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

ID: ALA2385400

PubChem CID: 71625779

Max Phase: Preclinical

Molecular Formula: C18H18O7

Molecular Weight: 346.34

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C18H18O7/c1-9-13(20)12-15(16(24-2)14(9)21)25-8-18(23,17(12)22)7-10-3-5-11(19)6-4-10/h3-6,19-21,23H,7-8H2,1-2H3/t18-/m0/s1

Standard InChI Key:  KJLKHEXGKXUNTN-SFHVURJKSA-N

Molfile:  

     RDKit          2D

 25 27  0  0  0  0  0  0  0  0999 V2000
   14.5956   -7.6166    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.7706   -7.6166    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1831   -8.3310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9025   -6.7957    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9014   -7.6230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6162   -8.0359    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6145   -6.3829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3298   -6.7921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3333   -7.6252    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0524   -8.0364    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7693   -6.7861    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0456   -6.3703    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.0547   -8.8614    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.1880   -6.3833    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.1867   -8.0349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6148   -8.8609    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.0081   -8.3310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4177   -9.0461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2420   -9.0465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6553   -8.3314    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2384   -7.6147    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4155   -7.6178    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4803   -8.3303    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.6119   -5.5579    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.3252   -5.1433    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
 24 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2385400

   (3S)-3,5,7-trihydroxy-3-[(4-hydroxyphenyl)methyl]-8-methoxy-6-methyl-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: 346.34

Molecular Weight (Monoisotopic): 346.1053

AlogP: 1.67

#Rotatable Bonds: 3

Polar Surface Area: 116.45

Molecular Species: NEUTRAL

HBA: 7

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.62

CX Basic pKa: ┄

CX LogP: 2.78

CX LogD: 2.75

Aromatic Rings: 2

Heavy Atoms: 25

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