(S)-3-((3S,6S)-3-((2S,3S)-2-acetamido-3-methylpentanamido)-4-oxo-1,2,3,4,6,7-hexahydroazepino[3,2,1-hi]indole-6-carboxamido)-4-oxo-4-(5-phenyl-1,3,4-oxadiazol-2-yl)butanoic acid

ID: ALA255387

PubChem CID: 44453613

Max Phase: Preclinical

Molecular Formula: C33H36N6O8

Molecular Weight: 644.69

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC[C@H](C)[C@H](NC(C)=O)C(=O)N[C@H]1CCc2cccc3c2N(C1=O)[C@H](C(=O)N[C@@H](CC(=O)O)C(=O)c1nnc(-c2ccccc2)o1)C3

Standard InChI:  InChI=1S/C33H36N6O8/c1-4-17(2)26(34-18(3)40)30(45)35-22-14-13-19-11-8-12-21-15-24(39(27(19)21)33(22)46)29(44)36-23(16-25(41)42)28(43)32-38-37-31(47-32)20-9-6-5-7-10-20/h5-12,17,22-24,26H,4,13-16H2,1-3H3,(H,34,40)(H,35,45)(H,36,44)(H,41,42)/t17-,22-,23-,24-,26-/m0/s1

Standard InChI Key:  JDSAQRQEFBZZNN-BTUHLANLSA-N

Molfile:  

     RDKit          2D

 47 51  0  0  1  0  0  0  0  0999 V2000
   -1.0205  -26.8719    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6094  -27.4850    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4920  -28.2813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1958  -26.9641    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2320  -27.6652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0617  -28.4704    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8106  -28.7191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4490  -26.9622    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0377  -26.2494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2113  -26.2523    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0382  -27.6735    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6297  -28.9344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2919  -28.4523    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1852  -28.7287    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9136  -29.5378    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6454  -29.7593    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0612  -30.1853    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3676  -30.1582    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0741  -29.7321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7963  -30.1309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0584  -28.9072    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7648  -28.4812    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7492  -27.6564    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4871  -28.8800    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8120  -30.9558    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5028  -29.7049    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1579  -31.4548    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4925  -31.4294    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2527  -32.2188    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4284  -32.2332    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9193  -28.3519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6125  -28.7992    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9600  -27.5279    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3465  -28.4224    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5718  -29.6232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2651  -30.0705    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8378  -30.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7971  -30.8239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3873  -27.5985    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1212  -27.2217    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6940  -27.1511    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9562  -32.9097    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1336  -32.8370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6615  -33.5127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0113  -34.2609    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8377  -34.3293    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3061  -33.6528    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 11  5  2  0
 22 23  2  0
  1  4  1  0
 22 24  1  0
  5  6  1  0
 20 25  1  0
  6  7  1  0
 20 26  2  0
 25 27  1  0
  6 12  1  0
 12 13  1  0
 27 30  1  0
 29 28  1  0
 28 25  2  0
 13 11  1  0
  7  3  1  0
 29 30  2  0
  3 14  1  1
 14 31  1  0
  4  5  1  0
 31 32  1  0
  7 15  2  0
 31 33  2  0
 32 34  1  6
 12 16  1  1
 32 35  1  0
 11  8  1  0
 35 36  1  6
 16 17  2  0
 35 37  1  0
  1  2  1  0
 37 38  1  0
 16 18  1  0
 34 39  1  0
  8  9  2  0
 39 40  1  0
 18 19  1  0
 39 41  2  0
  2  3  1  0
 30 42  1  0
 19 20  1  0
 42 43  2  0
  9 10  1  0
 43 44  1  0
 19 21  1  1
 44 45  2  0
 10  4  2  0
 45 46  1  0
 21 22  1  0
 46 47  2  0
 47 42  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA255387

   (3S)-3-[[(2S,11S)-11-[[(2S,3S)-2-acetamido-3-methylpentanoyl]amino]-12-oxo-1-azatricyclo[6.4.1.04,13]trideca-4,6,8(13)-triene-2-carbonyl]amino]-4-oxo-4-(5-phenyl-1,3,4-oxadiazol-2-yl)butanoic acid

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: 644.69

Molecular Weight (Monoisotopic): 644.2595

AlogP: 1.82

#Rotatable Bonds: 12

Polar Surface Area: 200.90

Molecular Species: ACID

HBA: 9

HBD: 4

#RO5 Violations: 1

HBA (Lipinski): 14

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 4.18

CX Basic pKa: ┄

CX LogP: 1.15

CX LogD: -1.89

Aromatic Rings: 3

Heavy Atoms: 47

QED Weighted: 0.21

Np Likeness Score: -0.35

References

1. Maryanoff BE, Costanzo MJ..  (2008)  Inhibitors of proteases and amide hydrolases that employ an alpha-ketoheterocycle as a key enabling functionality.,  16  (4): [PMID:18053726] [10.1016/j.bmc.2007.11.015]

Source

Source(1):

• Scientific Literature