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

ID: ALA2252770

PubChem CID: 11536109

Max Phase: Preclinical

Molecular Formula: C15H20O3

Molecular Weight: 248.32

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C15H20O3/c1-9-6-14(18)15(3)12(10(9)2)5-4-11(7-16)13(15)8-17/h4,7-9,12-14,18H,2,5-6H2,1,3H3/t9-,12-,13-,14+,15-/m0/s1

Standard InChI Key:  AKSBEXNBIJAHCH-MKJLKUPLSA-N

Molfile:  

     RDKit          2D

 18 19  0  0  0  0  0  0  0  0999 V2000
   19.3443   -4.6927    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3443   -5.5099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0496   -5.9143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0496   -4.2799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.7549   -4.6927    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.7559   -5.5098    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.4602   -5.9153    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.1680   -5.5080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.1670   -4.6909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.4582   -4.2809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.8746   -4.2821    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.5824   -4.6905    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.4560   -3.4637    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.1626   -3.0532    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.7476   -3.8755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6372   -5.9195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0496   -3.4627    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.0493   -6.7315    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
M  END

Alternative Forms

1. Parent:

   

   ALA2252770

   (1R,4aS,6S,8R,8aS)-8-hydroxy-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: 248.32

Molecular Weight (Monoisotopic): 248.1412

AlogP: 1.91

#Rotatable Bonds: 2

Polar Surface Area: 54.37

Molecular Species: NEUTRAL

HBA: 3

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 3

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 0.94

CX LogD: 0.94

Aromatic Rings: ┄

Heavy Atoms: 18

QED Weighted: 0.60

Np Likeness Score: 3.38

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