(S)-2-(4-fluoro-1H-indole-2-carboxamido)-3-(4-hydroxyphenyl)propanoic acid

ID: ALA4876740

PubChem CID: 164628698

Max Phase: Preclinical

Molecular Formula: C18H15FN2O4

Molecular Weight: 342.33

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  O=C(N[C@@H](Cc1ccc(O)cc1)C(=O)O)c1cc2c(F)cccc2[nH]1

Standard InChI:  InChI=1S/C18H15FN2O4/c19-13-2-1-3-14-12(13)9-15(20-14)17(23)21-16(18(24)25)8-10-4-6-11(22)7-5-10/h1-7,9,16,20,22H,8H2,(H,21,23)(H,24,25)/t16-/m0/s1

Standard InChI Key:  BAGCTYWKDRLPHT-INIZCTEOSA-N

Molfile:  

 
     RDKit          2D

 25 27  0  0  0  0  0  0  0  0999 V2000
    1.6949  -16.5501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6937  -17.3738    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4018  -17.7869    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1156  -17.3733    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1127  -16.5465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4000  -16.1413    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8280  -17.7850    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8293  -18.6063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1181  -19.0160    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5418  -19.0138    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4057  -18.6085    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1194  -19.8373    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2530  -18.6040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9655  -19.0115    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2517  -17.7827    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0536  -19.8262    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.7170  -18.6760    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2649  -19.2865    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8571  -19.9944    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2662  -20.7035    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0871  -20.7018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4971  -19.9851    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0815  -19.2830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4904  -18.5690    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    0.9871  -16.1417    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  1  1  0
  4  7  1  0
  8  7  1  6
  8  9  1  0
  8 10  1  0
  9 11  1  0
  9 12  2  0
 10 13  1  0
 13 14  1  0
 13 15  2  0
 14 16  1  0
 16 19  1  0
 18 17  1  0
 17 14  2  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 18  1  0
 23 24  1  0
  1 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4876740

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 342.33

Molecular Weight (Monoisotopic): 342.1016

AlogP: 2.44

#Rotatable Bonds: 5

Polar Surface Area: 102.42

Molecular Species: ACID

HBA: 3

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.74

CX Basic pKa: ┄

CX LogP: 2.61

CX LogD: -0.68

Aromatic Rings: 3

Heavy Atoms: 25

QED Weighted: 0.57

Np Likeness Score: -0.52

References

1. Gironda-Martínez A, Gorre ÉMD, Prati L, Gosalbes JF, Dakhel S, Cazzamalli S, Samain F, Donckele EJ, Neri D..  (2021)  Identification and Validation of New Interleukin-2 Ligands Using DNA-Encoded Libraries.,  64  (23.0): [PMID:34821503] [10.1021/acs.jmedchem.1c01693]

Source

Source(1):

• Scientific Literature