2N-[5-(3-amino-3-iminopropylcarbamoyl)-1-methyl-1H-3-pyrrolyl]-4-(4-formamido-1-methyl-1H-2-pyrrolylcarboxamido)-1-methyl-1H-2-pyrrolecarboxamide hydrochloride (congocidine)

ID: ALA115422

Cas Number: 18133-22-7

PubChem CID: 12303839

Max Phase: Preclinical

Molecular Formula: C18H28Cl2N10O3

Molecular Weight: 430.47

Molecule Type: Small molecule

Names and Identifiers

Synonyms: congocidine | Netropsin dihydrochloride|Netropsin (dihydrochloride)|18133-22-7|Congocidine|NETROPSIN DIHYDROCHLORIDE HYDRATE|CHEMBL115422|Netropsin hydrochloride (1:2)|SCHEMBL4953090|HY-N6800A|DTXSID90417704|CHEBI:201440|AKOS040733845|MS-29348|CS-0092637|Netropsin dihydrochloride, from Streptomyces netropsis, >=98% (HPLC and TLC), powder|N-[5-[(3-amino-3-iminopropyl)carbamoyl]-1-methylpyrrol-3-yl]-4-[[2-(diaminomethylideneamino)acetyl]amino]-1-methylpyrrole-2-carboxamide;dihydrochloride

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

Standard InChI:  InChI=1S/C18H26N10O3.2ClH/c1-27-9-11(6-12(27)16(30)23-4-3-14(19)20)26-17(31)13-5-10(8-28(13)2)25-15(29)7-24-18(21)22;;/h5-6,8-9H,3-4,7H2,1-2H3,(H3,19,20)(H,23,30)(H,25,29)(H,26,31)(H4,21,22,24);2*1H

Standard InChI Key:  SDRHUASONSRLFR-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 33 32  0  0  0  0  0  0  0  0999 V2000
   -1.9708   -2.8667    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.0875   -5.2417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5792   -4.0250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0875   -6.0542    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.8875   -3.6375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7875   -4.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1875   -4.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3875   -4.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5792   -4.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7125   -6.0542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1875   -4.0250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3875   -6.4667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4875   -5.2417    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.1417   -3.9917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2667   -3.6375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5583   -3.6167    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.8125   -4.0042    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.1250   -3.6167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1042   -6.4292    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5875   -6.0292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1167   -4.8375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7875   -4.0250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.4042   -4.0167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2667   -2.7292    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2875   -6.4542    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9792   -4.0250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.8417   -3.5792    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5875   -5.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1250   -2.7792    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.6792   -3.6167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7875   -6.4667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8875   -2.7917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2917   -4.1167    0.0000 Cl  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 21  1  0
 15  3  1  0
 16 14  2  0
 17 18  2  0
 18 23  1  0
 19 10  1  0
 20 19  1  0
 21 28  1  0
 22  6  2  0
 23 30  1  0
 24 15  2  0
 25 20  2  0
 26 15  1  0
 27 14  1  0
 28 20  1  0
 29 18  1  0
 30 26  1  0
 31  4  1  0
 32  5  1  0
 10 12  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: 430.47

Molecular Weight (Monoisotopic): 430.2189

AlogP: -0.91

#Rotatable Bonds: 9

Polar Surface Area: 208.93

Molecular Species: BASE

HBA: 7

HBD: 8

#RO5 Violations: 1

HBA (Lipinski): 13

HBD (Lipinski): 10

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 13.08

CX Basic pKa: 12.45

CX LogP: -2.81

CX LogD: -7.27

Aromatic Rings: 2

Heavy Atoms: 31

QED Weighted: 0.19

Np Likeness Score: -0.77

References

1. Bialer M, Yagen B, Mechoulam R, Becker Y..  (1980)  Structure-activity relationships of pyrrole amidine antiviral antibiotics. 2. Preparation of mono- and tripyrrole derivatives of congocidine.,  23  (10): [PMID:6252323] [10.1021/jm00184a018]

2. 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]

3. Lee M, Preti CS, Vinson E, Wyatt MD, Hartley JA..  (1994)  GC sequence specific recognition by an N-formamido, C-terminus-modified and imidazole-containing analogue of netropsin.,  37  (24): [PMID:7990106] [10.1021/jm00050a003]

Source

Source(1):

• Scientific Literature