2,3,5,8-Tetrahydroxy-1,4-naphthoquinone

Details

• Internal ID: 92ace960-608c-4416-9f38-645d24cc4933
• Taxonomy: Benzenoids > Naphthalenes > Naphthoquinones
• IUPAC Name: 2,3,5,8-tetrahydroxynaphthalene-1,4-dione
• SMILES (Canonical): C1=CC(=C2C(=C1O)C(=O)C(=C(C2=O)O)O)O
• SMILES (Isomeric): C1=CC(=C2C(=C1O)C(=O)C(=C(C2=O)O)O)O
• InChI: InChI=1S/C10H6O6/c11-3-1-2-4(12)6-5(3)7(13)9(15)10(16)8(6)14/h1-2,11-12,15-16H
• InChI Key: MECWRBUQZSSVHC-UHFFFAOYSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₁₀H₆O₆
• Molecular Weight: 222.15 g/mol
• Exact Mass: 222.01643791 g/mol
• Topological Polar Surface Area (TPSA): 115.00 Ų
• XlogP: 1.60
• Atomic LogP (AlogP): 0.80
• H-Bond Acceptor: 6
• H-Bond Donor: 4
• Rotatable Bonds: 0

Synonyms

• Oprea1_337611
• SCHEMBL5818577
• CHEMBL4746953

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9895	98.95%
Caco-2	-	0.7578	75.78%
Blood Brain Barrier	-	0.7250	72.50%
Human oral bioavailability	+	0.7000	70.00%
Subcellular localzation	Mitochondria	0.7309	73.09%
OATP2B1 inhibitior	-	0.7142	71.42%
OATP1B1 inhibitior	+	0.9721	97.21%
OATP1B3 inhibitior	+	0.9783	97.83%
MATE1 inhibitior	-	0.8200	82.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	-	0.9755	97.55%
P-glycoprotein inhibitior	-	0.9672	96.72%
P-glycoprotein substrate	-	0.9963	99.63%
CYP3A4 substrate	-	0.7981	79.81%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8530	85.30%
CYP3A4 inhibition	-	0.7861	78.61%
CYP2C9 inhibition	+	0.7874	78.74%
CYP2C19 inhibition	-	0.8037	80.37%
CYP2D6 inhibition	-	0.8533	85.33%
CYP1A2 inhibition	+	0.8711	87.11%
CYP2C8 inhibition	-	0.9858	98.58%
CYP inhibitory promiscuity	-	0.5467	54.67%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.8875	88.75%
Carcinogenicity (trinary)	Warning	0.4950	49.50%
Eye corrosion	-	0.9764	97.64%
Eye irritation	+	0.9794	97.94%
Skin irritation	+	0.7583	75.83%
Skin corrosion	-	0.8620	86.20%
Ames mutagenesis	+	0.8000	80.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.8600	86.00%
Micronuclear	+	0.8700	87.00%
Hepatotoxicity	+	0.8338	83.38%
skin sensitisation	+	0.7470	74.70%
Respiratory toxicity	-	0.5889	58.89%
Reproductive toxicity	+	0.5667	56.67%
Mitochondrial toxicity	+	0.5875	58.75%
Nephrotoxicity	+	0.7666	76.66%
Acute Oral Toxicity (c)	III	0.3647	36.47%
Estrogen receptor binding	-	0.5060	50.60%
Androgen receptor binding	-	0.5499	54.99%
Thyroid receptor binding	-	0.6714	67.14%
Glucocorticoid receptor binding	+	0.7909	79.09%
Aromatase binding	-	0.5616	56.16%
PPAR gamma	+	0.5935	59.35%
Honey bee toxicity	-	0.9430	94.30%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	-	0.6500	65.00%
Fish aquatic toxicity	+	0.9910	99.10%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	93.83%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.41%	95.56%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	84.83%	99.15%
CHEMBL2581	P07339	Cathepsin D	84.55%	98.95%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	82.42%	94.45%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	80.11%	99.23%

Plants that contains it

• Gluta usitata

Cross-Links

• PubChem: 135543374
• LOTUS: LTS0244508
• wikiData: Q105121574