(2S,5S,14S)-14-amino-5-benzyl-15-(4-hydroxyphenyl)-2-isobutyl-4,7,10,13-tetraoxo-6-oxa-3,9,12-triazapentadecan-1-oic acid

ID: ALA4572725

PubChem CID: 155563096

Max Phase: Preclinical

Molecular Formula: C28H36N4O8

Molecular Weight: 556.62

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CC(C)C[C@H](NC(=O)[C@H](Cc1ccccc1)OC(=O)CNC(=O)CNC(=O)[C@@H](N)Cc1ccc(O)cc1)C(=O)O

Standard InChI:  InChI=1S/C28H36N4O8/c1-17(2)12-22(28(38)39)32-27(37)23(14-18-6-4-3-5-7-18)40-25(35)16-30-24(34)15-31-26(36)21(29)13-19-8-10-20(33)11-9-19/h3-11,17,21-23,33H,12-16,29H2,1-2H3,(H,30,34)(H,31,36)(H,32,37)(H,38,39)/t21-,22-,23-/m0/s1

Standard InChI Key:  PSMDCSALCNYMEN-VABKMULXSA-N

Molfile:  

 
     RDKit          2D

 40 41  0  0  0  0  0  0  0  0999 V2000
   38.6556  -20.8219    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.3633  -20.4133    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.9479  -20.4133    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   37.2402  -20.8219    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.5325  -20.4133    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.8248  -20.8219    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   37.2402  -21.6391    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   36.5325  -19.5961    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.8248  -19.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.8280  -18.3692    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.1211  -17.9607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.4124  -18.3694    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.4151  -19.1908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.1225  -19.5956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.7042  -17.9617    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   40.0710  -20.8219    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   39.3633  -19.5961    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   40.7787  -20.4133    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.4865  -20.8219    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.1942  -20.4133    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   41.4865  -21.6391    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   42.9019  -20.8219    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   43.6096  -20.4133    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.9019  -21.6391    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   43.6096  -22.0477    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   43.6055  -22.8659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   44.3124  -23.2744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   45.0211  -22.8658    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   45.0185  -22.0444    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   44.3110  -21.6395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   44.3173  -20.8219    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   43.6096  -19.5961    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   45.0250  -20.4133    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   45.7327  -20.8219    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   46.4404  -20.4133    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   45.7327  -21.6391    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   45.0250  -19.5961    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   45.7327  -19.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   45.7327  -18.3703    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   46.4404  -19.5961    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  1  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  4  7  2  0
  5  8  1  1
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14  9  1  0
 12 15  1  0
  2 16  1  0
  2 17  2  0
 16 18  1  0
 18 19  1  0
 19 20  1  0
 19 21  2  0
 20 22  1  0
 22 23  1  0
 22 24  1  6
 24 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
 28 29  1  0
 29 30  2  0
 30 25  1  0
 23 31  1  0
 23 32  2  0
 31 33  1  0
 33 34  1  0
 34 35  1  0
 34 36  2  0
 33 37  1  1
 37 38  1  0
 38 39  1  0
 38 40  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4572725

   ---

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: 556.62

Molecular Weight (Monoisotopic): 556.2533

AlogP: 0.26

#Rotatable Bonds: 15

Polar Surface Area: 197.15

Molecular Species: ACID

HBA: 8

HBD: 6

#RO5 Violations: 2

HBA (Lipinski): 12

HBD (Lipinski): 7

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 3.90

CX Basic pKa: 7.73

CX LogP: -1.14

CX LogD: -1.28

Aromatic Rings: 2

Heavy Atoms: 40

QED Weighted: 0.17

Np Likeness Score: 0.17

References

1. Meanwell NA..  (2018)  Fluorine and Fluorinated Motifs in the Design and Application of Bioisosteres for Drug Design.,  61  (14): [PMID:29400967] [10.1021/acs.jmedchem.7b01788]

2. Kumari S,Carmona AV,Tiwari AK,Trippier PC.  (2020)  Amide Bond Bioisosteres: Strategies, Synthesis, and Successes.,  63  (21.0): [PMID:32686940] [10.1021/acs.jmedchem.0c00530]

Source

Source(1):

• Scientific Literature