N-(4-Amino-benzyl)-2-(3,5-dioxo-4-aza-tricyclo[5.2.1.0(2,6)]dec-4-yl)-acetamide

ID: ALA4471175

PubChem CID: 130476468

Max Phase: Preclinical

Molecular Formula: C18H21N3O3

Molecular Weight: 327.38

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  Nc1ccc(CNC(=O)CN2C(=O)C3C4CCC(C4)C3C2=O)cc1

Standard InChI:  InChI=1S/C18H21N3O3/c19-13-5-1-10(2-6-13)8-20-14(22)9-21-17(23)15-11-3-4-12(7-11)16(15)18(21)24/h1-2,5-6,11-12,15-16H,3-4,7-9,19H2,(H,20,22)

Standard InChI Key:  WFJPCFXBNDWOKM-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 24 27  0  0  0  0  0  0  0  0999 V2000
   18.7547  -17.4078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7535  -18.2351    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.4677  -18.6458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1836  -18.2346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1807  -17.4041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.4659  -16.9929    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0394  -18.6449    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.8931  -16.9868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.6085  -17.3986    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.3249  -16.9814    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.0403  -17.3932    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.3219  -16.1564    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.7527  -16.9759    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   24.5081  -17.3063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.8371  -16.1511    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.6432  -15.9756    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.0540  -16.6887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.8740  -16.6878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.2892  -15.9756    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.8742  -15.2626    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.0481  -15.2617    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.6861  -18.1119    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.2190  -15.6027    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.0417  -16.0845    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  1  1  0
  2  7  1  0
  5  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 10 12  2  0
 11 13  1  0
 13 14  1  0
 14 17  1  0
 16 15  1  0
 15 13  1  0
 16 17  1  0
 16 21  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 14 22  2  0
 15 23  2  0
 21 24  1  0
 24 18  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4471175

   ---

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: 327.38

Molecular Weight (Monoisotopic): 327.1583

AlogP: 0.92

#Rotatable Bonds: 4

Polar Surface Area: 92.50

Molecular Species: NEUTRAL

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 4.27

CX LogP: 0.20

CX LogD: 0.20

Aromatic Rings: 1

Heavy Atoms: 24

QED Weighted: 0.64

Np Likeness Score: -0.80

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