N-(3-bromo-4-fluorophenyl)-N'-hydroxy-4-[2-(sulfamoylamino)ethoxy]-1,2,5-oxadiazole-3-carboxamidine

ID: ALA4483087

PubChem CID: 137223162

Max Phase: Preclinical

Molecular Formula: C11H12BrFN6O5S

Molecular Weight: 439.22

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  NS(=O)(=O)NCCOc1nonc1/C(=N/O)Nc1ccc(F)c(Br)c1

Standard InChI:  InChI=1S/C11H12BrFN6O5S/c12-7-5-6(1-2-8(7)13)16-10(17-20)9-11(19-24-18-9)23-4-3-15-25(14,21)22/h1-2,5,15,20H,3-4H2,(H,16,17)(H2,14,21,22)

Standard InChI Key:  WGSXVCLSVMYHFM-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 25 26  0  0  0  0  0  0  0  0999 V2000
    9.3771  -28.0817    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.9590  -28.6636    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   10.1720  -27.8687    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7432  -28.5480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7420  -29.3675    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4501  -29.7765    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1598  -29.3671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1569  -28.5444    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4483  -28.1391    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8631  -28.1331    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.5723  -28.5391    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2785  -28.1278    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5754  -29.3563    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.8692  -29.7675    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0238  -28.4603    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5683  -27.8510    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.1570  -27.1448    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3583  -27.3178    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.1948  -29.2594    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0340  -29.7756    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    2.0354  -28.1396    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    7.9724  -29.5108    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5789  -28.9631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3565  -29.2144    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.7405  -28.9181    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  2  2  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9  4  1  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  2  0
 13 14  1  0
 12 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 18 12  2  0
 15 19  1  0
  5 20  1  0
  4 21  1  0
 19 22  1  0
 22 23  1  0
 23 24  1  0
 24  2  1  0
  2 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4483087

   ---

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: 439.22

Molecular Weight (Monoisotopic): 437.9757

AlogP: 0.39

#Rotatable Bonds: 7

Polar Surface Area: 164.96

Molecular Species: ACID

HBA: 8

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 11

HBD (Lipinski): 5

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 4.95

CX Basic pKa: ┄

CX LogP: 0.46

CX LogD: -1.65

Aromatic Rings: 2

Heavy Atoms: 25

QED Weighted: 0.16

Np Likeness Score: -2.00

References

1. Steeneck C, Kinzel O, Anderhub S, Hornberger M, Pinto S, Morschhaeuser B, Braun F, Kleymann G, Hoffmann T..  (2020)  Discovery of Hydroxyamidine Based Inhibitors of IDO1 for Cancer Immunotherapy with Reduced Potential for Glucuronidation.,  11  (2): [PMID:32071686] [10.1021/acsmedchemlett.9b00572]

Source

Source(1):

• Scientific Literature