N1,N3-bis(4-carbamimidoylphenethyl)malonamide

ID: ALA5265971

Max Phase: Preclinical

Molecular Formula: C21H26N6O2

Molecular Weight: 394.48

Names and Identifiers

Canonical SMILES:  N=C(N)c1ccc(CCNC(=O)CC(=O)NCCc2ccc(C(=N)N)cc2)cc1

Standard InChI:  InChI=1S/C21H26N6O2/c22-20(23)16-5-1-14(2-6-16)9-11-26-18(28)13-19(29)27-12-10-15-3-7-17(8-4-15)21(24)25/h1-8H,9-13H2,(H3,22,23)(H3,24,25)(H,26,28)(H,27,29)

Standard InChI Key:  UMWOKGIVZJWFOR-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 29 30  0  0  0  0  0  0  0  0999 V2000
   -5.0004    0.0007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2858    0.4130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5739    0.0010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5739   -0.8240    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2840   -1.2358    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0004   -0.8277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8592   -1.2366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1446   -0.8240    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4299   -1.2366    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7153   -0.8240    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0007   -1.2366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7153    0.0010    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7139   -0.8240    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4285   -1.2366    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7139    0.0010    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1431   -0.8240    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8578   -1.2366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.8240    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5726    0.0011    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2855    0.4118    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0004   -0.0008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0019   -0.8219    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2901   -1.2384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7150    0.4117    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7150    1.2369    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.4296   -0.0008    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7150    0.4133    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4296    0.0007    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7150    1.2384    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  2  1  0
  4  3  2  0
  5  4  1  0
  1  6  1  0
  6  5  2  0
  4  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 10 12  2  0
 11 13  1  0
 13 14  1  0
 13 15  2  0
 14 16  1  0
 16 17  1  0
 17 18  1  0
 19 18  2  0
 20 19  1  0
 21 20  2  0
 22 21  1  0
 23 22  2  0
 18 23  1  0
 21 24  1  0
 24 25  2  0
 24 26  1  0
  1 27  1  0
 27 28  1  0
 27 29  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA5265971

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type:

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 394.48

Molecular Weight (Monoisotopic): 394.2117

AlogP: 0.66

#Rotatable Bonds: 10

Polar Surface Area: 157.94

Molecular Species: BASE

HBA: 4

HBD: 6

#RO5 Violations: 1

HBA (Lipinski): 8

HBD (Lipinski): 8

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 13.23

CX Basic pKa: 11.79

CX LogP: 0.14

CX LogD: -4.44

Aromatic Rings: 2

Heavy Atoms: 29

QED Weighted: 0.20

Np Likeness Score: -0.26

References

1. Hammerschmidt SJ, Maus H, Weldert AC, Gütschow M, Kersten C..  (2023)  Improving binding entropy by higher ligand symmetry? - A case study with human matriptase.,  14  (5): [PMID:37252099] [10.1039/d3md00125c]

Source

Source(1):

• Scientific Literature