5-hydroxy-1,7-bis(4-hydroxy-3-methoxy-5-nitrophenyl)hepta-1,4,6-trien-3-one

ID: ALA3222136

PubChem CID: 90668286

Max Phase: Preclinical

Molecular Formula: C21H18N2O10

Molecular Weight: 458.38

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cc(/C=C/C(=O)/C=C(O)/C=C/c2cc(OC)c(O)c([N+](=O)[O-])c2)cc([N+](=O)[O-])c1O

Standard InChI:  InChI=1S/C21H18N2O10/c1-32-18-9-12(7-16(20(18)26)22(28)29)3-5-14(24)11-15(25)6-4-13-8-17(23(30)31)21(27)19(10-13)33-2/h3-11,24,26-27H,1-2H3/b5-3+,6-4+,14-11-

Standard InChI Key:  QRKTUJKCVIQROM-LJFKNHCYSA-N

Molfile:  

     RDKit          2D

 33 34  0  0  0  0  0  0  0  0999 V2000
    7.0214  -14.4054    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1432  -13.1727    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6042  -14.4045    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6047  -11.9529    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.2604  -12.7522    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2572  -11.9354    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6049  -12.7697    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.3118  -13.1818    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8987  -13.1824    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.3893  -13.9704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2115  -13.1316    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.4355  -12.7629    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3888  -13.1566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0196  -12.7690    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5101  -14.3655    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.0961  -14.3718    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4962  -11.9075    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.8448  -11.9408    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.5556  -13.1674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5022  -12.7243    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.3107  -15.6345    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8479  -12.7576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0885  -12.7380    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7337  -14.0004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9681  -13.1620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3107  -14.0008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6810  -12.7468    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7309  -13.1781    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8018  -13.9649    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0212  -15.2222    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.7961  -13.1439    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0988  -15.1849    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.3966  -15.5958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 20 17  2  0
  1 24  2  0
 27 13  1  0
  2 22  1  0
 30 21  1  0
 26  1  1  0
 23 13  1  0
 22 19  1  0
 12  2  2  0
 31 20  1  0
 22 18  2  0
  1 30  1  0
  5  6  1  0
  7  4  1  0
 14  8  1  0
  8  7  1  0
 19  5  2  0
 20 11  1  0
  7  9  2  0
 28 12  1  0
 25 27  2  0
 16 29  2  0
 31 23  2  0
  5 25  1  0
 13 10  2  0
 28 14  2  0
 24 28  1  0
 29 31  1  0
 29 15  1  0
  8 26  2  0
 10 16  1  0
 26  3  1  0
 16 32  1  0
 32 33  1  0
M  CHG  4   4  -1   7   1  11  -1  20   1
M  END

Alternative Forms

1. Parent:

   

   ALA3222136

   (1E,4Z,6E)-5-hydroxy-1,7-bis(4-hydroxy-3-methoxy-5-nitrophenyl)hepta-1,4,6-trien-3-one

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: 458.38

Molecular Weight (Monoisotopic): 458.0961

AlogP: 3.67

#Rotatable Bonds: 9

Polar Surface Area: 182.50

Molecular Species: NEUTRAL

HBA: 10

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 12

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 6.76

CX Basic pKa: ┄

CX LogP: 3.64

CX LogD: 2.64

Aromatic Rings: 2

Heavy Atoms: 33

QED Weighted: 0.16

Np Likeness Score: 0.33

References

1. Yap JL, Chauhan J, Jung K, Chen L, Prochownik EV, Fletcher S.  (2012)  Small-molecule inhibitors of dimeric transcription factors: Antagonism of proteinprotein and proteinDNA interactions,  3  (5): [10.1039/C2MD00289B]

2. Ye N, Ding Y, Wild C, Shen Q, Zhou J..  (2014)  Small molecule inhibitors targeting activator protein 1 (AP-1).,  57  (16): [PMID:24831826] [10.1021/jm5004733]

Source

Source(1):

• Scientific Literature