(R)-1-((5-ethyl-4-oxo-1,2,3,4,5,6-hexahydrobenzo[b][1,5]diazocin-8-yl)methyl)-3-(2-(2-(2-(methylthio)phenyl)pyrrolidin-1-yl)-2-oxoethyl)urea

ID: ALA4466871

PubChem CID: 130476250

Max Phase: Preclinical

Molecular Formula: C27H35N5O3S

Molecular Weight: 509.68

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CCN1Cc2cc(CNC(=O)NCC(=O)N3CCC[C@@H]3c3ccccc3SC)ccc2NCCC1=O

Standard InChI:  InChI=1S/C27H35N5O3S/c1-3-31-18-20-15-19(10-11-22(20)28-13-12-25(31)33)16-29-27(35)30-17-26(34)32-14-6-8-23(32)21-7-4-5-9-24(21)36-2/h4-5,7,9-11,15,23,28H,3,6,8,12-14,16-18H2,1-2H3,(H2,29,30,35)/t23-/m1/s1

Standard InChI Key:  KVRLCSQKFNRTCC-HSZRJFAPSA-N

Molfile:  

 
     RDKit          2D

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   15.4931   -1.9448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0681   -1.3656    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0682   -3.3520    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.8919   -3.3520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   17.4752   -1.9448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   18.1847   -1.5339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7333   -3.0799    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   14.9397   -4.2158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6081   -3.1797    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.3161   -2.7717    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.0276   -3.1809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.7398   -2.7729    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
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   23.8750   -3.1833    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   23.1642   -1.9527    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.9561   -3.9971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.7594   -4.1718    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.1686   -3.4603    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.6223   -2.8485    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.3456   -4.5461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.5643   -4.2898    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.9517   -4.8341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.1232   -5.6390    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.9086   -5.8966    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.5138   -5.3465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.2951   -5.5991    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   24.4691   -6.4026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
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  1 13  2  0
  4 14  1  0
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 17 18  1  0
 18 19  1  0
 18 20  2  0
 19 21  1  0
 21 22  1  0
 22 23  1  0
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 25 26  1  0
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 27 28  1  0
 28 23  1  0
 29 30  2  0
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 31 32  2  0
 32 33  1  0
 33 34  2  0
 34 29  1  0
 25 29  1  6
 34 35  1  0
 35 36  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4466871

   ---

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: 509.68

Molecular Weight (Monoisotopic): 509.2461

AlogP: 3.74

#Rotatable Bonds: 7

Polar Surface Area: 93.78

Molecular Species: NEUTRAL

HBA: 5

HBD: 3

#RO5 Violations: 1

HBA (Lipinski): 8

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: 3.91

CX LogP: 1.68

CX LogD: 1.68

Aromatic Rings: 2

Heavy Atoms: 36

QED Weighted: 0.49

Np Likeness Score: -1.10

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