4,5-dihydroxy-6,7-dimethoxy-3-[(E)-3-oxohex-1-enyl]naphthalene-1,2-dione

Details

• Internal ID: 4fd53ca2-9482-4b8c-94e7-2ba5f855955a
• Taxonomy: Benzenoids > Naphthalenes > Naphthoquinones
• IUPAC Name: 4,5-dihydroxy-6,7-dimethoxy-3-[(E)-3-oxohex-1-enyl]naphthalene-1,2-dione
• SMILES (Canonical): CCCC(=O)C=CC1=C(C2=C(C(=C(C=C2C(=O)C1=O)OC)OC)O)O
• SMILES (Isomeric): CCCC(=O)/C=C/C1=C(C2=C(C(=C(C=C2C(=O)C1=O)OC)OC)O)O
• InChI: InChI=1S/C18H18O7/c1-4-5-9(19)6-7-10-14(20)13-11(16(22)15(10)21)8-12(24-2)18(25-3)17(13)23/h6-8,20,23H,4-5H2,1-3H3/b7-6+
• InChI Key: PIMHFJPKESFSSO-VOTSOKGWSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₈H₁₈O₇
• Molecular Weight: 346.30 g/mol
• Exact Mass: 346.10525291 g/mol
• Topological Polar Surface Area (TPSA): 110.00 Ų
• XlogP: 1.90
• Atomic LogP (AlogP): 2.37
• H-Bond Acceptor: 7
• H-Bond Donor: 2
• Rotatable Bonds: 6

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9866	98.66%
Caco-2	+	0.7059	70.59%
Blood Brain Barrier	+	0.5149	51.49%
Human oral bioavailability	+	0.6000	60.00%
Subcellular localzation	Mitochondria	0.6907	69.07%
OATP2B1 inhibitior	-	0.8595	85.95%
OATP1B1 inhibitior	+	0.8534	85.34%
OATP1B3 inhibitior	+	0.9273	92.73%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	-	0.5926	59.26%
P-glycoprotein inhibitior	-	0.7606	76.06%
P-glycoprotein substrate	-	0.7231	72.31%
CYP3A4 substrate	+	0.5364	53.64%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8347	83.47%
CYP3A4 inhibition	-	0.5523	55.23%
CYP2C9 inhibition	+	0.5627	56.27%
CYP2C19 inhibition	-	0.5084	50.84%
CYP2D6 inhibition	-	0.7652	76.52%
CYP1A2 inhibition	+	0.7214	72.14%
CYP2C8 inhibition	+	0.7401	74.01%
CYP inhibitory promiscuity	+	0.6557	65.57%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9215	92.15%
Carcinogenicity (trinary)	Non-required	0.6632	66.32%
Eye corrosion	-	0.9870	98.70%
Eye irritation	-	0.7046	70.46%
Skin irritation	-	0.7820	78.20%
Skin corrosion	-	0.9394	93.94%
Ames mutagenesis	-	0.7100	71.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5476	54.76%
Micronuclear	-	0.5900	59.00%
Hepatotoxicity	-	0.6875	68.75%
skin sensitisation	-	0.6684	66.84%
Respiratory toxicity	-	0.5444	54.44%
Reproductive toxicity	+	0.7778	77.78%
Mitochondrial toxicity	+	0.6250	62.50%
Nephrotoxicity	-	0.6613	66.13%
Acute Oral Toxicity (c)	III	0.5275	52.75%
Estrogen receptor binding	+	0.8155	81.55%
Androgen receptor binding	-	0.6486	64.86%
Thyroid receptor binding	-	0.5000	50.00%
Glucocorticoid receptor binding	+	0.8679	86.79%
Aromatase binding	+	0.5646	56.46%
PPAR gamma	+	0.6813	68.13%
Honey bee toxicity	-	0.9024	90.24%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.6400	64.00%
Fish aquatic toxicity	+	0.9778	97.78%

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	98.49%	91.11%
CHEMBL1806	P11388	DNA topoisomerase II alpha	95.37%	89.00%
CHEMBL2581	P07339	Cathepsin D	93.69%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	93.16%	96.09%
CHEMBL3060	Q9Y345	Glycine transporter 2	92.45%	99.17%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.99%	95.56%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	91.42%	96.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	90.89%	86.33%
CHEMBL2085	P14174	Macrophage migration inhibitory factor	84.32%	80.78%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	83.20%	94.45%
CHEMBL2535	P11166	Glucose transporter	82.91%	98.75%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	82.72%	99.23%
CHEMBL5925	P22413	Ectonucleotide pyrophosphatase/phosphodiesterase family member 1	81.41%	92.38%
CHEMBL4208	P20618	Proteasome component C5	80.85%	90.00%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 10991599
• LOTUS: LTS0231314
• wikiData: Q77280747