(S)-5-(4-(5-butyl-3-methyl-2-oxo-1-oxa-3,9-diazaspiro[5.5]undecan-9-yl)-4-methylpiperidine-1-carbonyl)-4,6-dimethylpicolinonitrile

ID: ALA1078937

PubChem CID: 46883028

Max Phase: Preclinical

Molecular Formula: C28H41N5O3

Molecular Weight: 495.67

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCC[C@H]1CN(C)C(=O)OC12CCN(C1(C)CCN(C(=O)c3c(C)cc(C#N)nc3C)CC1)CC2

Standard InChI:  InChI=1S/C28H41N5O3/c1-6-7-8-22-19-31(5)26(35)36-28(22)11-15-33(16-12-28)27(4)9-13-32(14-10-27)25(34)24-20(2)17-23(18-29)30-21(24)3/h17,22H,6-16,19H2,1-5H3/t22-/m0/s1

Standard InChI Key:  LLQOAGQUGSEMLC-QFIPXVFZSA-N

Molfile:  

     RDKit          2D

 36 39  0  0  0  0  0  0  0  0999 V2000
   16.2667  -11.1542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6750  -11.8667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4917  -11.8693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9062  -11.1611    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.4979  -10.4486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6750  -10.4443    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.0139  -11.8316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8386  -11.8515    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8730  -10.4263    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0483  -10.4064    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6163  -11.1113    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.7938  -11.0900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3989  -10.3646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5777  -10.3439    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1453  -11.0469    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.5402  -11.7724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3675  -11.7948    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3206  -11.0250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8893  -11.7283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9272  -10.2999    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.0638  -11.7032    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6326  -12.4056    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.0261  -13.1318    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8551  -13.1511    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2826  -12.4480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1074  -12.4670    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6720  -10.9772    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2602  -12.5798    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6704  -13.2956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2557  -14.0088    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6659  -14.7245    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9134   -9.7358    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.7312  -11.1648    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3750  -10.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5957  -13.8356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1743  -14.5409    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 11 12  1  0
  2  3  1  0
 15 18  1  0
  3  4  1  0
 18 19  1  0
  7 11  1  0
 18 20  2  0
  8  1  1  0
 19 21  2  0
  1  9  1  0
 21 22  1  0
  9 10  1  0
 22 23  2  0
 10 11  1  0
 23 24  1  0
 12 13  1  0
 24 25  2  0
 25 19  1  0
  4  5  1  0
 25 26  1  0
  5  6  1  0
 21 27  1  0
  7  8  1  0
  2 28  1  6
 28 29  1  0
  1  2  1  0
 29 30  1  0
  1  6  1  0
 30 31  1  0
 12 17  1  0
  5 32  2  0
 13 14  1  0
  4 33  1  0
 14 15  1  0
 12 34  1  0
 15 16  1  0
 23 35  1  0
 16 17  1  0
 35 36  3  0
M  END

Alternative Forms

1. Parent:

   

   ALA1078937

   (S)-5-(4-(5-butyl-3-methyl-2-oxo-1-oxa-3,9-diazaspiro[5.5]undecan-9-yl)-4-methylpiperidine-1-carbonyl)-4,6-dimethylpicolinonitrile

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: 495.67

Molecular Weight (Monoisotopic): 495.3209

AlogP: 4.29

#Rotatable Bonds: 5

Polar Surface Area: 89.77

Molecular Species: BASE

HBA: 6

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 9.20

CX LogP: 2.75

CX LogD: 0.95

Aromatic Rings: 1

Heavy Atoms: 36

QED Weighted: 0.61

Np Likeness Score: -0.16

References

1. Rotstein DM, Gabriel SD, Makra F, Filonova L, Gleason S, Brotherton-Pleiss C, Setti LQ, Trejo-Martin A, Lee EK, Sankuratri S, Ji C, Derosier A, Dioszegi M, Heilek G, Jekle A, Berry P, Weller P, Mau CI..  (2009)  Spiropiperidine CCR5 antagonists.,  19  (18): [PMID:19674898] [10.1016/j.bmcl.2009.07.122]

Source

Source(1):

• Scientific Literature