(1R,3S,4aS,8R,8aS)-7,8-diformyl-3,8a-dimethyl-4-methylene-1,2,3,4,4a,5,8,8a-octahydronaphthalen-1-yl cinnamate

ID: ALA2252767

PubChem CID: 11682335

Max Phase: Preclinical

Molecular Formula: C24H26O4

Molecular Weight: 378.47

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](C=O)C(C=O)=CC[C@@H]12

Standard InChI:  InChI=1S/C24H26O4/c1-16-13-22(28-23(27)12-9-18-7-5-4-6-8-18)24(3)20(17(16)2)11-10-19(14-25)21(24)15-26/h4-10,12,14-16,20-22H,2,11,13H2,1,3H3/b12-9+/t16-,20-,21-,22+,24-/m0/s1

Standard InChI Key:  RIGSJIIZCIKSKY-PKCWWXAYSA-N

Molfile:  

     RDKit          2D

 28 30  0  0  0  0  0  0  0  0999 V2000
    2.3814   -4.9527    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3814   -5.7699    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0867   -6.1743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0867   -4.5400    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7920   -4.9527    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7930   -5.7699    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4973   -6.1753    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2051   -5.7681    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2041   -4.9509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4952   -4.5409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9117   -4.5421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6195   -4.9505    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4931   -3.7237    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1997   -3.3133    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7847   -4.1355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6743   -6.1795    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0867   -3.7228    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0864   -6.9915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3790   -3.3142    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3790   -2.4970    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6713   -3.7228    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6713   -2.0884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6713   -1.2712    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3847   -0.8622    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3851   -0.0457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6768    0.3637    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9668   -0.0493    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9699   -0.8644    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
  3  6  1  0
  5  4  1  0
  5  6  1  0
  5 10  1  0
  6  7  1  1
  7  8  1  0
  8  9  2  0
  9 10  1  0
  9 11  1  0
 11 12  2  0
 10 13  1  1
 13 14  2  0
  5 15  1  1
  2 16  1  1
  4 17  1  1
  3 18  2  0
 17 19  1  0
 19 20  1  0
 19 21  2  0
 20 22  2  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
 28 23  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2252767

   Paxidal

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: 378.47

Molecular Weight (Monoisotopic): 378.1831

AlogP: 4.17

#Rotatable Bonds: 5

Polar Surface Area: 60.44

Molecular Species: NEUTRAL

HBA: 4

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 3.98

CX LogD: 3.98

Aromatic Rings: 1

Heavy Atoms: 28

QED Weighted: 0.33

Np Likeness Score: 2.38

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