3-(4-(((2-(1H-indol-2-yl)ethyl)(2-hydroxyethyl)amino)methyl)phenyl)-N-hydroxyacrylamide

ID: ALA403323

Cas Number: 591207-53-3

PubChem CID: 44456564

Max Phase: Preclinical

Molecular Formula: C22H25N3O3

Molecular Weight: 379.46

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(/C=C/c1ccc(CN(CCO)CCc2cc3ccccc3[nH]2)cc1)NO

Standard InChI:  InChI=1S/C22H25N3O3/c26-14-13-25(12-11-20-15-19-3-1-2-4-21(19)23-20)16-18-7-5-17(6-8-18)9-10-22(27)24-28/h1-10,15,23,26,28H,11-14,16H2,(H,24,27)/b10-9+

Standard InChI Key:  FGJCGXHQLHHNFO-MDZDMXLPSA-N

Molfile:  

     RDKit          2D

 28 30  0  0  0  0  0  0  0  0999 V2000
    7.8618   -6.4434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2446   -7.1769    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0694   -7.2111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3010   -5.7475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1246   -5.7782    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5122   -6.5081    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3262   -6.3650    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.4416   -5.5466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6990   -5.1840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1703   -5.1596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8697   -5.5971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5983   -5.2101    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.2977   -5.6476    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6275   -4.3856    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3561   -3.9986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3852   -3.1741    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.0264   -5.2606    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7226   -5.7010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4507   -5.3147    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4803   -4.4893    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7759   -4.0518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0506   -4.4406    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2084   -4.1013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9084   -4.5379    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6365   -4.1500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3366   -4.5865    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.6646   -3.3254    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.0647   -4.1986    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  6  2  0
 12 14  1  0
  1  2  2  0
 14 15  1  0
  5  4  2  0
 15 16  1  0
  6  7  1  0
 13 17  1  0
  7  8  1  0
 17 18  2  0
  8  9  2  0
 18 19  1  0
  9  5  1  0
 19 20  2  0
  4  1  1  0
 20 21  1  0
  8 10  1  0
 21 22  2  0
 22 17  1  0
  5  6  1  0
 20 23  1  0
 10 11  1  0
 23 24  2  0
 24 25  1  0
 11 12  1  0
 25 26  1  0
  2  3  1  0
 25 27  2  0
 12 13  1  0
 26 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA403323

   2-Propenamide, N-hydroxy-3-(4-(((2-hydroxyethyl)(2-(1H-indol-2-yl)ethyl)amino)methyl)phenyl)-

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: 379.46

Molecular Weight (Monoisotopic): 379.1896

AlogP: 2.72

#Rotatable Bonds: 9

Polar Surface Area: 88.59

Molecular Species: BASE

HBA: 4

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.66

CX Basic pKa: 8.89

CX LogP: 1.98

CX LogD: 0.78

Aromatic Rings: 3

Heavy Atoms: 28

QED Weighted: 0.26

Np Likeness Score: -0.62

References

1. Paris M, Porcelloni M, Binaschi M, Fattori D..  (2008)  Histone deacetylase inhibitors: from bench to clinic.,  51  (6): [PMID:18247554] [10.1021/jm7011408]

Source

Source(1):

• Scientific Literature