(S,Z)-4-amino-N-(4-fluorobicyclo[4.2.0]octa-1(6),2,4-trien-7-yl)-N'-hydroxy-1,2,5-oxadiazole-3-carboximidamide

ID: ALA4475809

PubChem CID: 137297358

Max Phase: Preclinical

Molecular Formula: C11H10FN5O2

Molecular Weight: 263.23

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  Nc1nonc1/C(=N/O)N[C@H]1Cc2ccc(F)cc21

Standard InChI:  InChI=1S/C11H10FN5O2/c12-6-2-1-5-3-8(7(5)4-6)14-11(15-18)9-10(13)17-19-16-9/h1-2,4,8,18H,3H2,(H2,13,17)(H,14,15)/t8-/m0/s1

Standard InChI Key:  ZYPFVFRPQQRTIM-QMMMGPOBSA-N

Molfile:  

 
     RDKit          2D

 19 21  0  0  0  0  0  0  0  0999 V2000
   33.5420  -11.5852    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.3591  -11.5852    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.6135  -10.8085    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   33.9506  -10.3263    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   33.2918  -10.8085    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   34.8387  -12.2468    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   33.0608  -12.2457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.2482  -12.1592    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   33.3922  -12.9926    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   32.9110  -13.6531    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   31.9167  -11.4122    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.2114  -10.6505    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.1550  -11.1192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.4494  -10.3604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.9399   -9.7281    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.1359   -9.8533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.8440  -10.6165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.3554  -11.2456    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.0371  -10.7455    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  5  1  2  0
  2  6  1  0
  1  7  1  0
  7  8  1  0
  7  9  2  0
  9 10  1  0
 11  8  1  6
 11 12  1  0
 12 14  1  0
 13 11  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 13  1  0
 17 19  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4475809

   ---

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: 263.23

Molecular Weight (Monoisotopic): 263.0819

AlogP: 0.81

#Rotatable Bonds: 2

Polar Surface Area: 109.56

Molecular Species: ACID

HBA: 6

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 6.31

CX Basic pKa: ┄

CX LogP: 0.88

CX LogD: -0.22

Aromatic Rings: 2

Heavy Atoms: 19

QED Weighted: 0.32

Np Likeness Score: -1.30

References

1. Zhang H, Liu K, Pu Q, Achab A, Ardolino MJ, Cheng M, Deng Y, Doty AC, Ferguson H, Fradera X, Knemeyer I, Kurukulasuriya R, Lam YH, Lesburg CA, Martinot TA, McGowan MA, Miller JR, Otte K, Biju PJ, Sciammetta N, Solban N, Yu W, Zhou H, Wang X, Bennett DJ, Han Y..  (2019)  Discovery of Amino-cyclobutarene-derived Indoleamine-2,3-dioxygenase 1 (IDO1) Inhibitors for Cancer Immunotherapy.,  10  (11): [PMID:31749906] [10.1021/acsmedchemlett.9b00344]

Source

Source(1):

• Scientific Literature