N'-(1-(((3S)-2-hydroxy-5-oxo-tetrahydrofuran-3-yl)carbamoyl)cyclobutanecarbonyl)-3-methylbenzohydrazide

ID: ALA213784

PubChem CID: 44414592

Max Phase: Preclinical

Molecular Formula: C18H21N3O6

Molecular Weight: 375.38

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1cccc(C(=O)NNC(=O)C2(C(=O)N[C@H]3CC(=O)OC3O)CCC2)c1

Standard InChI:  InChI=1S/C18H21N3O6/c1-10-4-2-5-11(8-10)14(23)20-21-17(26)18(6-3-7-18)16(25)19-12-9-13(22)27-15(12)24/h2,4-5,8,12,15,24H,3,6-7,9H2,1H3,(H,19,25)(H,20,23)(H,21,26)/t12-,15?/m0/s1

Standard InChI Key:  QNNFJVOWDROYGA-SFVWDYPZSA-N

Molfile:  

     RDKit          2D

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   11.9035  -12.9708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3535  -12.2793    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6620  -11.8293    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1918  -13.3833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6194  -13.3833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3352  -12.9708    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.6194  -14.2083    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.1918  -14.2083    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.0484  -12.9696    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3325  -13.3821    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0484  -12.1446    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.0469  -13.3833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1353  -14.1994    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9413  -14.3718    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.3538  -13.6558    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8006  -13.0437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1762  -13.5667    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.5230  -14.7524    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6184  -12.9655    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6221  -14.6180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3345  -14.2038    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9019  -14.2044    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9013  -13.3792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6243  -15.4430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4770  -12.9714    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.7622  -13.3833    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  6  8  2  0
  5  9  2  0
 10 11  1  0
 10 12  2  0
 13  7  1  1
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 13  1  0
 16 18  2  0
 14 19  1  0
 11 20  2  0
 20 24  1  0
  1  2  1  0
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  2  3  1  0
 21 22  2  0
 22 11  1  0
  3  4  1  0
  4  1  1  0
 23 24  2  0
  5  2  1  0
 21 25  1  0
  2  6  1  0
  6  7  1  0
  5 26  1  0
 26 27  1  0
 27 10  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA213784

   N-[(3S)-2-hydroxy-5-oxooxolan-3-yl]-1-[[(3-methylbenzoyl)amino]carbamoyl]cyclobutane-1-carboxamide

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: 375.38

Molecular Weight (Monoisotopic): 375.1430

AlogP: -0.32

#Rotatable Bonds: 4

Polar Surface Area: 133.83

Molecular Species: NEUTRAL

HBA: 6

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.81

CX Basic pKa: ┄

CX LogP: 0.52

CX LogD: 0.52

Aromatic Rings: 1

Heavy Atoms: 27

QED Weighted: 0.32

Np Likeness Score: -0.51

References

1. Soper DL, Sheville J, O'Neil SV, Wang Y, Laufersweiler MC, Oppong KA, Wos JA, Ellis CD, Fancher AN, Lu W, Suchanek MK, Wang RL, De B, Demuth TP..  (2006)  Synthesis and evaluation of novel 1-(2-acylhydrazinocarbonyl)-cycloalkyl carboxamides as interleukin-1beta converting enzyme (ICE) inhibitors.,  16  (16): [PMID:16782334] [10.1016/j.bmcl.2006.05.076]

Source

Source(1):

• Scientific Literature