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

ID: ALA116694

PubChem CID: 49796526

Max Phase: Preclinical

Molecular Formula: C17H23ClFN7O3

Molecular Weight: 391.41

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C17H22FN7O3.ClH/c1-24-9-11(6-12(24)16(27)21-4-3-14(19)20)23-17(28)13-5-10(8-25(13)2)22-15(26)7-18;/h5-6,8-9H,3-4,7H2,1-2H3,(H3,19,20)(H,21,27)(H,22,26)(H,23,28);1H

Standard InChI Key:  MWLCXCQAAAEEJO-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 29 29  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
    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
    0.7667   -2.8417    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
    0.5167   -3.6292    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
    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
    0.2792   -2.1750    0.0000 N   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
    2.8042   -4.6875    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
   -1.0250   -1.5917    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
    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
   -1.6958   -3.1042    0.0000 F   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
  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 29  1  0
 29 18  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: 391.41

Molecular Weight (Monoisotopic): 391.1768

AlogP: 0.58

#Rotatable Bonds: 8

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: 12.87

CX Basic pKa: 12.27

CX LogP: -1.69

CX LogD: -3.54

Aromatic Rings: 2

Heavy Atoms: 28

QED Weighted: 0.33

Np Likeness Score: -0.81

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