(3S)-3,5,7-trihydroxyl-6,8-dimethyl-3-(4'-hydroxylbenzyl)-chroman-4-one

ID: ALA2385401

PubChem CID: 71625780

Max Phase: Preclinical

Molecular Formula: C18H18O6

Molecular Weight: 330.34

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1c(O)c(C)c2c(c1O)C(=O)[C@](O)(Cc1ccc(O)cc1)CO2

Standard InChI:  InChI=1S/C18H18O6/c1-9-14(20)10(2)16-13(15(9)21)17(22)18(23,8-24-16)7-11-3-5-12(19)6-4-11/h3-6,19-21,23H,7-8H2,1-2H3/t18-/m0/s1

Standard InChI Key:  TUXGIPNQUYTUBE-SFHVURJKSA-N

Molfile:  

     RDKit          2D

 24 26  0  0  0  0  0  0  0  0999 V2000
   22.4955   -7.3207    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.6705   -7.3207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.0830   -8.0351    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8025   -6.4998    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8013   -7.3272    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5161   -7.7400    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5143   -6.0871    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2297   -6.4962    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2331   -7.3293    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.9523   -7.7405    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.6692   -6.4903    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.9454   -6.0744    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.9545   -8.5655    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.0879   -6.0875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.0865   -7.7391    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5146   -8.5650    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.9080   -8.0351    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.3176   -8.7503    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.1418   -8.7506    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.5551   -8.0356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.1382   -7.3188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.3154   -7.3220    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.3801   -8.0345    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.5118   -5.2621    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6
  3  2  1  0
  4  5  2  0
  5  6  1  0
  6  9  2  0
  8  7  2  0
  7  4  1  0
  8  9  1  0
  8 12  1  0
  9 10  1  0
 10  2  1  0
  2 11  1  0
 11 12  1  0
 10 13  2  0
  4 14  1  0
  5 15  1  0
  6 16  1  0
  3 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 17  1  0
 20 23  1  0
  7 24  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2385401

   (3S)-3,5,7-trihydroxy-3-[(4-hydroxyphenyl)methyl]-6,8-dimethyl-2H-chromen-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: 330.34

Molecular Weight (Monoisotopic): 330.1103

AlogP: 1.97

#Rotatable Bonds: 2

Polar Surface Area: 107.22

Molecular Species: NEUTRAL

HBA: 6

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.47

CX Basic pKa: ┄

CX LogP: 3.45

CX LogD: 3.42

Aromatic Rings: 2

Heavy Atoms: 24

QED Weighted: 0.67

Np Likeness Score: 1.96

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