1-(3-Methoxycarbonyl-propyl)-4-(phenyl-propionyl-amino)-piperidine-4-carboxylic acid methyl ester

ID: ALA420187

Chembl Id: CHEMBL420187

PubChem CID: 14873781

Max Phase: Preclinical

Molecular Formula: C21H30N2O5

Molecular Weight: 390.48

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCC(=O)N(c1ccccc1)C1(C(=O)OC)CCN(CCCC(=O)OC)CC1

Standard InChI:  InChI=1S/C21H30N2O5/c1-4-18(24)23(17-9-6-5-7-10-17)21(20(26)28-3)12-15-22(16-13-21)14-8-11-19(25)27-2/h5-7,9-10H,4,8,11-16H2,1-3H3

Standard InChI Key:  GIHKCTJJULRQKV-UHFFFAOYSA-N

Alternative Forms

1. Parent:

   

   ALA420187

   methyl 1-(4-methoxy-4-oxobutyl)-4-(N-propanoylanilino)piperidine-4-carboxylate

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 390.48

Molecular Weight (Monoisotopic): 390.2155

AlogP: 2.39

#Rotatable Bonds: 8

Polar Surface Area: 76.15

Molecular Species: NEUTRAL

HBA: 6

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 7.44

CX LogP: 1.80

CX LogD: 1.48

Aromatic Rings: 1

Heavy Atoms: 28

QED Weighted: 0.63

Np Likeness Score: -0.44

References

1. Feldman PL, James MK, Brackeen MF, Bilotta JM, Schuster SV, Lahey AP, Lutz MW, Johnson MR, Leighton HJ..  (1991)  Design, synthesis, and pharmacological evaluation of ultrashort- to long-acting opioid analgetics.,  34  (7): [PMID:2066993] [10.1021/jm00111a041]

2. Metcalf MD, Aceto MD, Harris LS, Woods JH, Traynor JR, Coop A, May EL..  (2008)  The influence of esters and carboxylic acids as the N-substituent of opioids. Part 1: Benzomorphans.,  16  (2): [PMID:17962026] [10.1016/j.bmc.2007.10.030]

Source

Source(1):

• Scientific Literature