3-(4-nitrobenzamido)-9,10-dioxo-9,10-dihydroanthracene-2-carboxylic acid

ID: ALA1668296

PubChem CID: 53317020

Max Phase: Preclinical

Molecular Formula: C22H12N2O7

Molecular Weight: 416.35

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(Nc1cc2c(cc1C(=O)O)C(=O)c1ccccc1C2=O)c1ccc([N+](=O)[O-])cc1

Standard InChI:  InChI=1S/C22H12N2O7/c25-19-13-3-1-2-4-14(13)20(26)16-10-18(17(22(28)29)9-15(16)19)23-21(27)11-5-7-12(8-6-11)24(30)31/h1-10H,(H,23,27)(H,28,29)

Standard InChI Key:  SMPMQQJWCBELPW-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 31 34  0  0  0  0  0  0  0  0999 V2000
    7.2955  -17.0326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3197  -17.8569    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8266  -12.8937    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5447  -13.3001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5552  -14.1159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8371  -14.5382    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1192  -14.1299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1095  -13.3239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3934  -12.8937    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.4083  -12.0693    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6774  -13.2897    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2435  -14.5672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9532  -14.1297    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9961  -15.7826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0068  -16.5901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7391  -16.9975    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7015  -15.3453    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4261  -15.7389    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4473  -16.5653    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1633  -16.9601    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1271  -15.3071    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8532  -15.7047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8713  -16.5295    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5942  -16.9228    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2978  -16.4967    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2735  -15.6673    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5518  -15.2760    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1048  -14.4792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.1876  -17.7843    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2695  -15.3918    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.5944  -16.6132    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  3  1  0
  9 10  2  0
  9 11  1  0
  8  9  1  0
  5 12  1  0
 12 13  2  0
 14 15  2  0
 15 16  1  0
 16 19  2  0
 18 17  2  0
 17 14  1  0
 15  1  1  0
 18 19  1  0
 18 21  1  0
 19 20  1  0
 20 23  1  0
 22 21  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 27 22  1  0
 21 28  2  0
 20 29  2  0
  1  2  2  0
 12 30  1  0
 30 14  1  0
  1 31  1  0
M  CHG  2   9   1  11  -1
M  END

Alternative Forms

1. Parent:

   

   ALA1668296

   3-(4-Nitrobenzamido)-9,10-dioxo-9,10-dihydroanthracene-2-carboxylic acid

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: 416.35

Molecular Weight (Monoisotopic): 416.0645

AlogP: 3.32

#Rotatable Bonds: 4

Polar Surface Area: 143.68

Molecular Species: ACID

HBA: 6

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.08

CX Basic pKa: ┄

CX LogP: 4.26

CX LogD: 0.79

Aromatic Rings: 3

Heavy Atoms: 31

QED Weighted: 0.38

Np Likeness Score: -0.74

References

1. Chu Y, Chen X, Yang Y, Tang Y..  (2011)  Identification of small molecular inhibitors for Ero1p by structure-based virtual screening.,  21  (4): [PMID:21269829] [10.1016/j.bmcl.2010.12.129]

Source

Source(1):

• Scientific Literature