{(S)-15-[(S)-6-(3-Chlorophenyl)-2-oxo-[1,3]oxazinan-3-yl]-9-oxo-8,17,19-triaza-tricyclo[14.2.1.0(2,7)]nonadeca-1(18),2,4,6,12,16(19)-hexaen-5-yl}carbamic acid methyl ester

ID: ALA4552540

PubChem CID: 71260381

Max Phase: Preclinical

Molecular Formula: C28H28ClN5O5

Molecular Weight: 550.02

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  COC(=O)Nc1ccc2c(c1)NC(=O)CC/C=C/C[C@H](N1CC[C@@H](c3cccc(Cl)c3)OC1=O)c1nc-2c[nH]1

Standard InChI:  InChI=1S/C28H28ClN5O5/c1-38-27(36)31-19-10-11-20-21(15-19)32-25(35)9-4-2-3-8-23(26-30-16-22(20)33-26)34-13-12-24(39-28(34)37)17-6-5-7-18(29)14-17/h2-3,5-7,10-11,14-16,23-24H,4,8-9,12-13H2,1H3,(H,30,33)(H,31,36)(H,32,35)/b3-2+/t23-,24-/m0/s1

Standard InChI Key:  ZRELHZVMHRERCT-KOAGWOQNSA-N

Molfile:  

 
     RDKit          2D

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   25.4841  -24.4943    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.9276  -23.8841    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
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   22.0365  -23.8122    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.3260  -24.2211    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   19.8906  -27.5249    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1
  2  3  1  0
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  4  5  1  0
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 37 39  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4552540

   methyl N-[(12E,15S)-15-[(6S)-6-(3-chlorophenyl)-2-oxo-1,3-oxazinan-3-yl]-9-oxo-8,17,19-triazatricyclo[14.2.1.02,7]nonadeca-1(18),2(7),3,5,12,16-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: 550.02

Molecular Weight (Monoisotopic): 549.1779

AlogP: 6.21

#Rotatable Bonds: 3

Polar Surface Area: 125.65

Molecular Species: NEUTRAL

HBA: 6

HBD: 3

#RO5 Violations: 2

HBA (Lipinski): 10

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 12.25

CX Basic pKa: 5.03

CX LogP: 4.53

CX LogD: 4.53

Aromatic Rings: 3

Heavy Atoms: 39

QED Weighted: 0.33

Np Likeness Score: -0.43

References

1. Clark CG, Rossi KA, Corte JR, Fang T, Smallheer JM, De Lucca I, Nirschl DS, Orwat MJ, Pinto DJP, Hu Z, Wang Y, Yang W, Jeon Y, Ewing WR, Myers JE, Sheriff S, Lou Z, Bozarth JM, Wu Y, Rendina A, Harper T, Zheng J, Xin B, Xiang Q, Luettgen JM, Seiffert DA, Wexler RR, Lam PYS..  (2019)  Structure based design of macrocyclic factor XIa inhibitors: Discovery of cyclic P1 linker moieties with improved oral bioavailability.,  29  (19): [PMID:31445854] [10.1016/j.bmcl.2019.08.008]

Source

Source(1):

• Scientific Literature