N'-(1-(((3S)-2-hydroxy-5-oxo-tetrahydrofuran-3-yl)carbamoyl)cyclohexanecarbonyl)-3-methoxybenzohydrazide

ID: ALA214215

PubChem CID: 44414574

Max Phase: Preclinical

Molecular Formula: C20H25N3O7

Molecular Weight: 419.43

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cccc(C(=O)NNC(=O)C2(C(=O)N[C@H]3CC(=O)OC3O)CCCCC2)c1

Standard InChI:  InChI=1S/C20H25N3O7/c1-29-13-7-5-6-12(10-13)16(25)22-23-19(28)20(8-3-2-4-9-20)18(27)21-14-11-15(24)30-17(14)26/h5-7,10,14,17,26H,2-4,8-9,11H2,1H3,(H,21,27)(H,22,25)(H,23,28)/t14-,17?/m0/s1

Standard InChI Key:  WWJJTCYWVNPFIZ-MBIQTGHCSA-N

Molfile:  

     RDKit          2D

 30 32  0  0  1  0  0  0  0  0999 V2000
   11.7860   -5.2036    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0745   -5.6152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5021   -5.6152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2180   -5.2027    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.5021   -6.4402    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.0745   -6.4402    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.9311   -5.2015    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2153   -5.6140    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9311   -4.3765    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.9297   -5.6152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0180   -6.4313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8240   -6.6037    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.2366   -5.8877    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6834   -5.2756    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0589   -5.7986    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.4057   -6.9844    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5048   -6.8499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2172   -6.4357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4995   -5.1997    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7809   -6.4385    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7843   -5.6152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0740   -3.9702    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0740   -4.7952    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4980   -4.7952    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4980   -3.9702    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7860   -3.5536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5083   -7.6724    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.2248   -8.0814    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3597   -5.2033    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.6449   -5.6152    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 12 13  1  0
 13 14  1  0
 14 10  1  0
 13 15  2  0
 11 16  1  0
  8 19  2  0
 20 17  1  0
  2  1  1  0
 17 18  2  0
 18  8  1  0
  1  3  1  0
 21 19  1  0
  3  4  1  0
  3  5  2  0
 20 21  2  0
 22 23  1  0
  2  6  2  0
  7  8  1  0
 22 26  1  0
 23  1  1  0
  1 24  1  0
 24 25  1  0
 25 26  1  0
  7  9  2  0
 10  4  1  1
 27 28  1  0
 17 27  1  0
 10 11  1  0
 11 12  1  0
  2 29  1  0
 29 30  1  0
 30  7  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA214215

   N-[(3S)-2-hydroxy-5-oxooxolan-3-yl]-1-[[(3-methoxybenzoyl)amino]carbamoyl]cyclohexane-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: 419.43

Molecular Weight (Monoisotopic): 419.1693

AlogP: 0.16

#Rotatable Bonds: 5

Polar Surface Area: 143.06

Molecular Species: NEUTRAL

HBA: 7

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 10

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.43

CX Basic pKa: ┄

CX LogP: 0.74

CX LogD: 0.74

Aromatic Rings: 1

Heavy Atoms: 30

QED Weighted: 0.30

Np Likeness Score: -0.42

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