(2S)-4'-hydroxy-6,7,3'-trimethoxyflavan

ID: ALA2409054

PubChem CID: 71746243

Max Phase: Preclinical

Molecular Formula: C18H20O5

Molecular Weight: 316.35

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C18H20O5/c1-20-16-8-11(4-6-13(16)19)14-7-5-12-9-17(21-2)18(22-3)10-15(12)23-14/h4,6,8-10,14,19H,5,7H2,1-3H3/t14-/m0/s1

Standard InChI Key:  JLLHPTPUDAXLAG-AWEZNQCLSA-N

Molfile:  

     RDKit          2D

 23 25  0  0  0  0  0  0  0  0999 V2000
    3.5109   -3.5659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5097   -4.3854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2178   -4.7944    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2160   -3.1570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9246   -3.5623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9280   -4.3875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6403   -4.7949    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3539   -4.3816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3505   -3.5564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6336   -3.1445    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0595   -3.1480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7688   -3.5562    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4747   -3.1461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4726   -2.3280    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7587   -1.9248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0556   -2.3342    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8030   -3.1575    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8029   -2.3403    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1779   -1.9151    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8017   -4.7935    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0943   -4.3843    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1835   -3.5528    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.1856   -4.3700    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
 20 21  1  0
 13 22  1  0
 22 23  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2409054

   (2S)-4'-HYDROXY-6,7,3'-TRIMETHOXYFLAVAN

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: 316.35

Molecular Weight (Monoisotopic): 316.1311

AlogP: 3.48

#Rotatable Bonds: 4

Polar Surface Area: 57.15

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.91

CX Basic pKa: ┄

CX LogP: 3.31

CX LogD: 3.31

Aromatic Rings: 2

Heavy Atoms: 23

QED Weighted: 0.94

Np Likeness Score: 1.02

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