Methyl N-[(10R,14S)-14-[1-(3-Chlorophenyl)-5-oxopyrrolidine-3-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

ID: ALA4522419

PubChem CID: 71509334

Max Phase: Preclinical

Molecular Formula: C31H32ClN5O5

Molecular Weight: 590.08

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  COC(=O)Nc1ccc2c(c1)NC(=O)[C@H](C)CCC[C@H](NC(=O)C1CC(=O)N(c3cccc(Cl)c3)C1)c1cc-2ccn1

Standard InChI:  InChI=1S/C31H32ClN5O5/c1-18-5-3-8-25(35-30(40)20-14-28(38)37(17-20)23-7-4-6-21(32)15-23)27-13-19(11-12-33-27)24-10-9-22(34-31(41)42-2)16-26(24)36-29(18)39/h4,6-7,9-13,15-16,18,20,25H,3,5,8,14,17H2,1-2H3,(H,34,41)(H,35,40)(H,36,39)/t18-,20?,25+/m1/s1

Standard InChI Key:  GNMIMWHTQBWNQT-UWPXCJAKSA-N

Molfile:  

 
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M  END

Alternative Forms

1. Parent:

   

   ALA4522419

   methyl N-[(10R,14S)-14-[[1-(3-chlorophenyl)-5-oxopyrrolidine-3-carbonyl]amino]-10-methyl-9-oxo-8,16-diazatricyclo[13.3.1.02,7]nonadeca-1(19),2(7),3,5,15,17-hexaen-5-yl]carbamate

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: 590.08

Molecular Weight (Monoisotopic): 589.2092

AlogP: 5.55

#Rotatable Bonds: 4

Polar Surface Area: 129.73

Molecular Species: NEUTRAL

HBA: 6

HBD: 3

#RO5 Violations: 2

HBA (Lipinski): 10

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 12.52

CX Basic pKa: 3.76

CX LogP: 3.90

CX LogD: 3.90

Aromatic Rings: 3

Heavy Atoms: 42

QED Weighted: 0.37

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]

2. 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