(+/-)-rel-(1S,3aS,4R,6aR)-4-(2,6-dimethoxyphenoxy)-1-(2-methoxy-5-(2-methoxyethoxy)phenyl)hexahydrofuro[3,4-c]furan-3a-ol

ID: ALA2288238

PubChem CID: 76320214

Max Phase: Preclinical

Molecular Formula: C24H30O9

Molecular Weight: 462.50

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COCCOc1ccc(OC)c([C@H]2OC[C@]3(O)[C@@H](Oc4c(OC)cccc4OC)OC[C@H]23)c1

Standard InChI:  InChI=1S/C24H30O9/c1-26-10-11-30-15-8-9-18(27-2)16(12-15)21-17-13-31-23(24(17,25)14-32-21)33-22-19(28-3)6-5-7-20(22)29-4/h5-9,12,17,21,23,25H,10-11,13-14H2,1-4H3/t17-,21-,23-,24-/m1/s1

Standard InChI Key:  TZLCRRPJTRAHDB-BROLKAIQSA-N

Molfile:  

     RDKit          2D

 33 36  0  0  0  0  0  0  0  0999 V2000
    7.0772   -6.2250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0790   -7.0535    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7884   -7.4665    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5079   -7.0528    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5080   -6.2236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7911   -5.8121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7863   -4.9871    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0784   -4.5778    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2251   -7.4636    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.2232   -8.2886    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2202   -5.8070    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.2164   -4.9822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8067   -3.7163    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5472   -4.5023    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.6316   -3.7116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8904   -4.5019    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7171   -4.4996    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9719   -3.7077    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.2946   -3.2211    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2929   -2.3961    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1352   -5.2858    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.0157   -1.9855    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0176   -1.1646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3013   -0.7513    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5812   -1.1761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5866   -1.9929    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8740   -2.4059    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.1585   -1.9981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7280   -0.7512    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.4458   -1.1628    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1590   -0.7482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8746   -1.1584    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.5879   -0.7438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  1  1  0
  6  7  1  0
  7  8  1  0
  4  9  1  0
  9 10  1  0
  5 11  1  0
 12 11  1  1
 12 16  1  0
 15 13  1  6
 13 14  1  0
 14 12  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 15  1  0
 19 20  1  1
 16 21  1  1
 20 22  2  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 20  1  0
 26 27  1  0
 27 28  1  0
 23 29  1  0
 29 30  1  0
 30 31  1  0
 31 32  1  0
 32 33  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2288238

   (3R,3aS,6S,6aR)-3-(2,6-dimethoxyphenoxy)-6-[2-methoxy-5-(2-methoxyethoxy)phenyl]-3,4,6,6a-tetrahydro-1H-furo[3,4-c]furan-3a-ol

Molecule Features

Natural Product: No

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: 462.50

Molecular Weight (Monoisotopic): 462.1890

AlogP: 2.59

#Rotatable Bonds: 10

Polar Surface Area: 94.07

Molecular Species: NEUTRAL

HBA: 9

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 11.95

CX Basic pKa: ┄

CX LogP: 2.16

CX LogD: 2.16

Aromatic Rings: 2

Heavy Atoms: 33

QED Weighted: 0.53

Np Likeness Score: 0.83

References

1. YAMAUCHI S, TANIGUCHI E.  (1991)  Synthesis and Insecticidal Activity of Lignan Analogs. (1).,  55  (12): [10.1271/bbb1961.55.3075]

Source

Source(1):

• Scientific Literature