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

ID: ALA1094921

PubChem CID: 46886730

Max Phase: Preclinical

Molecular Formula: C18H18O6

Molecular Weight: 330.34

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1c(O)c(C)c(O)c2c1OC[C@@H](Cc1ccc(O)cc1)C2=O

Standard InChI:  InChI=1S/C18H18O6/c1-9-14(20)13-16(22)11(7-10-3-5-12(19)6-4-10)8-24-17(13)18(23-2)15(9)21/h3-6,11,19-21H,7-8H2,1-2H3/t11-/m1/s1

Standard InChI Key:  MDFVUCLEMCGDDE-LLVKDONJSA-N

Molfile:  

     RDKit          2D

 24 26  0  0  0  0  0  0  0  0999 V2000
   -4.3723  -20.2333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3734  -21.0607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6586  -21.4735    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6604  -19.8205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9450  -20.2297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9416  -21.0627    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2224  -21.4740    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5020  -21.0568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5055  -20.2238    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2293  -19.8079    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0882  -21.4726    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0868  -19.8210    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6601  -22.2985    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2202  -22.2990    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7864  -21.4674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0731  -21.0529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6385  -21.4666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3514  -21.0529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3496  -20.2270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6290  -19.8166    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0809  -20.2327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0624  -19.8116    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6629  -18.9955    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9496  -18.5809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  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
  2 11  1  0
 23 24  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1094921

   (3r)-5,7-Dihydroxy-6-methyl-8-methoxy-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: 330.34

Molecular Weight (Monoisotopic): 330.1103

AlogP: 2.55

#Rotatable Bonds: 3

Polar Surface Area: 96.22

Molecular Species: NEUTRAL

HBA: 6

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.71

CX Basic pKa: ┄

CX LogP: 3.53

CX LogD: 3.51

Aromatic Rings: 2

Heavy Atoms: 24

QED Weighted: 0.80

Np Likeness Score: 1.89

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