rac-5-fluoro-3-(2-phenylcyclopropanecarboxamido)-1H-indole-2-carboxylic acid

ID: ALA4089211

PubChem CID: 3784000

Max Phase: Preclinical

Molecular Formula: C19H15FN2O3

Molecular Weight: 338.34

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(O)c1[nH]c2ccc(F)cc2c1NC(=O)C1CC1c1ccccc1

Standard InChI:  InChI=1S/C19H15FN2O3/c20-11-6-7-15-14(8-11)16(17(21-15)19(24)25)22-18(23)13-9-12(13)10-4-2-1-3-5-10/h1-8,12-13,21H,9H2,(H,22,23)(H,24,25)

Standard InChI Key:  LBCNHUJFDVBZDB-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 25 28  0  0  0  0  0  0  0  0999 V2000
    8.5622   -4.7618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1467   -5.4773    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7992   -5.4736    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3851   -4.7612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3857   -6.1939    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5582   -6.1910    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2998   -6.9771    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.9676   -7.4658    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6386   -6.9817    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9644   -8.2934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2485   -8.7035    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.6774   -8.7083    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.4223   -7.2393    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.0373   -6.6893    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8211   -6.9469    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8685   -5.8817    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.3688   -7.5578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6264   -6.7741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5389   -8.3623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9225   -8.9124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0913   -9.7191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8760   -9.9770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4920   -9.4218    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3200   -8.6171    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7962   -4.0459    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  6  1  0
  5  3  1  0
  3  4  2  0
  4  1  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9  5  1  0
 10 11  1  0
 10 12  2  0
  8 10  1  0
  9 13  1  0
 13 14  1  0
 14 15  1  0
 14 16  2  0
 17 15  1  0
 18 17  1  0
 15 18  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 19  1  0
 17 19  1  0
  4 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4089211

   5-fluoro-3-[(2-phenylcyclopropanecarbonyl)amino]-1H-indole-2-carboxylic acid

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: 338.34

Molecular Weight (Monoisotopic): 338.1067

AlogP: 3.75

#Rotatable Bonds: 4

Polar Surface Area: 82.19

Molecular Species: ACID

HBA: 2

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.83

CX Basic pKa: ┄

CX LogP: 3.88

CX LogD: 0.63

Aromatic Rings: 3

Heavy Atoms: 25

QED Weighted: 0.68

Np Likeness Score: -1.07

References

1. Vulpetti A, Randl S, Rüdisser S, Ostermann N, Erbel P, Mac Sweeney A, Zoller T, Salem B, Gerhartz B, Cumin F, Hommel U, Dalvit C, Lorthiois E, Maibaum J..  (2017)  Structure-Based Library Design and Fragment Screening for the Identification of Reversible Complement Factor D Protease Inhibitors.,  60  (5): [PMID:28157311] [10.1021/acs.jmedchem.6b01684]

2. Dalvit C, Vulpetti A..  (2019)  Ligand-Based Fluorine NMR Screening: Principles and Applications in Drug Discovery Projects.,  62  (5): [PMID:30295487] [10.1021/acs.jmedchem.8b01210]

Source

Source(1):

• Scientific Literature