1-but-3-ynoyl-3,5-bis[(4-fluoro-3-nitrophenyl)methylene]azepan-4-one

ID: ALA4470335

PubChem CID: 155534324

Max Phase: Preclinical

Molecular Formula: C24H17F2N3O6

Molecular Weight: 481.41

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  C#CCC(=O)N1CC/C(=C\c2ccc(F)c([N+](=O)[O-])c2)C(=O)/C(=C/c2ccc(F)c([N+](=O)[O-])c2)C1

Standard InChI:  InChI=1S/C24H17F2N3O6/c1-2-3-23(30)27-9-8-17(10-15-4-6-19(25)21(12-15)28(32)33)24(31)18(14-27)11-16-5-7-20(26)22(13-16)29(34)35/h1,4-7,10-13H,3,8-9,14H2/b17-10+,18-11+

Standard InChI Key:  YZXJGQIHLWQTES-ODPUSEOTSA-N

Molfile:  

 
     RDKit          2D

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   19.5395  -11.9091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   24.4730  -11.6627    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.1152  -12.8913    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
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  1  2  1  0
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  7 31  1  0
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M  CHG  4  23   1  25  -1  26   1  28  -1
M  END

Alternative Forms

1. Parent:

   

   ALA4470335

   ---

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: 481.41

Molecular Weight (Monoisotopic): 481.1085

AlogP: 4.07

#Rotatable Bonds: 5

Polar Surface Area: 123.66

Molecular Species: NEUTRAL

HBA: 6

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 4.30

CX LogD: 4.30

Aromatic Rings: 2

Heavy Atoms: 35

QED Weighted: 0.27

Np Likeness Score: -0.95

References

1. Ward JA, Pinto-Fernandez A, Cornelissen L, Bonham S, Díaz-Sáez L, Riant O, Huber KVM, Kessler BM, Feron O, Tate EW..  (2020)  Re-Evaluating the Mechanism of Action of α,β-Unsaturated Carbonyl DUB Inhibitors b-AP15 and VLX1570: A Paradigmatic Example of Unspecific Protein Cross-linking with Michael Acceptor Motif-Containing Drugs.,  63  (7): [PMID:32109059] [10.1021/acs.jmedchem.0c00144]

Source

Source(1):

• Scientific Literature