(7R,8S,8'S)-3,3'-Dimethoxy-7,9'-epoxylignane-4,4',9-triol

ID: ALA487997

Cas Number: 83327-19-9

PubChem CID: 23815394

Product Number: L664417, Order Now?

Max Phase: Preclinical

Molecular Formula: C20H24O6

Molecular Weight: 360.41

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cc(C[C@@H]2CO[C@@H](c3ccc(O)c(OC)c3)[C@@H]2CO)ccc1O

Standard InChI:  InChI=1S/C20H24O6/c1-24-18-8-12(3-5-16(18)22)7-14-11-26-20(15(14)10-21)13-4-6-17(23)19(9-13)25-2/h3-6,8-9,14-15,20-23H,7,10-11H2,1-2H3/t14-,15-,20+/m1/s1

Standard InChI Key:  MHXCIKYXNYCMHY-SXGZJXTBSA-N

Molfile:  

     RDKit          2D

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    2.4891  -23.6690    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2039  -24.0819    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9203  -23.6685    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9175  -22.8380    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2021  -22.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6304  -22.4228    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3471  -22.8324    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6009  -23.6166    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4268  -23.6202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6854  -22.8367    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0201  -22.3489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7757  -22.4293    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7755  -21.6043    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7743  -24.0809    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9085  -24.2899    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1772  -24.3245    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3523  -24.3116    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5283  -25.0206    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9735  -25.7142    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7985  -25.6754    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1762  -24.9372    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7287  -24.2466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0001  -24.8951    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.4485  -25.5876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2454  -26.3689    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  6  1  1  0
  1 13  1  0
  1  2  2  0
 13 14  1  0
  5  7  1  0
  2 15  1  0
  3  4  2  0
 10 16  1  1
  8  7  1  6
  9 17  1  6
  8  9  1  0
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 16 19  2  0
  4  5  1  0
 19 20  1  0
  2  3  1  0
 20 21  2  0
  5  6  2  0
 21 22  1  0
  9 10  1  0
 22 23  2  0
 23 16  1  0
 10 11  1  0
 22 24  1  0
 11 12  1  0
 24 25  1  0
 12  8  1  0
 21 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA487997

   Lariciresinol

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: 360.41

Molecular Weight (Monoisotopic): 360.1573

AlogP: 2.65

#Rotatable Bonds: 6

Polar Surface Area: 88.38

Molecular Species: NEUTRAL

HBA: 6

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.75

CX Basic pKa: ┄

CX LogP: 2.31

CX LogD: 2.30

Aromatic Rings: 2

Heavy Atoms: 26

QED Weighted: 0.73

Np Likeness Score: 1.59

References

1. Nishiwaki H, Kumamoto M, Shuto Y, Yamauchi S..  (2011)  Stereoselective syntheses of all stereoisomers of lariciresinol and their plant growth inhibitory activities.,  59  (24): [PMID:22066904] [10.1021/jf203222w]

Source

Source(1):

• Scientific Literature