Structure Database (LMSD)
Common Name
guaiol
Systematic Name
guai-1(5)-en-11-ol
Synonyms
- 2-[(3S,5R,8S)-3,8-dimethyl-1,2,3,4,5,6,7,8-octahydroazulen-5-yl]propan-2-ol
- Guaiol
- [3S-(3alpha,5alpha,8alpha)]-1,2,3,4,5,6,7,8-octahydro-alpha,alpha,3,8-tetramethyl-5-azulenemethanol
- champaca camphor
- champacol
- guaiac alcohol
3D model of guaiol
Please note: Where there are chiral atoms but the stereochemistry is undefined, the 3D model takes an arbitrary conformation
Classification
Category
Main Class
Sub Class
Level 4 Class
Biological Context
(−)-Guaiol is a sesquiterpene alcohol that has been found in several traditional Chinese medicinal plants and has antiproliferative, pro-autophagic, insect repellent, and insecticidal biological activities.1,2,3 It selectively inhibits proliferation of A549 and H1299 non-small cell lung carcinoma (NSCLC) cells over BEAS-2B normal lung cells (IC50s = 121.7, 211.5, and 297.1 μM, respectively).1 It also dose-dependently induces formation of DNA double-strand breaks (DSBs) and autophagy in A549 and H1299 cells and increases levels of microtubule-associated protein 1 light chain 3 isoform II (LC3-II). (−)-Guaiol (8 mg/kg three times per week) inhibits tumor growth in an NSCLC mouse xenograft model. It deters A. aegypti and A. quadrimaculatus mosquitoes from feeding on a synthetic blood substitute with a biting-deterrent index (BDI) of 0.82 when used at a concentration of 25 nmol per cm2.2 (−)-Guaiol is also lethal to fourth instar M. separata and third instar P. xylostella larvae (LD50s = 0.07 and 8.9 mg/larva, respectively).3
This information has been provided by Cayman Chemical
References
String Representations
InChiKey (Click to copy)
TWVJWDMOZJXUID-SDDRHHMPSA-N
InChi (Click to copy)
InChI=1S/C15H26O/c1-10-5-7-12(15(3,4)16)9-14-11(2)6-8-13(10)14/h10-12,16H,5-9H2,1-4H3/t10-,11-,12+/m0/s1
SMILES (Click to copy)
C12CC[C@H](C)C=1C[C@H](C(O)(C)C)CC[C@@H]2C
Other Databases
Calculated Physicochemical Properties
Heavy Atoms
16
Rings
2
Aromatic Rings
0
Rotatable Bonds
1
Van der Waals Molecular Volume
249.49
Topological Polar Surface Area
20.23
Hydrogen Bond Donors
1
Hydrogen Bond Acceptors
1
logP
4.21
Molar Refractivity
68.74
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Updated at
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