(S)-3-((2S,3S)-3-cyclohexenyl-3-hydroxy-2-methylpropanoyl)-4-isopropyloxazolidin-2-one

ID: ALA3763533

PubChem CID: 49846981

Max Phase: Preclinical

Molecular Formula: C16H25NO4

Molecular Weight: 295.38

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(C)[C@H]1COC(=O)N1C(=O)[C@@H](C)[C@H](O)C1=CCCCC1

Standard InChI:  InChI=1S/C16H25NO4/c1-10(2)13-9-21-16(20)17(13)15(19)11(3)14(18)12-7-5-4-6-8-12/h7,10-11,13-14,18H,4-6,8-9H2,1-3H3/t11-,13+,14-/m0/s1

Standard InChI Key:  VKUFVKYLFZVBDA-YUTCNCBUSA-N

Molfile:  

     RDKit          2D

 21 22  0  0  0  0  0  0  0  0999 V2000
    4.6332   -7.5468    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1017   -6.1218    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8912   -5.2578    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6747   -6.1134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1332   -7.5416    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2421   -5.7482    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2561   -5.6316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0214   -4.4548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3540   -6.4230    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
    2.5973   -1.5031    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
    4.9336   -3.1588    0.0000 O   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
    3.6375   -0.9049    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
    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
 10 14  2  0
 11 15  1  1
 12 16  1  1
  3 10  1  0
 13 17  2  0
 13 21  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3763533

   (4S)-3-[(2S,3S)-3-(cyclohexen-1-yl)-3-hydroxy-2-methylpropanoyl]-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: 295.38

Molecular Weight (Monoisotopic): 295.1784

AlogP: 2.49

#Rotatable Bonds: 4

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: 2.74

CX LogD: 2.74

Aromatic Rings: ┄

Heavy Atoms: 21

QED Weighted: 0.81

Np Likeness Score: 0.62

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