(S,Z)-2-((4-(N-(4-fluorobicyclo[4.2.0]octa-1(6),2,4-trien-7-yl)-N'-hydroxycarbamimidoyl)-1,2,5-oxadiazol-3-yl)amino)-N-(2-hydroxyethyl)acetamide

ID: ALA4515137

PubChem CID: 137297350

Max Phase: Preclinical

Molecular Formula: C15H17FN6O4

Molecular Weight: 364.34

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  O=C(CNc1nonc1/C(=N/O)N[C@H]1Cc2ccc(F)cc21)NCCO

Standard InChI:  InChI=1S/C15H17FN6O4/c16-9-2-1-8-5-11(10(8)6-9)19-15(20-25)13-14(22-26-21-13)18-7-12(24)17-3-4-23/h1-2,6,11,23,25H,3-5,7H2,(H,17,24)(H,18,22)(H,19,20)/t11-/m0/s1

Standard InChI Key:  OLPQNOYGDGMZSU-NSHDSACASA-N

Molfile:  

 
     RDKit          2D

 26 28  0  0  0  0  0  0  0  0999 V2000
   17.4210   -4.1231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2382   -4.1231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4926   -3.3464    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.8296   -2.8643    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.1709   -3.3464    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.7178   -4.7848    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.9398   -4.7836    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1272   -4.6972    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.2712   -5.5306    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.7900   -6.1911    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.7958   -3.9502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0904   -3.1885    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0340   -3.6572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3285   -2.8984    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8189   -2.2660    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0149   -2.3913    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7230   -3.1544    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2344   -3.7835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9161   -3.2835    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   19.5306   -4.7003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0101   -5.3620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.8229   -5.2776    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.6769   -6.1082    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.3025   -5.9392    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.1153   -5.8548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.5949   -6.5164    0.0000 O   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
  6 20  1  0
 20 21  1  0
 21 22  1  0
 21 23  2  0
 22 24  1  0
 24 25  1  0
 25 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4515137

   ---

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: 364.34

Molecular Weight (Monoisotopic): 364.1295

AlogP: -0.25

#Rotatable Bonds: 7

Polar Surface Area: 144.90

Molecular Species: ACID

HBA: 8

HBD: 5

#RO5 Violations: ┄

HBA (Lipinski): 10

HBD (Lipinski): 5

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 6.47

CX Basic pKa: ┄

CX LogP: -0.62

CX LogD: -1.58

Aromatic Rings: 2

Heavy Atoms: 26

QED Weighted: 0.20

Np Likeness Score: -1.38

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]

2. Mancini RS, Barden CJ, Weaver DF, Reed MA..  (2021)  Furazans in Medicinal Chemistry.,  64  (4.0): [PMID:33569941] [10.1021/acs.jmedchem.0c01901]

Source

Source(1):

• Scientific Literature