8-[(2E)-4-hydroxy-4-methylpent-2-enoyl]-3-isopropyl-7-methylnaphthalene-1,2-dione

Details

• Internal ID: 9db6068a-2f0f-447f-9830-2b78ea52444a
• Taxonomy: Benzenoids > Naphthalenes > Naphthoquinones
• IUPAC Name: 8-(4-hydroxy-4-methylpent-2-enoyl)-7-methyl-3-propan-2-ylnaphthalene-1,2-dione
• SMILES (Canonical): CC1=C(C2=C(C=C1)C=C(C(=O)C2=O)C(C)C)C(=O)C=CC(C)(C)O
• SMILES (Isomeric): CC1=C(C2=C(C=C1)C=C(C(=O)C2=O)C(C)C)C(=O)C=CC(C)(C)O
• InChI: InChI=1S/C20H22O4/c1-11(2)14-10-13-7-6-12(3)16(17(13)19(23)18(14)22)15(21)8-9-20(4,5)24/h6-11,24H,1-5H3
• InChI Key: QRIJFKANMJMVFQ-UHFFFAOYSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₂₂O₄
• Molecular Weight: 326.40 g/mol
• Exact Mass: 326.15180918 g/mol
• Topological Polar Surface Area (TPSA): 71.40 Ų
• XlogP: 2.80
• Atomic LogP (AlogP): 3.31
• H-Bond Acceptor: 4
• H-Bond Donor: 1
• Rotatable Bonds: 4

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9961	99.61%
Caco-2	+	0.7182	71.82%
Blood Brain Barrier	+	0.5250	52.50%
Human oral bioavailability	+	0.5429	54.29%
Subcellular localzation	Mitochondria	0.8627	86.27%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9154	91.54%
OATP1B3 inhibitior	+	0.9352	93.52%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	+	0.7757	77.57%
P-glycoprotein inhibitior	-	0.6629	66.29%
P-glycoprotein substrate	-	0.7813	78.13%
CYP3A4 substrate	+	0.5114	51.14%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8849	88.49%
CYP3A4 inhibition	-	0.5227	52.27%
CYP2C9 inhibition	+	0.7049	70.49%
CYP2C19 inhibition	+	0.6066	60.66%
CYP2D6 inhibition	-	0.5638	56.38%
CYP1A2 inhibition	+	0.6705	67.05%
CYP2C8 inhibition	-	0.7123	71.23%
CYP inhibitory promiscuity	+	0.5946	59.46%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9071	90.71%
Carcinogenicity (trinary)	Non-required	0.5872	58.72%
Eye corrosion	-	0.9877	98.77%
Eye irritation	-	0.8550	85.50%
Skin irritation	-	0.5907	59.07%
Skin corrosion	-	0.9386	93.86%
Ames mutagenesis	-	0.5600	56.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5322	53.22%
Micronuclear	-	0.5500	55.00%
Hepatotoxicity	-	0.5271	52.71%
skin sensitisation	+	0.6081	60.81%
Respiratory toxicity	+	0.6778	67.78%
Reproductive toxicity	+	0.6778	67.78%
Mitochondrial toxicity	+	0.5500	55.00%
Nephrotoxicity	-	0.5610	56.10%
Acute Oral Toxicity (c)	III	0.6628	66.28%
Estrogen receptor binding	+	0.8740	87.40%
Androgen receptor binding	-	0.5178	51.78%
Thyroid receptor binding	+	0.6470	64.70%
Glucocorticoid receptor binding	+	0.6317	63.17%
Aromatase binding	+	0.5413	54.13%
PPAR gamma	+	0.7515	75.15%
Honey bee toxicity	-	0.9061	90.61%
Biodegradation	-	0.9750	97.50%
Crustacea aquatic toxicity	-	0.7300	73.00%
Fish aquatic toxicity	+	0.9928	99.28%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	96.07%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	94.66%	95.56%
CHEMBL3401	O75469	Pregnane X receptor	91.55%	94.73%
CHEMBL2265	P23141	Acyl coenzyme A:cholesterol acyltransferase	90.94%	85.94%
CHEMBL3359	P21462	Formyl peptide receptor 1	88.39%	93.56%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	88.34%	91.11%
CHEMBL1806	P11388	DNA topoisomerase II alpha	87.81%	89.00%
CHEMBL1907591	P30926	Neuronal acetylcholine receptor; alpha4/beta4	85.70%	100.00%
CHEMBL5409	Q8TDU6	G-protein coupled bile acid receptor 1	84.62%	93.65%
CHEMBL1907588	P02708	Acetylcholine receptor; alpha1/beta1/delta/gamma	84.34%	98.33%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	84.26%	85.14%
CHEMBL5966	P55899	IgG receptor FcRn large subunit p51	82.71%	90.93%
CHEMBL3180	O00748	Carboxylesterase 2	82.38%	90.00%

Plants that contains it

• Salvia prionitis

Cross-Links

• PubChem: 73001689
• LOTUS: LTS0035933
• wikiData: Q105226373