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

ID: ALA2252778

PubChem CID: 11625136

Max Phase: Preclinical

Molecular Formula: C24H30O4

Molecular Weight: 382.50

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]1CC=C(CO)[C@@H]2CO

Standard InChI:  InChI=1S/C24H30O4/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/h4-10,12,16,20-22,25-26H,2,11,13-15H2,1,3H3/b12-9+/t16-,20-,21-,22+,24-/m0/s1

Standard InChI Key:  VTIFJQDCHVYKFM-PKCWWXAYSA-N

Molfile:  

     RDKit          2D

 28 30  0  0  0  0  0  0  0  0999 V2000
   14.7837  -22.0600    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7837  -22.8772    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4890  -23.2817    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4890  -21.6473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1943  -22.0600    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1953  -22.8772    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8996  -23.2827    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6074  -22.8754    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1870  -21.2428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0766  -23.2868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4890  -20.8301    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.4888  -24.0989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7813  -20.4215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7813  -19.6043    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0736  -20.8301    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.0736  -19.1957    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0736  -18.3785    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7870  -17.9695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7874  -17.1531    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0792  -16.7447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3691  -17.1567    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3722  -17.9717    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8976  -21.6483    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6080  -22.0562    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8927  -20.8301    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5980  -20.4174    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.3153  -21.6470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0234  -22.0550    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
  3  6  1  0
  5  4  1  0
  5  6  1  0
  5 23  1  0
  6  7  1  1
  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
 14 16  2  0
 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  0
 23 25  1  1
 25 26  1  0
 24 27  1  0
 27 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2252778

   [(1R,3S,4aS,8S,8aS)-7,8-bis(hydroxymethyl)-3,8a-dimethyl-4-methylidene-1,2,3,4a,5,8-hexahydronaphthalen-1-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: 382.50

Molecular Weight (Monoisotopic): 382.2144

AlogP: 3.76

#Rotatable Bonds: 5

Polar Surface Area: 66.76

Molecular Species: NEUTRAL

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 3.53

CX LogD: 3.53

Aromatic Rings: 1

Heavy Atoms: 28

QED Weighted: 0.46

Np Likeness Score: 2.36

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