(3-Hydroxy-5-(3-(phenylamino)prop-1-yn-1-yl)-picolinoyl)glycine

ID: ALA4756775

PubChem CID: 129027326

Max Phase: Preclinical

Molecular Formula: C17H15N3O4

Molecular Weight: 325.32

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  O=C(O)CNC(=O)c1ncc(C#CCNc2ccccc2)cc1O

Standard InChI:  InChI=1S/C17H15N3O4/c21-14-9-12(5-4-8-18-13-6-2-1-3-7-13)10-19-16(14)17(24)20-11-15(22)23/h1-3,6-7,9-10,18,21H,8,11H2,(H,20,24)(H,22,23)

Standard InChI Key:  HTDCXHGZMOAJPP-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 24 25  0  0  0  0  0  0  0  0999 V2000
   19.6442  -13.3350    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6430  -14.1546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.3511  -14.5635    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.0608  -14.1541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.0579  -13.3314    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.3493  -12.9262    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.7641  -12.9202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.4733  -13.3261    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.7610  -12.1030    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.1795  -12.9148    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.8887  -13.3208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.5949  -12.9095    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.8918  -14.1380    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.7691  -14.5616    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.9350  -14.5626    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2217  -14.9653    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5101  -15.3671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5022  -16.1842    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.7906  -16.5860    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0903  -16.1682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3792  -16.5693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3709  -17.3873    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0796  -17.8026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7878  -17.3991    0.0000 C   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
  5  7  1  0
  7  8  1  0
  7  9  2  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  2  0
  4 14  1  0
  2 15  1  0
 15 16  3  0
 16 17  1  0
 17 18  1  0
 18 19  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
M  END

Alternative Forms

1. Parent:

   

   ALA4756775

   ---

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: 325.32

Molecular Weight (Monoisotopic): 325.1063

AlogP: 1.07

#Rotatable Bonds: 5

Polar Surface Area: 111.55

Molecular Species: ACID

HBA: 5

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 2.44

CX Basic pKa: 3.03

CX LogP: 0.93

CX LogD: -2.12

Aromatic Rings: 2

Heavy Atoms: 24

QED Weighted: 0.61

Np Likeness Score: -0.76

References

1. Zhang X,Lei Y,Hu T,Wu Y,Li Z,Jiang Z,Yang C,Zhang L,You Q.  (2020)  Discovery of Clinical Candidate (5-(3-(4-Chlorophenoxy)prop-1-yn-1-yl)-3-hydroxypicolinoyl)glycine, an Orally Bioavailable Prolyl Hydroxylase Inhibitor for the Treatment of Anemia.,  63  (17.0): [PMID:32787144] [10.1021/acs.jmedchem.0c01161]

Source

Source(1):

• Scientific Literature