N'-[(1S)-1-(3-methyl-2-pyridyl)ethyl]-N'-[[(3R)-1,2,3,4-tetrahydroisoquinolin-3-yl]methyl]butane-1,4-diamine

ID: ALA4164685

PubChem CID: 135313960

Max Phase: Preclinical

Molecular Formula: C22H32N4

Molecular Weight: 352.53

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1cccnc1[C@H](C)N(CCCCN)C[C@H]1Cc2ccccc2CN1

Standard InChI:  InChI=1S/C22H32N4/c1-17-8-7-12-24-22(17)18(2)26(13-6-5-11-23)16-21-14-19-9-3-4-10-20(19)15-25-21/h3-4,7-10,12,18,21,25H,5-6,11,13-16,23H2,1-2H3/t18-,21+/m0/s1

Standard InChI Key:  KTOPELDEHJBGPW-GHTZIAJQSA-N

Molfile:  

     RDKit          2D

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   41.7479   -2.9541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.7468   -3.7814    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.4616   -4.1943    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   42.4598   -2.5413    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   43.1751   -2.9505    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   43.1740   -3.7836    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   43.8909   -4.1988    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   44.6135   -3.7856    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   43.8886   -5.0238    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   43.1729   -5.4343    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   44.6018   -5.4383    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   44.5995   -6.2633    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   45.3128   -6.6778    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   45.3104   -7.5027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   46.0238   -7.9172    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   43.1706   -6.2593    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.4539   -6.6676    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   42.4496   -7.4890    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   43.8844   -6.6704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   43.8785   -7.4981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   43.1610   -7.9053    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   43.1560   -8.7285    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   43.8677   -9.1453    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   44.5859   -8.7330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   44.5874   -7.9113    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   43.8891   -2.5370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  6  2  0
  5  4  2  0
  4  1  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  1  6
  9 10  1  0
  9 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 16 10  1  1
 16 17  1  0
 16 19  1  0
 17 18  1  0
 18 21  1  0
 20 19  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 20  1  0
  5 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4164685

   ---

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: 352.53

Molecular Weight (Monoisotopic): 352.2627

AlogP: 3.21

#Rotatable Bonds: 8

Polar Surface Area: 54.18

Molecular Species: BASE

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 10.22

CX LogP: 3.10

CX LogD: -1.01

Aromatic Rings: 2

Heavy Atoms: 26

QED Weighted: 0.72

Np Likeness Score: -0.09

References

1. Wilson RJ, Jecs E, Miller EJ, Nguyen HH, Tahirovic YA, Truax VM, Kim MB, Kuo KM, Wang T, Sum CS, Cvijic ME, Paiva AA, Schroeder GM, Wilson LJ, Liotta DC..  (2018)  Synthesis and SAR of 1,2,3,4-Tetrahydroisoquinoline-Based CXCR4 Antagonists.,  9  (1): [PMID:29348805] [10.1021/acsmedchemlett.7b00381]

Source

Source(1):

• Scientific Literature