1,4-Dimethoxy-2,3-methylene-dioxyanthraquinone

Details

• Internal ID: 5a88f3bf-31ce-443b-ae61-313bafb61319
• Taxonomy: Benzenoids > Anthracenes > Anthraquinones
• IUPAC Name: 4,11-dimethoxynaphtho[3,2-f][1,3]benzodioxole-5,10-dione
• SMILES (Canonical): COC1=C2C(=C(C3=C1C(=O)C4=CC=CC=C4C3=O)OC)OCO2
• SMILES (Isomeric): COC1=C2C(=C(C3=C1C(=O)C4=CC=CC=C4C3=O)OC)OCO2
• InChI: InChI=1S/C17H12O6/c1-20-14-10-11(15(21-2)17-16(14)22-7-23-17)13(19)9-6-4-3-5-8(9)12(10)18/h3-6H,7H2,1-2H3
• InChI Key: UECQNAWZQLRCME-UHFFFAOYSA-N
• Popularity: 4 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₇H₁₂O₆
• Molecular Weight: 312.27 g/mol
• Exact Mass: 312.06338810 g/mol
• Topological Polar Surface Area (TPSA): 71.10 Ų
• XlogP: 2.60
• Atomic LogP (AlogP): 2.21
• H-Bond Acceptor: 6
• H-Bond Donor: 0
• Rotatable Bonds: 2

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9915	99.15%
Caco-2	+	0.8722	87.22%
Blood Brain Barrier	+	0.6500	65.00%
Human oral bioavailability	+	0.7429	74.29%
Subcellular localzation	Mitochondria	0.7066	70.66%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9642	96.42%
OATP1B3 inhibitior	+	0.9068	90.68%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	+	0.5829	58.29%
P-glycoprotein inhibitior	-	0.5342	53.42%
P-glycoprotein substrate	-	0.9758	97.58%
CYP3A4 substrate	-	0.5881	58.81%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.7501	75.01%
CYP3A4 inhibition	+	0.8409	84.09%
CYP2C9 inhibition	+	0.9402	94.02%
CYP2C19 inhibition	+	0.9033	90.33%
CYP2D6 inhibition	+	0.7053	70.53%
CYP1A2 inhibition	+	0.6448	64.48%
CYP2C8 inhibition	-	0.9540	95.40%
CYP inhibitory promiscuity	+	0.8417	84.17%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9343	93.43%
Carcinogenicity (trinary)	Non-required	0.4635	46.35%
Eye corrosion	-	0.9645	96.45%
Eye irritation	+	0.8537	85.37%
Skin irritation	-	0.7830	78.30%
Skin corrosion	-	0.9684	96.84%
Ames mutagenesis	+	0.5900	59.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5859	58.59%
Micronuclear	+	0.7474	74.74%
Hepatotoxicity	-	0.5000	50.00%
skin sensitisation	-	0.5339	53.39%
Respiratory toxicity	+	0.5444	54.44%
Reproductive toxicity	+	0.7333	73.33%
Mitochondrial toxicity	+	0.6375	63.75%
Nephrotoxicity	+	0.7577	75.77%
Acute Oral Toxicity (c)	III	0.6051	60.51%
Estrogen receptor binding	+	0.7560	75.60%
Androgen receptor binding	+	0.5686	56.86%
Thyroid receptor binding	-	0.5175	51.75%
Glucocorticoid receptor binding	+	0.7461	74.61%
Aromatase binding	-	0.5343	53.43%
PPAR gamma	+	0.6287	62.87%
Honey bee toxicity	-	0.7730	77.30%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	+	0.6000	60.00%
Fish aquatic toxicity	+	0.9583	95.83%

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	96.36%	95.56%
CHEMBL2581	P07339	Cathepsin D	96.07%	98.95%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	95.16%	91.11%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	89.19%	96.77%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	87.68%	99.23%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	85.39%	96.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	85.14%	86.33%
CHEMBL2378	P30307	Dual specificity phosphatase Cdc25C	84.99%	96.67%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	84.59%	82.69%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	84.43%	96.09%
CHEMBL3401	O75469	Pregnane X receptor	84.16%	94.73%
CHEMBL2535	P11166	Glucose transporter	83.53%	98.75%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	81.11%	97.14%

Plants that contains it

• Cinchona calisaya

Cross-Links

• PubChem: 11461106
• LOTUS: LTS0197509
• wikiData: Q105270787