(2S,3S)-3-hydroxy-1-(3-(2-hydroxyethyl)-1H-indol-1-yl)-2-methyl-4-methylenenonan-1-one

ID: ALA3764721

PubChem CID: 49847060

Max Phase: Preclinical

Molecular Formula: C21H29NO3

Molecular Weight: 343.47

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C=C(CCCCC)[C@@H](O)[C@H](C)C(=O)n1cc(CCO)c2ccccc21

Standard InChI:  InChI=1S/C21H29NO3/c1-4-5-6-9-15(2)20(24)16(3)21(25)22-14-17(12-13-23)18-10-7-8-11-19(18)22/h7-8,10-11,14,16,20,23-24H,2,4-6,9,12-13H2,1,3H3/t16-,20+/m0/s1

Standard InChI Key:  AUUJXQRFABCCQY-OXJNMPFZSA-N

Molfile:  

     RDKit          2D

 25 26  0  0  0  0  0  0  0  0999 V2000
    1.7138    1.2033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5889    0.0182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7138   -1.2033    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1855   -2.6254    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6552   -2.9294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1277   -4.3539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5974   -4.6579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3877   -3.5218    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4530   -2.0330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3299   -5.2503    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5396   -6.3865    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0699   -6.0824    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0120   -7.8110    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4817   -8.1150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8595   -9.2540    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3952   -3.7615    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2917   -0.7475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2917    0.7475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0028    1.5132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3155    0.7475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3155   -0.7475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0028   -1.5132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1812    2.6271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6500    2.9355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0244    4.0756    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3 17  1  0
  1 18  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  4  8  2  0
  5  9  1  1
  6 10  1  1
  3  4  1  0
  7 12  1  0
 11 12  1  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
  7 16  2  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 17  1  0
  1 23  1  0
 23 24  1  0
 24 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3764721

   (2S,3S)-3-hydroxy-1-[3-(2-hydroxyethyl)indol-1-yl]-2-methyl-4-methylidenenonan-1-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: 343.47

Molecular Weight (Monoisotopic): 343.2147

AlogP: 3.95

#Rotatable Bonds: 9

Polar Surface Area: 62.46

Molecular Species: NEUTRAL

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 3.69

CX LogD: 3.69

Aromatic Rings: 2

Heavy Atoms: 25

QED Weighted: 0.54

Np Likeness Score: 0.57

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