1-(2-((2-((3-chloro-2-fluorobenzyl)amino)-2-oxoethyl)(cyclopropyl)amino)-2-oxoethyl)-6-hydroxy-1H-indazole-3-carboxamide

ID: ALA5220699

PubChem CID: 137230917

Max Phase: Preclinical

Molecular Formula: C22H21ClFN5O4

Molecular Weight: 473.89

Names and Identifiers

Canonical SMILES:  NC(=O)c1nn(CC(=O)N(CC(=O)NCc2cccc(Cl)c2F)C2CC2)c2cc(O)ccc12

Standard InChI:  InChI=1S/C22H21ClFN5O4/c23-16-3-1-2-12(20(16)24)9-26-18(31)10-28(13-4-5-13)19(32)11-29-17-8-14(30)6-7-15(17)21(27-29)22(25)33/h1-3,6-8,13,30H,4-5,9-11H2,(H2,25,33)(H,26,31)

Standard InChI Key:  BDFWQTZENXBWRT-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 33 36  0  0  0  0  0  0  0  0999 V2000
   -5.0975    0.8831    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5182    1.4705    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7225    1.2628    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5030    0.4674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0781   -0.1183    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8772    0.0845    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6936   -0.8384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8791   -0.7074    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7578    0.0846    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0461    0.5024    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3285    0.0951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6170    0.5130    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.1005    0.1057    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8121    0.5235    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5298    0.1162    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.2414    0.5341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9590    0.1267    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6707    0.5444    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3859    0.1376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3920   -0.6876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6847   -1.1048    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9651   -0.7019    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0975    0.5555    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.6647    1.3695    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    0.8060    1.3487    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3225   -0.7299    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1009   -1.5561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6831   -2.2677    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9261   -1.5622    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6170    1.3382    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2036    2.0541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0288    2.0533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7318    2.2677    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  2  1  0
  4  3  2  0
  5  4  1  0
  6  5  2  0
  1  6  1  0
  5  7  1  0
  7  8  2  0
  9  8  1  0
  4  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 18 17  2  0
 19 18  1  0
 20 19  2  0
 21 20  1  0
 22 21  2  0
 17 22  1  0
 19 23  1  0
 18 24  1  0
 14 25  2  0
 11 26  2  0
  7 27  1  0
 27 28  2  0
 27 29  1  0
 30 12  1  0
 30 31  1  0
 30 32  1  0
 31 32  1  0
  2 33  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA5220699

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type:

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 473.89

Molecular Weight (Monoisotopic): 473.1266

AlogP: 1.94

#Rotatable Bonds: 8

Polar Surface Area: 130.55

Molecular Species: NEUTRAL

HBA: 6

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.39

CX Basic pKa: ┄

CX LogP: 1.30

CX LogD: 1.30

Aromatic Rings: 3

Heavy Atoms: 33

QED Weighted: 0.46

Np Likeness Score: -1.70

References

1. Zhang W, Wu M, Vadlakonda S, Juarez L, Cheng X, Muppa S, Chintareddy V, Vogeti L, Kellogg-Yelder D, Williams J, Polach K, Chen X, Raman K, Babu YS, Kotian P..  (2022)  Scaffold hopping via ring opening enables identification of acyclic compounds as new complement Factor D inhibitors.,  74  [PMID:36272185] [10.1016/j.bmc.2022.117034]

Source

Source(1):

• Scientific Literature