(1R,4aS,6S,8R,8aS)-8-methoxy-6,8a-dimethyl-5-methylene-1,4,4a,5,6,7,8,8a-octahydronaphthalene-1,2-dicarbaldehyde

ID: ALA2252771

PubChem CID: 11557991

Max Phase: Preclinical

Molecular Formula: C16H22O3

Molecular Weight: 262.35

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C16H22O3/c1-10-7-15(19-4)16(3)13(11(10)2)6-5-12(8-17)14(16)9-18/h5,8-10,13-15H,2,6-7H2,1,3-4H3/t10-,13-,14-,15+,16-/m0/s1

Standard InChI Key:  YXWNFPZXEUKCBB-AFWDSHEPSA-N

Molfile:  

     RDKit          2D

 19 20  0  0  0  0  0  0  0  0999 V2000
   24.5900   -4.8371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.5900   -5.6543    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.2953   -6.0588    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.2953   -4.4244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.0006   -4.8371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.0016   -5.6543    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.7059   -6.0597    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.4137   -5.6525    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.4127   -4.8353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.7039   -4.4254    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.1203   -4.4265    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.8281   -4.8349    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.7017   -3.6082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.4083   -3.1977    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.9933   -4.0199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.8829   -6.0639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.2953   -3.6072    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.2950   -6.8760    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.5876   -3.1986    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
M  END

Alternative Forms

1. Parent:

   

   ALA2252771

   (1R,4aS,6S,8R,8aS)-8-methoxy-6,8a-dimethyl-5-methylidene-1,4,4a,6,7,8-hexahydronaphthalene-1,2-dicarbaldehyde

Molecule Features

Natural Product: Yes

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: 262.35

Molecular Weight (Monoisotopic): 262.1569

AlogP: 2.56

#Rotatable Bonds: 3

Polar Surface Area: 43.37

Molecular Species: NEUTRAL

HBA: 3

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 3

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 1.58

CX LogD: 1.58

Aromatic Rings: ┄

Heavy Atoms: 19

QED Weighted: 0.58

Np Likeness Score: 3.03

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