(E)-1-[(3R,4R)-3,4-diacetylpyrrolidin-1-yl]-3-phenylprop-2-en-1-one

Details

• Internal ID: 06504945-e7b7-4b52-a970-1e27bfade2ee
• Taxonomy: Phenylpropanoids and polyketides > Cinnamic acids and derivatives
• IUPAC Name: (E)-1-[(3R,4R)-3,4-diacetylpyrrolidin-1-yl]-3-phenylprop-2-en-1-one
• SMILES (Canonical): CC(=O)C1CN(CC1C(=O)C)C(=O)C=CC2=CC=CC=C2
• SMILES (Isomeric): CC(=O)[C@H]1CN(C[C@@H]1C(=O)C)C(=O)/C=C/C2=CC=CC=C2
• InChI: InChI=1S/C17H19NO3/c1-12(19)15-10-18(11-16(15)13(2)20)17(21)9-8-14-6-4-3-5-7-14/h3-9,15-16H,10-11H2,1-2H3/b9-8+/t15-,16-/m1/s1
• InChI Key: SBZXUDQCWDMXCV-GUFYHEMZSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₇H₁₉NO₃
• Molecular Weight: 285.34 g/mol
• Exact Mass: 285.13649347 g/mol
• Topological Polar Surface Area (TPSA): 54.40 Ų
• XlogP: 1.00
• Atomic LogP (AlogP): 1.95
• H-Bond Acceptor: 3
• H-Bond Donor: 0
• Rotatable Bonds: 4

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9668	96.68%
Caco-2	+	0.9496	94.96%
Blood Brain Barrier	+	0.9080	90.80%
Human oral bioavailability	-	0.6000	60.00%
Subcellular localzation	Mitochondria	0.7010	70.10%
OATP2B1 inhibitior	-	0.7176	71.76%
OATP1B1 inhibitior	+	0.9581	95.81%
OATP1B3 inhibitior	+	0.9455	94.55%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.7817	78.17%
BSEP inhibitior	+	0.8265	82.65%
P-glycoprotein inhibitior	-	0.7602	76.02%
P-glycoprotein substrate	-	0.8725	87.25%
CYP3A4 substrate	-	0.6134	61.34%
CYP2C9 substrate	-	0.8000	80.00%
CYP2D6 substrate	-	0.8783	87.83%
CYP3A4 inhibition	-	0.8326	83.26%
CYP2C9 inhibition	-	0.7688	76.88%
CYP2C19 inhibition	+	0.6061	60.61%
CYP2D6 inhibition	-	0.8075	80.75%
CYP1A2 inhibition	-	0.5917	59.17%
CYP2C8 inhibition	-	0.7635	76.35%
CYP inhibitory promiscuity	-	0.5656	56.56%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.8400	84.00%
Carcinogenicity (trinary)	Non-required	0.5500	55.00%
Eye corrosion	-	0.9655	96.55%
Eye irritation	-	0.9732	97.32%
Skin irritation	-	0.6507	65.07%
Skin corrosion	-	0.9185	91.85%
Ames mutagenesis	-	0.8200	82.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.8488	84.88%
Micronuclear	+	0.5200	52.00%
Hepatotoxicity	+	0.5618	56.18%
skin sensitisation	-	0.8507	85.07%
Respiratory toxicity	+	0.5778	57.78%
Reproductive toxicity	+	0.6000	60.00%
Mitochondrial toxicity	+	0.6750	67.50%
Nephrotoxicity	-	0.6103	61.03%
Acute Oral Toxicity (c)	III	0.6825	68.25%
Estrogen receptor binding	+	0.6126	61.26%
Androgen receptor binding	+	0.6827	68.27%
Thyroid receptor binding	-	0.6247	62.47%
Glucocorticoid receptor binding	-	0.6844	68.44%
Aromatase binding	-	0.5377	53.77%
PPAR gamma	-	0.8249	82.49%
Honey bee toxicity	-	0.9640	96.40%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	-	0.5500	55.00%
Fish aquatic toxicity	+	0.8750	87.50%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.32%	96.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.11%	95.56%
CHEMBL2581	P07339	Cathepsin D	92.67%	98.95%
CHEMBL1293249	Q13887	Kruppel-like factor 5	91.35%	86.33%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	90.81%	96.00%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	87.13%	91.11%
CHEMBL5028	O14672	ADAM10	86.50%	97.50%
CHEMBL1806	P11388	DNA topoisomerase II alpha	81.95%	89.00%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	81.00%	93.00%
CHEMBL3192	Q9BY41	Histone deacetylase 8	80.63%	93.99%

Plants that contains it

• Piper sarmentosum

Cross-Links

• PubChem: 163190651
• LOTUS: LTS0187168
• wikiData: Q105249813