rac-2-(3,5-Dioxo-4-aza-tricyclo[5.2.1.0(2,6)]dec-4-yl)-N-(1,2,3,4-tetrahydro-quinolin-6-ylmethyl)-acetamide

ID: ALA4464178

PubChem CID: 130476467

Max Phase: Preclinical

Molecular Formula: C21H25N3O3

Molecular Weight: 367.45

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  O=C(CN1C(=O)C2C3CCC(C3)C2C1=O)NCc1ccc2c(c1)CCCN2

Standard InChI:  InChI=1S/C21H25N3O3/c25-17(23-10-12-3-6-16-13(8-12)2-1-7-22-16)11-24-20(26)18-14-4-5-15(9-14)19(18)21(24)27/h3,6,8,14-15,18-19,22H,1-2,4-5,7,9-11H2,(H,23,25)

Standard InChI Key:  ABTFDUSGCSGBMO-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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   32.2345   -5.4846    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.9499   -5.0737    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.9470   -4.2438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.2327   -3.8328    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.5208   -5.0742    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.5250   -4.2474    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.8155   -3.8306    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.0932   -4.2402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.0891   -5.0670    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.8072   -5.4842    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   33.6588   -3.8268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.3737   -4.2384    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   35.0856   -3.8214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.8047   -4.2329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.0824   -2.9970    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   36.5164   -3.8160    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   37.2695   -4.1503    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.5990   -2.9959    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.4045   -2.8205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.8192   -3.5402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.6431   -3.5374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.0586   -2.8165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.6398   -2.1011    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.8096   -2.1023    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.4428   -4.9564    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   35.9808   -2.4485    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   37.9134   -2.9335    0.0000 C   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
  8  9  1  0
  9 10  1  0
  3 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  2  0
 14 16  1  0
 16 17  1  0
 17 20  1  0
 19 18  1  0
 18 16  1  0
 19 20  1  0
 19 24  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 17 25  2  0
 18 26  2  0
 24 27  1  0
 27 21  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4464178

   ---

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: 367.45

Molecular Weight (Monoisotopic): 367.1896

AlogP: 1.69

#Rotatable Bonds: 4

Polar Surface Area: 78.51

Molecular Species: NEUTRAL

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 4.88

CX LogP: 0.98

CX LogD: 0.98

Aromatic Rings: 1

Heavy Atoms: 27

QED Weighted: 0.79

Np Likeness Score: -0.86

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