2-(2-(4-carbamimidoylphenylcarbamoyl)-6-methoxypyridin-3-yl)-5-(neopentylcarbamoyl)benzoic acid

ID: ALA2417905

PubChem CID: 10185526

Max Phase: Preclinical

Molecular Formula: C27H29N5O5

Molecular Weight: 503.56

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccc(-c2ccc(C(=O)NCC(C)(C)C)cc2C(=O)O)c(C(=O)Nc2ccc(C(=N)N)cc2)n1

Standard InChI:  InChI=1S/C27H29N5O5/c1-27(2,3)14-30-24(33)16-7-10-18(20(13-16)26(35)36)19-11-12-21(37-4)32-22(19)25(34)31-17-8-5-15(6-9-17)23(28)29/h5-13H,14H2,1-4H3,(H3,28,29)(H,30,33)(H,31,34)(H,35,36)

Standard InChI Key:  CATVOBGLOJBTJR-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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    5.4183  -17.6829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1328  -18.0954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8473  -17.6829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8473  -16.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1328  -16.4454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    8.2762  -17.6829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9907  -18.0954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    9.7051  -17.6829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7051  -16.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   11.8485  -16.4454    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.7051  -14.3829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4196  -13.9704    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.9907  -13.9704    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7039  -16.4454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9894  -16.8579    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.7039  -15.6204    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
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   11.8485  -13.9704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5630  -14.3829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8485  -13.1454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5648  -13.5568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7051  -20.1579    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.9907  -20.5705    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
  4  7  1  0
  7  8  1  0
  8  9  1  0
  8 10  2  0
  9 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15  9  1  0
 15 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
 17 22  1  0
 22 23  2  0
 22 24  1  0
 19 25  1  0
 25 26  1  0
 25 27  2  0
  1 28  1  0
 28 29  2  0
 28 30  1  0
 26 31  1  0
 31 32  1  0
 32 33  1  0
 32 34  1  0
 32 35  1  0
 12 36  1  0
 36 37  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2417905

   2-[2-[(4-Carbamimidoylphenyl)carbamoyl]-6-methoxypyridin-3-yl]-5-(2,2-dimethylpropylcarbamoyl)benzoic acid

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: 503.56

Molecular Weight (Monoisotopic): 503.2169

AlogP: 3.77

#Rotatable Bonds: 8

Polar Surface Area: 167.49

Molecular Species: ZWITTERION

HBA: 6

HBD: 5

#RO5 Violations: 1

HBA (Lipinski): 10

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 3.40

CX Basic pKa: 11.49

CX LogP: 1.95

CX LogD: 1.95

Aromatic Rings: 3

Heavy Atoms: 37

QED Weighted: 0.23

Np Likeness Score: -0.98

References

1. Bolton SA, Sutton JC, Anumula R, Bisacchi GS, Jacobson B, Slusarchyk WA, Treuner UD, Wu SC, Zhao G, Pi Z, Sheriff S, Smirk RA, Bisaha S, Cheney DL, Wei A, Schumacher WA, Hartl KS, Liu E, Zahler R, Seiler SM..  (2013)  Discovery of nonbenzamidine factor VIIa inhibitors using a biaryl acid scaffold.,  23  (18): [PMID:23927973] [10.1016/j.bmcl.2013.06.028]

Source

Source(1):

• Scientific Literature