Isopropyl N-[2-({4-[N-(3-bromo-4-fluorophenyl)-N'-hydroxycarbamimidoyl]-1,2,5-oxadiazol-3-yl}amino)ethyl]-P-methylphosphonamidate

ID: ALA4514159

PubChem CID: 155539196

Max Phase: Preclinical

Molecular Formula: C15H21BrFN6O4P

Molecular Weight: 479.25

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CC(C)OP(C)(=O)NCCNc1nonc1/C(=N/O)Nc1ccc(F)c(Br)c1

Standard InChI:  InChI=1S/C15H21BrFN6O4P/c1-9(2)26-28(3,25)19-7-6-18-14-13(22-27-23-14)15(21-24)20-10-4-5-12(17)11(16)8-10/h4-5,8-9,24H,6-7H2,1-3H3,(H,18,23)(H,19,25)(H,20,21)

Standard InChI Key:  GWFJYPOGGNSNNJ-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 28 29  0  0  0  0  0  0  0  0999 V2000
   33.8309  -30.4176    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   34.4939  -29.9397    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   34.2395  -29.1589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.4223  -29.1589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.1679  -29.9397    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   34.9452  -28.7461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.9407  -27.9290    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   35.6552  -29.1508    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   36.3606  -28.7382    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.6461  -27.5164    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   37.0700  -29.1454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.7750  -28.7335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.7708  -27.9155    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.0559  -27.5110    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.3539  -27.9252    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.4847  -29.1385    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   38.4757  -27.5020    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   32.7124  -28.7503    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   32.0052  -29.1598    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.2970  -28.7521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.5898  -29.1616    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   29.8816  -28.7539    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   29.1744  -29.1634    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   29.8770  -27.9331    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.8770  -29.5675    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   28.4662  -28.7558    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.7590  -29.1653    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.4651  -27.9386    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  4  5  2  0
  2  3  2  0
  1  2  1  0
  3  4  1  0
  5  1  1  0
  3  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  1  0
  7 10  1  0
  9 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15  9  1  0
 12 16  1  0
 13 17  1  0
  4 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 22 24  1  0
 22 25  2  0
 23 26  1  0
 26 27  1  0
 26 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4514159

   ---

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: 479.25

Molecular Weight (Monoisotopic): 478.0529

AlogP: 3.47

#Rotatable Bonds: 9

Polar Surface Area: 133.90

Molecular Species: ACID

HBA: 8

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 10

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 5.81

CX Basic pKa: ┄

CX LogP: 2.09

CX LogD: 0.57

Aromatic Rings: 2

Heavy Atoms: 28

QED Weighted: 0.11

Np Likeness Score: -1.48

References

1. Du Q, Feng X, Wang Y, Xu X, Zhang Y, Qu X, Li Z, Bian J..  (2019)  Discovery of phosphonamidate IDO1 inhibitors for the treatment of non-small cell lung cancer.,  182  [PMID:31445231] [10.1016/j.ejmech.2019.111629]

Source

Source(1):

• Scientific Literature