3-Ethyl-2,5-dihydroxy-1,4-benzoquinone

Details

• Internal ID: f76ab470-ef9a-448a-af7f-ac9ebdf86021
• Taxonomy: Organic oxygen compounds > Organooxygen compounds > Carbonyl compounds > Benzoquinones > P-benzoquinones
• IUPAC Name: 3-ethyl-2,5-dihydroxycyclohexa-2,5-diene-1,4-dione
• SMILES (Canonical): CCC1=C(C(=O)C=C(C1=O)O)O
• SMILES (Isomeric): CCC1=C(C(=O)C=C(C1=O)O)O
• InChI: InChI=1S/C8H8O4/c1-2-4-7(11)5(9)3-6(10)8(4)12/h3,9,12H,2H2,1H3
• InChI Key: WJSQCAWGGRFZJK-UHFFFAOYSA-N
• Popularity: 4 references in papers

Physical and Chemical Properties

• Molecular Formula: C₈H₈O₄
• Molecular Weight: 168.15 g/mol
• Exact Mass: 168.04225873 g/mol
• Topological Polar Surface Area (TPSA): 74.60 Ų
• XlogP: 0.50
• Atomic LogP (AlogP): 0.80
• H-Bond Acceptor: 4
• H-Bond Donor: 2
• Rotatable Bonds: 1

Synonyms

• CHEMBL222173
• SCHEMBL9175113
• 2,5-dihydroxy-3-ethylbenzoquinone
• AKOS006285928
• 3-ethyl-2,5-dihydroxybenzo-1,4-quinone
• AM-573/20891013

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9557	95.57%
Caco-2	-	0.5709	57.09%
Blood Brain Barrier	-	0.6750	67.50%
Human oral bioavailability	+	0.7286	72.86%
Subcellular localzation	Mitochondria	0.8569	85.69%
OATP2B1 inhibitior	-	0.8515	85.15%
OATP1B1 inhibitior	+	0.9267	92.67%
OATP1B3 inhibitior	+	0.9677	96.77%
MATE1 inhibitior	-	0.8600	86.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	-	0.9487	94.87%
P-glycoprotein inhibitior	-	0.9747	97.47%
P-glycoprotein substrate	-	0.9473	94.73%
CYP3A4 substrate	-	0.6484	64.84%
CYP2C9 substrate	-	0.8037	80.37%
CYP2D6 substrate	-	0.8667	86.67%
CYP3A4 inhibition	-	0.9220	92.20%
CYP2C9 inhibition	-	0.6456	64.56%
CYP2C19 inhibition	-	0.8558	85.58%
CYP2D6 inhibition	-	0.7454	74.54%
CYP1A2 inhibition	-	0.9000	90.00%
CYP2C8 inhibition	-	0.9711	97.11%
CYP inhibitory promiscuity	-	0.7813	78.13%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.7776	77.76%
Carcinogenicity (trinary)	Non-required	0.6137	61.37%
Eye corrosion	-	0.9131	91.31%
Eye irritation	+	0.9336	93.36%
Skin irritation	+	0.5389	53.89%
Skin corrosion	-	0.7738	77.38%
Ames mutagenesis	-	0.6900	69.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7913	79.13%
Micronuclear	+	0.6000	60.00%
Hepatotoxicity	+	0.6680	66.80%
skin sensitisation	+	0.5135	51.35%
Respiratory toxicity	-	0.6444	64.44%
Reproductive toxicity	+	0.6556	65.56%
Mitochondrial toxicity	-	0.5375	53.75%
Nephrotoxicity	+	0.7525	75.25%
Acute Oral Toxicity (c)	III	0.5482	54.82%
Estrogen receptor binding	-	0.6549	65.49%
Androgen receptor binding	+	0.6393	63.93%
Thyroid receptor binding	-	0.7523	75.23%
Glucocorticoid receptor binding	-	0.6040	60.40%
Aromatase binding	-	0.8326	83.26%
PPAR gamma	-	0.6904	69.04%
Honey bee toxicity	-	0.9465	94.65%
Biodegradation	+	0.6250	62.50%
Crustacea aquatic toxicity	-	0.7300	73.00%
Fish aquatic toxicity	+	0.9244	92.44%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL4198	P98170	Inhibitor of apoptosis protein 3	10400 nM	Ki	PMID: 16962773

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	95.35%	98.95%
CHEMBL4040	P28482	MAP kinase ERK2	84.54%	83.82%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	83.86%	96.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	83.75%	95.56%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	81.85%	91.11%

Plants that contains it

• Heliotropium indicum

Cross-Links

• PubChem: 821411
• NPASS: NPC137396
• ChEMBL: CHEMBL222173