11,12-Epoxynootkatone

ID: ALA2271435

PubChem CID: 11658706

Max Phase: Preclinical

Molecular Formula: C15H22O2

Molecular Weight: 234.34

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C[C@@H]1CC(=O)C=C2CC[C@@H](C3(C)CO3)C[C@]21C

Standard InChI:  InChI=1S/C15H22O2/c1-10-6-13(16)7-11-4-5-12(8-14(10,11)2)15(3)9-17-15/h7,10,12H,4-6,8-9H2,1-3H3/t10-,12-,14+,15?/m1/s1

Standard InChI Key:  JUWSZKSYEBPKOW-YIIBXEOUSA-N

Molfile:  

     RDKit          2D

 17 19  0  0  0  0  0  0  0  0999 V2000
   38.9487   -9.6784    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.3708  -10.2603    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.1637  -10.4697    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   34.8421   -9.0383    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.8421   -9.8558    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.5473  -10.2603    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.5473   -8.6259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.2526   -9.0386    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.2537   -9.8558    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.9580  -10.2613    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.6658   -9.8540    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.6647   -9.0368    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.9559   -8.6269    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.2494  -10.6689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.5471  -11.0775    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.3734  -11.0799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.1333   -8.6316    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  2  1  0
  1  3  1  0
  4  5  1  0
  4  7  1  0
  5  6  1  0
  6  9  1  0
  8  7  2  0
  8  9  1  0
  8 13  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
  9 14  1  6
  6 15  1  6
 11  2  1  1
  2 16  1  0
  4 17  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA2271435

   11,12-EPOXYNOOTKATONE

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: 234.34

Molecular Weight (Monoisotopic): 234.1620

AlogP: 3.12

#Rotatable Bonds: 1

Polar Surface Area: 29.60

Molecular Species: NEUTRAL

HBA: 2

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 2

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 2.77

CX LogD: 2.77

Aromatic Rings: ┄

Heavy Atoms: 17

QED Weighted: 0.65

Np Likeness Score: 2.77

References

1. Zhu BC, Henderson G, Sauer AM, Crowe W, Laine RA..  (2010)  Structural requirements for repellency: norsesquiterpenes and sesquiterpenoid derivatives of nootkatone against the Formosan subterranean termite (Isoptera: Rhinotermitidae).,  66  (8): [PMID:20602525] [10.1002/ps.1956]

Source

Source(1):

• Scientific Literature