6,7-Dihydroxy-2-methoxy-1,4-phenanthrenedione

Details

• Internal ID: 4bce15cb-6fe0-4977-86d0-5b04e58aee1b
• Taxonomy: Benzenoids > Phenanthrenes and derivatives > Phenanthrols
• IUPAC Name: 6,7-dihydroxy-2-methoxyphenanthrene-1,4-dione
• SMILES (Canonical): COC1=CC(=O)C2=C(C1=O)C=CC3=CC(=C(C=C32)O)O
• SMILES (Isomeric): COC1=CC(=O)C2=C(C1=O)C=CC3=CC(=C(C=C32)O)O
• InChI: InChI=1S/C15H10O5/c1-20-13-6-12(18)14-8(15(13)19)3-2-7-4-10(16)11(17)5-9(7)14/h2-6,16-17H,1H3
• InChI Key: PFKNMJHZSFZCQK-UHFFFAOYSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₁₀O₅
• Molecular Weight: 270.24 g/mol
• Exact Mass: 270.05282342 g/mol
• Topological Polar Surface Area (TPSA): 83.80 Ų
• XlogP: 2.20
• Atomic LogP (AlogP): 2.16
• H-Bond Acceptor: 5
• H-Bond Donor: 2
• Rotatable Bonds: 1

Synonyms

• CHEMBL486392

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9897	98.97%
Caco-2	+	0.5423	54.23%
Blood Brain Barrier	-	0.7500	75.00%
Human oral bioavailability	+	0.7714	77.14%
Subcellular localzation	Mitochondria	0.7529	75.29%
OATP2B1 inhibitior	-	0.7118	71.18%
OATP1B1 inhibitior	+	0.9153	91.53%
OATP1B3 inhibitior	+	0.9851	98.51%
MATE1 inhibitior	-	0.8000	80.00%
OCT2 inhibitior	-	1.0000	100.00%
BSEP inhibitior	-	0.7455	74.55%
P-glycoprotein inhibitior	-	0.9199	91.99%
P-glycoprotein substrate	-	0.8164	81.64%
CYP3A4 substrate	-	0.5401	54.01%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8159	81.59%
CYP3A4 inhibition	-	0.7725	77.25%
CYP2C9 inhibition	+	0.6991	69.91%
CYP2C19 inhibition	-	0.6107	61.07%
CYP2D6 inhibition	-	0.8598	85.98%
CYP1A2 inhibition	+	0.9363	93.63%
CYP2C8 inhibition	-	0.6986	69.86%
CYP inhibitory promiscuity	+	0.5235	52.35%
UGT catelyzed	-	0.7000	70.00%
Carcinogenicity (binary)	-	0.8638	86.38%
Carcinogenicity (trinary)	Non-required	0.4601	46.01%
Eye corrosion	-	0.9880	98.80%
Eye irritation	+	0.9384	93.84%
Skin irritation	-	0.5413	54.13%
Skin corrosion	-	0.9085	90.85%
Ames mutagenesis	+	0.7500	75.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.8218	82.18%
Micronuclear	+	0.8600	86.00%
Hepatotoxicity	+	0.5416	54.16%
skin sensitisation	-	0.7408	74.08%
Respiratory toxicity	-	0.5333	53.33%
Reproductive toxicity	+	0.6444	64.44%
Mitochondrial toxicity	+	0.5500	55.00%
Nephrotoxicity	+	0.5978	59.78%
Acute Oral Toxicity (c)	III	0.3874	38.74%
Estrogen receptor binding	+	0.8331	83.31%
Androgen receptor binding	+	0.7395	73.95%
Thyroid receptor binding	-	0.5531	55.31%
Glucocorticoid receptor binding	+	0.7817	78.17%
Aromatase binding	+	0.5372	53.72%
PPAR gamma	+	0.6989	69.89%
Honey bee toxicity	-	0.8768	87.68%
Biodegradation	-	0.9250	92.50%
Crustacea aquatic toxicity	-	0.6000	60.00%
Fish aquatic toxicity	+	0.9925	99.25%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL1951	P21397	Monoamine oxidase A	99.63%	91.49%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.20%	91.11%
CHEMBL2581	P07339	Cathepsin D	96.19%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.57%	95.56%
CHEMBL2378	P30307	Dual specificity phosphatase Cdc25C	89.94%	96.67%
CHEMBL2535	P11166	Glucose transporter	88.23%	98.75%
CHEMBL215	P09917	Arachidonate 5-lipoxygenase	88.18%	92.68%
CHEMBL1293249	Q13887	Kruppel-like factor 5	87.32%	86.33%
CHEMBL2085	P14174	Macrophage migration inhibitory factor	85.82%	80.78%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	85.46%	94.00%
CHEMBL4208	P20618	Proteasome component C5	84.94%	90.00%
CHEMBL241	Q14432	Phosphodiesterase 3A	82.40%	92.94%
CHEMBL1806	P11388	DNA topoisomerase II alpha	82.29%	89.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	81.75%	99.23%
CHEMBL1907	P15144	Aminopeptidase N	81.63%	93.31%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	81.26%	90.71%

Plants that contains it

• Dioscorea oppositifolia

Cross-Links

• PubChem: 135520438
• LOTUS: LTS0003015
• wikiData: Q105207809