1-(4-Aminobenzyl)-3-((S)-4-(methylthio)-1-((S)-2-(2-(methylthio)phenyl)pyrrolidin-1-yl)-1-oxobutan-2-yl)urea

ID: ALA3799661

PubChem CID: 127046107

Max Phase: Preclinical

Molecular Formula: C24H32N4O2S2

Molecular Weight: 472.68

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CSCC[C@H](NC(=O)NCc1ccc(N)cc1)C(=O)N1CCC[C@H]1c1ccccc1SC

Standard InChI:  InChI=1S/C24H32N4O2S2/c1-31-15-13-20(27-24(30)26-16-17-9-11-18(25)12-10-17)23(29)28-14-5-7-21(28)19-6-3-4-8-22(19)32-2/h3-4,6,8-12,20-21H,5,7,13-16,25H2,1-2H3,(H2,26,27,30)/t20-,21-/m0/s1

Standard InChI Key:  SXQHCTVKKRKZEF-SFTDATJTSA-N

Molfile:  

     RDKit          2D

 32 34  0  0  0  0  0  0  0  0999 V2000
    1.2990   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5973   -1.5031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5951   -3.0039    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8933   -3.7570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8912   -5.2578    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.9336   -3.1588    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1894   -6.0109    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1873   -7.5117    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4855   -8.2648    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1470   -8.1099    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2990    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2990    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2990   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3383    1.3500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.4920   -5.2654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7894   -6.0199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0920   -5.2745    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   10.1293   -5.8778    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0906  -10.0575    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6233   -9.7456    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8369   -7.6438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8406   -8.7585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5021  -10.7432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0506  -10.3861    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0127  -11.4690    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4315  -12.9093    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8883  -13.2668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9263  -12.1839    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6304   -8.9453    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.4649   -8.6595    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  4  6  2  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  8 10  2  0
  1 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15  1  1  0
 13 16  1  0
  7 17  1  1
 17 18  1  0
 18 19  1  0
 19 20  1  0
 21 22  1  0
 22  9  1  0
  9 23  1  0
 23 24  1  0
 24 21  1  0
 22 25  1  1
 25 26  2  0
 26 27  1  0
 27 28  2  0
 28 29  1  0
 29 30  2  0
 30 25  1  0
 26 31  1  0
 31 32  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3799661

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 472.68

Molecular Weight (Monoisotopic): 472.1967

AlogP: 4.28

#Rotatable Bonds: 9

Polar Surface Area: 87.46

Molecular Species: NEUTRAL

HBA: 5

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 4.25

CX LogP: 3.14

CX LogD: 3.14

Aromatic Rings: 2

Heavy Atoms: 32

QED Weighted: 0.37

Np Likeness Score: -1.11

References

1. Shore ER, Awais M, Kershaw NM, Gibson RR, Pandalaneni S, Latawiec D, Wen L, Javed MA, Criddle DN, Berry N, O'Neill PM, Lian LY, Sutton R..  (2016)  Small Molecule Inhibitors of Cyclophilin D To Protect Mitochondrial Function as a Potential Treatment for Acute Pancreatitis.,  59  (6): [PMID:26950392] [10.1021/acs.jmedchem.5b01801]

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