2-[(1-bromo-4-hydroxy-7-phenoxy-isoquinoline-3-carbonyl)amino]acetic acid

ID: ALA5209093

Cas Number: 808116-62-3

PubChem CID: 11384514

Max Phase: Preclinical

Molecular Formula: C18H13BrN2O5

Molecular Weight: 417.21

Names and Identifiers

Canonical SMILES:  O=C(O)CNC(=O)c1nc(Br)c2cc(Oc3ccccc3)ccc2c1O

Standard InChI:  InChI=1S/C18H13BrN2O5/c19-17-13-8-11(26-10-4-2-1-3-5-10)6-7-12(13)16(24)15(21-17)18(25)20-9-14(22)23/h1-8,24H,9H2,(H,20,25)(H,22,23)

Standard InChI Key:  MOOCHEISIIMJAU-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 26 28  0  0  0  0  0  0  0  0999 V2000
   -1.7855    0.4137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0709    0.8260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3590    0.4141    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3590   -0.4110    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0691   -0.8228    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7855   -0.4147    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3536    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0685    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0703   -0.4084    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3587   -0.8251    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3536    1.6502    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7831    0.8251    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7831    1.6503    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4978    0.4125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2124    0.8251    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9271    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6417    0.8251    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9271   -0.4126    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5001   -0.8272    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2148   -0.4147    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9296   -0.8271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6417   -0.4151    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6417    0.4103    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9313    0.8222    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2148    0.4140    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3587   -1.6503    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  2  1  0
  4  3  2  0
  5  4  1  0
  1  6  1  0
  6  5  2  0
  3  7  1  0
  8  7  2  0
  9  8  1  0
 10  9  2  0
  4 10  1  0
  7 11  1  0
  8 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 16 18  2  0
  6 19  1  0
 19 20  1  0
 21 20  2  0
 22 21  1  0
 23 22  2  0
 24 23  1  0
 25 24  2  0
 20 25  1  0
 10 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA5209093

   Glycine, N-[(1-bromo-4-hydroxy-7-phenoxy-3-isoquinolinyl)carbonyl]-

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: 417.21

Molecular Weight (Monoisotopic): 416.0008

AlogP: 3.31

#Rotatable Bonds: 5

Polar Surface Area: 108.75

Molecular Species: ACID

HBA: 5

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 2.45

CX Basic pKa: 0.27

CX LogP: 3.50

CX LogD: -0.43

Aromatic Rings: 3

Heavy Atoms: 26

QED Weighted: 0.55

Np Likeness Score: -0.43

References

1. Li Q, Yao B, Zhao S, Lu Z, Zhang Y, Xiang Q, Wu X, Yu H, Zhang C, Li J, Zhuang X, Wu D, Li Y, Xu Y..  (2022)  Discovery of a Highly Selective and H435R-Sensitive Thyroid Hormone Receptor β Agonist.,  65  (10.0): [PMID:35507418] [10.1021/acs.jmedchem.2c00144]

Source

Source(1):

• Scientific Literature