(S)-tert-Butyl 2-(4-Amino-3-(4-(4-hydroxyphenyl)butoxy)benzamido)-4-phenylbutanoate

ID: ALA3818365

PubChem CID: 90371446

Max Phase: Preclinical

Molecular Formula: C31H38N2O5

Molecular Weight: 518.65

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(C)(C)OC(=O)[C@H](CCc1ccccc1)NC(=O)c1ccc(N)c(OCCCCc2ccc(O)cc2)c1

Standard InChI:  InChI=1S/C31H38N2O5/c1-31(2,3)38-30(36)27(19-14-22-9-5-4-6-10-22)33-29(35)24-15-18-26(32)28(21-24)37-20-8-7-11-23-12-16-25(34)17-13-23/h4-6,9-10,12-13,15-18,21,27,34H,7-8,11,14,19-20,32H2,1-3H3,(H,33,35)/t27-/m0/s1

Standard InChI Key:  CTZJGSGPRDHDGU-MHZLTWQESA-N

Molfile:  

     RDKit          2D

 38 40  0  0  0  0  0  0  0  0999 V2000
    1.2990   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2990    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2990    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2990   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0031    3.0008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0351    3.6026    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3039    3.7494    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3070    5.2502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6078    5.9988    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0101    6.0056    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0149    7.5064    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0312    5.4092    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6109    7.4996    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9118    8.2481    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9171    9.7482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2187   10.4937    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5151    9.7392    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5099    8.2392    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2083    7.4937    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6003   -1.4978    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8990   -0.7455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2820    8.2617    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2782    9.4617    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3233    7.6654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3192    8.8652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2003   -1.4932    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.7000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4990   -0.7410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8003   -1.4887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0990   -0.7365    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.4007   -1.4819    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.6971   -0.7274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.6919    0.7726    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.3903    1.5181    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0939    0.7636    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.7291    1.3762    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  1  1  0
  3  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  1  0
 10 11  1  1
 10 12  1  0
 12 13  1  0
 12 14  2  0
 11 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 16  1  0
  5 22  1  0
 22 23  1  0
 13 24  1  0
 24 25  1  0
 24 26  1  0
 24 27  1  0
 23 28  1  0
  6 29  1  0
 28 30  1  0
 30 31  1  0
 31 32  1  0
 32 33  2  0
 33 34  1  0
 34 35  2  0
 35 36  1  0
 36 37  2  0
 37 32  1  0
 35 38  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3818365

   tert-butyl (2S)-2-[[4-amino-3-[4-(4-hydroxyphenyl)butoxy]benzoyl]amino]-4-phenylbutanoate

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: 518.65

Molecular Weight (Monoisotopic): 518.2781

AlogP: 5.45

#Rotatable Bonds: 12

Polar Surface Area: 110.88

Molecular Species: NEUTRAL

HBA: 6

HBD: 3

#RO5 Violations: 2

HBA (Lipinski): 7

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 10.31

CX Basic pKa: 3.38

CX LogP: 6.01

CX LogD: 6.01

Aromatic Rings: 3

Heavy Atoms: 38

QED Weighted: 0.17

Np Likeness Score: -0.19

References

1. Morin MD, Wang Y, Jones BT, Su L, Surakattula MM, Berger M, Huang H, Beutler EK, Zhang H, Beutler B, Boger DL..  (2016)  Discovery and Structure-Activity Relationships of the Neoseptins: A New Class of Toll-like Receptor-4 (TLR4) Agonists.,  59  (10): [PMID:27050713] [10.1021/acs.jmedchem.6b00177]

Source

Source(1):

• Scientific Literature