N-(3-(5-Hydroxy-6,7-trimethoxy-4-oxo-4H-chromen-2-yl)phenyl)benzo[d][1,3]dioxole-5-carboxamide

ID: ALA4474639

PubChem CID: 155537234

Max Phase: Preclinical

Molecular Formula: C25H19NO8

Molecular Weight: 461.43

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  COc1cc2oc(-c3cccc(NC(=O)c4ccc5c(c4)OCO5)c3)cc(=O)c2c(O)c1OC

Standard InChI:  InChI=1S/C25H19NO8/c1-30-21-11-20-22(23(28)24(21)31-2)16(27)10-18(34-20)13-4-3-5-15(8-13)26-25(29)14-6-7-17-19(9-14)33-12-32-17/h3-11,28H,12H2,1-2H3,(H,26,29)

Standard InChI Key:  YWMOJXZBCGKNKF-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 34 38  0  0  0  0  0  0  0  0999 V2000
    1.3317   -4.3418    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3305   -5.1613    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0386   -5.5703    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0368   -3.9329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7454   -4.3382    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7488   -5.1634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4612   -5.5708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1747   -5.1575    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1713   -4.3324    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4544   -3.9204    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4634   -6.3880    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8778   -3.9216    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5860   -4.3300    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2920   -3.9199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2899   -3.1019    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5759   -2.6956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8729   -3.1081    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0007   -4.3267    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.7074   -3.9162    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4161   -4.3230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7052   -3.0990    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0371   -6.3875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6225   -5.5694    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0885   -5.1602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6239   -3.9334    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6237   -3.1162    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4148   -5.1395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1227   -5.5461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1171   -3.9113    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8256   -4.3142    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8273   -5.1318    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6054   -5.3829    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.0847   -4.7204    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6027   -4.0600    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  6  2  0
  5  4  2  0
  4  1  1  0
  5  6  1  0
  5 10  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
  7 11  2  0
  9 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 12  1  0
 14 18  1  0
 18 19  1  0
 19 20  1  0
 19 21  2  0
  3 22  1  0
  2 23  1  0
 23 24  1  0
  1 25  1  0
 25 26  1  0
 20 27  2  0
 27 28  1  0
 28 31  2  0
 30 29  2  0
 29 20  1  0
 30 31  1  0
 31 32  1  0
 32 33  1  0
 33 34  1  0
 34 30  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4474639

   ---

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: 461.43

Molecular Weight (Monoisotopic): 461.1111

AlogP: 4.16

#Rotatable Bonds: 5

Polar Surface Area: 116.46

Molecular Species: NEUTRAL

HBA: 8

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 7.94

CX Basic pKa: ┄

CX LogP: 3.71

CX LogD: 3.60

Aromatic Rings: 4

Heavy Atoms: 34

QED Weighted: 0.46

Np Likeness Score: 0.11

References

1. Hassan AHE, Choi E, Yoon YM, Lee KW, Yoo SY, Cho MC, Yang JS, Kim HI, Hong JY, Shin JS, Chung KS, Lee JH, Lee KT, Lee YS..  (2019)  Natural products hybrids: 3,5,4'-Trimethoxystilbene-5,6,7-trimethoxyflavone chimeric analogs as potential cytotoxic agents against diverse human cancer cells.,  161  [PMID:30396104] [10.1016/j.ejmech.2018.10.062]

2. Hassan AHE, Yoo SY, Lee KW, Yoon YM, Ryu HW, Jeong Y, Shin JS, Kang SY, Kim SY, Lee HH, Park BY, Lee KT, Lee YS..  (2019)  Repurposing mosloflavone/5,6,7-trimethoxyflavone-resveratrol hybrids: Discovery of novel p38-α MAPK inhibitors as potent interceptors of macrophage-dependent production of proinflammatory mediators.,  180  [PMID:31310917] [10.1016/j.ejmech.2019.07.030]

3. Yun BH, Lee YH, Park KT, Jung SJ, Lee YS..  (2016)  Synthesis of novel flavone derivatives possessing substituted benzamides and their biological evaluation against human cancer cells.,  26  (17): [PMID:27503682] [10.1016/j.bmcl.2016.07.063]

Source

Source(1):

• Scientific Literature