N-(4-(3-(4-isopropylpiperazin-1-yl)prop-1-yn-1-yl)benzyl)-2-methoxy-N-neopentyl-pyrimidin-4-amine

ID: ALA4068102

PubChem CID: 137632699

Max Phase: Preclinical

Molecular Formula: C27H39N5O

Molecular Weight: 449.64

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1nccc(N(Cc2ccc(C#CCN3CCN(C(C)C)CC3)cc2)CC(C)(C)C)n1

Standard InChI:  InChI=1S/C27H39N5O/c1-22(2)31-18-16-30(17-19-31)15-7-8-23-9-11-24(12-10-23)20-32(21-27(3,4)5)25-13-14-28-26(29-25)33-6/h9-14,22H,15-21H2,1-6H3

Standard InChI Key:  RHRLEMPWTIKNII-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 33 35  0  0  0  0  0  0  0  0999 V2000
    3.0734  -11.9524    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0722  -12.7761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7844  -13.1850    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.4982  -12.7756    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4954  -11.9488    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7826  -11.5394    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7802  -10.7181    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.4908  -10.3074    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0671  -10.3116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0647   -9.4903    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3516   -9.0797    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7753   -9.0755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0583   -8.6672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1997  -10.7139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2000  -11.5326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9122  -11.9431    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6238  -11.5282    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6187  -10.7027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9059  -10.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3353  -11.9342    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0489  -12.3398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7625  -12.7494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4725  -12.3337    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.1801  -12.7452    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8881  -12.3329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8888  -11.5112    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.1753  -11.1035    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4653  -11.5134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6004  -11.1023    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3125  -11.5105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6000  -10.2809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2060  -13.1840    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2063  -14.0012    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  1  1  0
  6  7  1  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 10 12  1  0
 10 13  1  0
  8 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 14  1  0
 20 21  3  0
 17 20  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 23 28  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 26 29  1  0
 29 30  1  0
 29 31  1  0
  4 32  1  0
 32 33  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4068102

   ---

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: 449.64

Molecular Weight (Monoisotopic): 449.3155

AlogP: 3.92

#Rotatable Bonds: 7

Polar Surface Area: 44.73

Molecular Species: NEUTRAL

HBA: 6

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 8.29

CX LogP: 5.66

CX LogD: 4.71

Aromatic Rings: 2

Heavy Atoms: 33

QED Weighted: 0.60

Np Likeness Score: -1.32

References

1. Miltz W, Velcicky J, Dawson J, Littlewood-Evans A, Ludwig MG, Seuwen K, Feifel R, Oberhauser B, Meyer A, Gabriel D, Nash M, Loetscher P..  (2017)  Design and synthesis of potent and orally active GPR4 antagonists with modulatory effects on nociception, inflammation, and angiogenesis.,  25  (16): [PMID:28689977] [10.1016/j.bmc.2017.06.050]

Source

Source(1):

• Scientific Literature