(3E)-4-[3-(2-Hydroxyethyl)-1H-indol-5-yl]but-3-en-2-one

ID: ALA3259982

PubChem CID: 90675403

Max Phase: Preclinical

Molecular Formula: C14H15NO2

Molecular Weight: 229.28

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(=O)/C=C/c1ccc2[nH]cc(CCO)c2c1

Standard InChI:  InChI=1S/C14H15NO2/c1-10(17)2-3-11-4-5-14-13(8-11)12(6-7-16)9-15-14/h2-5,8-9,15-16H,6-7H2,1H3/b3-2+

Standard InChI Key:  WVZBZDMTKRSQSU-NSCUHMNNSA-N

Molfile:  

     RDKit          2D

 17 18  0  0  0  0  0  0  0  0999 V2000
   10.4461   -5.8587    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.9182   -5.1901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4247   -4.5390    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6516   -4.8039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9368   -4.4078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2357   -4.8299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2493   -5.6482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9641   -6.0443    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6652   -5.6222    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5209   -4.4337    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8205   -4.8547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1057   -4.4585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4053   -4.8795    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0914   -3.6415    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6632   -3.7574    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4593   -3.5731    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6977   -2.7914    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  1  9  1  0
  4  9  2  0
  6 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
  3 15  1  0
 15 16  1  0
 16 17  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3259982

   (3E)-4-[3-(2-hydroxyethyl)-1H-indol-5-yl]but-3-en-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: 229.28

Molecular Weight (Monoisotopic): 229.1103

AlogP: 2.30

#Rotatable Bonds: 4

Polar Surface Area: 53.09

Molecular Species: NEUTRAL

HBA: 2

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 3

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 2.09

CX LogD: 2.09

Aromatic Rings: 2

Heavy Atoms: 17

QED Weighted: 0.79

Np Likeness Score: 0.80

References

1. Jansen R, Mohr KI, Bernecker S, Stadler M, Müller R..  (2014)  Indothiazinone, an indolyl thiazolyl ketone from a novel myxobacterium belonging to the Sorangiineae.,  77  (4): [PMID:24697522] [10.1021/np500144t]

Source

Source(1):

• Scientific Literature