4-[(2S,3S)-4-(3-Hydroxy-4-methoxy-phenyl)-2,3-dimethyl-butyl]-6-methoxy-benzene-1,3-diol

ID: ALA363230

PubChem CID: 11290949

Max Phase: Preclinical

Molecular Formula: C20H26O5

Molecular Weight: 346.42

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccc(C[C@H](C)[C@@H](C)Cc2cc(OC)c(O)cc2O)cc1O

Standard InChI:  InChI=1S/C20H26O5/c1-12(7-14-5-6-19(24-3)17(22)9-14)13(2)8-15-10-20(25-4)18(23)11-16(15)21/h5-6,9-13,21-23H,7-8H2,1-4H3/t12-,13-/m0/s1

Standard InChI Key:  ZOOFDRPDTGLOSE-STQMWFEESA-N

Molfile:  

     RDKit          2D

 25 26  0  0  1  0  0  0  0  0999 V2000
    1.8292    0.1458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2542    0.1458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5417   -0.2667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2417    0.9750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8167    0.9625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5292    1.3833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1167   -0.2792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1708   -0.2875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4000    0.1375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1708   -1.1125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4583    0.1208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7458   -0.2875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0250    0.1333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3208   -0.2792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4583   -1.5250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7458   -1.1125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5417   -1.1000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9542    1.3875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8833    0.1208    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5167    2.2083    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8833   -1.5250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4000    0.9625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3208   -1.1000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8125    2.6125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8833   -2.3500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  1  0
  3  1  2  0
  4  6  1  0
  5  1  1  0
  6  5  2  0
  7  1  1  0
  8 11  1  0
  9  7  1  0
 10 15  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 14  9  1  0
 15 16  2  0
 16 12  1  0
 17  3  1  0
 18  4  1  0
 19  8  1  0
 20  6  1  0
 21 10  1  0
  9 22  1  1
 14 23  1  1
 24 20  1  0
 25 21  1  0
  2  4  2  0
  8 10  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA363230

   4-[(2S,3S)-4-(3-hydroxy-4-methoxyphenyl)-2,3-dimethylbutyl]-6-methoxybenzene-1,3-diol

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: 346.42

Molecular Weight (Monoisotopic): 346.1780

AlogP: 3.88

#Rotatable Bonds: 7

Polar Surface Area: 79.15

Molecular Species: NEUTRAL

HBA: 5

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.71

CX Basic pKa: ┄

CX LogP: 4.75

CX LogD: 4.74

Aromatic Rings: 2

Heavy Atoms: 25

QED Weighted: 0.71

Np Likeness Score: 1.00

References

1. Lee WS, Baek YI, Kim JR, Cho KH, Sok DE, Jeong TS..  (2004)  Antioxidant activities of a new lignan and a neolignan from Saururus chinensis.,  14  (22): [PMID:15482936] [10.1016/j.bmcl.2004.08.054]

Source

Source(1):

• Scientific Literature