2N-(3-amino-3-imminopropyl)-4-[4-(3-chloropropylcarboxamido)-1-methyl-1H-2-pyrrolylcarboxamido]-1-methyl-1H-2-pyrrolecarboxamide chloride

ID: ALA117594

PubChem CID: 49796524

Max Phase: Preclinical

Molecular Formula: C19H27Cl2N7O3

Molecular Weight: 435.92

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cl.Cn1cc(NC(=O)c2cc(NC(=O)CCCCl)cn2C)cc1C(=O)NCCC(=N)N

Standard InChI:  InChI=1S/C19H26ClN7O3.ClH/c1-26-11-13(9-14(26)18(29)23-7-5-16(21)22)25-19(30)15-8-12(10-27(15)2)24-17(28)4-3-6-20;/h8-11H,3-7H2,1-2H3,(H3,21,22)(H,23,29)(H,24,28)(H,25,30);1H

Standard InChI Key:  XAWZKXXPCNXZJC-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 31 31  0  0  0  0  0  0  0  0999 V2000
   11.9000   -5.9292    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.6292   -6.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8917   -7.1500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9542   -6.9000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2167   -7.6375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4167   -6.6667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8042   -6.3667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3667   -5.6250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6292   -6.3667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5417   -5.6250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5542   -7.1500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2917   -6.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0167   -6.1125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.6792   -7.4042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0792   -6.2542    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.4667   -6.8042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0542   -4.9542    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7583   -5.0417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5792   -7.4667    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6792   -6.5500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8417   -8.2125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2458   -4.3792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2917   -6.8500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.6417   -7.6125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.0667   -7.1042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2167   -8.4542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9542   -7.7250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0708   -6.7292    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -1.0958   -5.8000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2458   -6.6417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9125   -5.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  3  9  2  0
  4  2  1  0
  5 11  1  0
  6  2  1  0
  7 13  1  0
  8  2  2  0
  9  7  1  0
 10  8  1  0
 11  7  2  0
 12  4  1  0
 13  6  1  0
 14  3  1  0
 15 16  2  0
 16 20  1  0
 17 10  1  0
 18 17  1  0
 19  6  2  0
 20 25  1  0
 21 14  2  0
 22 18  2  0
 23 14  1  0
 24 16  1  0
 25 23  1  0
 26  5  1  0
 27  4  1  0
 28 30  1  0
 29 18  1  0
 30 31  1  0
 31 29  1  0
 12 10  2  0
  3  5  1  0
M  END

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: 435.92

Molecular Weight (Monoisotopic): 435.1786

AlogP: 1.63

#Rotatable Bonds: 10

Polar Surface Area: 147.03

Molecular Species: BASE

HBA: 6

HBD: 5

#RO5 Violations: ┄

HBA (Lipinski): 10

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 13.63

CX Basic pKa: 12.53

CX LogP: -0.35

CX LogD: -2.55

Aromatic Rings: 2

Heavy Atoms: 30

QED Weighted: 0.22

Np Likeness Score: -0.84

References

1. Krowicki K, Balzarini J, De Clercq E, Newman RA, Lown JW..  (1988)  Novel DNA groove binding alkylators: design, synthesis, and biological evaluation.,  31  (2): [PMID:2828620] [10.1021/jm00397a012]

Source

Source(1):

• Scientific Literature