(R)-3-(5-ethyl-4-oxo-1,2,3,4,5,6-hexahydrobenzo[b][1,5]diazocin-8-yl)-N-(3-(2-(2-(methylthio)phenyl)pyrrolidin-1-yl)-3-oxopropyl)propanamide

ID: ALA4526530

PubChem CID: 155544108

Max Phase: Preclinical

Molecular Formula: C29H38N4O3S

Molecular Weight: 522.72

Molecule Type: Unknown

Names and Identifiers

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

Standard InChI:  InChI=1S/C29H38N4O3S/c1-3-32-20-22-19-21(10-12-24(22)30-16-14-28(32)35)11-13-27(34)31-17-15-29(36)33-18-6-8-25(33)23-7-4-5-9-26(23)37-2/h4-5,7,9-10,12,19,25,30H,3,6,8,11,13-18,20H2,1-2H3,(H,31,34)/t25-/m1/s1

Standard InChI Key:  LFOHRMGRNIANAA-RUZDIDTESA-N

Molfile:  

 
     RDKit          2D

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   28.4085   -1.1592    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.4086   -3.1332    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
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   27.0778   -2.8653    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   33.3426   -3.7834    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   36.1741   -2.9686    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.8822   -2.5606    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   36.1734   -3.7858    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   37.6279   -2.8913    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.1752   -2.2845    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.7672   -1.5764    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.9678   -1.7457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   37.3580   -5.0336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.1360   -5.2866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.7445   -4.7348    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.5717   -3.9382    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.1773   -3.3895    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   39.9553   -3.6397    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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 32 33  2  0
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 35 30  1  0
 26 30  1  6
 35 36  1  0
 36 37  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4526530

   ---

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: 522.72

Molecular Weight (Monoisotopic): 522.2665

AlogP: 4.38

#Rotatable Bonds: 9

Polar Surface Area: 81.75

Molecular Species: NEUTRAL

HBA: 5

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 7

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: 3.93

CX LogP: 2.58

CX LogD: 2.58

Aromatic Rings: 2

Heavy Atoms: 37

QED Weighted: 0.48

Np Likeness Score: -0.83

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