(3-amino-1-methyl-1H-indol-2-yl)(3,4,5-trimethoxyphenyl)methanone

ID: ALA270309

PubChem CID: 24806274

Max Phase: Preclinical

Molecular Formula: C19H20N2O4

Molecular Weight: 340.38

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cc(C(=O)c2c(N)c3ccccc3n2C)cc(OC)c1OC

Standard InChI:  InChI=1S/C19H20N2O4/c1-21-13-8-6-5-7-12(13)16(20)17(21)18(22)11-9-14(23-2)19(25-4)15(10-11)24-3/h5-10H,20H2,1-4H3

Standard InChI Key:  AXKMPZBWJTYWTR-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 25 27  0  0  0  0  0  0  0  0999 V2000
   -4.7848  -23.9166    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7859  -24.7440    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0711  -25.1569    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0729  -23.5039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3575  -23.9130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3573  -24.7440    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5668  -25.0006    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0785  -24.3281    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5672  -23.6560    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2535  -24.3278    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8407  -25.0422    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8412  -23.6132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0159  -23.6162    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3963  -22.9024    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0165  -22.1871    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8458  -22.1900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2542  -22.9044    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2610  -21.4771    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8513  -20.7611    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3948  -21.4719    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2198  -21.4705    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2213  -22.9025    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6337  -23.6170    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3125  -22.8713    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3117  -25.7852    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 10 12  1  0
  2  3  1  0
 12 13  2  0
  3  6  2  0
 13 14  1  0
  1  2  2  0
 14 15  2  0
  5  4  2  0
 15 16  1  0
  6  7  1  0
 16 17  2  0
 17 12  1  0
  7  8  1  0
 16 18  1  0
  8  9  2  0
 18 19  1  0
  9  5  1  0
 15 20  1  0
  4  1  1  0
 20 21  1  0
  8 10  1  0
 14 22  1  0
  5  6  1  0
 22 23  1  0
 10 11  2  0
  9 24  1  0
  7 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA270309

   (3-Amino-1-methylindol-2-yl)-(3,4,5-trimethoxyphenyl)methanone

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: 340.38

Molecular Weight (Monoisotopic): 340.1423

AlogP: 3.02

#Rotatable Bonds: 5

Polar Surface Area: 75.71

Molecular Species: NEUTRAL

HBA: 6

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 3.02

CX LogD: 3.02

Aromatic Rings: 3

Heavy Atoms: 25

QED Weighted: 0.72

Np Likeness Score: -0.25

References

1. Romagnoli R, Baraldi PG, Sarkar T, Carrion MD, Cara CL, Cruz-Lopez O, Preti D, Tabrizi MA, Tolomeo M, Grimaudo S, Di Cristina A, Zonta N, Balzarini J, Brancale A, Hsieh HP, Hamel E..  (2008)  Synthesis and biological evaluation of 1-methyl-2-(3',4',5'-trimethoxybenzoyl)-3-aminoindoles as a new class of antimitotic agents and tubulin inhibitors.,  51  (5): [PMID:18260616] [10.1021/jm7011547]

Source

Source(1):

• Scientific Literature