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

ID: ALA2252776

PubChem CID: 11611881

Max Phase: Preclinical

Molecular Formula: C26H30O6

Molecular Weight: 438.52

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C=C1[C@@H]2C(=O)C=C3[C@@H](OC)O[C@@H](OC)[C@@H]3[C@@]2(C)[C@H](OC(=O)/C=C/c2ccccc2)C[C@@H]1C

Standard InChI:  InChI=1S/C26H30O6/c1-15-13-20(31-21(28)12-11-17-9-7-6-8-10-17)26(3)22(16(15)2)19(27)14-18-23(26)25(30-5)32-24(18)29-4/h6-12,14-15,20,22-25H,2,13H2,1,3-5H3/b12-11+/t15-,20+,22+,23+,24-,25+,26-/m0/s1

Standard InChI Key:  QUIOFBAKMJWQEO-UFQTXSPKSA-N

Molfile:  

     RDKit          2D

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    1.9646  -22.5099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.6698  -21.2800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.3762  -22.5099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    4.7883  -22.5081    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3678  -20.8755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2574  -22.9195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6698  -20.4628    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6696  -23.7316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.2600  -16.3773    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5499  -16.7893    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5531  -17.6044    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0784  -21.2810    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7888  -21.6889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3963  -21.1393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0614  -20.3917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2469  -20.4793    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6987  -19.8733    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9493  -19.0955    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1961  -21.3074    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4504  -22.0840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0804  -23.7325    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
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  5 23  1  0
  6  7  1  0
  7  8  1  0
  8 24  2  0
  5  9  1  1
  2 10  1  1
  4 11  1  1
  3 12  2  0
 11 13  1  0
 13 14  1  0
 13 15  2  0
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 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 17  1  0
 23 24  1  1
 24 25  1  0
 25 26  1  0
 26 27  1  0
 23 27  1  0
 27 28  1  6
 28 29  1  0
 25 30  1  6
 30 31  1  0
  7 32  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA2252776

   [(1R,3S,5aS,7S,9R,9aR,9bR)-1,3-dimethoxy-7,9a-dimethyl-6-methylidene-5-oxo-3,5a,7,8,9,9b-hexahydro-1H-benzo[e][2]benzofuran-9-yl] (E)-3-phenylprop-2-enoate

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: 438.52

Molecular Weight (Monoisotopic): 438.2042

AlogP: 3.93

#Rotatable Bonds: 5

Polar Surface Area: 71.06

Molecular Species: NEUTRAL

HBA: 6

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 4.57

CX LogD: 4.57

Aromatic Rings: 1

Heavy Atoms: 32

QED Weighted: 0.39

Np Likeness Score: 2.33

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