2-(3,4-Dimethoxy-phenyl)-5,7-dihydroxy-3-methoxy-chromen-4-one

ID: ALA350720

Cas Number: 14549-84-9

PubChem CID: 5383438

Max Phase: Preclinical

Molecular Formula: C18H16O7

Molecular Weight: 344.32

Molecule Type: Small molecule

Names and Identifiers

Synonyms: NSC-168804 | 14549-84-9|5,7-Dihydroxy-3,3',4'-trimethoxyflavone|Quercetin 3,3',4'-trimethyl ether|NSC-168804|4H-1-Benzopyran-4-one, 2-(3,4-dimethoxyphenyl)-5,7-dihydroxy-3-methoxy-|2-(3,4-dimethoxyphenyl)-5,7-dihydroxy-3-methoxychromen-4-one|2-(3,4-Dimethoxy-phenyl)-5,7-dihydroxy-3-methoxy-chromen-4-one|429X56Q8K5|2-(3,4-Dimethoxyphenyl)-5,7-dihydroxy-3-methoxy-4H-1-benzopyran-4-one|UNII-429X56Q8K5|NSC168804|NSC 168804|5,7-Dihydroxy-3,3',4'-trimethoxy flavone|5,3',4'-trimethoxy flavone|CHEMBL350Show More⌵

Canonical SMILES:  COc1ccc(-c2oc3cc(O)cc(O)c3c(=O)c2OC)cc1OC

Standard InChI:  InChI=1S/C18H16O7/c1-22-12-5-4-9(6-13(12)23-2)17-18(24-3)16(21)15-11(20)7-10(19)8-14(15)25-17/h4-8,19-20H,1-3H3

Standard InChI Key:  TWMBFWDMMIGYEO-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 25 27  0  0  0  0  0  0  0  0999 V2000
   -4.6973  -18.1333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6984  -18.9607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9836  -19.3735    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9854  -17.7205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2700  -18.1297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2712  -18.9581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5582  -19.3711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8396  -18.9602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8384  -18.1317    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5559  -17.7141    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5606  -20.1961    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1248  -17.7239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4110  -18.1398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4121  -16.4898    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1241  -16.9023    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3064  -16.9039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3046  -17.7254    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1263  -19.3747    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9819  -20.1985    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0212  -16.4919    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4118  -17.7210    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1286  -20.1997    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0188  -18.1382    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7353  -16.9049    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7335  -17.7260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  1  0
 12 13  2  0
 13 17  1  0
  3  6  2  0
 16 14  1  0
  1  2  2  0
 14 15  2  0
 15 12  1  0
  9 12  1  0
 16 17  2  0
  5  4  2  0
  4  1  1  0
  5 10  1  0
  8 18  1  0
  6  7  1  0
  3 19  1  0
  7  8  1  0
 16 20  1  0
  8  9  2  0
  1 21  1  0
  9 10  1  0
 18 22  1  0
  5  6  1  0
 17 23  1  0
  7 11  2  0
 20 24  1  0
 23 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA350720

   5,7-Dihydroxy-3,3',4'-trimethoxyflavone

Molecule Features

Natural Product: Yes

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: 344.32

Molecular Weight (Monoisotopic): 344.0896

AlogP: 2.90

#Rotatable Bonds: 4

Polar Surface Area: 98.36

Molecular Species: ACID

HBA: 7

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 6.38

CX Basic pKa: ┄

CX LogP: 2.56

CX LogD: 1.44

Aromatic Rings: 3

Heavy Atoms: 25

QED Weighted: 0.75

Np Likeness Score: 1.22

References

1. De Meyer N, Haemers A, Mishra L, Pandey HK, Pieters LA, Vanden Berghe DA, Vlietinck AJ..  (1991)  4'-Hydroxy-3-methoxyflavones with potent antipicornavirus activity.,  34  (2): [PMID:1847431] [10.1021/jm00106a039]

2. Daskiewicz JB, Depeint F, Viornery L, Bayet C, Comte-Sarrazin G, Comte G, Gee JM, Johnson IT, Ndjoko K, Hostettmann K, Barron D..  (2005)  Effects of flavonoids on cell proliferation and caspase activation in a human colonic cell line HT29: an SAR study.,  48  (8): [PMID:15828817] [10.1021/jm040770b]

3. Edwards JM, Raffauf RF, Le Quesne PW..  (1979)  Antineoplastic activity and cytotoxicity of flavones, isoflavones, and flavanones.,  42  (1): [PMID:469554] [10.1021/np50001a002]

Source

Source(1):

• Scientific Literature