(R)-1-(2-(2-(2-(methylthio)phenyl)pyrrolidin-1-yl)-2-oxoethyl)-3-((1,2,3,4-tetrahydroquinolin-6-yl)methyl)urea

ID: ALA4540033

PubChem CID: 155549580

Max Phase: Preclinical

Molecular Formula: C24H30N4O2S

Molecular Weight: 438.60

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CSc1ccccc1[C@H]1CCCN1C(=O)CNC(=O)NCc1ccc2c(c1)CCCN2

Standard InChI:  InChI=1S/C24H30N4O2S/c1-31-22-9-3-2-7-19(22)21-8-5-13-28(21)23(29)16-27-24(30)26-15-17-10-11-20-18(14-17)6-4-12-25-20/h2-3,7,9-11,14,21,25H,4-6,8,12-13,15-16H2,1H3,(H2,26,27,30)/t21-/m1/s1

Standard InChI Key:  AWMQVWTUQIZVPZ-OAQYLSRUSA-N

Molfile:  

 
     RDKit          2D

 31 34  0  0  0  0  0  0  0  0999 V2000
    3.5119   -5.2199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2205   -4.8048    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2140   -3.9826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5078   -3.5792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8007   -4.8059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8059   -3.9907    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1051   -3.5833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3951   -3.9849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3899   -4.8001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0968   -5.2137    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.9228   -3.5696    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6305   -3.9766    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.3414   -3.5677    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0491   -3.9747    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.3344   -2.7477    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7538   -3.5617    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4614   -3.9667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1724   -3.5537    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.4685   -4.7867    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.9218   -3.8833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4637   -3.2758    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0506   -2.5689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2544   -2.7370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0943   -4.6766    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4882   -5.2266    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6580   -6.0270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4430   -6.2758    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0420   -5.7205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8651   -4.9249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4741   -4.3705    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   12.2529   -4.6191    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
  9  8  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 18  1  0
 17 19  2  0
 18 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 18  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 27 28  1  0
 28 29  2  0
 29 24  1  0
 20 24  1  6
 29 30  1  0
 30 31  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4540033

   ---

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: 438.60

Molecular Weight (Monoisotopic): 438.2089

AlogP: 3.93

#Rotatable Bonds: 6

Polar Surface Area: 73.47

Molecular Species: NEUTRAL

HBA: 4

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 4.88

CX LogP: 2.70

CX LogD: 2.70

Aromatic Rings: 2

Heavy Atoms: 31

QED Weighted: 0.60

Np Likeness Score: -1.33

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