(S)-4-Hydroxy-N-(1-(4-methoxyphenyl)ethyl)-2-(1H-pyrazol-1-yl)pyrimidine-5-carboxamide

ID: ALA4781541

PubChem CID: 57878392

Max Phase: Preclinical

Molecular Formula: C17H17N5O3

Molecular Weight: 339.36

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  COc1ccc([C@H](C)NC(=O)c2cnc(-n3cccn3)nc2O)cc1

Standard InChI:  InChI=1S/C17H17N5O3/c1-11(12-4-6-13(25-2)7-5-12)20-15(23)14-10-18-17(21-16(14)24)22-9-3-8-19-22/h3-11H,1-2H3,(H,20,23)(H,18,21,24)/t11-/m0/s1

Standard InChI Key:  KIFFMHNSRWITIH-NSHDSACASA-N

Molfile:  

 
     RDKit          2D

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   10.9274  -21.7700    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9244  -20.9529    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.6299  -20.5422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3384  -20.9447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3414  -21.7618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6359  -22.1766    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.0440  -20.5340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7525  -20.9364    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.0410  -19.7169    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.2219  -22.1807    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.4759  -21.8569    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.9292  -22.4640    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3440  -23.1695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1409  -22.9959    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6228  -19.7251    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.7465  -19.3021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4574  -19.7051    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7400  -18.4849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4614  -20.5216    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1714  -20.9246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8769  -20.5104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8678  -19.6890    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1572  -19.2898    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5852  -20.9093    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.2891  -20.4942    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  1  6  2  0
  7  8  2  0
  7  9  1  0
  4  7  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 10 14  1  0
  1 10  1  0
  3 15  1  0
  9 16  1  0
 16 17  1  0
 16 18  1  1
 17 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 17  1  0
 24 25  1  0
 21 24  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4781541

   N-[(1S)-1-(4-methoxyphenyl)ethyl]-6-oxo-2-pyrazol-1-yl-1H-pyrimidine-5-carboxamide

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: 339.36

Molecular Weight (Monoisotopic): 339.1331

AlogP: 1.87

#Rotatable Bonds: 5

Polar Surface Area: 102.16

Molecular Species: NEUTRAL

HBA: 7

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 10.79

CX Basic pKa: 1.00

CX LogP: 2.81

CX LogD: 2.81

Aromatic Rings: 3

Heavy Atoms: 25

QED Weighted: 0.74

Np Likeness Score: -1.93

References

1. Debenham JS,Madsen-Duggan C,Clements MJ,Walsh TF,Kuethe JT,Reibarkh M,Salowe SP,Sonatore LM,Hajdu R,Milligan JA,Visco DM,Zhou D,Lingham RB,Stickens D,DeMartino JA,Tong X,Wolff M,Pang J,Miller RR,Sherer EC,Hale JJ.  (2016)  Discovery of N-[Bis(4-methoxyphenyl)methyl]-4-hydroxy-2-(pyridazin-3-yl)pyrimidine-5-carboxamide (MK-8617), an Orally Active Pan-Inhibitor of Hypoxia-Inducible Factor Prolyl Hydroxylase 1-3 (HIF PHD1-3) for the Treatment of Anemia.,  59  (24.0): [PMID:28002958] [10.1021/acs.jmedchem.6b01242]

Source

Source(1):

• Scientific Literature