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

ID: ALA1080988

PubChem CID: 44479559

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-/m1/s1

Standard InChI Key:  PIGMXBSUAPIWMM-BGTMTDRBSA-N

Molfile:  

     RDKit          2D

 26 27  0  0  0  0  0  0  0  0999 V2000
   -5.3136    1.8781    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3167    1.0485    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6058    0.6373    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6045    2.2889    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1632    3.1084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8800    3.5276    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6038    3.1171    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1701    2.2786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1982   -0.2023    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3163    3.5325    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9018    1.0429    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1861    0.6212    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4616    1.0345    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4579    1.8622    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8978    1.8678    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4899   -0.6251    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5020   -1.4499    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7696   -0.2232    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7938   -1.8728    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8059   -2.6976    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5277   -3.0946    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5402   -3.9187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8314   -4.3423    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1086   -3.9361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0997   -3.1133    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8424   -5.1672    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  6
 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:

   

   ALA1080988

   (R,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]

Source

Source(1):

• Scientific Literature