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

ID: ALA4168126

PubChem CID: 135313576

Max Phase: Preclinical

Molecular Formula: C21H30N4

Molecular Weight: 338.50

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C[C@@H](c1ccccn1)N(CCCCN)C[C@H]1Cc2ccccc2CN1

Standard InChI:  InChI=1S/C21H30N4/c1-17(21-10-4-6-12-23-21)25(13-7-5-11-22)16-20-14-18-8-2-3-9-19(18)15-24-20/h2-4,6,8-10,12,17,20,24H,5,7,11,13-16,22H2,1H3/t17-,20+/m0/s1

Standard InChI Key:  MEPBMCYDMSNDHL-FXAWDEMLSA-N

Molfile:  

     RDKit          2D

 25 27  0  0  0  0  0  0  0  0999 V2000
   27.6083   -2.7209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.6072   -3.5484    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.3220   -3.9612    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   28.3202   -2.3082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.0356   -2.7173    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.0344   -3.5504    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.7513   -3.9657    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.4741   -3.5525    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.7490   -4.7908    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   29.0333   -5.2013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.4623   -5.2052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.4600   -6.0303    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.1733   -6.4448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.1710   -7.2699    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.8844   -7.6844    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   29.0310   -6.0262    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.3142   -6.4346    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   28.3100   -7.2560    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.7449   -6.4376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.7390   -7.2652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.0214   -7.6725    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.0164   -8.4956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.7281   -8.9126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.4464   -8.5003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.4479   -7.6784    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
M  END

Alternative Forms

1. Parent:

   

   ALA4168126

   ---

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: 338.50

Molecular Weight (Monoisotopic): 338.2470

AlogP: 2.90

#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: 2.59

CX LogD: -1.49

Aromatic Rings: 2

Heavy Atoms: 25

QED Weighted: 0.73

Np Likeness Score: -0.37

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