(1R,2S)-2-(((2-Methyl-4-methoxymethylpyrimidin-5-yl)oxy)-methyl)-N-(5-fluoropyridin-2-yl)-2-(3-fluorophenyl)-cyclopropanecarboxamide

ID: ALA2425785

PubChem CID: 56944620

Max Phase: Preclinical

Molecular Formula: C23H22F2N4O3

Molecular Weight: 440.45

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COCc1nc(C)ncc1OC[C@@]1(c2cccc(F)c2)C[C@H]1C(=O)Nc1ccc(F)cn1

Standard InChI:  InChI=1S/C23H22F2N4O3/c1-14-26-11-20(19(28-14)12-31-2)32-13-23(15-4-3-5-16(24)8-15)9-18(23)22(30)29-21-7-6-17(25)10-27-21/h3-8,10-11,18H,9,12-13H2,1-2H3,(H,27,29,30)/t18-,23+/m0/s1

Standard InChI Key:  WRPGNWQVJUWOTB-FDDCHVKYSA-N

Molfile:  

     RDKit          2D

 32 35  0  0  0  0  0  0  0  0999 V2000
   18.9581  -13.1082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7831  -13.1082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3706  -12.3921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2439  -13.5210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5292  -13.1089    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.8150  -13.5218    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1030  -13.1050    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3893  -13.5172    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.3892  -14.3430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1089  -14.7550    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.8197  -14.3405    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6756  -14.7569    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4974  -13.5210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4970  -14.3460    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.2121  -13.1089    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.2112  -14.7589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.2090  -15.5842    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.9225  -15.9970    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.6381  -15.5848    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.6359  -14.7556    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.9220  -14.3465    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   23.3529  -15.9967    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   18.5347  -12.4001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9385  -11.6800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5158  -10.9724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6900  -10.9847    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2888  -11.7104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7138  -12.4150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9176  -10.2519    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   16.1055  -12.2800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3922  -11.8654    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.3946  -11.0404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  2  1  0
  1  3  1  0
  1  4  1  1
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11  6  1  0
  9 12  1  0
  2 13  1  1
 13 14  1  0
 13 15  2  0
 14 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 16  1  0
 19 22  1  0
  1 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
 28 23  1  0
 25 29  1  0
  7 30  1  0
 30 31  1  0
 31 32  1  0
M  END

Alternative Forms

1. Alternative Forms:

   

   ALA2425785

   (1R,2S)-2-(3-fluorophenyl)-N-(5-fluoropyridin-2-yl)-2-[[4-((111C)methoxymethyl)-2-methylpyrimidin-5-yl]oxymethyl]cyclopropane-1-carboxamide

2. Parent:

   

   ALA2425785

   (1R,2S)-2-(3-fluorophenyl)-N-(5-fluoropyridin-2-yl)-2-[[4-(methoxymethyl)-2-methylpyrimidin-5-yl]oxymethyl]cyclopropane-1-carboxamide

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 440.45

Molecular Weight (Monoisotopic): 440.1660

AlogP: 3.58

#Rotatable Bonds: 8

Polar Surface Area: 86.23

Molecular Species: NEUTRAL

HBA: 6

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.12

CX Basic pKa: 2.23

CX LogP: 3.11

CX LogD: 3.11

Aromatic Rings: 3

Heavy Atoms: 32

QED Weighted: 0.58

Np Likeness Score: -0.82

References

1. Oi N, Suzuki M, Terauchi T, Tokunaga M, Nakatani Y, Yamamoto N, Fukumura T, Zhang MR, Suhara T, Higuchi M..  (2013)  Synthesis and evaluation of novel radioligands for positron emission tomography imaging of the orexin-2 receptor.,  56  (16): [PMID:23879299] [10.1021/jm400772t]

Source

Source(1):

• Scientific Literature