(e)-2-(4,5-dihydroxy-2-{3-[(4-hydroxyphenethyl)amino]-3-oxopropyl}phenyl)-3-(4-hydroxy-3,5-dimethoxyphenyl)-N-(4-acetamidobutyl)-acrylamide

Details

• Internal ID: 2daa0400-f273-4e8e-88b4-2dd6d796cf00
• Taxonomy: Phenylpropanoids and polyketides > Stilbenes
• IUPAC Name: (E)-N-(4-acetamidobutyl)-2-[4,5-dihydroxy-2-[3-[2-(4-hydroxyphenyl)ethylamino]-3-oxopropyl]phenyl]-3-(4-hydroxy-3,5-dimethoxyphenyl)prop-2-enamide
• SMILES (Canonical): CC(=O)NCCCCNC(=O)C(=CC1=CC(=C(C(=C1)OC)O)OC)C2=CC(=C(C=C2CCC(=O)NCCC3=CC=C(C=C3)O)O)O
• SMILES (Isomeric): CC(=O)NCCCCNC(=O)/C(=C/C1=CC(=C(C(=C1)OC)O)OC)/C2=CC(=C(C=C2CCC(=O)NCCC3=CC=C(C=C3)O)O)O
• InChI: InChI=1S/C34H41N3O9/c1-21(38)35-13-4-5-14-37-34(44)27(16-23-17-30(45-2)33(43)31(18-23)46-3)26-20-29(41)28(40)19-24(26)8-11-32(42)36-15-12-22-6-9-25(39)10-7-22/h6-7,9-10,16-20,39-41,43H,4-5,8,11-15H2,1-3H3,(H,35,38)(H,36,42)(H,37,44)/b27-16+
• InChI Key: HJDHQNBCJWHUOS-JVWAILMASA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₄H₄₁N₃O₉
• Molecular Weight: 635.70 g/mol
• Exact Mass: 635.28427989 g/mol
• Topological Polar Surface Area (TPSA): 187.00 Ų
• XlogP: 3.30
• Atomic LogP (AlogP): 3.39
• H-Bond Acceptor: 9
• H-Bond Donor: 7
• Rotatable Bonds: 16

Synonyms

• SCHEMBL28355173
• (e)-2-(4,5-dihydroxy-2-{3-[(4-hydroxyphenethyl)amino]-3-oxopropyl}phenyl)-3-(4-hydroxy-3,5-dimethoxyphenyl)-N-(4-acetamidobutyl)-acrylamide

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9178	91.78%
Caco-2	-	0.8717	87.17%
Blood Brain Barrier	-	0.5250	52.50%
Human oral bioavailability	-	0.7429	74.29%
Subcellular localzation	Mitochondria	0.8459	84.59%
OATP2B1 inhibitior	+	0.5759	57.59%
OATP1B1 inhibitior	+	0.8363	83.63%
OATP1B3 inhibitior	+	0.9280	92.80%
MATE1 inhibitior	-	0.7486	74.86%
OCT2 inhibitior	-	0.7500	75.00%
BSEP inhibitior	+	0.9135	91.35%
P-glycoprotein inhibitior	+	0.8261	82.61%
P-glycoprotein substrate	+	0.8254	82.54%
CYP3A4 substrate	+	0.6632	66.32%
CYP2C9 substrate	-	0.8006	80.06%
CYP2D6 substrate	-	0.8230	82.30%
CYP3A4 inhibition	+	0.7041	70.41%
CYP2C9 inhibition	-	0.7929	79.29%
CYP2C19 inhibition	-	0.8065	80.65%
CYP2D6 inhibition	-	0.6798	67.98%
CYP1A2 inhibition	-	0.6851	68.51%
CYP2C8 inhibition	+	0.8647	86.47%
CYP inhibitory promiscuity	-	0.9624	96.24%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.8443	84.43%
Carcinogenicity (trinary)	Non-required	0.6919	69.19%
Eye corrosion	-	0.9916	99.16%
Eye irritation	-	0.9212	92.12%
Skin irritation	-	0.7293	72.93%
Skin corrosion	-	0.9399	93.99%
Ames mutagenesis	-	0.6400	64.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5560	55.60%
Micronuclear	+	0.6200	62.00%
Hepatotoxicity	-	0.6300	63.00%
skin sensitisation	-	0.8769	87.69%
Respiratory toxicity	-	0.5333	53.33%
Reproductive toxicity	+	0.8222	82.22%
Mitochondrial toxicity	+	0.8125	81.25%
Nephrotoxicity	-	0.6806	68.06%
Acute Oral Toxicity (c)	III	0.6689	66.89%
Estrogen receptor binding	+	0.8379	83.79%
Androgen receptor binding	+	0.7531	75.31%
Thyroid receptor binding	+	0.5862	58.62%
Glucocorticoid receptor binding	+	0.7167	71.67%
Aromatase binding	+	0.5672	56.72%
PPAR gamma	+	0.7073	70.73%
Honey bee toxicity	-	0.7089	70.89%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	+	0.5200	52.00%
Fish aquatic toxicity	+	0.9537	95.37%

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	99.68%	91.11%
CHEMBL2581	P07339	Cathepsin D	99.12%	98.95%
CHEMBL4657	Q6V1X1	Dipeptidyl peptidase VIII	97.77%	97.21%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.35%	96.09%
CHEMBL3060	Q9Y345	Glycine transporter 2	96.83%	99.17%
CHEMBL2107	P61073	C-X-C chemokine receptor type 4	96.11%	93.10%
CHEMBL2535	P11166	Glucose transporter	94.84%	98.75%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	94.29%	94.45%
CHEMBL5701	Q9H2K8	Serine/threonine-protein kinase TAO3	94.07%	96.67%
CHEMBL5261	Q7L7X3	Serine/threonine-protein kinase TAO1	93.16%	89.33%
CHEMBL3401	O75469	Pregnane X receptor	92.47%	94.73%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	92.08%	96.95%
CHEMBL4630	O14757	Serine/threonine-protein kinase Chk1	90.91%	97.03%
CHEMBL1293249	Q13887	Kruppel-like factor 5	90.27%	86.33%
CHEMBL3492	P49721	Proteasome Macropain subunit	89.64%	90.24%
CHEMBL1937	Q92769	Histone deacetylase 2	89.55%	94.75%
CHEMBL1255126	O15151	Protein Mdm4	89.40%	90.20%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	89.39%	95.50%
CHEMBL4208	P20618	Proteasome component C5	84.90%	90.00%
CHEMBL340	P08684	Cytochrome P450 3A4	84.70%	91.19%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	84.11%	95.56%
CHEMBL5163	Q9NY46	Sodium channel protein type III alpha subunit	83.27%	96.90%
CHEMBL5852	Q96P65	Pyroglutamylated RFamide peptide receptor	83.05%	85.00%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	82.69%	94.33%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	82.40%	96.00%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	82.24%	95.89%
CHEMBL1744525	P43490	Nicotinamide phosphoribosyltransferase	82.02%	96.25%
CHEMBL3437	Q16853	Amine oxidase, copper containing	80.64%	94.00%
CHEMBL2179	P04062	Beta-glucocerebrosidase	80.58%	85.31%
CHEMBL1163101	O75460	Serine/threonine-protein kinase/endoribonuclease IRE1	80.46%	98.11%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	80.03%	94.00%

Plants that contains it

• Lycium chinense

Cross-Links

• PubChem: 71524308
• NPASS: NPC127402
• LOTUS: LTS0049414
• wikiData: Q105029161