((1S,2S,4R)-4-(1-(4-bromophenyl)cyclobutylamino)-2-(thiophen-3-yl)cyclohexyl)(4-(5-chloropyridin-2-yl)piperazin-1-yl)methanone

ID: ALA1940530

PubChem CID: 57398361

Max Phase: Preclinical

Molecular Formula: C30H34BrClN4OS

Molecular Weight: 614.05

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C([C@H]1CC[C@@H](NC2(c3ccc(Br)cc3)CCC2)C[C@@H]1c1ccsc1)N1CCN(c2ccc(Cl)cn2)CC1

Standard InChI:  InChI=1S/C30H34BrClN4OS/c31-23-4-2-22(3-5-23)30(11-1-12-30)34-25-7-8-26(27(18-25)21-10-17-38-20-21)29(37)36-15-13-35(14-16-36)28-9-6-24(32)19-33-28/h2-6,9-10,17,19-20,25-27,34H,1,7-8,11-16,18H2/t25-,26+,27-/m1/s1

Standard InChI Key:  ACVQDOWULDOCRR-KWXIBIRDSA-N

Molfile:  

     RDKit          2D

 38 43  0  0  0  0  0  0  0  0999 V2000
    2.6833  -25.9231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0958  -26.5065    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6791  -27.0940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2666  -26.5106    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1667  -25.9167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1667  -26.7417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5454  -27.1500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2574  -26.7417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2574  -25.9167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5454  -25.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9730  -25.5063    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.4020  -25.5104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1156  -25.9307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8307  -25.5210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8336  -24.6951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1153  -24.2807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4031  -24.6928    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5449  -27.9753    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1225  -28.4602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1325  -29.2448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9575  -29.2448    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.2123  -28.4602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8805  -27.1552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5956  -26.7437    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8793  -27.9802    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5991  -25.9155    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3101  -25.5041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0264  -25.9141    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0272  -26.7401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3117  -27.1560    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7409  -25.4958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7376  -24.6697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4503  -24.2556    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1666  -24.6665    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1590  -25.4958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4527  -25.9061    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8824  -24.2563    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    5.5487  -24.2838    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 19 20  2  0
 20 21  1  0
 21 22  1  0
 22 18  2  0
  7 18  1  6
  9 11  1  1
  6 23  1  1
 11  1  1  0
 23 24  1  0
  1  2  1  0
 23 25  2  0
 24 26  1  0
  1 12  1  0
  2  3  1  0
 12 13  2  0
  3  4  1  0
 13 14  1  0
 24 30  1  0
 26 27  1  0
 27 28  1  0
 28 29  1  0
 29 30  1  0
  4  1  1  0
 14 15  2  0
 31 32  2  0
  5  6  1  0
 32 33  1  0
 15 16  1  0
 33 34  2  0
  5 10  1  0
 34 35  1  0
 16 17  2  0
 35 36  2  0
 36 31  1  0
 28 31  1  0
 17 12  1  0
 34 37  1  0
 18 19  1  0
 15 38  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1940530

   [(1S,2S,4R)-4-[[1-(4-bromophenyl)cyclobutyl]amino]-2-thiophen-3-ylcyclohexyl]-[4-(5-chloropyridin-2-yl)piperazin-1-yl]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: 614.05

Molecular Weight (Monoisotopic): 612.1325

AlogP: 6.83

#Rotatable Bonds: 6

Polar Surface Area: 48.47

Molecular Species: BASE

HBA: 5

HBD: 1

#RO5 Violations: 2

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 2

CX Acidic pKa: ┄

CX Basic pKa: 9.49

CX LogP: 6.72

CX LogD: 4.65

Aromatic Rings: 3

Heavy Atoms: 38

QED Weighted: 0.33

Np Likeness Score: -1.55

References

1. Anthony Romero F, Hastings NB, Moningka R, Guo Z, Wang M, Di Salvo J, Lei Y, Trusca D, Deng Q, Tong V, Terebetski JL, Ball RG, Ujjainwalla F..  (2012)  The discovery of potent antagonists of NPBWR1 (GPR7).,  22  (2): [PMID:22197390] [10.1016/j.bmcl.2011.11.126]

Source

Source(1):

• Scientific Literature