(1R,3S,5R)-2-Aza-bicyclo[3.1.0]hexane-2,3-dicarboxylic Acid-2-[(1-Carbamoyl-1H-indol-3-yl)-amide]-3-[(3-Chlorophenyl)-amide]

ID: ALA4095470

PubChem CID: 130301808

Max Phase: Preclinical

Molecular Formula: C22H20ClN5O3

Molecular Weight: 437.89

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  NC(=O)n1cc(NC(=O)N2[C@@H]3C[C@@H]3C[C@H]2C(=O)Nc2cccc(Cl)c2)c2ccccc21

Standard InChI:  InChI=1S/C22H20ClN5O3/c23-13-4-3-5-14(10-13)25-20(29)19-9-12-8-18(12)28(19)22(31)26-16-11-27(21(24)30)17-7-2-1-6-15(16)17/h1-7,10-12,18-19H,8-9H2,(H2,24,30)(H,25,29)(H,26,31)/t12-,18-,19+/m1/s1

Standard InChI Key:  AIORQXWESUEOLO-DPMMWBKBSA-N

Molfile:  

     RDKit          2D

 33 37  0  0  0  0  0  0  0  0999 V2000
   20.7664  -16.2443    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.5881  -16.2443    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.0654  -16.9111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.7337  -17.6621    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.8828  -16.8229    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   23.3684  -17.4898    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2792  -16.9100    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.4621  -16.8198    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.6173  -17.6617    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.9825  -17.4854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1649  -17.5699    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9952  -18.3741    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.2445  -18.7106    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.0328  -18.2394    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.5094  -18.9017    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.3277  -18.8180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.6669  -18.0621    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.1800  -17.4029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.4840  -17.9752    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   19.3118  -18.2352    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7011  -18.7811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8779  -19.5799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6565  -19.8299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2587  -19.2790    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0871  -18.4863    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5772  -18.2298    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.1530  -19.5280    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.8411  -15.4582    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.5174  -15.4629    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.1686  -14.9777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4228  -14.6564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.1644  -14.1605    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   19.7240  -15.2460    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2 28  1  0
 29  1  1  0
  2  3  1  1
  3  4  2  0
  3  5  1  0
  5  6  1  0
  1  7  1  0
  7  8  1  0
  7  9  2  0
  8 10  1  0
 20 10  1  0
 10 11  2  0
 11 12  1  0
 12 21  1  0
 12 13  1  0
  6 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18  6  1  0
 17 19  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 20  1  0
 13 26  2  0
 13 27  1  0
 28 30  1  0
 30 29  1  0
 31 30  1  0
 29 31  1  0
 30 32  1  1
 29 33  1  1
M  END

Alternative Forms

1. Parent:

   

   ALA4095470

   ---

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: 437.89

Molecular Weight (Monoisotopic): 437.1255

AlogP: 3.85

#Rotatable Bonds: 3

Polar Surface Area: 109.46

Molecular Species: NEUTRAL

HBA: 4

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.35

CX Basic pKa: ┄

CX LogP: 2.50

CX LogD: 2.50

Aromatic Rings: 3

Heavy Atoms: 31

QED Weighted: 0.58

Np Likeness Score: -1.05

References

1. Lorthiois E, Anderson K, Vulpetti A, Rogel O, Cumin F, Ostermann N, Steinbacher S, Mac Sweeney A, Delgado O, Liao SM, Randl S, Rüdisser S, Dussauge S, Fettis K, Kieffer L, de Erkenez A, Yang L, Hartwieg C, Argikar UA, La Bonte LR, Newton R, Kansara V, Flohr S, Hommel U, Jaffee B, Maibaum J..  (2017)  Discovery of Highly Potent and Selective Small-Molecule Reversible Factor D Inhibitors Demonstrating Alternative Complement Pathway Inhibition in Vivo.,  60  (13): [PMID:28621538] [10.1021/acs.jmedchem.7b00425]

Source

Source(1):

• Scientific Literature