[(1S,2R)-1-Benzyl-3-((3S,4aS,8aS)-3-tert-butylcarbamoyl-octahydro-isoquinolin-2-yl)-2-hydroxy-propyl]-carbamic acid (3R,3aR,6aS)-(hexahydro-cyclopenta[b]furan-3-yl) ester

ID: ALA331599

PubChem CID: 461022

Max Phase: Preclinical

Molecular Formula: C32H49N3O5

Molecular Weight: 555.76

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(C)(C)NC(=O)[C@@H]1C[C@@H]2CCCC[C@@H]2CN1C[C@@H](O)[C@H](Cc1ccccc1)NC(=O)O[C@H]1CO[C@H]2CCC[C@H]21

Standard InChI:  InChI=1S/C32H49N3O5/c1-32(2,3)34-30(37)26-17-22-12-7-8-13-23(22)18-35(26)19-27(36)25(16-21-10-5-4-6-11-21)33-31(38)40-29-20-39-28-15-9-14-24(28)29/h4-6,10-11,22-29,36H,7-9,12-20H2,1-3H3,(H,33,38)(H,34,37)/t22-,23+,24+,25-,26-,27+,28-,29-/m0/s1

Standard InChI Key:  LUICRMGYHPZLQE-XUSCARPCSA-N

Molfile:  

     RDKit          2D

 46 50  0  0  1  0  0  0  0  0999 V2000
    7.9542   -3.8042    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.6667   -4.2167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6667   -5.0542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3875   -4.2167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3792   -3.8167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2417   -4.2167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1000   -3.8042    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.9542   -2.9792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9542   -4.2042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3792   -5.4667    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0000   -5.0292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7042   -4.6917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8125   -4.2167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6750   -3.8042    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5292   -3.8042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3875   -2.9917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6750   -2.5792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2167   -5.3292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1542   -3.9917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9500   -5.4542    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3792   -5.0417    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8167   -5.0417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0917   -5.0542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5292   -2.9792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4000   -5.7542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5292   -5.6792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0750   -6.3792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2667   -6.1667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1000   -2.5917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6792   -1.7542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1000   -4.2292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3042   -5.8542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8042   -5.4667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8042   -6.4667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5667   -5.7417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4000   -1.3417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1042   -1.7667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1542   -6.4542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3875   -7.1792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5542   -7.1667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0500   -3.3917    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7667   -4.7417    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4542   -5.6292    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.4667   -4.4417    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.1000   -3.4042    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9542   -2.1667    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  2  1  0
  4  7  1  0
  5  2  1  0
  6  1  1  0
 13  7  1  6
  8  1  1  0
  9 14  1  0
 10  3  1  0
 11  9  1  0
 12 19  1  0
 13 15  1  0
 14  4  1  0
 15  6  1  0
 16 17  1  0
 17  8  1  0
 18 11  1  0
 19  9  1  0
 20  3  2  0
 21  4  2  0
 13 22  1  0
 23 10  1  0
 15 24  1  6
 25 22  1  0
 11 26  1  0
 27 26  1  0
 18 28  1  0
 29 16  1  0
 30 17  1  0
 31 23  1  0
 32 23  1  0
 33 23  1  0
 34 25  1  0
 35 25  2  0
 36 30  1  0
 37 36  1  0
 38 35  1  0
 39 34  2  0
 40 38  2  0
  9 41  1  1
 11 42  1  1
 18 43  1  1
  2 44  1  6
 16 45  1  6
 17 46  1  6
  5 16  1  0
 29 37  1  0
 39 40  1  0
 12 18  1  0
 28 27  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA331599

   [(3R,3aR,6aS)-3,3a,4,5,6,6a-hexahydro-2H-cyclopenta[b]furan-3-yl] N-[(1S,2R)-3-[(3S,4aS,8aS)-3-(tert-butylcarbamoyl)-3,4,4a,5,6,7,8,8a-octahydro-1H-isoquinolin-2-yl]-1-benzyl-2-hydroxy-propyl]carbamate

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 555.76

Molecular Weight (Monoisotopic): 555.3672

AlogP: 4.05

#Rotatable Bonds: 8

Polar Surface Area: 100.13

Molecular Species: NEUTRAL

HBA: 6

HBD: 3

#RO5 Violations: 1

HBA (Lipinski): 8

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 13.95

CX Basic pKa: 8.38

CX LogP: 4.22

CX LogD: 3.20

Aromatic Rings: 1

Heavy Atoms: 40

QED Weighted: 0.45

Np Likeness Score: 0.53

References

1. Ghosh AK, Kincaid JF, Walters DE, Chen Y, Chaudhuri NC, Thompson WJ, Culberson C, Fitzgerald PM, Lee HY, McKee SP, Munson PM, Duong TT, Darke PL, Zugay JA, Schleif WA, Axel MG, Lin J, Huff JR..  (1996)  Nonpeptidal P2 ligands for HIV protease inhibitors: structure-based design, synthesis, and biological evaluation.,  39  (17): [PMID:8765511] [10.1021/jm960128k]

2. Wu YJ, Meanwell NA..  (2021)  Geminal Diheteroatomic Motifs: Some Applications of Acetals, Ketals, and Their Sulfur and Nitrogen Homologues in Medicinal Chemistry and Drug Design.,  64  (14.0): [PMID:34213340] [10.1021/acs.jmedchem.1c00790]

Source

Source(1):

• Scientific Literature