N-hydroxy-3-(4-((1-(4-nitrophenyl)-9H-pyrido[3,4-b]indol-3-ylamino)methyl)phenyl)acrylamide

ID: ALA4475613

PubChem CID: 155537865

Max Phase: Preclinical

Molecular Formula: C27H21N5O4

Molecular Weight: 479.50

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  O=C(/C=C/c1ccc(CNc2cc3c([nH]c4ccccc43)c(-c3ccc([N+](=O)[O-])cc3)n2)cc1)NO

Standard InChI:  InChI=1S/C27H21N5O4/c33-25(31-34)14-9-17-5-7-18(8-6-17)16-28-24-15-22-21-3-1-2-4-23(21)29-27(22)26(30-24)19-10-12-20(13-11-19)32(35)36/h1-15,29,34H,16H2,(H,28,30)(H,31,33)/b14-9+

Standard InChI Key:  PSLBYNPIDJYPNR-NTEUORMPSA-N

Molfile:  

 
     RDKit          2D

 36 40  0  0  0  0  0  0  0  0999 V2000
   31.1155  -17.7572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.1153  -18.5815    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.8325  -18.9899    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.5484  -18.5760    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.5427  -17.7451    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.8249  -17.3362    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.2561  -17.3245    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.9755  -17.7346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.6889  -17.3141    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.4084  -17.7243    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   34.6830  -16.4875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   35.4144  -18.5509    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   28.9867  -21.4833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.7051  -21.0712    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   29.7023  -20.2390    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.9849  -19.8270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.4130  -19.8210    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   28.2700  -21.0717    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.2666  -20.2457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.4852  -21.3287    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   26.9952  -20.6617    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.4806  -19.9953    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.1475  -19.2495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.3293  -19.1606    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.8453  -19.8320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.1811  -20.5793    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.4064  -18.9985    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.9884  -22.3036    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.2744  -22.7141    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.2738  -23.5358    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.9866  -23.9481    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.7013  -23.5326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.6984  -22.7122    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.9857  -24.7748    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   29.6984  -25.1852    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   28.2738  -25.1868    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  1  1  0
  5  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
  9 11  2  0
 10 12  1  0
 18 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 19  1  0
 15 17  1  0
 18 19  2  0
 19 22  1  0
 21 20  1  0
 20 18  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 21  1  0
 17 27  1  0
 27  2  1  0
 28 29  2  0
 29 30  1  0
 30 31  2  0
 31 32  1  0
 32 33  2  0
 33 28  1  0
 13 28  1  0
 34 35  2  0
 34 36  1  0
 31 34  1  0
M  CHG  2  34   1  36  -1
M  END

Alternative Forms

1. Parent:

   

   ALA4475613

   ---

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: 479.50

Molecular Weight (Monoisotopic): 479.1594

AlogP: 5.42

#Rotatable Bonds: 7

Polar Surface Area: 133.18

Molecular Species: NEUTRAL

HBA: 6

HBD: 4

#RO5 Violations: 1

HBA (Lipinski): 9

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 9.56

CX Basic pKa: 5.52

CX LogP: 4.99

CX LogD: 4.98

Aromatic Rings: 5

Heavy Atoms: 36

QED Weighted: 0.11

Np Likeness Score: -0.58

References

1. Ling Y, Gao WJ, Ling C, Liu J, Meng C, Qian J, Liu S, Gan H, Wu H, Tao J, Dai H, Zhang Y..  (2019)  β-Carboline and N-hydroxycinnamamide hybrids as anticancer agents for drug-resistant hepatocellular carcinoma.,  168  [PMID:30851694] [10.1016/j.ejmech.2019.02.054]

Source

Source(1):

• Scientific Literature