(4S)-4-((S)-2-amino-3-carboxypropanamido)-5-oxo-5-(1-oxo-1-((S)-1-oxo-3-phenylpropan-2-ylamino)hexan-2-ylamino)pentanoic acid

ID: ALA4100180

PubChem CID: 137660044

Max Phase: Preclinical

Molecular Formula: C24H34N4O8

Molecular Weight: 506.56

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C24H34N4O8/c1-2-3-9-18(23(35)26-16(14-29)12-15-7-5-4-6-8-15)28-24(36)19(10-11-20(30)31)27-22(34)17(25)13-21(32)33/h4-8,14,16-19H,2-3,9-13,25H2,1H3,(H,26,35)(H,27,34)(H,28,36)(H,30,31)(H,32,33)/t16-,17-,18?,19-/m0/s1

Standard InChI Key:  WVGXVDCSNQQEEL-WPOPZESYSA-N

Molfile:  

     RDKit          2D

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   16.6162  -10.6999    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3287  -11.9434    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.3287  -11.1146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6162   -9.8806    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3253   -9.4704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3253   -8.6354    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   19.4996   -9.8615    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.4996  -10.6992    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7794  -11.9358    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5021  -12.3547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5021  -13.1737    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   22.3674  -10.6922    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   23.0893  -11.1075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.8144   -9.8509    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.8144  -10.6914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.0893  -11.9252    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.8240  -13.1631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.8144  -12.3455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.5346  -11.9179    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.2549  -12.3225    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.2598  -13.1516    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.5444  -13.5718    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.9395   -9.8758    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.6538   -9.4630    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.6536   -8.6380    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.3678   -8.2254    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  4  9  1  0
 12 18  1  0
 21 22  1  0
  1  2  1  0
  2  4  1  0
  4  3  2  0
  2  5  1  1
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  6  7  2  0
  6  8  1  0
  9 10  1  0
 10 12  1  0
 12 11  2  0
 10 13  1  6
 13 14  1  0
 14 15  1  0
 15 16  2  0
 15 17  1  0
 18 19  1  0
 19 21  1  0
 21 20  2  0
 22 23  1  0
 23 25  1  0
 25 24  2  0
 23 26  1  6
 26 28  1  0
 27 28  2  0
 28 29  1  0
 29 30  2  0
 30 31  1  0
 31 32  2  0
 32 27  1  0
 19 33  1  0
 33 34  1  0
 34 35  1  0
 35 36  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4100180

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 506.56

Molecular Weight (Monoisotopic): 506.2377

AlogP: -0.26

#Rotatable Bonds: 17

Polar Surface Area: 204.99

Molecular Species: ACID

HBA: 7

HBD: 6

#RO5 Violations: 2

HBA (Lipinski): 12

HBD (Lipinski): 7

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 3.43

CX Basic pKa: 8.23

CX LogP: -2.89

CX LogD: -5.79

Aromatic Rings: 1

Heavy Atoms: 36

QED Weighted: 0.15

Np Likeness Score: 0.53

References

1. Swedberg JE, Li CY, de Veer SJ, Wang CK, Craik DJ..  (2017)  Design of Potent and Selective Cathepsin G Inhibitors Based on the Sunflower Trypsin Inhibitor-1 Scaffold.,  60  (2): [PMID:28045523] [10.1021/acs.jmedchem.6b01509]

Source

Source(1):

• Scientific Literature