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

ID: ALA2288236

PubChem CID: 76334683

Max Phase: Preclinical

Molecular Formula: C21H24O8

Molecular Weight: 404.42

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccc(O)cc1[C@H]1OC[C@]2(O)[C@H](Oc3c(OC)cccc3OC)OC[C@H]12

Standard InChI:  InChI=1S/C21H24O8/c1-24-15-8-7-12(22)9-13(15)18-14-10-27-20(21(14,23)11-28-18)29-19-16(25-2)5-4-6-17(19)26-3/h4-9,14,18,20,22-23H,10-11H2,1-3H3/t14-,18-,20+,21-/m1/s1

Standard InChI Key:  CTHZSAFLAXYHKF-MLCUKSTJSA-N

Molfile:  

     RDKit          2D

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   25.4936  -17.0690    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.4937  -16.2477    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.7836  -15.8400    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.7789  -15.0228    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   26.2041  -17.4759    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   27.9778  -12.0495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.9796  -11.2364    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.2701  -10.8271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.5568  -11.2479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.5622  -12.0569    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.8563  -12.4660    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.1475  -12.0621    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.6833  -10.8269    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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 16 21  1  1
 20 22  2  0
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 27 28  1  0
 23 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2288236

   (3S,3aS,6S,6aR)-3-(2,6-dimethoxyphenoxy)-6-(5-hydroxy-2-methoxyphenyl)-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: 404.42

Molecular Weight (Monoisotopic): 404.1471

AlogP: 2.27

#Rotatable Bonds: 6

Polar Surface Area: 95.84

Molecular Species: NEUTRAL

HBA: 8

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.78

CX Basic pKa: ┄

CX LogP: 2.06

CX LogD: 2.06

Aromatic Rings: 2

Heavy Atoms: 29

QED Weighted: 0.76

Np Likeness Score: 1.48

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