2,5-Dimethoxy-4-hydroxy-4-[(E)-3-phenyl-2-propenyl]-2,5-cyclohexadiene-1-one

Details

• Internal ID: ee8cdb9e-1fad-46a7-9488-c729cf1951c7
• Taxonomy: Benzenoids > Benzene and substituted derivatives > Styrenes
• IUPAC Name: 4-hydroxy-2,5-dimethoxy-4-[(E)-3-phenylprop-2-enyl]cyclohexa-2,5-dien-1-one
• SMILES (Canonical): COC1=CC(=O)C(=CC1(CC=CC2=CC=CC=C2)O)OC
• SMILES (Isomeric): COC1=CC(=O)C(=CC1(C/C=C/C2=CC=CC=C2)O)OC
• InChI: InChI=1S/C17H18O4/c1-20-15-12-17(19,16(21-2)11-14(15)18)10-6-9-13-7-4-3-5-8-13/h3-9,11-12,19H,10H2,1-2H3/b9-6+
• InChI Key: UJUNVNYVYMHQIS-RMKNXTFCSA-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): 55.80 Ų
• XlogP: 2.30
• Atomic LogP (AlogP): 2.46
• H-Bond Acceptor: 4
• H-Bond Donor: 1
• Rotatable Bonds: 5

Synonyms

• 2,5-Dimethoxy-4-hydroxy-4-[(E)-3-phenyl-2-propenyl]-2,5-cyclohexadiene-1-one

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9902	99.02%
Caco-2	+	0.8222	82.22%
Blood Brain Barrier	+	0.6250	62.50%
Human oral bioavailability	+	0.5857	58.57%
Subcellular localzation	Mitochondria	0.8234	82.34%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8810	88.10%
OATP1B3 inhibitior	+	0.9584	95.84%
MATE1 inhibitior	-	0.8200	82.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	+	0.5807	58.07%
P-glycoprotein inhibitior	-	0.7029	70.29%
P-glycoprotein substrate	-	0.9140	91.40%
CYP3A4 substrate	+	0.5065	50.65%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8159	81.59%
CYP3A4 inhibition	-	0.7959	79.59%
CYP2C9 inhibition	-	0.8825	88.25%
CYP2C19 inhibition	-	0.5200	52.00%
CYP2D6 inhibition	-	0.9000	90.00%
CYP1A2 inhibition	-	0.8251	82.51%
CYP2C8 inhibition	-	0.6577	65.77%
CYP inhibitory promiscuity	-	0.6622	66.22%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.7500	75.00%
Carcinogenicity (trinary)	Non-required	0.6292	62.92%
Eye corrosion	-	0.9826	98.26%
Eye irritation	-	0.5980	59.80%
Skin irritation	-	0.6691	66.91%
Skin corrosion	-	0.9754	97.54%
Ames mutagenesis	-	0.6008	60.08%
Human Ether-a-go-go-Related Gene inhibition	+	0.6848	68.48%
Micronuclear	-	0.5582	55.82%
Hepatotoxicity	+	0.5177	51.77%
skin sensitisation	+	0.5198	51.98%
Respiratory toxicity	+	0.6111	61.11%
Reproductive toxicity	+	0.5778	57.78%
Mitochondrial toxicity	-	0.6750	67.50%
Nephrotoxicity	+	0.6946	69.46%
Acute Oral Toxicity (c)	III	0.5984	59.84%
Estrogen receptor binding	+	0.8310	83.10%
Androgen receptor binding	+	0.6687	66.87%
Thyroid receptor binding	-	0.5432	54.32%
Glucocorticoid receptor binding	-	0.5430	54.30%
Aromatase binding	+	0.5843	58.43%
PPAR gamma	-	0.6375	63.75%
Honey bee toxicity	-	0.8926	89.26%
Biodegradation	-	0.9250	92.50%
Crustacea aquatic toxicity	+	0.5200	52.00%
Fish aquatic toxicity	+	0.8275	82.75%

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	98.35%	91.11%
CHEMBL1293249	Q13887	Kruppel-like factor 5	95.56%	86.33%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	95.43%	96.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	95.12%	95.56%
CHEMBL2581	P07339	Cathepsin D	93.47%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	91.15%	96.09%
CHEMBL4208	P20618	Proteasome component C5	90.24%	90.00%
CHEMBL3192	Q9BY41	Histone deacetylase 8	89.16%	93.99%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	85.38%	94.62%
CHEMBL1821	P08173	Muscarinic acetylcholine receptor M4	83.12%	94.08%
CHEMBL2288	Q13526	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	82.17%	91.71%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	82.04%	85.14%

Plants that contains it

• Dalbergia sissoo

Cross-Links

• PubChem: 24761040
• NPASS: NPC473347
• ChEMBL: CHEMBL402025
• LOTUS: LTS0076506
• wikiData: Q105274230