2-(5-Oxo-1,3-hexadienyl)-3,5,8-trihydroxy-6-methoxy-1,4-naphthoquinone

Details

• Internal ID: a4ac4683-62b9-4323-8826-6c18fd02b182
• Taxonomy: Benzenoids > Naphthalenes > Naphthoquinones
• IUPAC Name: 5,7,8-trihydroxy-2-methoxy-6-[(1E,3E)-5-oxohexa-1,3-dienyl]naphthalene-1,4-dione
• SMILES (Canonical): CC(=O)C=CC=CC1=C(C2=C(C(=C1O)O)C(=O)C(=CC2=O)OC)O
• SMILES (Isomeric): CC(=O)/C=C/C=C/C1=C(C2=C(C(=C1O)O)C(=O)C(=CC2=O)OC)O
• InChI: InChI=1S/C17H14O7/c1-8(18)5-3-4-6-9-14(20)12-10(19)7-11(24-2)16(22)13(12)17(23)15(9)21/h3-7,20-21,23H,1-2H3/b5-3+,6-4+
• InChI Key: VCZWDDRTRQBHBT-GGWOSOGESA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₇H₁₄O₇
• Molecular Weight: 330.29 g/mol
• Exact Mass: 330.07395278 g/mol
• Topological Polar Surface Area (TPSA): 121.00 Ų
• XlogP: 2.40
• Atomic LogP (AlogP): 1.87
• H-Bond Acceptor: 7
• H-Bond Donor: 3
• Rotatable Bonds: 4

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9784	97.84%
Caco-2	+	0.5400	54.00%
Blood Brain Barrier	-	0.7250	72.50%
Human oral bioavailability	+	0.5857	58.57%
Subcellular localzation	Mitochondria	0.6226	62.26%
OATP2B1 inhibitior	-	0.7039	70.39%
OATP1B1 inhibitior	+	0.8931	89.31%
OATP1B3 inhibitior	+	0.9738	97.38%
MATE1 inhibitior	-	0.7400	74.00%
OCT2 inhibitior	-	0.9588	95.88%
BSEP inhibitior	-	0.5000	50.00%
P-glycoprotein inhibitior	-	0.6948	69.48%
P-glycoprotein substrate	-	0.8961	89.61%
CYP3A4 substrate	+	0.5215	52.15%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8636	86.36%
CYP3A4 inhibition	-	0.5228	52.28%
CYP2C9 inhibition	+	0.5524	55.24%
CYP2C19 inhibition	-	0.6974	69.74%
CYP2D6 inhibition	-	0.7917	79.17%
CYP1A2 inhibition	+	0.8764	87.64%
CYP2C8 inhibition	-	0.6452	64.52%
CYP inhibitory promiscuity	+	0.6149	61.49%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9218	92.18%
Carcinogenicity (trinary)	Non-required	0.5770	57.70%
Eye corrosion	-	0.9788	97.88%
Eye irritation	-	0.6874	68.74%
Skin irritation	-	0.5497	54.97%
Skin corrosion	-	0.8735	87.35%
Ames mutagenesis	-	0.6123	61.23%
Human Ether-a-go-go-Related Gene inhibition	-	0.5643	56.43%
Micronuclear	+	0.8300	83.00%
Hepatotoxicity	+	0.6283	62.83%
skin sensitisation	-	0.6056	60.56%
Respiratory toxicity	-	0.5111	51.11%
Reproductive toxicity	+	0.7111	71.11%
Mitochondrial toxicity	+	0.5625	56.25%
Nephrotoxicity	+	0.7159	71.59%
Acute Oral Toxicity (c)	III	0.4413	44.13%
Estrogen receptor binding	+	0.7865	78.65%
Androgen receptor binding	+	0.6529	65.29%
Thyroid receptor binding	-	0.6566	65.66%
Glucocorticoid receptor binding	+	0.7699	76.99%
Aromatase binding	-	0.5654	56.54%
PPAR gamma	+	0.6851	68.51%
Honey bee toxicity	-	0.8598	85.98%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.7200	72.00%
Fish aquatic toxicity	+	0.9833	98.33%

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	96.62%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.41%	95.56%
CHEMBL1806	P11388	DNA topoisomerase II alpha	89.82%	89.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	89.46%	94.45%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	89.45%	96.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	87.87%	86.33%
CHEMBL2581	P07339	Cathepsin D	86.17%	98.95%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	85.47%	85.14%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	83.70%	96.09%
CHEMBL3401	O75469	Pregnane X receptor	81.15%	94.73%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 101036747
• LOTUS: LTS0035052
• wikiData: Q77625122