(S,E)-N-(4-chlorobenzyl)-2-(5,12-dioxo-1-oxa-4-azacyclododec-8-en-6-yl)acetamide

ID: ALA1080091

PubChem CID: 44479802

Max Phase: Preclinical

Molecular Formula: C19H23ClN2O4

Molecular Weight: 378.86

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(C[C@@H]1C/C=C/CCC(=O)OCCNC1=O)NCc1ccc(Cl)cc1

Standard InChI:  InChI=1S/C19H23ClN2O4/c20-16-8-6-14(7-9-16)13-22-17(23)12-15-4-2-1-3-5-18(24)26-11-10-21-19(15)25/h1-2,6-9,15H,3-5,10-13H2,(H,21,25)(H,22,23)/b2-1+/t15-/m0/s1

Standard InChI Key:  PIGMXBSUAPIWMM-YLSAJCSVSA-N

Molfile:  

     RDKit          2D

 26 27  0  0  0  0  0  0  0  0999 V2000
   11.6775    2.1236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6745    1.2941    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3853    0.8830    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.3867    2.5344    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.8277    3.3537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1109    3.7729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3873    3.3624    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8207    2.5241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7926    0.0436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6748    3.7778    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.0891    1.2885    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8047    0.8668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5291    1.2801    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5329    2.1076    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0932    2.1132    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.5008   -0.3793    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4887   -1.2039    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.2209    0.0226    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.1967   -1.6267    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1846   -2.4513    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4630   -2.8484    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4506   -3.6722    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1593   -4.0959    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8818   -3.6896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8907   -2.8671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1482   -4.9205    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  8  5  1  0
 13 14  1  0
 14  8  2  0
  5  6  1  0
 11 15  2  0
  6  7  1  0
  9 16  1  0
  3 11  1  0
 16 17  1  0
 16 18  2  0
 12  9  1  1
 17 19  1  0
  1  2  1  0
 19 20  1  0
  7 10  2  0
 20 21  2  0
  1  4  1  0
 21 22  1  0
  2  3  1  0
 22 23  2  0
 11 12  1  0
 23 24  1  0
  4  7  1  0
 24 25  2  0
 25 20  1  0
 12 13  1  0
 23 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1080091

   (S,E)-N-(4-chlorobenzyl)-2-(5,12-dioxo-1-oxa-4-azacyclododec-8-en-6-yl)acetamide

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: 378.86

Molecular Weight (Monoisotopic): 378.1346

AlogP: 2.36

#Rotatable Bonds: 4

Polar Surface Area: 84.50

Molecular Species: NEUTRAL

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 1.82

CX LogD: 1.82

Aromatic Rings: 1

Heavy Atoms: 26

QED Weighted: 0.62

Np Likeness Score: -0.02

References

1. Peng LF, Stanton BZ, Maloof N, Wang X, Schreiber SL..  (2009)  Syntheses of aminoalcohol-derived macrocycles leading to a small-molecule binder to and inhibitor of Sonic Hedgehog.,  19  (22): [PMID:19819139] [10.1016/j.bmcl.2009.09.089]

2. Dockendorff C, Nagiec MM, Weïwer M, Buhrlage S, Ting A, Nag PP, Germain A, Kim HJ, Youngsaye W, Scherer C, Bennion M, Xue L, Stanton BZ, Lewis TA, Macpherson L, Palmer M, Foley MA, Perez JR, Schreiber SL..  (2012)  Macrocyclic Hedgehog Pathway Inhibitors: Optimization of Cellular Activity and Mode of Action Studies.,  3  (10): [PMID:23074541] [10.1021/ml300172p]

Source

Source(1):

• Scientific Literature