3-(2-aminoethylamino)-1-methyl-4-(1-methyl-1H-indol-3-yl)-1H-pyrrole-2,5-dione hydrochloride

ID: ALA4280743

PubChem CID: 145981248

Max Phase: Preclinical

Molecular Formula: C16H19ClN4O2

Molecular Weight: 298.35

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CN1C(=O)C(NCCN)=C(c2cn(C)c3ccccc23)C1=O.Cl

Standard InChI:  InChI=1S/C16H18N4O2.ClH/c1-19-9-11(10-5-3-4-6-12(10)19)13-14(18-8-7-17)16(22)20(2)15(13)21;/h3-6,9,18H,7-8,17H2,1-2H3;1H

Standard InChI Key:  LSSCXPYOGQVZEC-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 23 24  0  0  0  0  0  0  0  0999 V2000
   17.1777   -6.6589    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   10.0814   -7.5817    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0803   -8.4012    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7883   -8.8102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7865   -7.1728    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4951   -7.5781    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4999   -8.3967    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2800   -8.6451    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.7573   -7.9800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2722   -7.3206    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5177   -6.5425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2933   -6.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2885   -5.4682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5098   -5.2202    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.0335   -5.8842    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5370   -9.4209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2163   -5.8890    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.9468   -4.9840    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.2527   -4.4445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9573   -6.7618    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.7018   -6.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3658   -6.9015    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1103   -6.5647    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  2  0
  3  4  1  0
  4  7  2  0
  6  5  2  0
  5  2  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10  6  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 11  1  0
 10 11  1  0
  8 16  1  0
 15 17  2  0
 13 18  2  0
 14 19  1  0
 12 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  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: 298.35

Molecular Weight (Monoisotopic): 298.1430

AlogP: 0.44

#Rotatable Bonds: 4

Polar Surface Area: 80.36

Molecular Species: BASE

HBA: 5

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 9.07

CX LogP: 0.06

CX LogD: -1.60

Aromatic Rings: 2

Heavy Atoms: 22

QED Weighted: 0.80

Np Likeness Score: -0.41

References

1. Dodo K, Shimizu T, Sasamori J, Aihara K, Terayama N, Nakao S, Iuchi K, Takahashi M, Sodeoka M..  (2018)  Indolylmaleimide Derivative IM-17 Shows Cardioprotective Effects in Ischemia-Reperfusion Injury.,  9  (3): [PMID:29541357] [10.1021/acsmedchemlett.7b00454]

2. Dodo K, Kuboki E, Shimizu T, Imamura R, Magarisawa M, Takahashi M, Tokuhiro T, Yotsumoto S, Asano K, Nakao S, Terayama N, Suda T, Tanaka M, Sodeoka M..  (2019)  Development of a Water-Soluble Indolylmaleimide Derivative IM-93 Showing Dual Inhibition of Ferroptosis and NETosis.,  10  (9): [PMID:31531196] [10.1021/acsmedchemlett.9b00142]

Source

Source(1):

• Scientific Literature