(R)-5,7-dihydroxy-3-(4-hydroxybenzyl)-6,8-dimethylchroman-4-one

ID: ALA1094629

PubChem CID: 46886731

Max Phase: Preclinical

Molecular Formula: C18H18O5

Molecular Weight: 314.34

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C18H18O5/c1-9-15(20)10(2)18-14(16(9)21)17(22)12(8-23-18)7-11-3-5-13(19)6-4-11/h3-6,12,19-21H,7-8H2,1-2H3/t12-/m1/s1

Standard InChI Key:  OQJXNTUJUHDHSF-GFCCVEGCSA-N

Molfile:  

     RDKit          2D

 23 25  0  0  0  0  0  0  0  0999 V2000
    3.5611  -20.5166    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5599  -21.3440    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2747  -21.7569    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2729  -20.1039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9883  -20.5130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9917  -21.3461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7109  -21.7574    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4313  -21.3402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4279  -20.5071    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7041  -20.0912    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8451  -21.7559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8465  -20.1043    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2733  -22.5819    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7132  -22.5824    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1469  -21.7507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8602  -21.3363    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5719  -21.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2847  -21.3362    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2829  -20.5103    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5623  -20.0999    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8524  -20.5161    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9957  -20.0949    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2705  -19.2789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2 11  1  0
  1 12  1  0
  2  3  1  0
  3 13  1  0
  3  6  2  0
  7 14  2  0
  1  2  2  0
  8 15  1  1
  5  4  2  0
 15 16  1  0
  4  1  1  0
 16 17  2  0
  5 10  1  0
 17 18  1  0
  6  7  1  0
 18 19  2  0
  7  8  1  0
 19 20  1  0
  8  9  1  0
 20 21  2  0
 21 16  1  0
  9 10  1  0
 19 22  1  0
  5  6  1  0
  4 23  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1094629

   (3r)-5,7-Dihydroxy-6,8-dimethyl-3-(4'-hydroxybenzyl)chroman-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: 314.34

Molecular Weight (Monoisotopic): 314.1154

AlogP: 2.85

#Rotatable Bonds: 2

Polar Surface Area: 86.99

Molecular Species: NEUTRAL

HBA: 5

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.57

CX Basic pKa: ┄

CX LogP: 4.20

CX LogD: 4.17

Aromatic Rings: 2

Heavy Atoms: 23

QED Weighted: 0.79

Np Likeness Score: 1.88

References

1. Zhang H, Yang F, Qi J, Song XC, Hu ZF, Zhu DN, Yu BY..  (2010)  Homoisoflavonoids from the fibrous roots of Polygonatum odoratum with glucose uptake-stimulatory activity in 3T3-L1 adipocytes.,  73  (4): [PMID:20158245] [10.1021/np900588q]

2. 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