5-Hydroxy-3-(hydroxymethyl)-2-methylnaphthalene-1,4-dione

Details

• Internal ID: 14bd6585-427e-43f0-8be5-760a7dccd931
• Taxonomy: Benzenoids > Naphthalenes > Naphthoquinones
• IUPAC Name: 5-hydroxy-3-(hydroxymethyl)-2-methylnaphthalene-1,4-dione
• SMILES (Canonical): CC1=C(C(=O)C2=C(C1=O)C=CC=C2O)CO
• SMILES (Isomeric): CC1=C(C(=O)C2=C(C1=O)C=CC=C2O)CO
• InChI: InChI=1S/C12H10O4/c1-6-8(5-13)12(16)10-7(11(6)15)3-2-4-9(10)14/h2-4,13-14H,5H2,1H3
• InChI Key: ZJGBSBNSGINTNE-UHFFFAOYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₂H₁₀O₄
• Molecular Weight: 218.20 g/mol
• Exact Mass: 218.05790880 g/mol
• Topological Polar Surface Area (TPSA): 74.60 Ų
• XlogP: 1.10
• Atomic LogP (AlogP): 1.08
• H-Bond Acceptor: 4
• H-Bond Donor: 2
• Rotatable Bonds: 1

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9974	99.74%
Caco-2	+	0.5460	54.60%
Blood Brain Barrier	-	0.7322	73.22%
Human oral bioavailability	+	0.7143	71.43%
Subcellular localzation	Mitochondria	0.8251	82.51%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9210	92.10%
OATP1B3 inhibitior	+	0.9510	95.10%
MATE1 inhibitior	-	0.7200	72.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	-	0.9111	91.11%
P-glycoprotein inhibitior	-	0.9829	98.29%
P-glycoprotein substrate	-	0.9076	90.76%
CYP3A4 substrate	-	0.5547	55.47%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8530	85.30%
CYP3A4 inhibition	-	0.7799	77.99%
CYP2C9 inhibition	+	0.8644	86.44%
CYP2C19 inhibition	+	0.7100	71.00%
CYP2D6 inhibition	-	0.6339	63.39%
CYP1A2 inhibition	+	0.9332	93.32%
CYP2C8 inhibition	-	0.9302	93.02%
CYP inhibitory promiscuity	+	0.8100	81.00%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.8252	82.52%
Carcinogenicity (trinary)	Non-required	0.6891	68.91%
Eye corrosion	-	0.9890	98.90%
Eye irritation	+	0.9019	90.19%
Skin irritation	-	0.5724	57.24%
Skin corrosion	-	0.9291	92.91%
Ames mutagenesis	+	0.8000	80.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.8321	83.21%
Micronuclear	-	0.5300	53.00%
Hepatotoxicity	+	0.5927	59.27%
skin sensitisation	+	0.4930	49.30%
Respiratory toxicity	+	0.5333	53.33%
Reproductive toxicity	+	0.6444	64.44%
Mitochondrial toxicity	+	0.6250	62.50%
Nephrotoxicity	+	0.6609	66.09%
Acute Oral Toxicity (c)	III	0.5109	51.09%
Estrogen receptor binding	-	0.6206	62.06%
Androgen receptor binding	-	0.5219	52.19%
Thyroid receptor binding	-	0.8057	80.57%
Glucocorticoid receptor binding	+	0.5633	56.33%
Aromatase binding	-	0.6405	64.05%
PPAR gamma	-	0.5423	54.23%
Honey bee toxicity	-	0.9740	97.40%
Biodegradation	-	0.5250	52.50%
Crustacea aquatic toxicity	-	0.6800	68.00%
Fish aquatic toxicity	+	0.9921	99.21%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	98.65%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	95.54%	95.56%
CHEMBL3401	O75469	Pregnane X receptor	90.20%	94.73%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	88.67%	99.23%
CHEMBL1937	Q92769	Histone deacetylase 2	87.08%	94.75%
CHEMBL1951	P21397	Monoamine oxidase A	86.45%	91.49%
CHEMBL3492	P49721	Proteasome Macropain subunit	85.89%	90.24%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	83.97%	96.09%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	83.82%	99.15%
CHEMBL1806	P11388	DNA topoisomerase II alpha	83.71%	89.00%
CHEMBL2378	P30307	Dual specificity phosphatase Cdc25C	83.23%	96.67%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	83.15%	91.11%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	82.62%	93.03%
CHEMBL1293249	Q13887	Kruppel-like factor 5	80.11%	86.33%

Plants that contains it

• Dionaea muscipula

Cross-Links

• PubChem: 11481367
• LOTUS: LTS0209096
• wikiData: Q105377869