2-(3,4,5-trimethoxybenzoyl)-3-amino-6-methyl-1H-indole

ID: ALA406682

PubChem CID: 24805456

Max Phase: Preclinical

Molecular Formula: C19H20N2O4

Molecular Weight: 340.38

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cc(C(=O)c2[nH]c3cc(C)ccc3c2N)cc(OC)c1OC

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

Standard InChI Key:  UGTAEPITBWMZEN-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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   -4.1193   -6.6648    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4044   -7.0777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4062   -5.4247    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6909   -5.8338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6906   -6.6649    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9001   -6.9215    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4118   -6.2490    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9006   -5.5768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5868   -6.2487    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1741   -6.9630    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1746   -5.5341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6508   -5.5370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0630   -4.8232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6502   -4.1079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1791   -4.1108    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5875   -4.8252    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5944   -3.3980    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1846   -2.6819    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0615   -3.3927    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8865   -3.3914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8880   -4.8233    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3004   -5.5379    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6459   -4.7921    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8341   -7.0768    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
  2 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA406682

   (3-amino-6-methyl-1H-indol-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: 3.32

#Rotatable Bonds: 5

Polar Surface Area: 86.57

Molecular Species: NEUTRAL

HBA: 5

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 3.31

CX LogD: 3.31

Aromatic Rings: 3

Heavy Atoms: 25

QED Weighted: 0.70

Np Likeness Score: -0.17

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