5,7-dihydroxyl-8-methoxyl-3-(2'-hydroxyl-4'-methoxylbenzyl)-chroman-4-one

ID: ALA2385399

PubChem CID: 71625778

Max Phase: Preclinical

Molecular Formula: C18H18O7

Molecular Weight: 346.34

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccc(CC2COc3c(OC)c(O)cc(O)c3C2=O)c(O)c1

Standard InChI:  InChI=1S/C18H18O7/c1-23-11-4-3-9(12(19)6-11)5-10-8-25-18-15(16(10)22)13(20)7-14(21)17(18)24-2/h3-4,6-7,10,19-21H,5,8H2,1-2H3

Standard InChI Key:  CGKORFWCUPPJCO-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 25 27  0  0  0  0  0  0  0  0999 V2000
    4.1039   -7.8287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2360   -7.0079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2348   -7.8352    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9496   -8.2481    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9478   -6.5951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6632   -7.0043    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6666   -7.8373    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3857   -8.2486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1026   -6.9983    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3789   -6.5825    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3880   -9.0735    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5215   -6.5955    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9481   -9.0730    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8197   -8.2387    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5327   -7.8237    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2453   -8.2348    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9579   -7.8206    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9554   -6.9947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2345   -6.5849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5251   -7.0016    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6679   -6.5788    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9453   -5.7702    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6585   -5.3556    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3843   -6.9878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2468   -9.0597    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  2  0
  3  4  1  0
  4  7  2  0
  6  5  2  0
  5  2  1  0
  6  7  1  0
  6 10  1  0
  7  8  1  0
  8  1  1  0
  1  9  1  0
  9 10  1  0
  8 11  2  0
  2 12  1  0
  4 13  1  0
  1 14  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 15  1  0
 18 21  1  0
  5 22  1  0
 22 23  1  0
 21 24  1  0
 16 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2385399

   5,7-Dihydroxy-3-[(2-hydroxy-4-methoxyphenyl)methyl]-8-methoxy-2,3-dihydrochromen-4-one

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: 346.34

Molecular Weight (Monoisotopic): 346.1053

AlogP: 2.25

#Rotatable Bonds: 4

Polar Surface Area: 105.45

Molecular Species: NEUTRAL

HBA: 7

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.33

CX Basic pKa: ┄

CX LogP: 2.86

CX LogD: 2.81

Aromatic Rings: 2

Heavy Atoms: 25

QED Weighted: 0.78

Np Likeness Score: 1.75

References

1. Guo H, Zhao H, Kanno Y, Li W, Mu Y, Kuang X, Inouye Y, Koike K, Jiang H, Bai H..  (2013)  A dihydrochalcone and several homoisoflavonoids from Polygonatum odoratum are activators of adenosine monophosphate-activated protein kinase.,  23  (11): [PMID:23639538] [10.1016/j.bmcl.2013.04.027]

Source

Source(1):

• Scientific Literature