9,10-Anthracenedione, 1,3-dihydroxy-4-methoxy-2-methyl-

Details

• Internal ID: ef5933c0-3a2f-41a5-80e6-cc5b209886f9
• Taxonomy: Benzenoids > Anthracenes > Anthraquinones > Hydroxyanthraquinones
• IUPAC Name: 1,3-dihydroxy-4-methoxy-2-methylanthracene-9,10-dione
• SMILES (Canonical): CC1=C(C2=C(C(=C1O)OC)C(=O)C3=CC=CC=C3C2=O)O
• SMILES (Isomeric): CC1=C(C2=C(C(=C1O)OC)C(=O)C3=CC=CC=C3C2=O)O
• InChI: InChI=1S/C16H12O5/c1-7-12(17)10-11(16(21-2)13(7)18)15(20)9-6-4-3-5-8(9)14(10)19/h3-6,17-18H,1-2H3
• InChI Key: SYBVTSFWLPOQKR-UHFFFAOYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₆H₁₂O₅
• Molecular Weight: 284.26 g/mol
• Exact Mass: 284.06847348 g/mol
• Topological Polar Surface Area (TPSA): 83.80 Ų
• XlogP: 3.00
• Atomic LogP (AlogP): 2.19
• H-Bond Acceptor: 5
• H-Bond Donor: 2
• Rotatable Bonds: 1

Synonyms

• SYBVTSFWLPOQKR-UHFFFAOYSA-N
• 1,3-Dihydroxy-4-methoxy-2-methylanthra-9,10-quinone #

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9719	97.19%
Caco-2	+	0.6325	63.25%
Blood Brain Barrier	-	0.7250	72.50%
Human oral bioavailability	+	0.7571	75.71%
Subcellular localzation	Mitochondria	0.6989	69.89%
OATP2B1 inhibitior	-	0.7198	71.98%
OATP1B1 inhibitior	+	0.8852	88.52%
OATP1B3 inhibitior	+	0.9036	90.36%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	1.0000	100.00%
BSEP inhibitior	-	0.7243	72.43%
P-glycoprotein inhibitior	-	0.8249	82.49%
P-glycoprotein substrate	-	0.9599	95.99%
CYP3A4 substrate	-	0.5457	54.57%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.7976	79.76%
CYP3A4 inhibition	-	0.6524	65.24%
CYP2C9 inhibition	+	0.5754	57.54%
CYP2C19 inhibition	-	0.6607	66.07%
CYP2D6 inhibition	-	0.6948	69.48%
CYP1A2 inhibition	+	0.8581	85.81%
CYP2C8 inhibition	-	0.8823	88.23%
CYP inhibitory promiscuity	-	0.5358	53.58%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	0.9075	90.75%
Carcinogenicity (trinary)	Non-required	0.6173	61.73%
Eye corrosion	-	0.9813	98.13%
Eye irritation	+	0.9152	91.52%
Skin irritation	-	0.5739	57.39%
Skin corrosion	-	0.8895	88.95%
Ames mutagenesis	+	0.7300	73.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7917	79.17%
Micronuclear	+	0.8300	83.00%
Hepatotoxicity	+	0.5625	56.25%
skin sensitisation	-	0.8550	85.50%
Respiratory toxicity	-	0.5889	58.89%
Reproductive toxicity	+	0.6222	62.22%
Mitochondrial toxicity	+	0.5250	52.50%
Nephrotoxicity	+	0.5303	53.03%
Acute Oral Toxicity (c)	III	0.5551	55.51%
Estrogen receptor binding	+	0.6771	67.71%
Androgen receptor binding	-	0.5822	58.22%
Thyroid receptor binding	-	0.5186	51.86%
Glucocorticoid receptor binding	+	0.8383	83.83%
Aromatase binding	+	0.5508	55.08%
PPAR gamma	+	0.7035	70.35%
Honey bee toxicity	-	0.9045	90.45%
Biodegradation	-	0.6750	67.50%
Crustacea aquatic toxicity	-	0.5400	54.00%
Fish aquatic toxicity	+	0.9701	97.01%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	97.10%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	96.44%	95.56%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	92.71%	91.11%
CHEMBL1951	P21397	Monoamine oxidase A	91.29%	91.49%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	90.46%	99.23%
CHEMBL2378	P30307	Dual specificity phosphatase Cdc25C	86.39%	96.67%
CHEMBL2535	P11166	Glucose transporter	86.37%	98.75%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	83.32%	99.15%
CHEMBL1293249	Q13887	Kruppel-like factor 5	83.20%	86.33%
CHEMBL1806	P11388	DNA topoisomerase II alpha	82.61%	89.00%
CHEMBL3401	O75469	Pregnane X receptor	82.30%	94.73%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	81.14%	94.00%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	81.02%	96.00%
CHEMBL2002	P12268	Inosine-5'-monophosphate dehydrogenase 2	80.35%	98.21%

Plants that contains it

• Digitalis lanata
• Digitalis purpurea

Cross-Links

• PubChem: 625092
• LOTUS: LTS0047160
• wikiData: Q105263470