N-Carbamimidoyl-2-{3-[2-(morpholin-4-yl)pyrimidin-5-yl]phenyl}acetamide (2R,3R)-tartrate

ID: ALA4103619

PubChem CID: 146029979

Max Phase: Preclinical

Molecular Formula: C21H26N6O8

Molecular Weight: 340.39

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  N=C(N)NC(=O)Cc1cccc(-c2cnc(N3CCOCC3)nc2)c1.O=C(O)[C@H](O)[C@@H](O)C(=O)O

Standard InChI:  InChI=1S/C17H20N6O2.C4H6O6/c18-16(19)22-15(24)9-12-2-1-3-13(8-12)14-10-20-17(21-11-14)23-4-6-25-7-5-23;5-1(3(7)8)2(6)4(9)10/h1-3,8,10-11H,4-7,9H2,(H4,18,19,22,24);1-2,5-6H,(H,7,8)(H,9,10)/t;1-,2-/m.1/s1

Standard InChI Key:  GNMWSWRBHZFPRI-LREBCSMRSA-N

Molfile:  

     RDKit          2D

 35 36  0  0  0  0  0  0  0  0999 V2000
    9.8405  -11.0764    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5496   -9.8465    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.2587  -11.8978    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.5496  -10.6679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   12.6810  -11.0764    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.5685   -7.9495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8554   -8.3522    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2693   -8.3681    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.5807   -7.1324    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.1546   -7.9336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    7.6097   -8.2919    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.3228   -7.8934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0236   -8.3120    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0155   -9.1291    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3024   -9.5276    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.8844   -9.5116    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.8763  -10.3287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1633  -10.7272    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4583  -10.3087    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4706   -9.4916    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1836   -9.0931    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2938   -6.7339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3019   -5.9169    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.9946   -7.1525    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  4  1  0
  4  2  1  6
  4  5  1  0
  5  3  1  6
  5  6  1  0
  1  7  2  0
  1  8  1  0
  6  9  2  0
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 15 20  2  0
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 27 28  1  0
 28 29  1  0
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 31 32  1  0
 27 32  1  0
 21 27  1  0
 17 24  1  0
 12 15  1  0
 33 34  1  0
 33 35  2  0
 14 33  1  0
M  END

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: 340.39

Molecular Weight (Monoisotopic): 340.1648

AlogP: 0.53

#Rotatable Bonds: 4

Polar Surface Area: 117.22

Molecular Species: BASE

HBA: 6

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 11.44

CX Basic pKa: 8.80

CX LogP: 0.82

CX LogD: -0.56

Aromatic Rings: 2

Heavy Atoms: 25

QED Weighted: 0.55

Np Likeness Score: -1.33

References

1. Yamaki S, Yamada H, Nagashima A, Kondo M, Shimada Y, Kadono K, Yoshihara K..  (2017)  Synthesis and structure activity relationships of carbamimidoylcarbamate derivatives as novel vascular adhesion protein-1 inhibitors.,  25  (21): [PMID:28988626] [10.1016/j.bmc.2017.09.036]

Source

Source(1):

• Scientific Literature