(S)-4-((S)-2-((S)-2-Acetamido-3-phenylpropanamido)-propanamido)-5-(((S)-1-amino-4-(methylthio)-1-oxobutan-2-yl)amino)-5-oxopentanoic Acid

ID: ALA4553664

PubChem CID: 155510391

Max Phase: Preclinical

Molecular Formula: C24H35N5O7S

Molecular Weight: 537.64

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CSCC[C@H](NC(=O)[C@H](CCC(=O)O)NC(=O)[C@H](C)NC(=O)[C@H](Cc1ccccc1)NC(C)=O)C(N)=O

Standard InChI:  InChI=1S/C24H35N5O7S/c1-14(26-24(36)19(27-15(2)30)13-16-7-5-4-6-8-16)22(34)29-18(9-10-20(31)32)23(35)28-17(21(25)33)11-12-37-3/h4-8,14,17-19H,9-13H2,1-3H3,(H2,25,33)(H,26,36)(H,27,30)(H,28,35)(H,29,34)(H,31,32)/t14-,17-,18-,19-/m0/s1

Standard InChI Key:  BYTFPOUVGJUVFP-QZHFEQFPSA-N

Molfile:  

 
     RDKit          2D

 37 37  0  0  0  0  0  0  0  0999 V2000
    2.4740  -12.7980    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1834  -12.3895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8887  -13.6152    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8887  -12.7980    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1834  -11.5723    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7687  -11.5723    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4740  -11.1637    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4740  -10.3465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7687   -9.9338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0552  -10.3465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0552  -11.1637    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5981  -12.3895    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.3034  -12.7980    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0128  -11.5723    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3034  -13.6152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0128  -12.3895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7181  -12.7980    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.4316  -12.3895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8463  -12.3895    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.1410  -12.7980    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4316  -11.5723    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1410  -11.1637    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1410  -10.3465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4316   -9.9338    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.8463   -9.9338    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.1410  -13.6152    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.8463  -14.0238    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5557  -15.2537    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.8463  -14.8410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5557  -13.6152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2610  -14.0238    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2610  -14.8410    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   10.9704  -15.2537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1410  -15.2537    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4740  -13.6152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1834  -14.0238    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7687  -14.0238    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  4 12  1  0
 16 17  1  0
 20 26  1  0
 29 34  1  0
  1  2  1  0
  2  4  1  0
  4  3  2  0
  2  5  1  1
  5  7  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11  6  1  0
 12 13  1  0
 13 16  1  0
 16 14  2  0
 13 15  1  6
 17 18  1  0
 18 20  1  0
 20 19  2  0
 18 21  1  1
 21 22  1  0
 22 23  1  0
 23 24  2  0
 23 25  1  0
 27 26  1  1
 27 29  1  0
 29 28  2  0
 27 30  1  0
 30 31  1  0
 31 32  1  0
 32 33  1  0
  1 35  1  0
 35 36  1  0
 35 37  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA4553664

   ---

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: 537.64

Molecular Weight (Monoisotopic): 537.2257

AlogP: -0.69

#Rotatable Bonds: 16

Polar Surface Area: 196.79

Molecular Species: ACID

HBA: 7

HBD: 6

#RO5 Violations: 2

HBA (Lipinski): 12

HBD (Lipinski): 7

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 4.10

CX Basic pKa: ┄

CX LogP: -1.22

CX LogD: -4.32

Aromatic Rings: 1

Heavy Atoms: 37

QED Weighted: 0.16

Np Likeness Score: -0.22

References

1. Trifonov L, Nudelman V, Zhenin M, Matsree E, Afri M, Schmerling B, Cohen G, Jozwiak K, Weitman M, Korshin E, Senderowitz H, Shainberg A, Hochhauser E, Gruzman A..  (2018)  Structurally Simple, Readily Available Peptidomimetic 1-Benzyl-5-methyl-4-( n-octylamino)pyrimidin-2(1 H)-one Exhibited Efficient Cardioprotection in a Myocardial Ischemia (MI) Mouse Model.,  61  (24): [PMID:30507195] [10.1021/acs.jmedchem.8b01471]

Source

Source(1):

• Scientific Literature