(S)-4-benzyl-3-[(2S,3S)-3-hydroxy-2-methyl-4-ethylenenonanoyl]oxazolidin-2-one

ID: ALA3763273

PubChem CID: 49846983

Max Phase: Preclinical

Molecular Formula: C21H29NO4

Molecular Weight: 359.47

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C21H29NO4/c1-4-5-7-10-15(2)19(23)16(3)20(24)22-18(14-26-21(22)25)13-17-11-8-6-9-12-17/h6,8-9,11-12,16,18-19,23H,2,4-5,7,10,13-14H2,1,3H3/t16-,18-,19+/m0/s1

Standard InChI Key:  JSIYFMCFASVUJH-YTQUADARSA-N

Molfile:  

     RDKit          2D

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    6.2544   -0.2640    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5052    1.0356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0378    0.7246    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8990   -0.7562    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2500   -1.3780    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9940    2.1315    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
    2.5923   -3.0039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9154    1.7169    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4920    1.2410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3675    2.2350    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0558    1.7590    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1545    2.8928    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2529    0.0650    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6066    3.4109    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6037    2.2771    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1803    2.7530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7282    3.2711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1515    2.7952    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0506    3.5899    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8873   -3.7609    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8792   -5.2609    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5761   -6.0039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2812   -5.2469    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2892   -3.7469    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2551    0.7791    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
  4  7  1  6
  9 10  1  0
 10 11  1  0
 11 12  1  0
  9 13  2  0
 10 14  1  1
 11 15  1  1
  3  9  1  0
 12 17  1  0
 16 17  1  0
 16 18  1  0
 18 19  1  0
 19 20  1  0
  8 21  2  0
 21 22  1  0
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 23 24  1  0
 24 25  2  0
 25  8  1  0
 12 26  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA3763273

   (4S)-4-benzyl-3-[(2S,3S)-3-hydroxy-2-methyl-4-methylidenenonanoyl]-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: 359.47

Molecular Weight (Monoisotopic): 359.2097

AlogP: 3.71

#Rotatable Bonds: 9

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: 4.48

CX LogD: 4.48

Aromatic Rings: 1

Heavy Atoms: 26

QED Weighted: 0.54

Np Likeness Score: 0.60

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