2-(3,4-Dihydroxyphenyl)-7-hydroxy-3,5-dimethoxy-4Hchromen-4-one

ID: ALA2043331

Cas Number: 1486-66-4

PubChem CID: 5489501

Max Phase: Preclinical

Molecular Formula: C17H14O7

Molecular Weight: 330.29

Molecule Type: Small molecule

Names and Identifiers

Synonyms: 3,5-O-dimethylquercetin | Caryatin|1486-66-4|3,5-Di-O-methylquercetin|2-(3,4-dihydroxyphenyl)-7-hydroxy-3,5-dimethoxychromen-4-one|2-(3,4-Dihydroxyphenyl)-7-hydroxy-3,5-dimethoxy-4H-1-benzopyran-4-one|3,5-DIMETHOXY-7,3',4'-TRIHYDROXYFLAVONE|7,3',4'-Trihydroxy-3,5-dimethoxyflavone|4H-1-Benzopyran-4-one, 2-(3,4-dihydroxyphenyl)-7-hydroxy-3,5-dimethoxy-|3,5-O-dimethylquercetin|AT4UXB9ZR8|Di-O-Methylquercetin, 3,5-|CHEMBL2043331|SCHEMBL11149169|DTXSID60164031|CHEBI:174457|HY-N10602|LMPK12112730|AKOSShow More⌵

Canonical SMILES:  COc1c(-c2ccc(O)c(O)c2)oc2cc(O)cc(OC)c2c1=O

Standard InChI:  InChI=1S/C17H14O7/c1-22-12-6-9(18)7-13-14(12)15(21)17(23-2)16(24-13)8-3-4-10(19)11(20)5-8/h3-7,18-20H,1-2H3

Standard InChI Key:  AOFQCVDYMNHCKD-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 24 26  0  0  0  0  0  0  0  0999 V2000
    2.5807   -9.1094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5807   -9.9340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2941  -10.3484    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0075   -9.9340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0075   -9.1094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2941   -8.6950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7250   -8.6950    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4426   -9.1094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4426   -9.9340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7250  -10.3484    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7250  -11.1705    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1545  -10.3493    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1545   -8.6983    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8679   -9.1085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5855   -8.6983    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5855   -7.8696    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8679   -7.4552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1545   -7.8696    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2973   -7.4585    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.2973   -9.1094    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2941  -11.1705    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8646   -8.6983    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0082  -11.5828    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1508  -11.1739    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  1  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
 12 24  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2043331

   Caryatin

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: 330.29

Molecular Weight (Monoisotopic): 330.0740

AlogP: 2.59

#Rotatable Bonds: 3

Polar Surface Area: 109.36

Molecular Species: ACID

HBA: 7

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 6.38

CX Basic pKa: ┄

CX LogP: 1.77

CX LogD: 0.71

Aromatic Rings: 3

Heavy Atoms: 24

QED Weighted: 0.63

Np Likeness Score: 1.57

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