2N-(3-amino-3-imminopropyl)-1-methyl-4-(1-methyl-4-trichloromethylcarboxamido-1H-2-pyrrolylcarboxamido)-1H-2-pyrrolecarboxamide chloride

ID: ALA116032

PubChem CID: 49796528

Max Phase: Preclinical

Molecular Formula: C17H21Cl4N7O3

Molecular Weight: 476.75

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C17H20Cl3N7O3.ClH/c1-26-7-9(5-11(26)14(28)23-4-3-13(21)22)24-15(29)12-6-10(8-27(12)2)25-16(30)17(18,19)20;/h5-8H,3-4H2,1-2H3,(H3,21,22)(H,23,28)(H,24,29)(H,25,30);1H

Standard InChI Key:  QTIRYPVJBNVXRR-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 31 31  0  0  0  0  0  0  0  0999 V2000
   11.9917   -4.1167    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.8500   -3.6292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1167   -4.3667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1792   -4.1167    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.4417   -4.8542    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6375   -3.8792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0292   -3.5792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7667   -2.8417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5917   -2.8417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8542   -3.5792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8708   -3.0167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5375   -2.2625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5167   -3.6292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7792   -4.3667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2417   -3.3292    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.9000   -4.6167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2792   -2.1750    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.3042   -3.4667    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.6917   -4.0167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8042   -4.6875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0250   -1.5917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9042   -3.7667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0667   -5.4292    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5125   -4.0667    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6958   -3.1042    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -0.3875   -3.6792    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -1.5125   -2.5000    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    8.8667   -4.8292    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.2917   -4.3167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4417   -5.6792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1792   -4.9417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  3 10  2  0
  4  2  1  0
  5 14  1  0
  6  2  1  0
  7 15  1  0
  8  9  1  0
  9  2  2  0
 10  7  1  0
 11 12  1  0
 12 17  1  0
 13  4  1  0
 14  7  2  0
 15  6  1  0
 16  3  1  0
 17  8  1  0
 18 19  2  0
 19 22  1  0
 20  6  2  0
 21 12  2  0
 22 29  1  0
 23 16  2  0
 24 16  1  0
 25 11  1  0
 26 11  1  0
 27 11  1  0
 28 19  1  0
 29 24  1  0
 30  5  1  0
 31  4  1  0
 13  8  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: 476.75

Molecular Weight (Monoisotopic): 475.0693

AlogP: 1.98

#Rotatable Bonds: 7

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: 11.91

CX Basic pKa: 12.67

CX LogP: -0.12

CX LogD: -1.86

Aromatic Rings: 2

Heavy Atoms: 30

QED Weighted: 0.24

Np Likeness Score: -0.79

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