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
LM ID
LMPR0103410007
Formula
Exact Mass
Calculate m/z
222.198365
Status
Curated

Classification

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

1. Yang, Q., Wu, J., Luo, Y., et al. (−)-Guaiol regulates RAD51 stability via autophagy to induce cell apoptosis in non-small cell lung cancer. Oncotarget 7(38), 62585-62597 (2016).
3. Ali, A., Tabanca, N., Demirci, B., et al. Chemical composition and biological activity of four salvia essential oils and individual compounds against two species of mosquitoes. J. Agric. Food Chem. 63(2), 447-456 (2015).

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

KEGG ID
CHEBI ID
PubChem CID
Cayman ID

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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Created at
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Updated at
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