(3S,4S)-1-Cyclohexyl-4-([5-(2,4-difluoro-phenyl)-isoxazole-3-carbonyl]-amino)piperidine-3-carboxylic acid (1-pyridin-2-yl-cyclopropyl)-amide

ID: ALA4789874

PubChem CID: 141677978

Max Phase: Preclinical

Molecular Formula: C30H33F2N5O3

Molecular Weight: 549.62

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  O=C(N[C@H]1CCN(C2CCCCC2)C[C@@H]1C(=O)NC1(c2ccccn2)CC1)c1cc(-c2ccc(F)cc2F)on1

Standard InChI:  InChI=1S/C30H33F2N5O3/c31-19-9-10-21(23(32)16-19)26-17-25(36-40-26)29(39)34-24-11-15-37(20-6-2-1-3-7-20)18-22(24)28(38)35-30(12-13-30)27-8-4-5-14-33-27/h4-5,8-10,14,16-17,20,22,24H,1-3,6-7,11-13,15,18H2,(H,34,39)(H,35,38)/t22-,24-/m0/s1

Standard InChI Key:  DOLXGWIZOQOXAE-UPVQGACJSA-N

Molfile:  

 
     RDKit          2D

 40 45  0  0  0  0  0  0  0  0999 V2000
   23.4427  -28.6347    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.0382  -29.3446    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.8552  -29.3399    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.3559  -25.6644    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.0664  -25.2606    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.8081  -25.5945    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   24.3590  -24.9908    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.9551  -24.2804    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.1547  -24.4450    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.2899  -23.5373    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.1044  -23.4584    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.4417  -22.7150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.9656  -22.0497    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.1484  -22.1328    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.8148  -22.8765    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.3020  -21.3049    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   23.0018  -22.9587    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   21.6510  -25.2511    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.3504  -26.4816    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.6400  -26.8854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.9364  -26.4694    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2281  -26.8698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2184  -27.6873    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.9232  -28.1028    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.6377  -27.7008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5096  -28.0888    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8064  -27.6706    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0966  -28.0683    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0838  -28.8858    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7870  -29.3039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5030  -28.9047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.3425  -28.1144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.0530  -27.7107    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.3368  -28.9315    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   23.0359  -30.1622    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.3225  -30.5622    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.3165  -31.3786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.0218  -31.7930    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.7348  -31.3850    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.7373  -30.5699    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  2  1  0
  1  3  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9  5  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 10  1  0
  8 10  1  0
 13 16  1  0
 15 17  1  0
  4 18  2  0
  4 19  1  0
 20 19  1  6
 20 21  1  0
 20 25  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 26 27  1  0
 26 31  1  0
 27 28  1  0
 28 29  1  0
 29 30  1  0
 30 31  1  0
 23 26  1  0
 25 32  1  1
 32 33  2  0
 32 34  1  0
 34  2  1  0
  2 35  1  0
 35 36  2  0
 36 37  1  0
 37 38  2  0
 38 39  1  0
 39 40  2  0
 40 35  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4789874

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 549.62

Molecular Weight (Monoisotopic): 549.2551

AlogP: 4.57

#Rotatable Bonds: 7

Polar Surface Area: 100.36

Molecular Species: BASE

HBA: 6

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 8

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 12.40

CX Basic pKa: 9.41

CX LogP: 3.78

CX LogD: 1.78

Aromatic Rings: 3

Heavy Atoms: 40

QED Weighted: 0.45

Np Likeness Score: -1.49

References

1. Richard-Bildstein S,Aissaoui H,Pothier J,Schäfer G,Gnerre C,Lindenberg E,Lehembre F,Pouzol L,Guerry P.  (2020)  Discovery of the Potent, Selective, Orally Available CXCR7 Antagonist ACT-1004-1239.,  63  (24): [PMID:33314938] [10.1021/acs.jmedchem.0c01588]

Source

Source(1):

• Scientific Literature