(E)-4-Acetyl-3-ethyl-N-(3-[3-(hydroxyamino)-3-oxoprop-1-en-1-yl]phenyl)-5-methyl-1H-pyrrole-2-carboxamide

ID: ALA5094795

PubChem CID: 166635550

Max Phase: Preclinical

Molecular Formula: C19H21N3O4

Molecular Weight: 355.39

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CCc1c(C(=O)Nc2cccc(/C=C/C(=O)NO)c2)[nH]c(C)c1C(C)=O

Standard InChI:  InChI=1S/C19H21N3O4/c1-4-15-17(12(3)23)11(2)20-18(15)19(25)21-14-7-5-6-13(10-14)8-9-16(24)22-26/h5-10,20,26H,4H2,1-3H3,(H,21,25)(H,22,24)/b9-8+

Standard InChI Key:  GVORXNGLOKKWIC-CMDGGOBGSA-N

Molfile:  

 
     RDKit          2D

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   14.8212   -3.9367    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6224   -3.7525    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6994   -2.9347    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9423   -2.6105    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.4019   -3.2300    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4974   -4.6911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6816   -4.7858    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.9852   -5.3467    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2401   -4.2963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0795   -5.1017    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5840   -3.1553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4065   -2.5180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1229   -2.9186    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.3972   -1.6968    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.8301   -2.5020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5430   -2.9054    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2455   -2.4895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2367   -1.6674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5153   -1.2629    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8157   -1.6853    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9618   -2.8904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6691   -2.4741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.3854   -2.8750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.0927   -2.4587    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.8089   -2.8596    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.3942   -3.6963    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  1  2  0
  1  6  1  0
  6  7  2  0
  6  8  1  0
  2  9  1  0
  9 10  1  0
  5 11  1  0
  3 12  1  0
 12 13  1  0
 12 14  2  0
 13 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 15  1  0
 17 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 23 26  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA5094795

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 355.39

Molecular Weight (Monoisotopic): 355.1532

AlogP: 2.86

#Rotatable Bonds: 6

Polar Surface Area: 111.29

Molecular Species: NEUTRAL

HBA: 4

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.55

CX Basic pKa: ┄

CX LogP: 2.13

CX LogD: 2.13

Aromatic Rings: 2

Heavy Atoms: 26

QED Weighted: 0.28

Np Likeness Score: -0.91

References

1. Schäker-Hübner L, Warstat R, Ahlert H, Mishra P, Kraft FB, Schliehe-Diecks J, Schöler A, Borkhardt A, Breit B, Bhatia S, Hügle M, Günther S, Hansen FK..  (2021)  4-Acyl Pyrrole Capped HDAC Inhibitors: A New Scaffold for Hybrid Inhibitors of BET Proteins and Histone Deacetylases as Antileukemia Drug Leads.,  64  (19.0): [PMID:34582215] [10.1021/acs.jmedchem.1c01119]

Source

Source(1):

• Scientific Literature