Methyl N-[(10R,14S)-14-[1-(3-Chloro-2-fluorophenyl)-5-methyl-1H-pyrazole-4-amido]-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 Hydrochloric Acid

ID: ALA4534617

PubChem CID: 155547007

Max Phase: Preclinical

Molecular Formula: C31H31Cl2FN6O4

Molecular Weight: 605.07

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  COC(=O)Nc1ccc2c(c1)NC(=O)[C@H](C)CCC[C@H](NC(=O)c1cnn(-c3cccc(Cl)c3F)c1C)c1cc-2ccn1.Cl

Standard InChI:  InChI=1S/C31H30ClFN6O4.ClH/c1-17-6-4-8-24(37-30(41)22-16-35-39(18(22)2)27-9-5-7-23(32)28(27)33)26-14-19(12-13-34-26)21-11-10-20(36-31(42)43-3)15-25(21)38-29(17)40;/h5,7,9-17,24H,4,6,8H2,1-3H3,(H,36,42)(H,37,41)(H,38,40);1H/t17-,24+;/m1./s1

Standard InChI Key:  PADDCQHTOGPCRK-NDZTXGRGSA-N

Molfile:  

     RDKit          2D

 44 47  0  0  0  0  0  0  0  0999 V2000
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    8.0986   -3.1531    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8141   -2.7383    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0986   -3.9787    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8141   -1.9127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5296   -1.5019    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2452   -1.9127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9608   -1.5019    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.2452   -2.7383    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.9608   -3.1531    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9584   -3.9798    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6732   -4.3905    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3856   -3.9796    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3829   -3.1498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6718   -2.7388    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    8.8132   -5.2130    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
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   10.2458   -5.2135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3836   -4.3908    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.6715   -3.9812    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9567   -4.3933    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6700   -3.1556    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.5296   -0.6762    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0970   -2.7324    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.8140   -3.1448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8169   -3.9704    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.5281   -2.7274    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.2452   -3.1397    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2047   -4.0624    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6522   -4.6751    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.0643   -5.3901    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.8714   -5.2190    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7295   -6.1389    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9113   -6.2230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5766   -6.9724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0592   -7.6383    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8802   -7.5498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2110   -6.8003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3649   -8.2131    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    6.0278   -6.7126    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    6.4821   -5.7683    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  1  0
  4  2  1  0
  3  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 10  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
 11 16  1  0
 18  4  1  0
  4 22  1  1
 22 23  1  0
 23 24  1  0
 23 25  2  0
  6 26  1  1
 14 27  1  0
 27 28  1  0
 28 29  2  0
 28 30  1  0
 30 31  1  0
 24 32  1  0
 32 33  2  0
 33 34  1  0
 34 35  1  0
 35 24  2  0
 36 37  2  0
 37 38  1  0
 38 39  2  0
 39 40  1  0
 40 41  2  0
 41 36  1  0
 34 36  1  0
 40 42  1  0
 41 43  1  0
 35 44  1  0
M  END

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: 605.07

Molecular Weight (Monoisotopic): 604.2001

AlogP: 6.44

#Rotatable Bonds: 4

Polar Surface Area: 127.24

Molecular Species: NEUTRAL

HBA: 7

HBD: 3

#RO5 Violations: 2

HBA (Lipinski): 10

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 12.45

CX Basic pKa: 3.76

CX LogP: 5.28

CX LogD: 5.28

Aromatic Rings: 4

Heavy Atoms: 43

QED Weighted: 0.25

Np Likeness Score: -1.26

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