1-(2-((1R,3S,5R)-3-(((R)-1-(3-Chloro-2-fluorophenyl)ethyl)carbamoyl)-2-azabicyclo[3.1.0]hexan-2-yl)-2-oxoethyl)-1H-pyrazolo[3,4-c]pyridine-3-carboxamide (6)::US9085555, 702

ID: ALA3678914

Cas Number: 1386455-51-1

PubChem CID: 68283608

Max Phase: Preclinical

Molecular Formula: C23H22ClFN6O3

Molecular Weight: 484.92

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C[C@@H](NC(=O)[C@@H]1C[C@H]2C[C@H]2N1C(=O)Cn1nc(C(N)=O)c2ccncc21)c1cccc(Cl)c1F

Standard InChI:  InChI=1S/C23H22ClFN6O3/c1-11(13-3-2-4-15(24)20(13)25)28-23(34)17-8-12-7-16(12)31(17)19(32)10-30-18-9-27-6-5-14(18)21(29-30)22(26)33/h2-6,9,11-12,16-17H,7-8,10H2,1H3,(H2,26,33)(H,28,34)/t11-,12-,16-,17+/m1/s1

Standard InChI Key:  YAALCKJNOOFODD-SKNMWMDOSA-N

Molfile:  

     RDKit          2D

 34 38  0  0  1  0  0  0  0  0999 V2000
   -5.0816   -2.8014    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6880   -3.8370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9451   -5.1410    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4443   -5.1507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8380   -4.1152    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7027   -6.4525    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3131   -7.8227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1985   -8.8266    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9030   -9.5710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8994   -8.0768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2256   -6.6258    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2234   -5.5086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9507   -5.7562    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6890   -4.0818    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3114   -2.9665    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8032   -3.1233    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4133   -1.7530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8794   -1.4442    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6813   -2.3370    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2520   -0.3035    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2990   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2990    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2990    0.7500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2990   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1888   -3.8273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9287   -2.5224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.4287   -2.5107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.1888   -3.8039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.4490   -5.1087    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.0571   -6.1432    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -7.9490   -5.1204    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3572   -6.1643    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1
  2  3  1  0
  3  4  1  0
  4  5  2  0
  6  4  1  1
  6  7  1  0
  8  7  1  6
  8  9  1  0
 10  9  1  6
 10  8  1  0
 10 11  1  0
 11  6  1  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
 17 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 15  1  0
 26 21  1  0
  2 27  1  0
 27 28  2  0
 28 29  1  0
 29 30  2  0
 30 31  1  0
 31 32  1  0
 31 33  2  0
 33 27  1  0
 33 34  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3678914

   Factor D inhibitor 6

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 484.92

Molecular Weight (Monoisotopic): 484.1426

AlogP: 2.19

#Rotatable Bonds: 6

Polar Surface Area: 123.21

Molecular Species: NEUTRAL

HBA: 6

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.75

CX Basic pKa: 1.93

CX LogP: 0.91

CX LogD: 0.91

Aromatic Rings: 3

Heavy Atoms: 34

QED Weighted: 0.55

Np Likeness Score: -1.20

References

1.  (2015)  Complement pathway modulators and uses thereof, 

2. 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(2):

• Scientific Literature
• BindingDB Database