(2S,3S)-2-(2-(hydroxy(methyl)amino)-4-oxo-3-thioxocyclobut-1-enylamino)-3-methyl-N-((S)-1-(methylamino)-1-oxo-3-phenylpropan-2-yl)pentanamide

ID: ALA5220101

PubChem CID: 11711713

Max Phase: Preclinical

Molecular Formula: C21H28N4O4S

Molecular Weight: 432.55

Names and Identifiers

Canonical SMILES:  CC[C@H](C)[C@H](Nc1c(N(C)O)c(=S)c1=O)C(=O)N[C@@H](Cc1ccccc1)C(=O)NC

Standard InChI:  InChI=1S/C21H28N4O4S/c1-5-12(2)15(24-16-17(25(4)29)19(30)18(16)26)21(28)23-14(20(27)22-3)11-13-9-7-6-8-10-13/h6-10,12,14-15,24,29H,5,11H2,1-4H3,(H,22,27)(H,23,28)/t12-,14-,15-/m0/s1

Standard InChI Key:  VWOPOYQMVVOTAG-QEJZJMRPSA-N

Molfile:  

 
     RDKit          2D

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   -2.5641    0.2067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5641    1.0317    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7253    1.0317    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7253    0.2067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0111   -0.2054    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1475    1.6151    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2965    0.2069    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4209   -0.2073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9932    0.2067    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2787   -1.0307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1353    0.2050    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.4209   -1.0323    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8498   -0.2073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5642    0.2050    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8498   -1.0323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5642   -1.4448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5642    1.0301    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2787   -0.2073    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.9932    0.2050    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789   -1.0325    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9908   -1.4443    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9908   -2.2697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2807   -2.6814    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5642   -2.2734    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2965    1.0319    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4338    1.4153    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2403    1.6991    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0026    1.4586    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0026    2.2836    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  3  2  1  0
  4  3  1  0
  4  5  1  0
  2  5  2  0
  5  6  1  0
  3  7  2  0
  6  8  1  0
  8  9  1  1
  1 10  1  0
  1 11  1  0
  9 12  1  0
  9 13  2  0
 12 14  1  0
 14 15  1  0
 14 16  1  6
 16 17  1  0
 15 18  2  0
 15 19  1  0
 19 20  1  0
 21 17  2  0
 22 21  1  0
 23 22  2  0
 24 23  1  0
 25 24  2  0
 17 25  1  0
  8 26  1  0
 26 27  1  6
  4 28  2  0
 26 29  1  0
 29 30  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA5220101

   (2S,3S)-2-[[2-[hydroxy(methyl)amino]-4-oxo-3-sulfanylidenecyclobuten-1-yl]amino]-3-methyl-N-[(2S)-1-(methylamino)-1-oxo-3-phenylpropan-2-yl]pentanamide

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: 432.55

Molecular Weight (Monoisotopic): 432.1831

AlogP: 1.78

#Rotatable Bonds: 10

Polar Surface Area: 110.77

Molecular Species: NEUTRAL

HBA: 7

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.57

CX Basic pKa: ┄

CX LogP: 1.78

CX LogD: 1.78

Aromatic Rings: 2

Heavy Atoms: 30

QED Weighted: 0.33

Np Likeness Score: -0.30

References

1. Chasák J, Šlachtová V, Urban M, Brulíková L..  (2021)  Squaric acid analogues in medicinal chemistry.,  209  [PMID:33035923] [10.1016/j.ejmech.2020.112872]

Source

Source(1):

• Scientific Literature