N1,N1'-((5-(methylamino)-1,3-phenylene)bis(methylene))bis(N3-cyclohexylpropane-1,3-diamine)

ID: ALA5283630

Max Phase: Preclinical

Molecular Formula: C27H49N5

Molecular Weight: 443.72

Names and Identifiers

Canonical SMILES:  CNc1cc(CNCCCNC2CCCCC2)cc(CNCCCNC2CCCCC2)c1

Standard InChI:  InChI=1S/C27H49N5/c1-28-27-19-23(21-29-14-8-16-31-25-10-4-2-5-11-25)18-24(20-27)22-30-15-9-17-32-26-12-6-3-7-13-26/h18-20,25-26,28-32H,2-17,21-22H2,1H3

Standard InChI Key:  KIVIBJLRCRUXBC-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 32 34  0  0  0  0  0  0  0  0999 V2000
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    0.0013    0.8266    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7132    0.4147    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7132   -0.4104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.7132   -0.4141    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4278   -0.8267    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1425   -0.4141    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8571   -0.8267    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5717   -0.4141    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2864   -0.8267    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0010   -0.4141    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7156   -0.8267    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7156   -1.6518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4303   -2.0644    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1449   -1.6518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1449   -0.8267    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4303   -0.4141    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4278   -0.8230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1424   -0.4104    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8571   -0.8230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5717   -0.4104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2863   -0.8230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0010   -0.4104    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.7156   -0.8230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -0.4104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1449   -0.8230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1449   -1.6482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -2.0608    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7156   -1.6482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0013    1.6518    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7132    2.0644    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
  6  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
  4 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 26 25  1  0
 27 26  1  0
 28 27  1  0
 29 28  1  0
 30 29  1  0
 25 30  1  0
  2 31  1  0
 31 32  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA5283630

   ---

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: 443.72

Molecular Weight (Monoisotopic): 443.3988

AlogP: 4.53

#Rotatable Bonds: 15

Polar Surface Area: 60.15

Molecular Species: BASE

HBA: 5

HBD: 5

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 5

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 10.89

CX LogP: 3.55

CX LogD: -3.15

Aromatic Rings: 1

Heavy Atoms: 32

QED Weighted: 0.26

Np Likeness Score: -0.23

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