(S)-tert-Butyl 2-(4-Amino-3-(3-fluoro-4-hydroxyphenethoxy)benzamido)-4-phenylbutanoate

ID: ALA3818304

PubChem CID: 90371504

Max Phase: Preclinical

Molecular Formula: C29H33FN2O5

Molecular Weight: 508.59

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(C)(C)OC(=O)[C@H](CCc1ccccc1)NC(=O)c1ccc(N)c(OCCc2ccc(O)c(F)c2)c1

Standard InChI:  InChI=1S/C29H33FN2O5/c1-29(2,3)37-28(35)24(13-9-19-7-5-4-6-8-19)32-27(34)21-11-12-23(31)26(18-21)36-16-15-20-10-14-25(33)22(30)17-20/h4-8,10-12,14,17-18,24,33H,9,13,15-16,31H2,1-3H3,(H,32,34)/t24-/m0/s1

Standard InChI Key:  VZRXGVBXJWGDLT-DEOSSOPVSA-N

Molfile:  

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M  END

Alternative Forms

1. Parent:

   

   ALA3818304

   tert-butyl (2S)-2-[[4-amino-3-[2-(3-fluoro-4-hydroxyphenyl)ethoxy]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: 508.59

Molecular Weight (Monoisotopic): 508.2374

AlogP: 4.81

#Rotatable Bonds: 10

Polar Surface Area: 110.88

Molecular Species: NEUTRAL

HBA: 6

HBD: 3

#RO5 Violations: 1

HBA (Lipinski): 7

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 8.66

CX Basic pKa: 3.22

CX LogP: 5.26

CX LogD: 5.24

Aromatic Rings: 3

Heavy Atoms: 37

QED Weighted: 0.27

Np Likeness Score: -0.43

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