(S)-tert-Butyl 2-(6-amino-4'-hydroxy-[1,1'-biphenyl]-3-ylcarboxamido)-4-phenylbutanoate

ID: ALA3819353

PubChem CID: 90371371

Max Phase: Preclinical

Molecular Formula: C27H30N2O4

Molecular Weight: 446.55

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(C)(C)OC(=O)[C@H](CCc1ccccc1)NC(=O)c1ccc(N)c(-c2ccc(O)cc2)c1

Standard InChI:  InChI=1S/C27H30N2O4/c1-27(2,3)33-26(32)24(16-9-18-7-5-4-6-8-18)29-25(31)20-12-15-23(28)22(17-20)19-10-13-21(30)14-11-19/h4-8,10-15,17,24,30H,9,16,28H2,1-3H3,(H,29,31)/t24-/m0/s1

Standard InChI Key:  DXAULABOJYNMLR-DEOSSOPVSA-N

Molfile:  

     RDKit          2D

 33 35  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
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    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
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   -2.5987   -1.5004    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
    0.0000   -2.7000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8991   -0.7525    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1969   -1.5046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1945   -3.0046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8943   -3.7525    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5964   -3.0004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2328   -3.6062    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
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  9 10  1  0
 10 11  1  1
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  5 22  1  0
 13 23  1  0
 23 24  1  0
 23 25  1  0
 23 26  1  0
  6 27  1  0
 22 28  2  0
 28 29  1  0
 29 30  2  0
 30 31  1  0
 31 32  2  0
 32 22  1  0
 30 33  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3819353

   tert-butyl (2S)-2-[[4-amino-3-(4-hydroxyphenyl)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: 446.55

Molecular Weight (Monoisotopic): 446.2206

AlogP: 4.71

#Rotatable Bonds: 7

Polar Surface Area: 101.65

Molecular Species: NEUTRAL

HBA: 5

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.86

CX Basic pKa: 2.93

CX LogP: 4.91

CX LogD: 4.91

Aromatic Rings: 3

Heavy Atoms: 33

QED Weighted: 0.36

Np Likeness Score: -0.17

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