N1-cyclopentyl-N2-(2-((2R,3R,6R)-3-hydroxy-2,3,4,6-tetrahydro-1H-2,6-methanobenzo [c][1,5]oxazocin-8-yl)ethyl)oxalamide

ID: ALA4464825

PubChem CID: 130476037

Max Phase: Preclinical

Molecular Formula: C20H27N3O4

Molecular Weight: 373.45

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  O=C(NCCc1ccc2c(c1)[C@H]1C[C@@H](N2)[C@H](O)CO1)C(=O)NC1CCCC1

Standard InChI:  InChI=1S/C20H27N3O4/c24-17-11-27-18-10-16(17)23-15-6-5-12(9-14(15)18)7-8-21-19(25)20(26)22-13-3-1-2-4-13/h5-6,9,13,16-18,23-24H,1-4,7-8,10-11H2,(H,21,25)(H,22,26)/t16-,17-,18-/m1/s1

Standard InChI Key:  TWJNDXFEOOUBGG-KZNAEPCWSA-N

Molfile:  

 
     RDKit          2D

 29 32  0  0  0  0  0  0  0  0999 V2000
   32.1093  -11.0205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.8214  -10.6106    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.8171   -9.7851    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.1066   -9.3774    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.3997  -10.6113    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.4018   -9.7932    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.7003   -9.3843    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.9901   -9.7867    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.9839  -10.6048    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.6921  -11.0205    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   29.2707  -10.1908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.9831   -8.9756    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   29.2760   -9.3875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.5280   -9.3725    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.2394   -9.7812    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.9461   -9.3685    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   35.6575   -9.7772    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.3684   -9.3646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.6622  -10.5944    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   37.0798   -9.7691    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   36.3637   -8.5433    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   37.7866   -9.3565    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.5366   -9.6825    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.0851   -9.0729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.6724   -8.3661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.8709   -8.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.5596  -10.6001    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   29.9720  -11.4260    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   30.6888   -8.5631    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  5  1  1  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  6  1  0
  5  6  2  0
  5 10  1  0
  6  7  1  0
  7  8  1  0
  9  8  1  0
  9 10  1  0
  9 11  1  0
  7 12  1  0
 11 13  1  0
 12 13  1  0
  3 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 17 19  2  0
 18 20  1  0
 18 21  2  0
 20 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 26 22  1  0
 11 27  1  6
  9 28  1  6
  7 29  1  6
M  END

Alternative Forms

1. Parent:

   

   ALA4464825

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 373.45

Molecular Weight (Monoisotopic): 373.2002

AlogP: 1.02

#Rotatable Bonds: 4

Polar Surface Area: 99.69

Molecular Species: NEUTRAL

HBA: 5

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.65

CX Basic pKa: 2.88

CX LogP: 0.49

CX LogD: 0.49

Aromatic Rings: 1

Heavy Atoms: 27

QED Weighted: 0.59

Np Likeness Score: -0.04

References

1. Grädler U, Schwarz D, Blaesse M, Leuthner B, Johnson TL, Bernard F, Jiang X, Marx A, Gilardone M, Lemoine H, Roche D, Jorand-Lebrun C..  (2019)  Discovery of novel Cyclophilin D inhibitors starting from three dimensional fragments with millimolar potencies.,  29  (23): [PMID:31635932] [10.1016/j.bmcl.2019.126717]

2. Gaali, Steffen S, Kozany, Christian C, Hoogeland, Bastiaan B, Klein, Marielle M and Hausch, Felix F.  2010-12-09  Facile synthesis of a fluorescent cyclosporin a analogue to study cyclophilin 40 and cyclophilin 18 ligands.  [PMID:24900244]

3. Shore, Emma R ER and 12 more authors.  2016-03-24  Small Molecule Inhibitors of Cyclophilin D To Protect Mitochondrial Function as a Potential Treatment for Acute Pancreatitis.  [PMID:26950392]

4. Valasani, Koteswara Rao KR and 8 more authors.  2016-03-10  Identification of a Small Molecule Cyclophilin D Inhibitor for Rescuing Aβ-Mediated Mitochondrial Dysfunction.  [PMID:26985318]

Source

Source(1):

• Scientific Literature