(2R,Z)-N-(2-Bromophenyl)-2-((4-(hydroxyimino)-1-oxo-1,4-dihydronaphthalen-2-yl)amino)-3-phenylpropanamide

ID: ALA4513280

PubChem CID: 141744845

Max Phase: Preclinical

Molecular Formula: C25H20BrN3O3

Molecular Weight: 490.36

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  O=C1C(N[C@H](Cc2ccccc2)C(=O)Nc2ccccc2Br)=C/C(=N/O)c2ccccc21

Standard InChI:  InChI=1S/C25H20BrN3O3/c26-19-12-6-7-13-20(19)28-25(31)23(14-16-8-2-1-3-9-16)27-22-15-21(29-32)17-10-4-5-11-18(17)24(22)30/h1-13,15,23,27,32H,14H2,(H,28,31)/b29-21-/t23-/m1/s1

Standard InChI Key:  ADBKJTBBPTWYPX-WEHFJGPMSA-N

Molfile:  

 
     RDKit          2D

 32 35  0  0  0  0  0  0  0  0999 V2000
    3.6718  -25.3040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6707  -26.1235    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3787  -26.5325    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3769  -24.8951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    5.0844  -26.1256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7945  -26.5369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5103  -26.1276    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5115  -25.3025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7968  -24.8865    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7969  -24.0694    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7922  -27.3541    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.0833  -27.7607    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2202  -24.8956    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.9269  -25.3059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6356  -24.8991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9249  -26.1231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6316  -26.5334    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6253  -27.3481    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3312  -27.7583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0408  -27.3514    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0402  -26.5300    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3338  -26.1234    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3423  -25.3094    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.6376  -24.0819    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.0510  -24.9025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7541  -25.3153    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4623  -24.9091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4648  -24.0911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7531  -23.6809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0478  -24.0894    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7500  -26.1325    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  6  2  0
  5  4  2  0
  4  1  1  0
  5  6  1  0
  5 10  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
  7 12  2  0
 12 13  1  0
  9 14  1  0
 15 14  1  1
 15 16  1  0
 15 17  1  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 18  1  0
 16 24  1  0
 16 25  2  0
 24 26  1  0
 26 27  2  0
 27 28  1  0
 28 29  2  0
 29 30  1  0
 30 31  2  0
 31 26  1  0
 27 32  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4513280

   ---

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: 490.36

Molecular Weight (Monoisotopic): 489.0688

AlogP: 4.55

#Rotatable Bonds: 6

Polar Surface Area: 90.79

Molecular Species: ACID

HBA: 5

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 5.69

CX Basic pKa: ┄

CX LogP: 4.69

CX LogD: 3.05

Aromatic Rings: 3

Heavy Atoms: 32

QED Weighted: 0.35

Np Likeness Score: -0.44

References

1. Huang R, Jing X, Huang X, Pan Y, Fang Y, Liang G, Liao Z, Wang H, Chen Z, Zhang Y..  (2020)  Bifunctional Naphthoquinone Aromatic Amide-Oxime Derivatives Exert Combined Immunotherapeutic and Antitumor Effects through Simultaneous Targeting of Indoleamine-2,3-dioxygenase and Signal Transducer and Activator of Transcription 3.,  63  (4): [PMID:31999451] [10.1021/acs.jmedchem.9b01386]

Source

Source(1):

• Scientific Literature