(S)-1-((R)-2-amino-3-phenylpropanoyl)-N-(4-(aminomethyl)benzyl)pyrrolidine-2-carboxamide

ID: ALA4761989

PubChem CID: 69989551

Max Phase: Preclinical

Molecular Formula: C22H28N4O2

Molecular Weight: 380.49

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  NCc1ccc(CNC(=O)[C@@H]2CCCN2C(=O)[C@H](N)Cc2ccccc2)cc1

Standard InChI:  InChI=1S/C22H28N4O2/c23-14-17-8-10-18(11-9-17)15-25-21(27)20-7-4-12-26(20)22(28)19(24)13-16-5-2-1-3-6-16/h1-3,5-6,8-11,19-20H,4,7,12-15,23-24H2,(H,25,27)/t19-,20+/m1/s1

Standard InChI Key:  MTUGEKUGFKKRIV-UXHICEINSA-N

Molfile:  

 
     RDKit          2D

 28 30  0  0  0  0  0  0  0  0999 V2000
   21.3625  -14.0161    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.3584  -13.1989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6486  -12.7939    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.6445  -11.9767    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9348  -11.5717    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.3502  -11.5645    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.8419  -10.7601    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0418  -10.5942    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6367  -11.3040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1867  -11.9084    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.0205  -12.7085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2445  -12.9647    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6303  -13.2525    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.6346  -12.4207    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.0783  -13.7648    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3023  -14.0210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6947  -13.4740    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9193  -13.7296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7525  -14.5305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3672  -15.0753    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1402  -14.8168    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6546  -14.4264    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6584  -15.2428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.3687  -15.6487    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.0766  -15.2321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.0694  -14.4170    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.3739  -16.4658    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.0842  -16.8699    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  5  4  1  1
  4  6  2  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10  5  1  0
 10 11  1  0
 11 12  1  0
 11 13  2  0
 12 14  1  0
 12 15  1  1
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 16  1  0
  1 22  2  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26  1  1  0
 24 27  1  0
 27 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4761989

   (2~{S})-~{N}-[[4-(aminomethyl)phenyl]methyl]-1-[(2~{R})-2-azanyl-3-phenyl-propanoyl]pyrrolidine-2-carboxamide

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: 380.49

Molecular Weight (Monoisotopic): 380.2212

AlogP: 1.32

#Rotatable Bonds: 7

Polar Surface Area: 101.45

Molecular Species: BASE

HBA: 4

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 5

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 9.29

CX LogP: 1.08

CX LogD: -1.25

Aromatic Rings: 2

Heavy Atoms: 28

QED Weighted: 0.67

Np Likeness Score: -0.59

References

1. Sandner A,Ngo K,Schiebel J,Pizarroso AIM,Schmidt L,Wenzel B,Steinmetzer T,Ostermann A,Heine A,Klebe G.  (2021)  How a Fragment Draws Attention to Selectivity Discriminating Features between the Related Proteases Trypsin and Thrombin.,  64  (3.0): [PMID:33471524] [10.1021/acs.jmedchem.0c01809]

Source

Source(1):

• Scientific Literature