(3-tert-Butyl-pyrrolidin-1-yl)-(4-hexyloxy-phenyl)-methanone

ID: ALA121822

PubChem CID: 10892912

Max Phase: Preclinical

Molecular Formula: C21H33NO2

Molecular Weight: 331.50

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCCCCOc1ccc(C(=O)N2CCC(C(C)(C)C)C2)cc1

Standard InChI:  InChI=1S/C21H33NO2/c1-5-6-7-8-15-24-19-11-9-17(10-12-19)20(23)22-14-13-18(16-22)21(2,3)4/h9-12,18H,5-8,13-16H2,1-4H3

Standard InChI Key:  MFKDNMHZILMJII-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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    6.6292   -3.5500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.1125   -3.2542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7042   -4.1417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2917   -4.2667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5917   -3.5542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1792   -3.3042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5375   -4.8167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1042   -2.6542    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5875   -3.7417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5917   -4.1625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0750   -3.2542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5542   -4.1625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0750   -4.4625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5542   -3.5625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0375   -4.4625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1875   -5.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1292   -4.8750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8292   -5.3292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5167   -4.1625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0000   -4.4625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4417   -4.1542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9542   -4.4542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4792   -4.1542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9167   -4.4542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  1  1  0
  4  3  1  0
  5  2  1  0
  6  1  1  0
  7  4  1  0
  8  2  2  0
  9  6  1  0
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 11  5  2  0
 12 14  2  0
 13 10  2  0
 14 11  1  0
 15 12  1  0
 16  7  1  0
 17  7  1  0
 18  7  1  0
 19 15  1  0
 20 19  1  0
 21 22  1  0
 22 23  1  0
 23 20  1  0
 24 21  1  0
  9  4  1  0
 13 12  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA121822

   (3-tert-Butyl-pyrrolidin-1-yl)-(4-hexyloxy-phenyl)-methanone

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: 331.50

Molecular Weight (Monoisotopic): 331.2511

AlogP: 5.15

#Rotatable Bonds: 7

Polar Surface Area: 29.54

Molecular Species: NEUTRAL

HBA: 2

HBD: ┄

#RO5 Violations: 1

HBA (Lipinski): 3

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 5.13

CX LogD: 5.13

Aromatic Rings: 1

Heavy Atoms: 24

QED Weighted: 0.65

Np Likeness Score: -0.93

References

1. Lloyd J, Schmidt JB, Rovnyak G, Ahmad S, Atwal KS, Bisaha SN, Doweyko LM, Stein PD, Traeger SC, Mathur A, Conder ML, DiMarco J, Harper TW, Jenkins-West T, Levesque PC, Normandin DE, Russell AD, Serafino RP, Smith MA, Lodge NJ..  (2001)  Design and synthesis of 4-substituted benzamides as potent, selective, and orally bioavailable I(Ks) blockers.,  44  (23): [PMID:11689063] [10.1021/jm015505u]

Source

Source(1):

• Scientific Literature