3,3'-Methylenebis(2-methyl-5-hydroxy-1,4-naphthoquinone)

Details

• Internal ID: 44a10be1-6b68-4f03-b4d2-efc231fd789e
• Taxonomy: Benzenoids > Naphthalenes > Naphthoquinones
• IUPAC Name: 5-hydroxy-3-[(8-hydroxy-3-methyl-1,4-dioxonaphthalen-2-yl)methyl]-2-methylnaphthalene-1,4-dione
• SMILES (Canonical): CC1=C(C(=O)C2=C(C1=O)C=CC=C2O)CC3=C(C(=O)C4=C(C3=O)C(=CC=C4)O)C
• SMILES (Isomeric): CC1=C(C(=O)C2=C(C1=O)C=CC=C2O)CC3=C(C(=O)C4=C(C3=O)C(=CC=C4)O)C
• InChI: InChI=1S/C23H16O6/c1-10-14(22(28)18-12(20(10)26)5-3-7-16(18)24)9-15-11(2)21(27)13-6-4-8-17(25)19(13)23(15)29/h3-8,24-25H,9H2,1-2H3
• InChI Key: XICSGZYDUFXNEH-UHFFFAOYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₃H₁₆O₆
• Molecular Weight: 388.40 g/mol
• Exact Mass: 388.09468823 g/mol
• Topological Polar Surface Area (TPSA): 109.00 Ų
• XlogP: 4.10
• Atomic LogP (AlogP): 3.58
• H-Bond Acceptor: 6
• H-Bond Donor: 2
• Rotatable Bonds: 2

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9965	99.65%
Caco-2	+	0.5464	54.64%
Blood Brain Barrier	-	0.6000	60.00%
Human oral bioavailability	+	0.8000	80.00%
Subcellular localzation	Mitochondria	0.8350	83.50%
OATP2B1 inhibitior	+	0.5731	57.31%
OATP1B1 inhibitior	+	0.9183	91.83%
OATP1B3 inhibitior	+	0.9434	94.34%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	-	0.6151	61.51%
P-glycoprotein inhibitior	-	0.7568	75.68%
P-glycoprotein substrate	-	0.9327	93.27%
CYP3A4 substrate	-	0.5563	55.63%
CYP2C9 substrate	-	0.8009	80.09%
CYP2D6 substrate	-	0.8218	82.18%
CYP3A4 inhibition	-	0.7109	71.09%
CYP2C9 inhibition	+	0.9243	92.43%
CYP2C19 inhibition	+	0.7485	74.85%
CYP2D6 inhibition	+	0.5338	53.38%
CYP1A2 inhibition	+	0.9279	92.79%
CYP2C8 inhibition	-	0.9224	92.24%
CYP inhibitory promiscuity	+	0.8582	85.82%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.8145	81.45%
Carcinogenicity (trinary)	Non-required	0.6191	61.91%
Eye corrosion	-	0.9948	99.48%
Eye irritation	+	0.6288	62.88%
Skin irritation	-	0.5970	59.70%
Skin corrosion	-	0.9222	92.22%
Ames mutagenesis	+	0.7900	79.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5000	50.00%
Micronuclear	+	0.6000	60.00%
Hepatotoxicity	+	0.7677	76.77%
skin sensitisation	-	0.5545	55.45%
Respiratory toxicity	-	0.5111	51.11%
Reproductive toxicity	+	0.6556	65.56%
Mitochondrial toxicity	+	0.6625	66.25%
Nephrotoxicity	+	0.6797	67.97%
Acute Oral Toxicity (c)	III	0.5443	54.43%
Estrogen receptor binding	+	0.8090	80.90%
Androgen receptor binding	-	0.5986	59.86%
Thyroid receptor binding	-	0.6779	67.79%
Glucocorticoid receptor binding	+	0.7571	75.71%
Aromatase binding	-	0.5758	57.58%
PPAR gamma	+	0.6486	64.86%
Honey bee toxicity	-	0.9537	95.37%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	-	0.6500	65.00%
Fish aquatic toxicity	+	1.0000	100.00%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	98.40%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	95.22%	95.56%
CHEMBL3401	O75469	Pregnane X receptor	91.40%	94.73%
CHEMBL1951	P21397	Monoamine oxidase A	88.86%	91.49%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	87.81%	99.23%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	85.33%	99.15%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	84.05%	96.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	83.39%	89.00%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	83.20%	93.03%
CHEMBL2378	P30307	Dual specificity phosphatase Cdc25C	82.36%	96.67%
CHEMBL1293249	Q13887	Kruppel-like factor 5	80.34%	86.33%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	80.15%	91.11%

Plants that contains it

• Diospyros maritima
• Diospyros wallichii
• Plumbago zeylanica

Cross-Links

• PubChem: 12232587
• NPASS: NPC17100
• LOTUS: LTS0089376
• wikiData: Q105328420