3,3'-Methanediylbis(4-hydroxynaphthalene-1,2-dione)

Details

• Internal ID: bc1cdd47-76ef-4611-9e64-11828e2569a8
• Taxonomy: Benzenoids > Naphthalenes > Naphthoquinones
• IUPAC Name: 4-hydroxy-3-[(1-hydroxy-3,4-dioxonaphthalen-2-yl)methyl]naphthalene-1,2-dione
• InChI: InChI=1S/C21H12O6/c22-16-10-5-1-3-7-12(10)18(24)20(26)14(16)9-15-17(23)11-6-2-4-8-13(11)19(25)21(15)27/h1-8,22-23H,9H2
• InChI Key: QOZDSCOMMADWQX-UHFFFAOYSA-N
• Popularity: 6 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₁H₁₂O₆
• Molecular Weight: 360.30 g/mol
• Exact Mass: 360.06338810 g/mol
• Topological Polar Surface Area (TPSA): 109.00 Ų
• XlogP: 1.70
• Atomic LogP (AlogP): 2.85
• H-Bond Acceptor: 6
• H-Bond Donor: 2
• Rotatable Bonds: 2

Synonyms

• 3,3'-methanediylbis(4-hydroxynaphthalene-1,2-dione)
• NSC91834
• Methylene-bis-lawsone
• SCHEMBL1520566
• DTXSID30291207
• NSC74050
• 1, 2,2'-methylenebis[3-hydroxy-
• NSC-74050
• NSC-91834
• 2,2'-methylenebis(3-hydroxy-1,4-naphthoquinone)
• 1,4-Naphthalenedione, 2,2'-methylenebis[3-hydroxy-
• 2-hydroxy-3-[(3-hydroxy-1,4-dioxo-2-naphthyl)methyl]naphthalene-1,4-dione

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9874	98.74%
Caco-2	-	0.7353	73.53%
Blood Brain Barrier	-	0.6750	67.50%
Human oral bioavailability	+	0.7143	71.43%
Subcellular localzation	Mitochondria	0.7520	75.20%
OATP2B1 inhibitior	-	0.5689	56.89%
OATP1B1 inhibitior	+	0.9077	90.77%
OATP1B3 inhibitior	+	0.9138	91.38%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	-	0.7117	71.17%
P-glycoprotein inhibitior	-	0.9357	93.57%
P-glycoprotein substrate	-	0.9768	97.68%
CYP3A4 substrate	-	0.6881	68.81%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8250	82.50%
CYP3A4 inhibition	-	0.8931	89.31%
CYP2C9 inhibition	+	0.9027	90.27%
CYP2C19 inhibition	-	0.8238	82.38%
CYP2D6 inhibition	-	0.8773	87.73%
CYP1A2 inhibition	+	0.8121	81.21%
CYP2C8 inhibition	-	0.9505	95.05%
CYP inhibitory promiscuity	+	0.6306	63.06%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.8754	87.54%
Carcinogenicity (trinary)	Non-required	0.5896	58.96%
Eye corrosion	-	0.9902	99.02%
Eye irritation	+	0.8724	87.24%
Skin irritation	-	0.5121	51.21%
Skin corrosion	-	0.9614	96.14%
Ames mutagenesis	-	0.7354	73.54%
Human Ether-a-go-go-Related Gene inhibition	-	0.7888	78.88%
Micronuclear	+	0.7059	70.59%
Hepatotoxicity	+	0.6250	62.50%
skin sensitisation	+	0.6091	60.91%
Respiratory toxicity	-	0.5000	50.00%
Reproductive toxicity	+	0.6778	67.78%
Mitochondrial toxicity	+	0.7000	70.00%
Nephrotoxicity	+	0.6753	67.53%
Acute Oral Toxicity (c)	II	0.3641	36.41%
Estrogen receptor binding	+	0.7874	78.74%
Androgen receptor binding	-	0.5287	52.87%
Thyroid receptor binding	-	0.7390	73.90%
Glucocorticoid receptor binding	-	0.4684	46.84%
Aromatase binding	-	0.6588	65.88%
PPAR gamma	+	0.6760	67.60%
Honey bee toxicity	-	0.8460	84.60%
Biodegradation	-	0.9000	90.00%
Crustacea aquatic toxicity	-	0.5500	55.00%
Fish aquatic toxicity	+	0.9934	99.34%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	96.76%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.26%	95.56%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	91.08%	91.11%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	88.93%	82.69%
CHEMBL2378	P30307	Dual specificity phosphatase Cdc25C	81.59%	96.67%
CHEMBL1951	P21397	Monoamine oxidase A	81.21%	91.49%

Plants that contains it

• Impatiens balsamina

Cross-Links

• PubChem: 252335
• LOTUS: LTS0211173
• wikiData: Q82029087