(3R)-5,7-dihydroxyl-6-methyl-3-(4'-hydroxylbenzyl)-chroman-4-one

ID: ALA2385398

Cas Number: 84638-48-2

PubChem CID: 71585044

Max Phase: Preclinical

Molecular Formula: C17H16O5

Molecular Weight: 300.31

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1c(O)cc2c(c1O)C(=O)[C@H](Cc1ccc(O)cc1)CO2

Standard InChI:  InChI=1S/C17H16O5/c1-9-13(19)7-14-15(16(9)20)17(21)11(8-22-14)6-10-2-4-12(18)5-3-10/h2-5,7,11,18-20H,6,8H2,1H3/t11-/m1/s1

Standard InChI Key:  BFVOQLBTLZMHPR-LLVKDONJSA-N

Molfile:  

     RDKit          2D

 22 24  0  0  0  0  0  0  0  0999 V2000
   21.8556   -2.8663    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9879   -2.0455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9867   -2.8728    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7015   -3.2856    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6997   -1.6329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4150   -2.0419    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4184   -2.8749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.1375   -3.2861    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.8544   -2.0360    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.1307   -1.6201    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.1398   -4.1110    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.2735   -1.6333    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.2721   -3.2847    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7001   -4.1105    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.5715   -3.2763    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.2844   -2.8613    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.9971   -3.2724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.7095   -2.8581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.7071   -2.0324    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.9863   -1.6226    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.2767   -2.0392    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.4195   -1.6165    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
  3 13  1  0
  4 14  1  0
  1 15  1  1
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 16  1  0
 19 22  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2385398

   (3R)-5,7-Dihydroxy-3-(4-hydroxybenzyl)-6-methyl-2,3-dihydro-4H-1-benzopyran-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: 300.31

Molecular Weight (Monoisotopic): 300.0998

AlogP: 2.55

#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: 8.21

CX Basic pKa: ┄

CX LogP: 3.69

CX LogD: 3.62

Aromatic Rings: 2

Heavy Atoms: 22

QED Weighted: 0.79

Np Likeness Score: 1.88

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