N-Cyclopentyl-N'-[2-((1S,9S,10S)-10-hydroxy-12-oxa-8-aza-tricyclo[7.3.1.0(2,7)]trideca-2(7),3,5-trien-4-yl)-ethyl]-oxalamide

ID: ALA4570230

PubChem CID: 130476052

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-/m0/s1

Standard InChI Key:  TWJNDXFEOOUBGG-KSZLIROESA-N

Molfile:  

 
     RDKit          2D

 29 32  0  0  0  0  0  0  0  0999 V2000
   31.1807  -18.6270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.8927  -18.2171    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.8885  -17.3916    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.1780  -16.9839    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.4711  -18.2178    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.4731  -17.3997    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.7717  -16.9908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.0614  -17.3932    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.0552  -18.2113    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.7635  -18.6270    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   28.3421  -17.7973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.0545  -16.5820    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   28.3473  -16.9940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.5993  -16.9790    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.3107  -17.3876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.0175  -16.9750    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   34.7289  -17.3837    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.4398  -16.9711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.7336  -18.2009    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   36.1512  -17.3756    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   35.4351  -16.1498    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   36.8579  -16.9630    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.6079  -17.2890    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.1564  -16.6794    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.7438  -15.9726    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.9423  -16.1439    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.6310  -18.2066    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   29.0434  -19.0325    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   29.7601  -16.1696    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  1
  7 29  1  1
M  END

Alternative Forms

1. Parent:

   

   ALA4570230

   ---

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