((4R,5S)-2-oxo-4-((4-phenylpiperazin-1-yl)methyl)oxazolidin-5-yl)methyl 2-phenylacetate

ID: ALA258476

Chembl Id: CHEMBL258476

PubChem CID: 24821056

Max Phase: Preclinical

Molecular Formula: C23H27N3O4

Molecular Weight: 409.49

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(Cc1ccccc1)OC[C@H]1OC(=O)N[C@@H]1CN1CCN(c2ccccc2)CC1

Standard InChI:  InChI=1S/C23H27N3O4/c27-22(15-18-7-3-1-4-8-18)29-17-21-20(24-23(28)30-21)16-25-11-13-26(14-12-25)19-9-5-2-6-10-19/h1-10,20-21H,11-17H2,(H,24,28)/t20-,21-/m1/s1

Standard InChI Key:  PEYFDUDIYDGOOB-NHCUHLMSSA-N

Alternative Forms

1. Parent:

   

   ALA258476

   [(4R,5S)-2-oxo-4-[(4-phenylpiperazin-1-yl)methyl]-1,3-oxazolidin-5-yl]methyl 2-phenylacetate

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: 409.49

Molecular Weight (Monoisotopic): 409.2002

AlogP: 2.07

#Rotatable Bonds: 7

Polar Surface Area: 71.11

Molecular Species: NEUTRAL

HBA: 6

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.72

CX Basic pKa: 7.36

CX LogP: 3.10

CX LogD: 2.82

Aromatic Rings: 2

Heavy Atoms: 30

QED Weighted: 0.71

Np Likeness Score: -0.36

References

1. Anupam R, Nayek A, Green NJ, Grundy FJ, Henkin TM, Means JA, Bergmeier SC, Hines JV..  (2008)  4,5-Disubstituted oxazolidinones: High affinity molecular effectors of RNA function.,  18  (12): [PMID:18502126] [10.1016/j.bmcl.2008.05.015]

2. Maciagiewicz I, Zhou S, Bergmeier SC, Hines JV..  (2011)  Structure-activity studies of RNA-binding oxazolidinone derivatives.,  21  (15): [PMID:21733684] [10.1016/j.bmcl.2011.05.130]

3. Orac CM, Zhou S, Means JA, Boehm D, Bergmeier SC, Hines JV..  (2011)  Synthesis and stereospecificity of 4,5-disubstituted oxazolidinone ligands binding to T-box riboswitch RNA.,  54  (19): [PMID:21812425] [10.1021/jm2006904]

4. Armstrong I,Aldhumani AH,Schopis JL,Fang F,Parsons E,Zeng C,Hossain MI,Bergmeier SC,Hines JV.  (2020)  RNA drug discovery: Conformational restriction enhances specific modulation of the T-box riboswitch function.,  28  (20.0): [PMID:33069065] [10.1016/j.bmc.2020.115696]

Source

Source(1):

• Scientific Literature