(1R,3S,5S,5aS,7S,9R,9aS,9bR)-1,3,5-trimethoxy-7,9a-dimethyl-6-methylene-1,3,5,5a,6,7,8,9,9a,9b-decahydronaphtho[2,1-c]furan-9-ol

ID: ALA2252777

PubChem CID: 11551567

Max Phase: Preclinical

Molecular Formula: C18H28O5

Molecular Weight: 324.42

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C=C1[C@@H]2[C@@H](OC)C=C3[C@@H](OC)O[C@@H](OC)[C@@H]3[C@@]2(C)[C@H](O)C[C@@H]1C

Standard InChI:  InChI=1S/C18H28O5/c1-9-7-13(19)18(3)14(10(9)2)12(20-4)8-11-15(18)17(22-6)23-16(11)21-5/h8-9,12-17,19H,2,7H2,1,3-6H3/t9-,12-,13+,14+,15+,16-,17+,18-/m0/s1

Standard InChI Key:  WWKLNYZIVVPDBN-JOLFBPBZSA-N

Molfile:  

     RDKit          2D

 23 25  0  0  0  0  0  0  0  0999 V2000
    8.5269  -21.8991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5269  -22.7163    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2321  -23.1207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2321  -21.4864    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9374  -21.8991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9385  -22.7163    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6428  -23.1217    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3506  -22.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9301  -21.0819    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8197  -23.1259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2321  -20.6692    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.2319  -23.9379    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6407  -21.4873    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3511  -21.8953    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9586  -21.3457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6237  -20.5980    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.8092  -20.6857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2610  -20.0797    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.5116  -19.3019    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7583  -21.5138    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.0127  -22.2904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6427  -23.9389    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.3503  -24.3476    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  1  4  1  0
  2  3  1  0
  6  3  1  1
  5  4  1  0
  5  6  1  0
  5 13  1  0
  6  7  1  0
  7  8  1  0
  8 14  2  0
  5  9  1  1
  2 10  1  1
  4 11  1  1
  3 12  2  0
 13 14  1  1
 14 15  1  0
 15 16  1  0
 16 17  1  0
 13 17  1  0
 17 18  1  6
 18 19  1  0
 15 20  1  6
 20 21  1  0
  7 22  1  6
 22 23  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2252777

   (1R,3S,5S,5aS,7S,9R,9aS,9bR)-1,3,5-trimethoxy-7,9a-dimethyl-6-methylidene-1,3,5,5a,7,8,9,9b-octahydrobenzo[e][2]benzofuran-9-ol

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: 324.42

Molecular Weight (Monoisotopic): 324.1937

AlogP: 2.11

#Rotatable Bonds: 3

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: 1.59

CX LogD: 1.59

Aromatic Rings: ┄

Heavy Atoms: 23

QED Weighted: 0.81

Np Likeness Score: 2.89

References

1. Brennan NJ, Larsen L, Lorimer SD, Perry NB, Chapin EL, Werk TL, Henry MJ, Hahn DR..  (2006)  Fungicidal sesquiterpene dialdehyde cinnamates from Pseudowintera axillaris.,  54  (2): [PMID:16417306] [10.1021/jf052585s]

Source

Source(1):

• Scientific Literature