(S)-3-[(2S,3S)-4-benzyl-3-hydroxy-2-methylpent-4-enoyl]-4-isopropyloxazolidin-2-one

ID: ALA3764217

PubChem CID: 49846980

Max Phase: Preclinical

Molecular Formula: C19H25NO4

Molecular Weight: 331.41

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C=C(Cc1ccccc1)[C@@H](O)[C@H](C)C(=O)N1C(=O)OC[C@@H]1C(C)C

Standard InChI:  InChI=1S/C19H25NO4/c1-12(2)16-11-24-19(23)20(16)18(22)14(4)17(21)13(3)10-15-8-6-5-7-9-15/h5-9,12,14,16-17,21H,3,10-11H2,1-2,4H3/t14-,16+,17+/m0/s1

Standard InChI Key:  HWOIMKFOLFJYFQ-USXIJHARSA-N

Molfile:  

     RDKit          2D

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    5.9293   -9.8007    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3978   -8.3758    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1873   -7.5117    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.9707   -8.3673    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4293   -9.7955    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5381   -8.0021    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5521   -7.8856    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3175   -6.7087    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -8.6769    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1894   -6.0109    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8912   -5.2578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8933   -3.7570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5951   -3.0039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5548   -3.6021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2297   -5.4127    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5973   -1.5031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8509   -5.8560    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9336   -3.1588    0.0000 O   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
    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
   -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  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  1  5  1  0
  2  6  2  0
  7  8  1  0
  7  9  1  0
  4  7  1  6
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 10 15  2  0
 13 16  1  0
 11 17  1  1
 12 18  1  1
  3 10  1  0
 16 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 19  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3764217

   (4S)-3-[(2S,3S)-4-benzyl-3-hydroxy-2-methylpent-4-enoyl]-4-propan-2-yl-1,3-oxazolidin-2-one

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: 331.41

Molecular Weight (Monoisotopic): 331.1784

AlogP: 2.79

#Rotatable Bonds: 6

Polar Surface Area: 66.84

Molecular Species: NEUTRAL

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 3.51

CX LogD: 3.51

Aromatic Rings: 1

Heavy Atoms: 24

QED Weighted: 0.81

Np Likeness Score: 0.51

References

1. Singh S, Gajulapati V, Gajulapati K, Goo JI, Park YH, Jung HY, Lee SY, Choi JH, Kim YK, Lee K, Heo TH, Choi Y..  (2016)  Structure-activity relationship study of a series of novel oxazolidinone derivatives as IL-6 signaling blockers.,  26  (4): [PMID:26810262] [10.1016/j.bmcl.2016.01.016]

Source

Source(1):

• Scientific Literature