beta-Nootkatol

ID: ALA2398793

Cas Number: 50763-67-2

PubChem CID: 182645

Max Phase: Preclinical

Molecular Formula: C15H24O

Molecular Weight: 220.36

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C15H24O/c1-10(2)12-5-6-13-8-14(16)7-11(3)15(13,4)9-12/h8,11-12,14,16H,1,5-7,9H2,2-4H3/t11-,12-,14+,15+/m1/s1

Standard InChI Key:  GFNWRKNVTHDNPV-UXOAXIEHSA-N

Molfile:  

     RDKit          2D

 16 17  0  0  0  0  0  0  0  0999 V2000
   21.3857   -5.8965    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9605   -7.5467    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.0983   -7.1341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2521   -6.3132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2521   -7.1382    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9643   -5.8965    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6764   -6.3132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6774   -7.1382    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.3885   -7.5477    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.1021   -6.3113    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.8127   -7.5470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6731   -7.9592    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9564   -8.3718    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5364   -5.9027    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.8124   -8.3720    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.5274   -7.1346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  4  5  1  0
  4  6  1  0
  5  2  1  0
  2  8  1  0
  7  6  2  0
  7  8  1  0
  7  1  1  0
  8  9  1  0
  9  3  1  0
 10  1  1  0
 10  3  1  0
  3 11  1  1
  8 12  1  6
  2 13  1  6
  4 14  1  6
 11 15  2  0
 11 16  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2398793

   BETA-NOOTKATOL

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: 220.36

Molecular Weight (Monoisotopic): 220.1827

AlogP: 3.70

#Rotatable Bonds: 1

Polar Surface Area: 20.23

Molecular Species: NEUTRAL

HBA: 1

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 1

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 3.29

CX LogD: 3.29

Aromatic Rings: ┄

Heavy Atoms: 16

QED Weighted: 0.67

Np Likeness Score: 3.11

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]

2. Jiang B, Wang WJ, Li MP, Huang XJ, Huang F, Gao H, Sun PH, He MF, Jiang ZJ, Zhang XQ, Ye WC..  (2013)  New eudesmane sesquiterpenes from Alpinia oxyphylla and determination of their inhibitory effects on microglia.,  23  (13): [PMID:23711917] [10.1016/j.bmcl.2013.04.072]

Source

Source(1):

• Scientific Literature