(2S,3S)-2-acetamido-N-((S)-1-((S)-1-amino-1-oxopropan-2-ylamino)-1-oxo-3-phenylpropan-2-yl)-3-methylpentanamide

ID: ALA4442410

PubChem CID: 101137783

Max Phase: Preclinical

Molecular Formula: C20H30N4O4

Molecular Weight: 390.48

Molecule Type: Unknown

Names and Identifiers

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

Standard InChI:  InChI=1S/C20H30N4O4/c1-5-12(2)17(23-14(4)25)20(28)24-16(11-15-9-7-6-8-10-15)19(27)22-13(3)18(21)26/h6-10,12-13,16-17H,5,11H2,1-4H3,(H2,21,26)(H,22,27)(H,23,25)(H,24,28)/t12-,13-,16-,17-/m0/s1

Standard InChI Key:  DDMGTSYQYDHCGY-PYTWLRIVSA-N

Molfile:  

 
     RDKit          2D

 28 28  0  0  0  0  0  0  0  0999 V2000
   21.9016  -19.1914    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.3102  -19.9009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.5360  -19.1914    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.1274  -19.9009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.9016  -20.6061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.0844  -20.6061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.3102  -21.3155    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.9016  -22.0208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.5360  -20.6061    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   24.3532  -20.6061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.3532  -19.1914    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.7618  -19.9009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.7618  -21.3155    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.9876  -22.0208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.5790  -21.3155    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.9876  -20.6061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.8047  -20.6061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.2133  -21.3155    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.8047  -22.0208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.5790  -19.9009    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   25.9876  -19.1914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.2133  -19.9009    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.5790  -18.4820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.8047  -19.1914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.2133  -18.4820    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.0844  -19.1914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6758  -19.9009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6758  -18.4820    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  4  9  1  0
 12 20  1  0
 24 25  1  0
  2  1  1  6
  2  4  1  0
  4  3  2  0
  2  5  1  0
  5  6  1  6
  5  7  1  0
  7  8  1  0
  9 10  1  0
 10 12  1  0
 12 11  2  0
 10 13  1  6
 13 15  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 14  1  0
 20 21  1  0
 21 24  1  0
 24 22  2  0
 21 23  1  1
  1 26  1  0
 26 27  1  0
 26 28  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA4442410

   Ac-Ile-Phe-Ala-NH2

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: 390.48

Molecular Weight (Monoisotopic): 390.2267

AlogP: 0.25

#Rotatable Bonds: 10

Polar Surface Area: 130.39

Molecular Species: NEUTRAL

HBA: 4

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 5

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.21

CX Basic pKa: ┄

CX LogP: 0.35

CX LogD: 0.35

Aromatic Rings: 1

Heavy Atoms: 28

QED Weighted: 0.46

Np Likeness Score: -0.20

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