(S)-tert-Butyl 2-(4-Amino-3-phenethylbenzamido)-4-phenylbutanoate

ID: ALA3818032

PubChem CID: 90371385

Max Phase: Preclinical

Molecular Formula: C29H34N2O3

Molecular Weight: 458.60

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(C)(C)OC(=O)[C@H](CCc1ccccc1)NC(=O)c1ccc(N)c(CCc2ccccc2)c1

Standard InChI:  InChI=1S/C29H34N2O3/c1-29(2,3)34-28(33)26(19-15-22-12-8-5-9-13-22)31-27(32)24-17-18-25(30)23(20-24)16-14-21-10-6-4-7-11-21/h4-13,17-18,20,26H,14-16,19,30H2,1-3H3,(H,31,32)/t26-/m0/s1

Standard InChI Key:  GRRNVRFXIXNAEG-SANMLTNESA-N

Molfile:  

     RDKit          2D

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   -5.2003   -1.4932    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -6.4995   -3.7433    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2004   -2.9933    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.0000   -2.7000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
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 13 30  1  0
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 30 32  1  0
 30 33  1  0
  6 34  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3818032

   tert-butyl (2S)-2-[[4-amino-3-(2-phenylethyl)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: 458.60

Molecular Weight (Monoisotopic): 458.2569

AlogP: 5.13

#Rotatable Bonds: 9

Polar Surface Area: 81.42

Molecular Species: NEUTRAL

HBA: 4

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 5

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: 3.08

CX LogP: 6.10

CX LogD: 6.10

Aromatic Rings: 3

Heavy Atoms: 34

QED Weighted: 0.34

Np Likeness Score: -0.14

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