N-[2-[[4-[N-[3-(difluoromethyl)phenyl]-N'-hydroxycarbamimidoyl]-1,2,5-oxadiazol-3-yl]sulfanyl]ethyl]-2-sulfamoylacetamide

ID: ALA4475499

PubChem CID: 142342024

Max Phase: Preclinical

Molecular Formula: C14H16F2N6O5S2

Molecular Weight: 450.45

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  NS(=O)(=O)CC(=O)NCCSc1nonc1/C(=N/O)Nc1cccc(C(F)F)c1

Standard InChI:  InChI=1S/C14H16F2N6O5S2/c15-12(16)8-2-1-3-9(6-8)19-13(20-24)11-14(22-27-21-11)28-5-4-18-10(23)7-29(17,25)26/h1-3,6,12,24H,4-5,7H2,(H,18,23)(H,19,20)(H2,17,25,26)

Standard InChI Key:  SRGIOYOXVRHLHA-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 29 30  0  0  0  0  0  0  0  0999 V2000
    9.7939  -15.2749    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.3759  -15.8568    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   10.5889  -15.0619    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7733  -16.0384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7721  -16.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4802  -17.2669    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1899  -16.8574    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1870  -16.0348    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4784  -15.6295    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8932  -15.6235    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.6024  -16.0294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3086  -15.6182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6055  -16.8466    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8993  -17.2579    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0539  -15.9507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5984  -15.3413    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.1871  -14.6351    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3885  -14.8082    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.2249  -16.7498    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    7.0025  -17.0011    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6090  -16.4534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3866  -16.7048    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.9930  -16.1571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7706  -16.4085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8219  -15.3580    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.1547  -16.1121    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.0655  -15.6299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0653  -14.8128    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    0.3579  -16.0387    0.0000 F   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
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24  2  1  0
 23 25  2  0
  2 26  1  0
  4 27  1  0
 27 28  1  0
 27 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4475499

   ---

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: 450.45

Molecular Weight (Monoisotopic): 450.0592

AlogP: 0.75

#Rotatable Bonds: 9

Polar Surface Area: 172.80

Molecular Species: ACID

HBA: 9

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 11

HBD (Lipinski): 5

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 5.88

CX Basic pKa: ┄

CX LogP: 0.05

CX LogD: -1.43

Aromatic Rings: 2

Heavy Atoms: 29

QED Weighted: 0.11

Np Likeness Score: -1.89

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