rel-(7S,8R,8'R)-3,4:3',4'-bis(methylenedioxy)lignan-7-ol

ID: ALA1077913

PubChem CID: 44254704

Max Phase: Preclinical

Molecular Formula: C20H22O5

Molecular Weight: 342.39

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C[C@H]([C@H](C)Cc1ccc2c(c1)OCO2)[C@H](O)c1ccc2c(c1)OCO2

Standard InChI:  InChI=1S/C20H22O5/c1-12(7-14-3-5-16-18(8-14)24-10-22-16)13(2)20(21)15-4-6-17-19(9-15)25-11-23-17/h3-6,8-9,12-13,20-21H,7,10-11H2,1-2H3/t12-,13-,20+/m1/s1

Standard InChI Key:  SDXLCXZRXWWAGW-IZDJOXEWSA-N

Molfile:  

     RDKit          2D

 25 28  0  0  0  0  0  0  0  0999 V2000
   -2.2878    0.3806    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5742    1.6245    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2896    2.0336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0026    0.7935    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0013    1.6224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7893    1.8798    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2776    1.2099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7913    0.5386    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8613    2.0397    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1453    1.6299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8644    2.8647    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1421    0.8049    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5677    2.0451    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5739    0.3951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8551    0.3897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5711    0.7995    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8520   -0.4353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5666   -0.8457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5639   -1.6700    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1383   -0.8381    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1320   -1.6610    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8502   -2.0787    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6749   -2.8909    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1518   -2.9751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4872   -2.2149    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 10 12  1  0
 16  2  1  0
 10 13  1  6
  4  1  1  0
 12 14  1  6
  2  3  2  0
 12 15  1  0
  5  6  1  0
  6  7  1  0
 15 17  1  0
  7  8  1  0
 17 18  2  0
  8  4  1  0
 18 19  1  0
 19 22  2  0
  3  5  1  0
 21 20  2  0
 20 17  1  0
 21 22  1  0
  2  9  1  0
  4  5  2  0
  9 10  1  0
  1 16  2  0
  9 11  1  1
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 21  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1077913

   MAGNOVATIN A

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: 342.39

Molecular Weight (Monoisotopic): 342.1467

AlogP: 3.69

#Rotatable Bonds: 5

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: ┄

CX Basic pKa: ┄

CX LogP: 4.07

CX LogD: 4.07

Aromatic Rings: 2

Heavy Atoms: 25

QED Weighted: 0.90

Np Likeness Score: 0.78

References

1. Barros LF, Barison A, Salvador MJ, de Mello-Silva R, Cabral EC, Eberlin MN, Stefanello ME..  (2009)  Constituents of the leaves of Magnolia ovata.,  72  (8): [PMID:19658431] [10.1021/np900203y]

Source

Source(1):

• Scientific Literature