2-(3,4-Dimethoxyphenyl)-3,7-dihydroxy-5-methoxy-4Hchromen-4-one

ID: ALA2043333

PubChem CID: 14234929

Max Phase: Preclinical

Molecular Formula: C18H16O7

Molecular Weight: 344.32

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccc(-c2oc3cc(O)cc(OC)c3c(=O)c2O)cc1OC

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

Standard InChI Key:  JVPXWOZUJXXSRX-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 25 27  0  0  0  0  0  0  0  0999 V2000
    3.9215  -15.1476    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9215  -15.9720    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6349  -16.3865    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3483  -15.9720    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3483  -15.1476    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6349  -14.7333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0658  -14.7333    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7833  -15.1476    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7833  -15.9720    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0658  -16.3865    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0658  -17.2085    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4952  -16.3873    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4952  -14.7366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2086  -15.1468    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9260  -14.7366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9260  -13.9078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2086  -13.4935    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4952  -13.9078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6380  -13.4968    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.6380  -15.1476    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6349  -17.2085    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2055  -14.7366    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9208  -17.6208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6380  -12.6722    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6380  -15.9721    0.0000 C   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  1  1  0
  7  5  1  0
  8  7  1  0
  9  8  2  0
 10  9  1  0
  4 10  1  0
 10 11  2  0
  9 12  1  0
  8 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 13  1  0
 16 19  1  0
 15 20  1  0
  3 21  1  0
  1 22  1  0
 21 23  1  0
  1  2  2  0
 19 24  1  0
  2  3  1  0
 20 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2043333

   3,7-Dihydroxy-5,3',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: 1.94

CX LogD: 0.91

Aromatic Rings: 3

Heavy Atoms: 25

QED Weighted: 0.75

Np Likeness Score: 1.22

References

1. 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