Chabrolonaphthoquinone A

Details

• Internal ID: 206504cc-fc5b-48f0-8641-136446fdf3a1
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Sesquiterpenoids
• IUPAC Name: (2E,6E)-6-methyl-9-(7-methyl-5,8-dioxonaphthalen-2-yl)-2-(4-methylpent-3-enyl)nona-2,6-dienoic acid
• SMILES (Canonical): CC1=CC(=O)C2=C(C1=O)C=C(C=C2)CCC=C(C)CCC=C(CCC=C(C)C)C(=O)O
• SMILES (Isomeric): CC1=CC(=O)C2=C(C1=O)C=C(C=C2)CC/C=C(\C)/CC/C=C(\CCC=C(C)C)/C(=O)O
• InChI: InChI=1S/C27H32O4/c1-18(2)8-5-12-22(27(30)31)13-7-10-19(3)9-6-11-21-14-15-23-24(17-21)26(29)20(4)16-25(23)28/h8-9,13-17H,5-7,10-12H2,1-4H3,(H,30,31)/b19-9+,22-13+
• InChI Key: UQVKETMBFLZESD-ZEGMUUQVSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₇H₃₂O₄
• Molecular Weight: 420.50 g/mol
• Exact Mass: 420.23005950 g/mol
• Topological Polar Surface Area (TPSA): 71.40 Ų
• XlogP: 6.50
• Atomic LogP (AlogP): 6.43
• H-Bond Acceptor: 3
• H-Bond Donor: 1
• Rotatable Bonds: 10

Synonyms

• (2E,6E)-6-methyl-9-(7-methyl-5,8-dioxonaphthalen-2-yl)-2-(4-methylpent-3-enyl)nona-2,6-dienoic acid
• CHEBI:188737

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9934	99.34%
Caco-2	-	0.6205	62.05%
Blood Brain Barrier	-	0.5000	50.00%
Human oral bioavailability	-	0.6000	60.00%
Subcellular localzation	Mitochondria	0.8826	88.26%
OATP2B1 inhibitior	-	0.8579	85.79%
OATP1B1 inhibitior	+	0.8882	88.82%
OATP1B3 inhibitior	-	0.2925	29.25%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	+	0.9830	98.30%
P-glycoprotein inhibitior	+	0.8589	85.89%
P-glycoprotein substrate	-	0.6925	69.25%
CYP3A4 substrate	+	0.5753	57.53%
CYP2C9 substrate	-	0.7056	70.56%
CYP2D6 substrate	-	0.8984	89.84%
CYP3A4 inhibition	-	0.6511	65.11%
CYP2C9 inhibition	+	0.6075	60.75%
CYP2C19 inhibition	-	0.5684	56.84%
CYP2D6 inhibition	-	0.8435	84.35%
CYP1A2 inhibition	+	0.7134	71.34%
CYP2C8 inhibition	-	0.6215	62.15%
CYP inhibitory promiscuity	-	0.6717	67.17%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.8911	89.11%
Carcinogenicity (trinary)	Non-required	0.7298	72.98%
Eye corrosion	-	0.9946	99.46%
Eye irritation	-	0.8743	87.43%
Skin irritation	-	0.6669	66.69%
Skin corrosion	-	0.9555	95.55%
Ames mutagenesis	-	0.5200	52.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7176	71.76%
Micronuclear	-	0.8200	82.00%
Hepatotoxicity	-	0.5250	52.50%
skin sensitisation	-	0.5486	54.86%
Respiratory toxicity	+	0.6778	67.78%
Reproductive toxicity	+	0.8222	82.22%
Mitochondrial toxicity	+	0.7500	75.00%
Nephrotoxicity	-	0.7374	73.74%
Acute Oral Toxicity (c)	III	0.6123	61.23%
Estrogen receptor binding	+	0.7350	73.50%
Androgen receptor binding	+	0.7607	76.07%
Thyroid receptor binding	+	0.5248	52.48%
Glucocorticoid receptor binding	+	0.6784	67.84%
Aromatase binding	+	0.5986	59.86%
PPAR gamma	+	0.7818	78.18%
Honey bee toxicity	-	0.8516	85.16%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	-	0.6252	62.52%
Fish aquatic toxicity	+	1.0000	100.00%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	98.86%	98.95%
CHEMBL4769	O95749	Geranylgeranyl pyrophosphate synthetase	96.89%	92.08%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.43%	95.56%
CHEMBL2039	P27338	Monoamine oxidase B	90.48%	92.51%
CHEMBL3401	O75469	Pregnane X receptor	90.37%	94.73%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	87.90%	90.71%
CHEMBL1293249	Q13887	Kruppel-like factor 5	87.51%	86.33%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	87.01%	91.11%
CHEMBL3060	Q9Y345	Glycine transporter 2	86.60%	99.17%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	82.75%	96.95%
CHEMBL2216739	Q92523	Carnitine O-palmitoyltransferase 1, muscle isoform	81.08%	88.33%
CHEMBL5163	Q9NY46	Sodium channel protein type III alpha subunit	80.84%	96.90%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 11464291
• LOTUS: LTS0188317
• wikiData: Q105277490