2-((1R,2S,6R,7S)-3,5-Dioxo-4-aza-tricyclo[5.2.1.0(2,6)]dec-4-yl)-N-(5-ethyl-4-oxo-1,2,3,4,5,6-hexahydro-benzo[b][1,5]diazocin-8-ylmethyl)-acetamide

ID: ALA4579041

PubChem CID: 131971481

Max Phase: Preclinical

Molecular Formula: C24H30N4O4

Molecular Weight: 438.53

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CCN1Cc2cc(CNC(=O)CN3C(=O)[C@@H]4[C@H]5CC[C@H](C5)[C@@H]4C3=O)ccc2NCCC1=O

Standard InChI:  InChI=1S/C24H30N4O4/c1-2-27-12-17-9-14(3-6-18(17)25-8-7-20(27)30)11-26-19(29)13-28-23(31)21-15-4-5-16(10-15)22(21)24(28)32/h3,6,9,15-16,21-22,25H,2,4-5,7-8,10-13H2,1H3,(H,26,29)/t15-,16+,21+,22-

Standard InChI Key:  HXBMMMFMSLLSBS-WGKKAQPQSA-N

Molfile:  

 
     RDKit          2D

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   17.8334   -2.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4096   -1.7258    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.4098   -3.6932    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2265   -3.6932    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
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   20.5020   -1.8942    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0783   -1.9850    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   18.5942   -0.3264    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.9099   -1.8896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.6157   -2.2968    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   23.3198   -1.8867    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.0256   -2.2939    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.3222   -1.0736    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.7338   -1.8879    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   25.4742   -2.2152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.8127   -1.0760    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.6107   -0.9034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.0160   -1.6101    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.8284   -1.6103    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.2406   -0.9061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.8311   -0.1994    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.0135   -0.1967    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.6459   -3.0133    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.2080   -0.5308    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.1177   -1.2049    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.3101   -0.1474    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   26.5563   -2.2229    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   25.9777    0.6231    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   27.6421   -1.5507    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
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 24 33  1  1
 25 34  1  1
 29 35  1  6
 26 36  1  6
M  END

Alternative Forms

1. Parent:

   

   ALA4579041

   ---

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: 438.53

Molecular Weight (Monoisotopic): 438.2267

AlogP: 1.50

#Rotatable Bonds: 5

Polar Surface Area: 98.82

Molecular Species: NEUTRAL

HBA: 5

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 3.91

CX LogP: -0.04

CX LogD: -0.04

Aromatic Rings: 1

Heavy Atoms: 32

QED Weighted: 0.68

Np Likeness Score: -0.69

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