N-(3-(dimethylamino)propyl)-1-methyl-4-(1-methyl-4-(1-methyl-4-nitro-1H-pyrrole-2-carboxamido)-1H-pyrrole-2-carboxamido)-1H-pyrrole-2-carboxamide hydrochloride

ID: ALA4758715

PubChem CID: 10324848

Max Phase: Preclinical

Molecular Formula: C23H31ClN8O5

Molecular Weight: 498.54

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CN(C)CCCNC(=O)c1cc(NC(=O)c2cc(NC(=O)c3cc([N+](=O)[O-])cn3C)cn2C)cn1C.Cl

Standard InChI:  InChI=1S/C23H30N8O5.ClH/c1-27(2)8-6-7-24-21(32)18-9-15(12-28(18)3)25-22(33)19-10-16(13-29(19)4)26-23(34)20-11-17(31(35)36)14-30(20)5;/h9-14H,6-8H2,1-5H3,(H,24,32)(H,25,33)(H,26,34);1H

Standard InChI Key:  HUPDDIXFGOHDJZ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 37 38  0  0  0  0  0  0  0  0999 V2000
   16.4284   -4.2814    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   12.2707   -9.2124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0956   -9.2124    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.3525   -8.4283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6832   -7.9416    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0181   -8.4283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5798   -9.8804    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1375   -8.1745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7498   -8.7273    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.3101   -7.3678    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.0950   -7.1139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2677   -6.3071    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0527   -6.0533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2253   -5.2466    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.2334   -8.1737    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.6206   -8.7260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8358   -8.4715    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7925   -9.5329    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.5807   -7.6900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7557   -7.6903    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5012   -8.4751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1688   -8.9596    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.1705   -9.7846    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2705   -7.0231    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.4500   -7.1097    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9649   -6.4425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1149   -7.8636    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2177   -5.6601    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5500   -5.1754    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8827   -5.6607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1381   -6.4451    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.6545   -7.1135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6130   -4.6937    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0103   -4.9927    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5462   -4.3479    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.8315   -3.9357    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2605   -3.9351    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  2  2  0
  3  7  1  0
  4  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
  6 15  1  0
 15 16  1  0
 16 17  1  0
 16 18  2  0
 17 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 17  1  0
 22 23  1  0
 20 24  1  0
 24 25  1  0
 25 26  1  0
 25 27  2  0
 26 28  2  0
 28 29  1  0
 29 30  2  0
 30 31  1  0
 31 26  1  0
 31 32  1  0
 14 33  1  0
 14 34  1  0
 35 36  2  0
 35 37  1  0
 29 35  1  0
M  CHG  2  35   1  37  -1
M  END

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 498.54

Molecular Weight (Monoisotopic): 498.2339

AlogP: 1.80

#Rotatable Bonds: 10

Polar Surface Area: 148.47

Molecular Species: BASE

HBA: 9

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 13

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: 9.30

CX LogP: 0.92

CX LogD: -0.97

Aromatic Rings: 3

Heavy Atoms: 36

QED Weighted: 0.22

Np Likeness Score: -1.00

References

1. Kumari S,Carmona AV,Tiwari AK,Trippier PC.  (2020)  Amide Bond Bioisosteres: Strategies, Synthesis, and Successes.,  63  (21.0): [PMID:32686940] [10.1021/acs.jmedchem.0c00530]

Source

Source(1):

• Scientific Literature