1beta,3beta-Dibromotetrahydronootkatone

ID: ALA2271436

PubChem CID: 76319741

Max Phase: Preclinical

Molecular Formula: C15H24Br2O

Molecular Weight: 380.16

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(C)[C@@H]1CCC2[C@H](Br)C(=O)[C@H](Br)[C@@H](C)[C@]2(C)C1

Standard InChI:  InChI=1S/C15H24Br2O/c1-8(2)10-5-6-11-13(17)14(18)12(16)9(3)15(11,4)7-10/h8-13H,5-7H2,1-4H3/t9-,10-,11?,12-,13+,15+/m1/s1

Standard InChI Key:  RTJPAEUNQXSQFC-VPLFLSBKSA-N

Molfile:  

     RDKit          2D

 18 19  0  0  0  0  0  0  0  0999 V2000
    1.8407  -13.4589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8407  -14.2761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5460  -14.6806    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5460  -13.0462    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2513  -13.4589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2523  -14.2761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9567  -14.6815    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6645  -14.2743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6634  -13.4571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9546  -13.0471    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5460  -12.2290    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    1.1336  -14.6857    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    1.1318  -13.0524    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5458  -15.4977    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2481  -15.0891    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3721  -14.6830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3720  -15.5001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0799  -14.2744    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  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  4 11  1  1
  2 12  1  1
  1 13  2  0
  3 14  1  6
  6 15  1  6
  8 16  1  1
 16 17  1  0
 16 18  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2271436

   1BETA,3BETA-DIBROMOTETRAHYDRONOOTKATONE

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: 380.16

Molecular Weight (Monoisotopic): 378.0194

AlogP: 4.81

#Rotatable Bonds: 1

Polar Surface Area: 17.07

Molecular Species: NEUTRAL

HBA: 1

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 1

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 5.59

CX LogD: 5.59

Aromatic Rings: ┄

Heavy Atoms: 18

QED Weighted: 0.60

Np Likeness Score: 1.36

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