(S)-N-(4-carbamimidoylbenzyl)-1-(2-phenylacetyl)pyrrolidine-2-carboxamide

ID: ALA4519966

PubChem CID: 155542064

Max Phase: Preclinical

Molecular Formula: C21H24N4O2

Molecular Weight: 364.45

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  N=C(N)c1ccc(CNC(=O)[C@@H]2CCCN2C(=O)Cc2ccccc2)cc1

Standard InChI:  InChI=1S/C21H24N4O2/c22-20(23)17-10-8-16(9-11-17)14-24-21(27)18-7-4-12-25(18)19(26)13-15-5-2-1-3-6-15/h1-3,5-6,8-11,18H,4,7,12-14H2,(H3,22,23)(H,24,27)/t18-/m0/s1

Standard InChI Key:  LPZOJXOENRGTKT-SFHVURJKSA-N

Molfile:  

 
     RDKit          2D

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   25.9933   -3.6980    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.9878   -2.8817    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   26.6437   -2.3943    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.3845   -1.6191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.5648   -1.6276    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.3237   -2.4075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.4233   -2.6393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.6009   -3.4369    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   28.0252   -2.0866    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   28.3805   -3.6820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.5581   -4.4796    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.9534   -5.0286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.1305   -5.8256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.9108   -6.0713    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.5141   -5.5138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.3339   -4.7189    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.0894   -6.8687    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.4882   -7.4221    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   29.8694   -7.1127    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   25.2917   -4.1142    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.5802   -3.7123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.5777   -2.8960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.8670   -2.4942    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.1622   -2.9096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.1727   -3.7310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.8839   -4.1290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.7048   -4.1000    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  1  0
  5  6  1  0
  6  2  1  0
  3  7  1  1
  7  8  1  0
  7  9  2  0
  8 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 11  1  0
 14 17  1  0
 17 18  1  0
 17 19  2  0
  2  1  1  0
  1 20  1  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 21  1  0
  1 27  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA4519966

   ---

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: 364.45

Molecular Weight (Monoisotopic): 364.1899

AlogP: 1.82

#Rotatable Bonds: 6

Polar Surface Area: 99.28

Molecular Species: BASE

HBA: 3

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 11.48

CX LogP: 1.41

CX LogD: -1.00

Aromatic Rings: 2

Heavy Atoms: 27

QED Weighted: 0.54

Np Likeness Score: -0.95

References

1. Said AM, Hangauer DG..  (2016)  Ligand binding cooperativity: Bioisosteric replacement of CO with SO2 among thrombin inhibitors.,  26  (16): [PMID:27445170] [10.1016/j.bmcl.2016.07.024]

Source

Source(1):

• Scientific Literature