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

ID: ALA5220812

PubChem CID: 130299610

Max Phase: Preclinical

Molecular Formula: C23H23ClFN5O4

Molecular Weight: 487.92

Names and Identifiers

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

Standard InChI:  InChI=1S/C23H23ClFN5O4/c24-17-3-1-2-14(21(17)25)9-27-19(32)10-29(15-5-6-15)20(33)11-30-18-8-13(12-31)4-7-16(18)22(28-30)23(26)34/h1-4,7-8,15,31H,5-6,9-12H2,(H2,26,34)(H,27,32)

Standard InChI Key:  UYOQIJAROUNQLT-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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   -0.8129    1.9463    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4012    1.2312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4012    0.4061    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1127   -0.0116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.5419   -0.0221    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.5065    1.1560    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3022    1.3636    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8813    0.7762    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6611   -0.0222    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8620   -0.2251    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4776   -0.9452    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6632   -0.8140    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8849   -1.6628    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7100   -1.6689    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4671   -2.3742    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    1.0277    0.4166    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0217    1.2418    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7454    0.0094    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4568    0.4271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1744    0.0199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8861    0.4375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8801    1.2627    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    4.6013    0.0309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3128    0.4486    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    4.6073   -0.7943    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9001   -1.2115    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1805   -0.8085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5158    2.1607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3128    2.3742    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  3  1  1  0
  3  2  1  0
  3  4  1  0
  5  4  1  0
  6  5  1  0
  7  6  1  0
  8  7  1  0
  8  9  2  0
  9 10  1  0
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 13  8  1  0
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  7 15  1  0
 14 16  1  0
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  5 19  2  0
  4 20  1  0
 20 21  1  0
 21 22  2  0
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 23 24  1  0
 24 25  1  0
 26 25  2  0
 26 27  1  0
 28 26  1  0
 28 29  1  0
 30 28  2  0
 31 30  1  0
 25 32  1  0
 32 31  2  0
 10 33  1  0
 33 34  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA5220812

   ---

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: 487.92

Molecular Weight (Monoisotopic): 487.1423

AlogP: 1.73

#Rotatable Bonds: 9

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: 13.39

CX Basic pKa: ┄

CX LogP: 0.84

CX LogD: 0.84

Aromatic Rings: 3

Heavy Atoms: 34

QED Weighted: 0.42

Np Likeness Score: -1.74

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