3,4-Dihydroxy-1-methoxy-9,10-dioxoanthracene-2-carbaldehyde

Details

• Internal ID: b732d2df-b8dc-416a-a667-c3f695bce7ac
• Taxonomy: Benzenoids > Anthracenes > Anthraquinones > Hydroxyanthraquinones
• IUPAC Name: 3,4-dihydroxy-1-methoxy-9,10-dioxoanthracene-2-carbaldehyde
• SMILES (Canonical): COC1=C2C(=C(C(=C1C=O)O)O)C(=O)C3=CC=CC=C3C2=O
• SMILES (Isomeric): COC1=C2C(=C(C(=C1C=O)O)O)C(=O)C3=CC=CC=C3C2=O
• InChI: InChI=1S/C16H10O6/c1-22-16-9(6-17)14(20)15(21)10-11(16)13(19)8-5-3-2-4-7(8)12(10)18/h2-6,20-21H,1H3
• InChI Key: RAHSTXHHUJYBPE-UHFFFAOYSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₁₆H₁₀O₆
• Molecular Weight: 298.25 g/mol
• Exact Mass: 298.04773803 g/mol
• Topological Polar Surface Area (TPSA): 101.00 Ų
• XlogP: 2.70
• Atomic LogP (AlogP): 1.69
• H-Bond Acceptor: 6
• H-Bond Donor: 2
• Rotatable Bonds: 2

Synonyms

• SCHEMBL1149730

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9794	97.94%
Caco-2	-	0.6074	60.74%
Blood Brain Barrier	-	0.7750	77.50%
Human oral bioavailability	+	0.6000	60.00%
Subcellular localzation	Mitochondria	0.8085	80.85%
OATP2B1 inhibitior	-	0.7138	71.38%
OATP1B1 inhibitior	+	0.7970	79.70%
OATP1B3 inhibitior	+	0.9826	98.26%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	-	0.7703	77.03%
P-glycoprotein inhibitior	-	0.8626	86.26%
P-glycoprotein substrate	-	0.9402	94.02%
CYP3A4 substrate	-	0.5386	53.86%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8014	80.14%
CYP3A4 inhibition	-	0.8955	89.55%
CYP2C9 inhibition	-	0.6228	62.28%
CYP2C19 inhibition	-	0.8272	82.72%
CYP2D6 inhibition	-	0.8951	89.51%
CYP1A2 inhibition	+	0.9280	92.80%
CYP2C8 inhibition	-	0.8045	80.45%
CYP inhibitory promiscuity	-	0.8085	80.85%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.8595	85.95%
Carcinogenicity (trinary)	Warning	0.4773	47.73%
Eye corrosion	-	0.9813	98.13%
Eye irritation	+	0.7990	79.90%
Skin irritation	+	0.5321	53.21%
Skin corrosion	-	0.8809	88.09%
Ames mutagenesis	+	0.5200	52.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.8887	88.87%
Micronuclear	+	0.8500	85.00%
Hepatotoxicity	+	0.6125	61.25%
skin sensitisation	-	0.8800	88.00%
Respiratory toxicity	-	0.5333	53.33%
Reproductive toxicity	+	0.5556	55.56%
Mitochondrial toxicity	+	0.5750	57.50%
Nephrotoxicity	+	0.6481	64.81%
Acute Oral Toxicity (c)	III	0.5443	54.43%
Estrogen receptor binding	+	0.7366	73.66%
Androgen receptor binding	-	0.4825	48.25%
Thyroid receptor binding	-	0.6684	66.84%
Glucocorticoid receptor binding	+	0.8225	82.25%
Aromatase binding	-	0.4886	48.86%
PPAR gamma	+	0.6123	61.23%
Honey bee toxicity	-	0.8595	85.95%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	-	0.5600	56.00%
Fish aquatic toxicity	+	0.9750	97.50%

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	98.46%	95.56%
CHEMBL1951	P21397	Monoamine oxidase A	97.41%	91.49%
CHEMBL2581	P07339	Cathepsin D	97.12%	98.95%
CHEMBL1163101	O75460	Serine/threonine-protein kinase/endoribonuclease IRE1	95.68%	98.11%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	94.03%	91.11%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	87.80%	99.23%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	87.78%	96.00%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	85.18%	82.69%
CHEMBL1293249	Q13887	Kruppel-like factor 5	84.52%	86.33%
CHEMBL3401	O75469	Pregnane X receptor	83.30%	94.73%
CHEMBL2535	P11166	Glucose transporter	82.78%	98.75%
CHEMBL1806	P11388	DNA topoisomerase II alpha	82.61%	89.00%
CHEMBL2378	P30307	Dual specificity phosphatase Cdc25C	81.98%	96.67%
CHEMBL2085	P14174	Macrophage migration inhibitory factor	81.78%	80.78%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	80.66%	96.09%

Plants that contains it

• Saprosma fragrans

Cross-Links

• PubChem: 16007210
• LOTUS: LTS0247517
• wikiData: Q105232626