N1,N1'-((2-amino-1,4-phenylene)bis(methylene))bis(N3-cyclohexylpropane-1,3-diamine)

ID: ALA5277914

Max Phase: Preclinical

Molecular Formula: C26H47N5

Molecular Weight: 429.70

Names and Identifiers

Canonical SMILES:  Nc1cc(CNCCCNC2CCCCC2)ccc1CNCCCNC1CCCCC1

Standard InChI:  InChI=1S/C26H47N5/c27-26-19-22(20-28-15-7-17-30-24-9-3-1-4-10-24)13-14-23(26)21-29-16-8-18-31-25-11-5-2-6-12-25/h13-14,19,24-25,28-31H,1-12,15-18,20-21,27H2

Standard InChI Key:  LNDFVHJUTHVAAE-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 31 33  0  0  0  0  0  0  0  0999 V2000
   -0.7132    0.4124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0013    0.8246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7132    0.4127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7132   -0.4124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0031   -0.8242    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7132   -0.4161    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4278   -0.8249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1424   -0.4124    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8571   -0.8249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5717   -0.4124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2863   -0.8249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0010   -0.4124    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.7156   -0.8249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -0.4124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1449   -0.8249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1449   -1.6502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -2.0627    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7156   -1.6502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0013    1.6498    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4278    0.8249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1425    0.4124    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8571    0.8249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5717    0.4124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2864    0.8249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0011    0.4124    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7156    0.8249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4303    0.4124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1449    0.8249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1449    1.6501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4303    2.0627    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7156    1.6501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  2  1  0
  4  3  2  0
  5  4  1  0
  6  5  2  0
  1  6  1  0
  4  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 14 13  1  0
 15 14  1  0
 16 15  1  0
 17 16  1  0
 18 17  1  0
 13 18  1  0
 19  2  1  0
  1 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 27 26  1  0
 28 27  1  0
 29 28  1  0
 30 29  1  0
 31 30  1  0
 26 31  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA5277914

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type:

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 429.70

Molecular Weight (Monoisotopic): 429.3831

AlogP: 4.07

#Rotatable Bonds: 14

Polar Surface Area: 74.14

Molecular Species: BASE

HBA: 5

HBD: 5

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: 10.88

CX LogP: 3.25

CX LogD: -3.32

Aromatic Rings: 1

Heavy Atoms: 31

QED Weighted: 0.23

Np Likeness Score: -0.30

References

1. Fang X, Meng Q, Zhang H, Liang B, Zhu S, Wang J, Zhang C, Huang LS, Zhang X, Schooley RT, An J, Xu Y, Huang Z..  (2020)  Design, synthesis, and biological characterization of a new class of symmetrical polyamine-based small molecule CXCR4 antagonists.,  200  [PMID:32492596] [10.1016/j.ejmech.2020.112410]

Source

Source(1):

• Scientific Literature