(aR)-(3S)-1-{4-[{4-Chloro-2-[(S)-hydroxy(2-methoxyphenyl)methyl]-6-(propan-2-yloxy)phenyl}(2,2-dimethylpropyl)amino]-4-oxobutanoyl}piperidine-3-carboxylic acid

ID: ALA1819577

PubChem CID: 53379397

Max Phase: Preclinical

Molecular Formula: C32H43ClN2O7

Molecular Weight: 603.16

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccccc1[C@@H](O)c1cc(Cl)cc(OC(C)C)c1N(CC(C)(C)C)C(=O)CCC(=O)N1CCC[C@H](C(=O)O)C1

Standard InChI:  InChI=1S/C32H43ClN2O7/c1-20(2)42-26-17-22(33)16-24(30(38)23-11-7-8-12-25(23)41-6)29(26)35(19-32(3,4)5)28(37)14-13-27(36)34-15-9-10-21(18-34)31(39)40/h7-8,11-12,16-17,20-21,30,38H,9-10,13-15,18-19H2,1-6H3,(H,39,40)/t21-,30+/m0/s1

Standard InChI Key:  CLELLBMJLWSCHW-URAOTHONSA-N

Molfile:  

     RDKit          2D

 42 44  0  0  0  0  0  0  0  0999 V2000
   -5.0139  -26.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0151  -27.1273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3003  -27.5402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5838  -27.1269    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5867  -26.2963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3021  -25.8872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7285  -25.8876    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -2.8738  -25.8811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8687  -27.5382    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8674  -28.3632    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1549  -27.1246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1523  -28.7746    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1510  -29.5996    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4385  -28.3610    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4417  -29.1833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4398  -27.5360    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8769  -25.0561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1562  -26.2996    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1622  -24.6458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1650  -23.8215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8815  -23.4109    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5968  -23.8306    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5905  -24.6534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4475  -25.0579    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7333  -24.6451    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1625  -25.4625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7260  -27.1224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0108  -27.5337    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7030  -27.1201    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0095  -28.3587    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4130  -27.5346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1247  -27.1245    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1277  -26.2992    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4127  -25.8856    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6948  -26.2974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4146  -25.0587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1298  -24.6475    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7009  -24.6449    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3005  -28.3652    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0150  -28.7775    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7294  -28.3649    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0153  -29.6025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 20 21  2  0
  2  3  1  0
 21 22  1  0
  9 11  1  0
 22 23  2  0
 23 17  1  0
  5  6  2  0
 19 24  1  0
 10 12  1  0
 24 25  1  0
  6  1  1  0
  8 26  1  1
 12 13  1  0
 16 27  1  0
  1  2  2  0
 27 28  1  0
 12 14  1  0
 28 29  1  0
  1  7  1  0
 28 30  2  0
 29 31  1  0
 12 15  1  0
  3  4  2  0
 11 16  1  0
  5  8  1  0
  8 17  1  0
 29 35  1  0
 31 32  1  0
 32 33  1  0
 33 34  1  0
 34 35  1  0
 11 18  2  0
  4  9  1  0
 36 37  1  0
 36 38  2  0
 34 36  1  1
 17 19  2  0
  3 39  1  0
  4  5  1  0
 39 40  1  0
 19 20  1  0
 40 41  1  0
  9 10  1  0
 40 42  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1819577

   (3S)-1-[4-[4-chloro-N-(2,2-dimethylpropyl)-2-[(S)-hydroxy-(2-methoxyphenyl)methyl]-6-propan-2-yloxyanilino]-4-oxobutanoyl]piperidine-3-carboxylic acid

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: 603.16

Molecular Weight (Monoisotopic): 602.2759

AlogP: 5.70

#Rotatable Bonds: 11

Polar Surface Area: 116.61

Molecular Species: ACID

HBA: 6

HBD: 2

#RO5 Violations: 2

HBA (Lipinski): 9

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 3.95

CX Basic pKa: ┄

CX LogP: 4.47

CX LogD: 1.28

Aromatic Rings: 2

Heavy Atoms: 42

QED Weighted: 0.34

Np Likeness Score: -1.06

References

1. Ichikawa M, Yokomizo A, Itoh M, Haginoya N, Sugita K, Usui H, Terayama K, Kanda A..  (2011)  Discovery of atrop fixed alkoxy-aminobenzhydrol derivatives: novel, highly potent and orally efficacious squalene synthase inhibitors.,  19  (17): [PMID:21802309] [10.1016/j.bmc.2011.07.007]

Source

Source(1):

• Scientific Literature