(5S)-5-butyl-3-((4,4-difluorocyclohexyl)methyl)-9-(1-(4,6-dimethylpyrimidine-5-carbonyl)-4-methylpiperidin-4-yl)-1-oxa-3,9-diazaspiro[5.5]undecan-2-one

ID: ALA1078714

PubChem CID: 44555482

Max Phase: Preclinical

Molecular Formula: C32H49F2N5O3

Molecular Weight: 589.77

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCC[C@H]1CN(CC2CCC(F)(F)CC2)C(=O)OC12CCN(C1(C)CCN(C(=O)c3c(C)ncnc3C)CC1)CC2

Standard InChI:  InChI=1S/C32H49F2N5O3/c1-5-6-7-26-21-38(20-25-8-10-32(33,34)11-9-25)29(41)42-31(26)14-18-39(19-15-31)30(4)12-16-37(17-13-30)28(40)27-23(2)35-22-36-24(27)3/h22,25-26H,5-21H2,1-4H3/t26-/m0/s1

Standard InChI Key:  ZOUBVRYFOBAGOI-SANMLTNESA-N

Molfile:  

     RDKit          2D

 42 46  0  0  0  0  0  0  0  0999 V2000
    5.4250  -23.5958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3083  -25.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7167  -25.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5333  -25.7151    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9479  -25.0069    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5395  -24.2944    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7167  -24.2901    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0555  -25.6775    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8803  -25.6974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9147  -24.2722    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0899  -24.2522    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3420  -24.9571    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1646  -24.9359    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5594  -24.2104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3806  -24.1898    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8130  -24.8927    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4182  -25.6182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5909  -25.6407    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6378  -24.8709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0691  -25.5741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0312  -24.1457    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8945  -25.5490    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3257  -26.2515    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9323  -26.9776    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1032  -26.9970    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6757  -26.2938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8510  -26.3129    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2863  -24.8230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3019  -26.4256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7121  -27.1414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2973  -27.8546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7075  -28.5704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9550  -23.5817    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7729  -25.0107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1886  -24.2981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0121  -24.3051    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1961  -22.8721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7758  -23.5851    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5833  -24.3458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0220  -22.8778    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8085  -22.0809    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    5.8189  -22.6643    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  1  0
 16 19  1  0
 19 20  1  0
 19 21  2  0
  2  7  1  0
 20 22  2  0
  8 12  1  0
 22 23  1  0
  9  2  1  0
 23 24  2  0
  2 10  1  0
 24 25  1  0
 10 11  1  0
 25 26  2  0
 26 20  1  0
 11 12  1  0
 26 27  1  0
 13 14  1  0
 22 28  1  0
  3  4  1  0
  3 29  1  6
  4  5  1  0
 29 30  1  0
  5  6  1  0
 30 31  1  0
  6  7  1  0
 31 32  1  0
  8  9  1  0
  6 33  2  0
  5 34  1  0
 13 18  1  0
 34 35  1  0
 35 36  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 35 38  1  0
 36  1  1  0
  1 40  1  0
 40 37  1  0
 37 38  1  0
 12 13  1  0
 13 39  1  0
 40 41  1  0
 40 42  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1078714

   (5S)-5-butyl-3-((4,4-difluorocyclohexyl)methyl)-9-(1-(4,6-dimethylpyrimidine-5-carbonyl)-4-methylpiperidin-4-yl)-1-oxa-3,9-diazaspiro[5.5]undecan-2-one

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: 589.77

Molecular Weight (Monoisotopic): 589.3803

AlogP: 6.01

#Rotatable Bonds: 7

Polar Surface Area: 78.87

Molecular Species: BASE

HBA: 6

HBD: ┄

#RO5 Violations: 2

HBA (Lipinski): 8

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): 2

CX Acidic pKa: ┄

CX Basic pKa: 9.18

CX LogP: 3.02

CX LogD: 1.24

Aromatic Rings: 1

Heavy Atoms: 42

QED Weighted: 0.39

Np Likeness Score: -0.15

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