4-Hydroxy-N-(2-phenylpropan-2-yl)-2-(pyridazin-3-yl)-pyrimidine-5-carboxamide

ID: ALA4789540

PubChem CID: 44230661

Max Phase: Preclinical

Molecular Formula: C18H17N5O2

Molecular Weight: 335.37

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CC(C)(NC(=O)c1cnc(-c2cccnn2)nc1O)c1ccccc1

Standard InChI:  InChI=1S/C18H17N5O2/c1-18(2,12-7-4-3-5-8-12)22-17(25)13-11-19-15(21-16(13)24)14-9-6-10-20-23-14/h3-11H,1-2H3,(H,22,25)(H,19,21,24)

Standard InChI Key:  HIJYTFKLKFBPSJ-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 25 27  0  0  0  0  0  0  0  0999 V2000
    8.9728  -20.2438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9885  -19.4295    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.7052  -19.0306    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4103  -19.4585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3948  -20.2659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6820  -20.6648    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.1152  -19.0499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8243  -19.4585    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.1152  -18.2327    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.8243  -17.8241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8243  -17.0069    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1152  -16.5983    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1152  -15.7811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8243  -15.3725    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5334  -15.7811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5334  -16.5983    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7052  -18.2135    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.2329  -18.5332    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6415  -17.8241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2605  -20.6404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5591  -20.2190    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.8455  -20.6157    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.8322  -21.4337    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5384  -21.8533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2491  -21.4541    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
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 11 16  2  0
 10 11  1  0
  9 10  1  0
  3 17  1  0
 10 18  1  0
 19 10  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 20  1  0
  1 20  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4789540

   6-oxo-N-(2-phenylpropan-2-yl)-2-pyridazin-3-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: 335.37

Molecular Weight (Monoisotopic): 335.1382

AlogP: 2.30

#Rotatable Bonds: 4

Polar Surface Area: 100.89

Molecular Species: NEUTRAL

HBA: 6

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 10.57

CX Basic pKa: 0.51

CX LogP: 2.72

CX LogD: 2.72

Aromatic Rings: 3

Heavy Atoms: 25

QED Weighted: 0.76

Np Likeness Score: -1.52

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