Methyl N-[(10R,14S)-14-(2,6-Difluoro-4-methylbenzamido)-10-methyl-9-oxo-8,16-diazatricyclo[13.3.1.0(2,7)]nonadeca-1-(19),2(7),3,5,15,17-hexaen-5-yl]carbamate

ID: ALA4585824

PubChem CID: 155567050

Max Phase: Preclinical

Molecular Formula: C28H28F2N4O4

Molecular Weight: 522.55

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  COC(=O)Nc1ccc2c(c1)NC(=O)[C@H](C)CCC[C@H](NC(=O)c1c(F)cc(C)cc1F)c1cc-2ccn1

Standard InChI:  InChI=1S/C28H28F2N4O4/c1-15-11-20(29)25(21(30)12-15)27(36)33-22-6-4-5-16(2)26(35)34-23-14-18(32-28(37)38-3)7-8-19(23)17-9-10-31-24(22)13-17/h7-14,16,22H,4-6H2,1-3H3,(H,32,37)(H,33,36)(H,34,35)/t16-,22+/m1/s1

Standard InChI Key:  UFXJPWDSTBLEDM-ZHRRBRCNSA-N

Molfile:  

 
     RDKit          2D

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    8.1326  -27.1943    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4208  -28.4284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1326  -26.3730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8444  -25.9644    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5563  -26.3730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   10.2681  -27.6070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    9.5569  -28.8388    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8454  -28.4273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    8.1317  -29.6563    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
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    5.2901  -28.8407    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9998  -27.6096    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5808  -28.4332    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8702  -28.8424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8712  -29.6646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5887  -30.0759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2964  -29.6602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5804  -27.6119    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    6.0110  -30.0682    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    3.1606  -30.0795    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8444  -25.1431    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3932  -27.1885    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.1065  -27.5987    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1094  -28.4201    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.8169  -27.1835    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.5302  -27.5937    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  3  1  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  1  0
  9 10  2  0
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 15 16  2  0
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 18 19  1  0
 19 20  2  0
 20 15  1  0
 10 15  1  0
 17  3  1  0
  3 21  1  1
 21 22  1  0
 22 23  1  0
 22 24  2  0
 23 25  2  0
 25 26  1  0
 26 27  2  0
 27 28  1  0
 28 29  2  0
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 25 30  1  0
 29 31  1  0
 27 32  1  0
  5 33  1  1
 13 34  1  0
 34 35  1  0
 35 36  2  0
 35 37  1  0
 37 38  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4585824

   ---

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: 522.55

Molecular Weight (Monoisotopic): 522.2079

AlogP: 5.74

#Rotatable Bonds: 3

Polar Surface Area: 109.42

Molecular Species: NEUTRAL

HBA: 5

HBD: 3

#RO5 Violations: 2

HBA (Lipinski): 8

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 11.58

CX Basic pKa: 3.76

CX LogP: 5.05

CX LogD: 5.05

Aromatic Rings: 3

Heavy Atoms: 38

QED Weighted: 0.41

Np Likeness Score: -0.77

References

1. Corte JR, Pinto DJP, Fang T, Osuna H, Yang W, Wang Y, Lai A, Clark CG, Sun JH, Rampulla R, Mathur A, Kaspady M, Neithnadka PR, Li YC, Rossi KA, Myers JE, Sheriff S, Lou Z, Harper TW, Huang C, Zheng JJ, Bozarth JM, Wu Y, Wong PC, Crain EJ, Seiffert DA, Luettgen JM, Lam PYS, Wexler RR, Ewing WR..  (2020)  Potent, Orally Bioavailable, and Efficacious Macrocyclic Inhibitors of Factor XIa. Discovery of Pyridine-Based Macrocycles Possessing Phenylazole Carboxamide P1 Groups.,  63  (2): [PMID:31833761] [10.1021/acs.jmedchem.9b01768]

Source

Source(1):

• Scientific Literature