2-((1R,7S)-3,5-Dioxo-4-aza-tricyclo[5.2.1.0(2,6)]dec-4-yl)-N-(5-ethyl-4-oxo-1,2,3,4,5,6-hexahydro-benzo[b][1,5]diazocin-8-yl)-acetamide

ID: ALA4473560

PubChem CID: 155536278

Max Phase: Preclinical

Molecular Formula: C23H28N4O4

Molecular Weight: 424.50

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CCN1Cc2cc(NC(=O)CN3C(=O)C4C(C3=O)[C@H]3CC[C@@H]4C3)ccc2NCCC1=O

Standard InChI:  InChI=1S/C23H28N4O4/c1-2-26-11-15-10-16(5-6-17(15)24-8-7-19(26)29)25-18(28)12-27-22(30)20-13-3-4-14(9-13)21(20)23(27)31/h5-6,10,13-14,20-21,24H,2-4,7-9,11-12H2,1H3,(H,25,28)/t13-,14+,20?,21?

Standard InChI Key:  PYWBLYOFWYINQO-ZXPDZVFASA-N

Molfile:  

 
     RDKit          2D

 33 37  0  0  0  0  0  0  0  0999 V2000
   17.6888  -10.1488    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6890   -9.3316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2613   -8.7584    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2615  -10.7213    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.0785  -10.7213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0785   -8.7582    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.6454   -9.3316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6445  -10.1465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.3467  -10.5529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.0530  -10.1491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.0511   -9.3311    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.3475   -8.9270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9364  -10.4577    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.9526  -11.4736    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1413  -11.5818    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.7568  -10.5608    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.4639  -10.1548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.1677  -10.5623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.4672   -9.3370    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.8748  -10.1563    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   24.6177  -10.4848    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.9628   -9.3408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.7623   -9.1770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.1630   -9.8822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.9731   -9.8912    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.3878   -9.1894    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.9830   -8.4800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.1677   -8.4726    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.7890  -11.2837    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.3580   -8.7984    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.8886   -8.9714    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.1403   -7.6603    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   25.9582  -10.7041    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  1  4  1  0
  4  5  1  0
  5  8  1  0
  7  6  1  0
  6  3  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
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  1 13  2  0
  4 14  1  0
 14 15  1  0
 10 16  1  0
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 17 18  1  0
 17 19  2  0
 18 20  1  0
 20 21  1  0
 21 24  1  0
 23 22  1  0
 22 20  1  0
 23 24  1  0
 23 28  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 21 29  2  0
 22 30  2  0
 28 31  1  0
 25 31  1  0
 28 32  1  6
 25 33  1  6
M  END

Alternative Forms

1. Parent:

   

   ALA4473560

   ---

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: 424.50

Molecular Weight (Monoisotopic): 424.2111

AlogP: 1.82

#Rotatable Bonds: 4

Polar Surface Area: 98.82

Molecular Species: NEUTRAL

HBA: 5

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.19

CX Basic pKa: 3.90

CX LogP: 0.26

CX LogD: 0.26

Aromatic Rings: 1

Heavy Atoms: 31

QED Weighted: 0.72

Np Likeness Score: -0.87

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