methyl 4-hydroxy-1,2,3-trimethoxy-5-[(E)-3-phenylprop-2-enoyl]cyclopenta-2,4-diene-1-carboxylate

Details

• Internal ID: b2acf1ed-5cd4-453b-8ab0-f5272c512a7f
• Taxonomy: Benzenoids > Benzene and substituted derivatives > Styrenes
• IUPAC Name: methyl 4-hydroxy-1,2,3-trimethoxy-5-[(E)-3-phenylprop-2-enoyl]cyclopenta-2,4-diene-1-carboxylate
• SMILES (Canonical): COC1=C(C(C(=C1O)C(=O)C=CC2=CC=CC=C2)(C(=O)OC)OC)OC
• SMILES (Isomeric): COC1=C(C(C(=C1O)C(=O)/C=C/C2=CC=CC=C2)(C(=O)OC)OC)OC
• InChI: InChI=1S/C19H20O7/c1-23-16-15(21)14(13(20)11-10-12-8-6-5-7-9-12)19(26-4,17(16)24-2)18(22)25-3/h5-11,21H,1-4H3/b11-10+
• InChI Key: IYNWJCIJDFPPAH-ZHACJKMWSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₁₉H₂₀O₇
• Molecular Weight: 360.40 g/mol
• Exact Mass: 360.12090297 g/mol
• Topological Polar Surface Area (TPSA): 91.30 Ų
• XlogP: 2.00
• Atomic LogP (AlogP): 2.16
• H-Bond Acceptor: 7
• H-Bond Donor: 1
• Rotatable Bonds: 7

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9761	97.61%
Caco-2	+	0.6708	67.08%
Blood Brain Barrier	+	0.6250	62.50%
Human oral bioavailability	-	0.5857	58.57%
Subcellular localzation	Mitochondria	0.8417	84.17%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8982	89.82%
OATP1B3 inhibitior	+	0.9385	93.85%
MATE1 inhibitior	-	0.7800	78.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	+	0.6434	64.34%
P-glycoprotein inhibitior	+	0.6700	67.00%
P-glycoprotein substrate	-	0.8493	84.93%
CYP3A4 substrate	+	0.5142	51.42%
CYP2C9 substrate	-	0.8020	80.20%
CYP2D6 substrate	-	0.8797	87.97%
CYP3A4 inhibition	-	0.8930	89.30%
CYP2C9 inhibition	-	0.9276	92.76%
CYP2C19 inhibition	-	0.8526	85.26%
CYP2D6 inhibition	-	0.9432	94.32%
CYP1A2 inhibition	-	0.8926	89.26%
CYP2C8 inhibition	+	0.6953	69.53%
CYP inhibitory promiscuity	-	0.8917	89.17%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.7435	74.35%
Carcinogenicity (trinary)	Non-required	0.5055	50.55%
Eye corrosion	-	0.9641	96.41%
Eye irritation	-	0.5953	59.53%
Skin irritation	-	0.6466	64.66%
Skin corrosion	-	0.9802	98.02%
Ames mutagenesis	-	0.6700	67.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4883	48.83%
Micronuclear	-	0.5000	50.00%
Hepatotoxicity	-	0.5519	55.19%
skin sensitisation	-	0.6585	65.85%
Respiratory toxicity	-	0.6667	66.67%
Reproductive toxicity	+	0.6444	64.44%
Mitochondrial toxicity	-	0.6625	66.25%
Nephrotoxicity	-	0.5545	55.45%
Acute Oral Toxicity (c)	III	0.4452	44.52%
Estrogen receptor binding	+	0.8182	81.82%
Androgen receptor binding	+	0.6554	65.54%
Thyroid receptor binding	+	0.7140	71.40%
Glucocorticoid receptor binding	-	0.5961	59.61%
Aromatase binding	-	0.4938	49.38%
PPAR gamma	+	0.6570	65.70%
Honey bee toxicity	-	0.8915	89.15%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	+	0.5100	51.00%
Fish aquatic toxicity	+	0.9645	96.45%

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	98.64%	91.11%
CHEMBL221	P23219	Cyclooxygenase-1	93.75%	90.17%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.14%	95.56%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	92.35%	96.00%
CHEMBL1821	P08173	Muscarinic acetylcholine receptor M4	91.97%	94.08%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	90.36%	96.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	89.42%	86.33%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	89.20%	94.62%
CHEMBL5028	O14672	ADAM10	85.15%	97.50%
CHEMBL2581	P07339	Cathepsin D	84.17%	98.95%
CHEMBL2563	Q9UQL6	Histone deacetylase 5	82.76%	89.67%
CHEMBL3060	Q9Y345	Glycine transporter 2	81.32%	99.17%
CHEMBL3401	O75469	Pregnane X receptor	80.98%	94.73%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	80.68%	95.50%

Plants that contains it

• Fissistigma oldhamii

Cross-Links

• PubChem: 101021545
• LOTUS: LTS0149131
• wikiData: Q105122847