(18aS)-2-Chloro-13-1-(1r,3S)-3-hydroxycyclobutyl]-11-methyl-8,9,10,11,19,20,21,22-octahydro-18aH,24H-18,15-(metheno)pyrido[2,1-l]pyrimido(6,1-h][1,4,7,9,10,13]benzoxapentaazacyclohexadecine-7,24(6H)-dione

ID: ALA4740044

PubChem CID: 154970072

Max Phase: Preclinical

Molecular Formula: C27H31ClN6O4

Molecular Weight: 539.04

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CN1CCNC(=O)COc2ccc(Cl)cc2C(=O)N2CCCC[C@H]2c2cc3nc([C@H]4C[C@H](O)C4)cc1n3n2

Standard InChI:  InChI=1S/C27H31ClN6O4/c1-32-9-7-29-25(36)15-38-23-6-5-17(28)12-19(23)27(37)33-8-3-2-4-22(33)21-13-24-30-20(16-10-18(35)11-16)14-26(32)34(24)31-21/h5-6,12-14,16,18,22,35H,2-4,7-11,15H2,1H3,(H,29,36)/t16-,18-,22-/m0/s1

Standard InChI Key:  HIRKVDNSABOJID-ZJBJCVSYSA-N

Molfile:  

 
     RDKit          2D

 39 44  0  0  0  0  0  0  0  0999 V2000
    4.2541  -22.1246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2541  -22.9496    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9661  -23.3578    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.9661  -21.7080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6781  -22.1246    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.6827  -22.9506    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4696  -23.2015    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9515  -22.5305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4622  -21.8650    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.7741  -22.5256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1894  -23.2395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0108  -23.2369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4231  -22.5221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0079  -21.8080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1803  -21.8090    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5409  -23.3648    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7438  -23.1524    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5314  -23.9496    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3286  -24.1620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9661  -20.8830    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2517  -20.4705    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7645  -21.0964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1738  -20.3800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9396  -21.1001    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.9986  -20.3781    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4078  -19.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9919  -18.9490    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1627  -18.9555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7573  -19.6715    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9324  -19.6782    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4766  -19.0988    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.0741  -19.8458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5382  -20.3818    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2328  -19.6592    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    7.3541  -23.2371    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2874  -20.0954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1624  -19.2830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8073  -18.7685    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8176  -24.3631    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  1  4  2  0
  2  3  2  0
  3  6  1  0
  5  4  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9  5  1  0
 10 11  1  0
 10 15  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
  8 10  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 16  1  0
 16  2  1  1
  4 20  1  0
 20 33  1  0
 20 21  1  0
 15 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
 29 23  1  0
 29 30  1  0
 31 32  1  0
 32 33  1  0
 26 34  1  0
 10 35  1  6
 30 36  1  0
 36 37  1  0
 37 31  1  0
 37 38  2  0
 18 39  1  6
M  END

Alternative Forms

1. Parent:

   

   ALA4740044

   ---

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: 539.04

Molecular Weight (Monoisotopic): 538.2095

AlogP: 2.93

#Rotatable Bonds: 1

Polar Surface Area: 112.30

Molecular Species: NEUTRAL

HBA: 8

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 10

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 13.27

CX Basic pKa: 2.09

CX LogP: 2.16

CX LogD: 2.16

Aromatic Rings: 3

Heavy Atoms: 38

QED Weighted: 0.49

Np Likeness Score: -0.53

References

1. Yamaguchi-Sasaki T,Kawaguchi T,Okada A,Tokura S,Tanaka-Yamamoto N,Takeuchi T,Ogata Y,Takahashi R,Kurimoto-Tsuruta R,Tamaoki T,Sugaya Y,Abe-Kumasaka T,Arikawa K,Yoshida I,Sugiyama H,Kanuma K,Yoshinaga M.  (2020)  Discovery of a potent dual inhibitor of wild-type and mutant respiratory syncytial virus fusion proteins through the modulation of atropisomer interconversion properties.,  28  (24): [PMID:33190073] [10.1016/j.bmc.2020.115818]

Source

Source(1):

• Scientific Literature