2-((1R,2R,6S,7S)-3,5-Dioxo-4-aza-tricyclo[5.2.1.0(2,6)]dec-4-yl)-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)-acetamide

ID: ALA4520315

PubChem CID: 155541962

Max Phase: Preclinical

Molecular Formula: C23H27N3O5

Molecular Weight: 425.49

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  O=C(CN1C(=O)[C@@H]2[C@@H]3CC[C@@H](C3)[C@@H]2C1=O)NCc1ccc2c(c1)[C@H]1C[C@@H](N2)[C@H](O)CO1

Standard InChI:  InChI=1S/C23H27N3O5/c27-17-10-31-18-7-16(17)25-15-4-1-11(5-14(15)18)8-24-19(28)9-26-22(29)20-12-2-3-13(6-12)21(20)23(26)30/h1,4-5,12-13,16-18,20-21,25,27H,2-3,6-10H2,(H,24,28)/t12-,13+,16-,17-,18-,20-,21+/m1/s1

Standard InChI Key:  BOGJVTQQRCPUBE-RMVSDHFHSA-N

Molfile:  

 
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M  END

Alternative Forms

1. Parent:

   

   ALA4520315

   ---

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: 425.49

Molecular Weight (Monoisotopic): 425.1951

AlogP: 0.95

#Rotatable Bonds: 4

Polar Surface Area: 107.97

Molecular Species: NEUTRAL

HBA: 6

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.78

CX Basic pKa: 2.87

CX LogP: -0.42

CX LogD: -0.42

Aromatic Rings: 1

Heavy Atoms: 31

QED Weighted: 0.62

Np Likeness Score: -0.12

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