1-(2-((1H-Indol-5-yl)oxy)ethyl)-4,4-dimethyl-6-(3-nitrophenyl)-1,2,3,4-tetrahydroquinoline

ID: ALA4104556

PubChem CID: 137658298

Max Phase: Preclinical

Molecular Formula: C27H27N3O3

Molecular Weight: 441.53

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC1(C)CCN(CCOc2ccc3c(ccn3-c3cccc([N+](=O)[O-])c3)c2)c2ccccc21

Standard InChI:  InChI=1S/C27H27N3O3/c1-27(2)13-15-28(26-9-4-3-8-24(26)27)16-17-33-23-10-11-25-20(18-23)12-14-29(25)21-6-5-7-22(19-21)30(31)32/h3-12,14,18-19H,13,15-17H2,1-2H3

Standard InChI Key:  ZLNWOBWUKXQNGJ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 33 37  0  0  0  0  0  0  0  0999 V2000
   29.6830   -8.8488    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.2786   -8.1430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.8696   -8.8462    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.1642   -7.7365    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.8697   -8.1470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.8671   -6.5126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.1622   -6.9218    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.5792   -6.9220    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.5769   -7.7384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.9876   -7.7423    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.9899   -6.9260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.2834   -6.5135    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   29.2846   -5.6963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.9928   -5.2887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.9940   -4.4716    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   30.7023   -4.0639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.4067   -4.4749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.4039   -2.8405    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.6990   -3.2498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.1160   -3.2499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.1128   -4.0674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.8893   -4.3231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.3725   -3.6636    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.8945   -3.0004    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   33.1467   -2.2266    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.9480   -2.0610    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.2037   -1.2856    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.6591   -0.6752    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.8555   -0.8454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.6035   -1.6206    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.0049   -1.1187    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   35.2608   -0.3426    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   35.5490   -1.7284    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  2  1  0
  4  5  2  0
  5  9  1  0
  8  6  1  0
  6  7  2  0
  7  4  1  0
  8  9  2  0
  8 12  1  0
  9  2  1  0
  2 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 17 21  1  0
 20 18  1  0
 18 19  2  0
 19 16  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 20  1  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
 28 29  1  0
 29 30  2  0
 30 25  1  0
 24 25  1  0
 31 32  2  0
 31 33  1  0
 27 31  1  0
M  CHG  2  31   1  33  -1
M  END

Alternative Forms

1. Parent:

   

   ALA4104556

   ---

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: 441.53

Molecular Weight (Monoisotopic): 441.2052

AlogP: 6.11

#Rotatable Bonds: 6

Polar Surface Area: 60.54

Molecular Species: NEUTRAL

HBA: 5

HBD: ┄

#RO5 Violations: 1

HBA (Lipinski): 6

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: 3.09

CX LogP: 6.72

CX LogD: 6.72

Aromatic Rings: 4

Heavy Atoms: 33

QED Weighted: 0.27

Np Likeness Score: -1.11

References

1. Juen L, Brachet-Botineau M, Parmenon C, Bourgeais J, Hérault O, Gouilleux F, Viaud-Massuard MC, Prié G..  (2017)  New Inhibitor Targeting Signal Transducer and Activator of Transcription 5 (STAT5) Signaling in Myeloid Leukemias.,  60  (14): [PMID:28654259] [10.1021/acs.jmedchem.7b00369]

Source

Source(1):

• Scientific Literature