N-[(1S)-2-[4-[(2S)-2-[[2-(2-bromophenyl)acetyl]amino]-6-(prop-2-enoylamino)hexanoyl]piperazin-1-yl]-1-methyl-2-oxo-ethyl]naphthalene-1-carboxamide

ID: ALA5278546

Max Phase: Preclinical

Molecular Formula: C35H40BrN5O5

Molecular Weight: 690.64

Names and Identifiers

Canonical SMILES:  C=CC(=O)NCCCC[C@H](NC(=O)Cc1ccccc1Br)C(=O)N1CCN(C(=O)[C@H](C)NC(=O)c2cccc3ccccc23)CC1

Standard InChI:  InChI=1S/C35H40BrN5O5/c1-3-31(42)37-18-9-8-17-30(39-32(43)23-26-12-5-7-16-29(26)36)35(46)41-21-19-40(20-22-41)34(45)24(2)38-33(44)28-15-10-13-25-11-4-6-14-27(25)28/h3-7,10-16,24,30H,1,8-9,17-23H2,2H3,(H,37,42)(H,38,44)(H,39,43)/t24-,30-/m0/s1

Standard InChI Key:  AFNFQGFWVDQHQD-NGQVCNFZSA-N

Molfile:  

 
     RDKit          2D

 46 49  0  0  0  0  0  0  0  0999 V2000
   -5.0016    1.6496    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2872    2.0621    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5726    1.6494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    2.0621    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5726    0.8242    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1432    1.6494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4286    2.0621    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7140    1.6494    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4286    2.8871    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1432    0.8242    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4286    0.4116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4286   -0.4135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1432   -0.8261    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1432   -1.6513    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4286   -2.0639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4286   -2.8891    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7140   -1.6513    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0005   -2.0639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0019    0.8243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7148    0.4136    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4296    0.8263    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4311    1.6475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7194    2.0640    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0005    2.0621    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7151    1.6494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7151    0.8242    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0005    0.4116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7140    0.8242    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4299    0.4116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1445    0.8242    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4299   -0.4135    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8592    0.4116    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5738    0.8242    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2884    0.4116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5738    1.6494    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0032    0.8240    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7154    0.4120    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7154   -0.4133    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0051   -0.8252    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2884   -0.4170    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0045    1.6442    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7175    2.0552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4269    1.6468    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4311    0.8247    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7194    2.8891    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    2.1445    1.6494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  3  5  2  0
  4  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  2  0
  6 10  1  6
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 15 17  1  0
 17 18  2  0
 19  1  2  0
 20 19  1  0
 21 20  2  0
 22 21  1  0
 23 22  2  0
  1 23  1  0
 24  8  1  0
 25 24  1  0
 26 25  1  0
 27 26  1  0
 28 27  1  0
  8 28  1  0
 26 29  1  0
 29 30  1  0
 29 31  2  0
 30 32  1  0
 32 33  1  0
 33 34  1  0
 33 35  2  0
 36 34  2  0
 37 36  1  0
 38 37  2  0
 39 38  1  0
 40 39  2  0
 34 40  1  0
 36 41  1  0
 42 41  2  0
 43 42  1  0
 44 43  2  0
 37 44  1  0
 23 45  1  0
 30 46  1  6
M  END

Alternative Forms

1. Parent:

   

   ALA5278546

   ---

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: 690.64

Molecular Weight (Monoisotopic): 689.2213

AlogP: 3.59

#Rotatable Bonds: 13

Polar Surface Area: 127.92

Molecular Species: NEUTRAL

HBA: 5

HBD: 3

#RO5 Violations: 1

HBA (Lipinski): 10

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 12.52

CX Basic pKa: ┄

CX LogP: 3.31

CX LogD: 3.31

Aromatic Rings: 3

Heavy Atoms: 46

QED Weighted: 0.19

Np Likeness Score: -0.80

References

1. Cundy NJ, Arciszewski J, Gates EWJ, Acton SL, Passley KD, Awoonor-Williams E, Boyd EK, Xu N, Pierson É, Fernandez-Ansieta C, Albert MR, McNeil NMR, Adhikary G, Eckert RL, Keillor JW..  (2023)  Novel irreversible peptidic inhibitors of transglutaminase 2.,  14  (2.0): [PMID:36846375] [10.1039/d2md00417h]

Source

Source(1):

• Scientific Literature