N-((1R,9R,10S)-10-Hydroxy-12-oxa-8-aza-tricyclo[7.3.1.0(2,7)]trideca-2(7),3,5-trien-4-ylmethyl)-2-[(S)-2-(2-methylsulfanyl-phenyl)-pyrrolidin-1-yl]-2-oxo-acetamide

ID: ALA4585544

PubChem CID: 155557873

Max Phase: Preclinical

Molecular Formula: C25H29N3O4S

Molecular Weight: 467.59

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CSc1ccccc1[C@@H]1CCCN1C(=O)C(=O)NCc1ccc2c(c1)[C@H]1C[C@@H](N2)[C@H](O)CO1

Standard InChI:  InChI=1S/C25H29N3O4S/c1-33-23-7-3-2-5-16(23)20-6-4-10-28(20)25(31)24(30)26-13-15-8-9-18-17(11-15)22-12-19(27-18)21(29)14-32-22/h2-3,5,7-9,11,19-22,27,29H,4,6,10,12-14H2,1H3,(H,26,30)/t19-,20+,21-,22-/m1/s1

Standard InChI Key:  QNURHBKOBGDDTR-CIAFKFPVSA-N

Molfile:  

 
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M  END

Alternative Forms

1. Parent:

   

   ALA4585544

   ---

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: 467.59

Molecular Weight (Monoisotopic): 467.1879

AlogP: 3.00

#Rotatable Bonds: 4

Polar Surface Area: 90.90

Molecular Species: NEUTRAL

HBA: 6

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.38

CX Basic pKa: 2.87

CX LogP: 1.89

CX LogD: 1.89

Aromatic Rings: 2

Heavy Atoms: 33

QED Weighted: 0.47

Np Likeness Score: -0.45

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