitochondrial toxicity	-	0.5125	51.25%
Nephrotoxicity	-	0.6372	63.72%
Acute Oral Toxicity (c)	II	0.5649	56.49%
Estrogen receptor binding	+	0.8171	81.71%
Androgen receptor binding	-	0.5323	53.23%
Thyroid receptor binding	-	0.5349	53.49%
Glucocorticoid receptor binding	+	0.7943	79.43%
Aromatase binding	+	0.5956	59.56%
PPAR gamma	+	0.6242	62.42%
Honey bee toxicity	-	0.9329	93.29%
Biodegradation	-	0.6750	67.50%
Crustacea aquatic toxicity	-	0.6100	61.00%
Fish aquatic toxicity	+	0.9782	97.82%

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	96.41%	91.11%
CHEMBL2581	P07339	Cathepsin D	92.86%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.91%	95.56%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	90.38%	99.15%
CHEMBL1806	P11388	DNA topoisomerase II alpha	88.62%	89.00%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	87.85%	94.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	86.64%	99.23%
CHEMBL1951	P21397	Monoamine oxidase A	84.30%	91.49%
CHEMBL4208	P20618	Proteasome component C5	84.10%	90.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	83.19%	86.33%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	82.23%	85.14%
CHEMBL2056	P21728	Dopamine D1 receptor	80.77%	91.00%
CHEMBL2378	P30307	Dual specificity phosphatase Cdc25C	80.49%	96.67%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	80.45%	96.21%

Plants that contains it

• Chamaecrista greggii

Cross-Links

• PubChem: 101676227
• LOTUS: LTS0073850
• wikiData: Q105217011