(S)-benzyl 2-((S)-2-(benzyloxycarbonylamino)propanamido)-5-((2R,3S)-4-oxo-3-propyloxetane-2-carboxamido)pentanoate

ID: ALA4081658

PubChem CID: 11541428

Max Phase: Preclinical

Molecular Formula: C30H37N3O8

Molecular Weight: 567.64

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCC[C@@H]1C(=O)O[C@H]1C(=O)NCCC[C@H](NC(=O)[C@H](C)NC(=O)OCc1ccccc1)C(=O)OCc1ccccc1

Standard InChI:  InChI=1S/C30H37N3O8/c1-3-11-23-25(41-28(23)36)27(35)31-17-10-16-24(29(37)39-18-21-12-6-4-7-13-21)33-26(34)20(2)32-30(38)40-19-22-14-8-5-9-15-22/h4-9,12-15,20,23-25H,3,10-11,16-19H2,1-2H3,(H,31,35)(H,32,38)(H,33,34)/t20-,23-,24-,25+/m0/s1

Standard InChI Key:  LYBGSJVQPXDWND-WAABAYLZSA-N

Molfile:  

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M  END

Alternative Forms

1. Parent:

   

   ALA4081658

   benzyl (2S)-5-[[(2R,3S)-4-oxo-3-propyloxetane-2-carbonyl]amino]-2-[[(2S)-2-(phenylmethoxycarbonylamino)propanoyl]amino]pentanoate

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: 567.64

Molecular Weight (Monoisotopic): 567.2581

AlogP: 2.77

#Rotatable Bonds: 15

Polar Surface Area: 149.13

Molecular Species: NEUTRAL

HBA: 8

HBD: 3

#RO5 Violations: 1

HBA (Lipinski): 11

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 12.02

CX Basic pKa: ┄

CX LogP: 3.37

CX LogD: 3.37

Aromatic Rings: 2

Heavy Atoms: 41

QED Weighted: 0.17

Np Likeness Score: -0.07

References

1. Zhu M, Harshbarger WD, Robles O, Krysiak J, Hull KG, Cho SW, Richardson RD, Yang Y, Garcia A, Spiegelman L, Ramirez B, Wilson CT, Yau JA, Moore JT, Walker CB, Sacchettini JC, Liu WR, Sieber SA, Smith JW, Romo D..  (2017)  A strategy for dual inhibition of the proteasome and fatty acid synthase with belactosin C-orlistat hybrids.,  25  (11): [PMID:28236510] [10.1016/j.bmc.2017.01.020]

Source

Source(1):

• Scientific Literature