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

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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Updated at
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