(1R,3S,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-9-yl cinnamate

ID: ALA2252772

PubChem CID: 11626008

Max Phase: Preclinical

Molecular Formula: C26H32O5

Molecular Weight: 424.54

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C=C1[C@@H](C)C[C@@H](OC(=O)/C=C/c2ccccc2)[C@]2(C)[C@@H]3C(=CC[C@@H]12)[C@@H](OC)O[C@H]3OC

Standard InChI:  InChI=1S/C26H32O5/c1-16-15-21(30-22(27)14-11-18-9-7-6-8-10-18)26(3)20(17(16)2)13-12-19-23(26)25(29-5)31-24(19)28-4/h6-12,14,16,20-21,23-25H,2,13,15H2,1,3-5H3/b14-11+/t16-,20-,21+,23+,24-,25+,26+/m0/s1

Standard InChI Key:  ZMBQTUOUZGMUDO-JEQLIRSJSA-N

Molfile:  

     RDKit          2D

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    4.8177  -13.3684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4252  -12.8188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0903  -12.0712    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    3.7275  -11.5528    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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 30 31  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2252772

   [(1R,3S,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-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: 424.54

Molecular Weight (Monoisotopic): 424.2250

AlogP: 4.75

#Rotatable Bonds: 5

Polar Surface Area: 53.99

Molecular Species: NEUTRAL

HBA: 5

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 5.13

CX LogD: 5.13

Aromatic Rings: 1

Heavy Atoms: 31

QED Weighted: 0.39

Np Likeness Score: 2.49

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