2-(3,4-dimethoxyphenyl)-3,5-dihydroxy-7-methoxy-4H-chromen-4-one

ID: ALA1689343

Cas Number: 6068-80-0

PubChem CID: 5748558

Max Phase: Preclinical

Molecular Formula: C18H16O7

Molecular Weight: 344.32

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cc(O)c2c(=O)c(O)c(-c3ccc(OC)c(OC)c3)oc2c1

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

Standard InChI Key:  OEEUHNAUMMATJT-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 25 27  0  0  0  0  0  0  0  0999 V2000
    6.5073  -21.3999    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5061  -22.2267    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2205  -22.6394    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2187  -20.9874    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2203  -23.4639    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7931  -20.9878    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9336  -21.3962    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9370  -22.2288    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6558  -22.6399    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3758  -22.2229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3724  -21.3903    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6490  -20.9747    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.6581  -23.4644    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.0852  -20.9759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7997  -21.3880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5119  -20.9743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5098  -20.1489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7896  -19.7390    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0802  -20.1551    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2221  -19.7334    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7929  -20.1632    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0910  -22.6333    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.9380  -20.1425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2271  -21.3846    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.2292  -22.2091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 11 12  1  0
  2  3  1  0
  9 13  2  0
  1  6  1  0
 11 14  1  0
  7  8  1  0
 14 15  2  0
  3  8  2  0
 15 16  1  0
  1  2  2  0
 16 17  2  0
  7  4  2  0
 17 18  1  0
  4  1  1  0
 18 19  2  0
 19 14  1  0
 17 20  1  0
  3  5  1  0
  6 21  1  0
  7 12  1  0
 10 22  1  0
  8  9  1  0
 20 23  1  0
  9 10  1  0
 16 24  1  0
 10 11  2  0
 24 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1689343

   Quercetin 7,3',4'-trimethyl ether

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: NEUTRAL

HBA: 7

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 7.15

CX Basic pKa: ┄

CX LogP: 2.59

CX LogD: 2.15

Aromatic Rings: 3

Heavy Atoms: 25

QED Weighted: 0.75

Np Likeness Score: 1.07

References

1. Versiani MA, Diyabalanage T, Ratnayake R, Henrich CJ, Bates SE, McMahon JB, Gustafson KR..  (2011)  Flavonoids from eight tropical plant species that inhibit the multidrug resistance transporter ABCG2.,  74  (2): [PMID:21275386] [10.1021/np100797y]

2. Shi ZH, Li NG, Tang YP, Wei-Li, Lian-Yin, Yang JP, Hao-Tang, Duan JA..  (2012)  Metabolism-based synthesis, biologic evaluation and SARs analysis of O-methylated analogs of quercetin as thrombin inhibitors.,  54  [PMID:22647223] [10.1016/j.ejmech.2012.04.044]

Source

Source(1):

• Scientific Literature