(2S)-6,4'-dihydroxy-7,3'-dimethoxyflavan

ID: ALA2409055

PubChem CID: 71746244

Max Phase: Preclinical

Molecular Formula: C17H18O5

Molecular Weight: 302.33

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cc([C@@H]2CCc3cc(O)c(OC)cc3O2)ccc1O

Standard InChI:  InChI=1S/C17H18O5/c1-20-16-8-11(3-5-12(16)18)14-6-4-10-7-13(19)17(21-2)9-15(10)22-14/h3,5,7-9,14,18-19H,4,6H2,1-2H3/t14-/m0/s1

Standard InChI Key:  JKEOWRFBUPMWAZ-AWEZNQCLSA-N

Molfile:  

     RDKit          2D

 22 24  0  0  0  0  0  0  0  0999 V2000
   14.1550   -3.4173    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1538   -4.2368    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8619   -4.6458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8601   -3.0084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5687   -3.4137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5721   -4.2389    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2845   -4.6463    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9980   -4.2330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9946   -3.4079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2777   -2.9959    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.7036   -2.9995    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4129   -3.4076    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1188   -2.9975    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1167   -2.1794    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4028   -1.7762    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6998   -2.1856    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4472   -3.0089    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.4470   -2.1917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8220   -1.7666    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.4458   -4.6449    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.8276   -3.4042    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.8297   -4.2214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  6  2  0
  5  4  2  0
  4  1  1  0
  5  6  1  0
  5 10  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 11  1  0
  9 11  1  6
  1 17  1  0
 17 18  1  0
 14 19  1  0
  2 20  1  0
 13 21  1  0
 21 22  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2409055

   (2S)-2-(4-hydroxy-3-methoxyphenyl)-7-methoxy-3,4-dihydro-2H-chromen-6-ol

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: 302.33

Molecular Weight (Monoisotopic): 302.1154

AlogP: 3.18

#Rotatable Bonds: 3

Polar Surface Area: 68.15

Molecular Species: NEUTRAL

HBA: 5

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.80

CX Basic pKa: ┄

CX LogP: 3.16

CX LogD: 3.16

Aromatic Rings: 2

Heavy Atoms: 22

QED Weighted: 0.91

Np Likeness Score: 1.18

References

1. Moosophon P, Kanokmedhakul S, Kanokmedhakul K, Buayairaksa M, Noichan J, Poopasit K..  (2013)  Antiplasmodial and cytotoxic flavans and diarylpropanes from the stems of Combretum griffithii.,  76  (7): [PMID:23795891] [10.1021/np400266h]

Source

Source(1):

• Scientific Literature