2-(4-Methyl-3-pentenyl)-5-methoxy-8-hydroxy-1,4-naphthoquinone

Details

• Internal ID: 9754163e-99e5-4370-9851-b12944fba859
• Taxonomy: Benzenoids > Naphthalenes > Naphthoquinones
• IUPAC Name: 8-hydroxy-5-methoxy-2-(4-methylpent-3-enyl)naphthalene-1,4-dione
• SMILES (Canonical): CC(=CCCC1=CC(=O)C2=C(C=CC(=C2C1=O)O)OC)C
• SMILES (Isomeric): CC(=CCCC1=CC(=O)C2=C(C=CC(=C2C1=O)O)OC)C
• InChI: InChI=1S/C17H18O4/c1-10(2)5-4-6-11-9-13(19)15-14(21-3)8-7-12(18)16(15)17(11)20/h5,7-9,18H,4,6H2,1-3H3
• InChI Key: DOQSBOUHOPLRMV-UHFFFAOYSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₁₇H₁₈O₄
• Molecular Weight: 286.32 g/mol
• Exact Mass: 286.12050905 g/mol
• Topological Polar Surface Area (TPSA): 63.60 Ų
• XlogP: 3.80
• Atomic LogP (AlogP): 3.45
• H-Bond Acceptor: 4
• H-Bond Donor: 1
• Rotatable Bonds: 4

Synonyms

• 2-(4-Methyl-3-pentenyl)-5-methoxy-8-hydroxy-1,4-naphthoquinone

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9968	99.68%
Caco-2	+	0.9118	91.18%
Blood Brain Barrier	+	0.5750	57.50%
Human oral bioavailability	+	0.5714	57.14%
Subcellular localzation	Mitochondria	0.8538	85.38%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9179	91.79%
OATP1B3 inhibitior	+	0.9011	90.11%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.7750	77.50%
BSEP inhibitior	+	0.5699	56.99%
P-glycoprotein inhibitior	-	0.8157	81.57%
P-glycoprotein substrate	-	0.8559	85.59%
CYP3A4 substrate	+	0.5252	52.52%
CYP2C9 substrate	-	0.7958	79.58%
CYP2D6 substrate	-	0.8231	82.31%
CYP3A4 inhibition	-	0.8330	83.30%
CYP2C9 inhibition	+	0.6719	67.19%
CYP2C19 inhibition	+	0.6864	68.64%
CYP2D6 inhibition	-	0.8076	80.76%
CYP1A2 inhibition	+	0.8648	86.48%
CYP2C8 inhibition	-	0.7171	71.71%
CYP inhibitory promiscuity	+	0.7023	70.23%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.8703	87.03%
Carcinogenicity (trinary)	Non-required	0.7005	70.05%
Eye corrosion	-	0.9897	98.97%
Eye irritation	+	0.8521	85.21%
Skin irritation	-	0.7377	73.77%
Skin corrosion	-	0.9547	95.47%
Ames mutagenesis	+	0.5800	58.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5674	56.74%
Micronuclear	-	0.6900	69.00%
Hepatotoxicity	+	0.5552	55.52%
skin sensitisation	-	0.7082	70.82%
Respiratory toxicity	-	0.6000	60.00%
Reproductive toxicity	+	0.7556	75.56%
Mitochondrial toxicity	+	0.6750	67.50%
Nephrotoxicity	+	0.6942	69.42%
Acute Oral Toxicity (c)	III	0.6769	67.69%
Estrogen receptor binding	+	0.8862	88.62%
Androgen receptor binding	+	0.7256	72.56%
Thyroid receptor binding	-	0.5000	50.00%
Glucocorticoid receptor binding	+	0.7866	78.66%
Aromatase binding	+	0.6807	68.07%
PPAR gamma	+	0.8964	89.64%
Honey bee toxicity	-	0.8466	84.66%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	-	0.7600	76.00%
Fish aquatic toxicity	+	0.9936	99.36%

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	96.04%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	94.58%	94.45%
CHEMBL2581	P07339	Cathepsin D	93.28%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.12%	95.56%
CHEMBL1293249	Q13887	Kruppel-like factor 5	89.19%	86.33%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	87.59%	96.09%
CHEMBL1937	Q92769	Histone deacetylase 2	86.66%	94.75%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	85.10%	96.00%
CHEMBL3401	O75469	Pregnane X receptor	83.37%	94.73%
CHEMBL4208	P20618	Proteasome component C5	81.88%	90.00%

Plants that contains it

• Alkanna cappadocica

Cross-Links

• PubChem: 46833119
• NPASS: NPC22222
• ChEMBL: CHEMBL1099068
• LOTUS: LTS0103987
• wikiData: Q104986140