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

ID: ALA2252775

PubChem CID: 11522458

Max Phase: Preclinical

Molecular Formula: C17H26O5

Molecular Weight: 310.39

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C=C1[C@@H]2[C@@H](O)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/C17H26O5/c1-8-6-12(19)17(3)13(9(8)2)11(18)7-10-14(17)16(21-5)22-15(10)20-4/h7-8,11-16,18-19H,2,6H2,1,3-5H3/t8-,11-,12+,13+,14+,15-,16+,17-/m0/s1

Standard InChI Key:  KFRZYNUEUBAILG-UQHHHJTPSA-N

Molfile:  

     RDKit          2D

 22 24  0  0  0  0  0  0  0  0999 V2000
   22.2251  -13.9665    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.2251  -14.7837    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.9304  -15.1882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.9304  -13.5538    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.6357  -13.9665    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.6367  -14.7837    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.3410  -15.1892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.0488  -14.7819    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.6284  -13.1494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.5180  -15.1934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.9304  -12.7366    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.9301  -16.0054    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.3390  -13.5548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.0494  -13.9627    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.6569  -13.4132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.3219  -12.6655    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.5075  -12.7531    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.9592  -12.1471    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.2099  -11.3693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.4566  -13.5812    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.7109  -14.3578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.3410  -16.0064    0.0000 O   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
M  END

Alternative Forms

1. Parent:

   

   ALA2252775

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

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: 310.39

Molecular Weight (Monoisotopic): 310.1780

AlogP: 1.46

#Rotatable Bonds: 2

Polar Surface Area: 68.15

Molecular Species: NEUTRAL

HBA: 5

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 0.94

CX LogD: 0.94

Aromatic Rings: ┄

Heavy Atoms: 22

QED Weighted: 0.76

Np Likeness Score: 2.96

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