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

ID: ALA2252769

PubChem CID: 11682657

Max Phase: Preclinical

Molecular Formula: C24H26O5

Molecular Weight: 394.47

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C24H26O5/c1-15-11-21(29-22(28)10-9-17-7-5-4-6-8-17)24(3)19(14-26)18(13-25)12-20(27)23(24)16(15)2/h4-10,12-15,19-21,23,27H,2,11H2,1,3H3/b10-9+/t15-,19-,20-,21+,23+,24-/m0/s1

Standard InChI Key:  OKDTYBVVAITUOQ-HNESARCWSA-N

Molfile:  

     RDKit          2D

 29 31  0  0  0  0  0  0  0  0999 V2000
   13.6900   -4.7298    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6900   -5.5470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3953   -5.9515    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3953   -4.3171    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1006   -4.7298    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1016   -5.5470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8059   -5.9524    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5137   -5.5452    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5127   -4.7280    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8038   -4.3181    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2203   -4.3192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9281   -4.7276    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.8017   -3.5009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5083   -3.0904    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.0933   -3.9126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9829   -5.9566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3953   -3.4999    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.3950   -6.7687    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6876   -3.0913    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6876   -2.2741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9799   -3.4999    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.9799   -1.8655    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9799   -1.0483    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6933   -0.6393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6937    0.1778    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9854    0.5866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2754    0.1814    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2785   -0.6415    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8058   -6.7696    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 10  1  0
  6  7  1  0
  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
  7 29  1  6
M  END

Alternative Forms

1. Parent:

   

   ALA2252769

   [(1R,3S,4aS,5S,8R,8aS)-7,8-diformyl-5-hydroxy-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: 394.47

Molecular Weight (Monoisotopic): 394.1780

AlogP: 3.15

#Rotatable Bonds: 5

Polar Surface Area: 80.67

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 2.82

CX LogD: 2.82

Aromatic Rings: 1

Heavy Atoms: 29

QED Weighted: 0.36

Np Likeness Score: 2.18

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