[(3S,4S)-4-acetyloxy-1-[(E)-3-phenylprop-2-enoyl]pyrrolidin-3-yl] acetate

Details

• Internal ID: 3eb26d9c-b0b5-4200-9349-43601de547ea
• Taxonomy: Phenylpropanoids and polyketides > Cinnamic acids and derivatives
• IUPAC Name: [(3S,4S)-4-acetyloxy-1-[(E)-3-phenylprop-2-enoyl]pyrrolidin-3-yl] acetate
• SMILES (Canonical): CC(=O)OC1CN(CC1OC(=O)C)C(=O)C=CC2=CC=CC=C2
• SMILES (Isomeric): CC(=O)O[C@H]1CN(C[C@@H]1OC(=O)C)C(=O)/C=C/C2=CC=CC=C2
• InChI: InChI=1S/C17H19NO5/c1-12(19)22-15-10-18(11-16(15)23-13(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-/m0/s1
• InChI Key: BLUFKOASZPTGNZ-FHQWLQQXSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₁₇H₁₉NO₅
• Molecular Weight: 317.34 g/mol
• Exact Mass: 317.12632271 g/mol
• Topological Polar Surface Area (TPSA): 72.90 Ų
• XlogP: 1.50
• Atomic LogP (AlogP): 1.41
• H-Bond Acceptor: 5
• 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	+	0.8330	83.30%
Caco-2	+	0.8111	81.11%
Blood Brain Barrier	+	0.8500	85.00%
Human oral bioavailability	-	0.5429	54.29%
Subcellular localzation	Mitochondria	0.6765	67.65%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9552	95.52%
OATP1B3 inhibitior	+	0.9378	93.78%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.7164	71.64%
BSEP inhibitior	+	0.7596	75.96%
P-glycoprotein inhibitior	-	0.5370	53.70%
P-glycoprotein substrate	-	0.8906	89.06%
CYP3A4 substrate	-	0.5417	54.17%
CYP2C9 substrate	-	0.7936	79.36%
CYP2D6 substrate	-	0.8807	88.07%
CYP3A4 inhibition	-	0.9030	90.30%
CYP2C9 inhibition	-	0.7383	73.83%
CYP2C19 inhibition	+	0.6478	64.78%
CYP2D6 inhibition	-	0.8818	88.18%
CYP1A2 inhibition	-	0.6860	68.60%
CYP2C8 inhibition	-	0.8032	80.32%
CYP inhibitory promiscuity	+	0.5271	52.71%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.8900	89.00%
Carcinogenicity (trinary)	Non-required	0.5397	53.97%
Eye corrosion	-	0.9858	98.58%
Eye irritation	-	0.8674	86.74%
Skin irritation	-	0.8008	80.08%
Skin corrosion	-	0.9468	94.68%
Ames mutagenesis	-	0.7700	77.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7888	78.88%
Micronuclear	+	0.6600	66.00%
Hepatotoxicity	+	0.5993	59.93%
skin sensitisation	-	0.8667	86.67%
Respiratory toxicity	+	0.5444	54.44%
Reproductive toxicity	+	0.7222	72.22%
Mitochondrial toxicity	+	0.7500	75.00%
Nephrotoxicity	+	0.4798	47.98%
Acute Oral Toxicity (c)	III	0.6858	68.58%
Estrogen receptor binding	+	0.5890	58.90%
Androgen receptor binding	+	0.5835	58.35%
Thyroid receptor binding	-	0.5247	52.47%
Glucocorticoid receptor binding	-	0.5828	58.28%
Aromatase binding	-	0.5420	54.20%
PPAR gamma	-	0.7901	79.01%
Honey bee toxicity	-	0.9153	91.53%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.5555	55.55%
Fish aquatic toxicity	+	0.7933	79.33%

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	96.09%	96.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	94.01%	86.33%
CHEMBL1821	P08173	Muscarinic acetylcholine receptor M4	93.58%	94.08%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.26%	95.56%
CHEMBL2581	P07339	Cathepsin D	92.86%	98.95%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	92.76%	96.00%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	90.55%	94.62%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	88.49%	91.11%
CHEMBL5028	O14672	ADAM10	87.99%	97.50%
CHEMBL221	P23219	Cyclooxygenase-1	87.79%	90.17%
CHEMBL216	P11229	Muscarinic acetylcholine receptor M1	86.28%	94.23%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	80.21%	93.00%

Plants that contains it

• Acanthosyris paulo-alvinii
• Aglaia perviridis
• Ardisia japonica
• Betula alnoides
• Phoebe grandis
• Piper sarmentosum
• Rubus pileatus

Cross-Links

• PubChem: 11638279
• NPASS: NPC93641
• LOTUS: LTS0236486
• wikiData: Q103818516