Cannabis Compound Database: Showing Compound Card for Guaiol (CDB000079)

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Identification Taxonomy Ontology Physical properties Spectra Protein target Pathways Concentrations Links References XML

Record Information

Version

1.0

Created at

2020-03-18 23:23:59 UTC

Updated at

2020-12-07 19:07:04 UTC

CannabisDB ID

CDB000079

Secondary Accession Numbers

Not Available

Cannabis Compound Identification

Common Name

Guaiol

Description

Guaiol belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes that contain 15 carbon atoms and are comprised of three isoprene units. The biosynthesis of sesquiterpenes is known to occur mainly through the mevalonic acid pathway (MVA), in the cytosol (PMID: 17467679 ). Farnesyl diphosphate (FPP) is a key intermediate in the biosynthesis of cyclic sesquiterpenes. FPP undergoes several cyclization reactions to yield a diverse number of cyclic arrangements. Guaiol is an essentially neutral compound with low solubility in water but soluble in alcohol. Guaiol is found in several plants, especially in the oil of guaiacum and cypress pine. Guaiol is one of many terpenes found in Cannabis and it has been associated with decreased anxiolytic activity (PMID: 30405331 ). (-)-Guaiol, a sesquiterpene alcohol with the guaiane skeleton, has been found in many Chinese medicinal plants and been reported to comprise various guaiane natural products that are well known for their antibacterial activities. (-)-Guaiol has anti-cancer properties inhibiting the proliferation of non small cell lung cancer (NSCLC) cells (PMID:29611762 ) and inducing autophagy ( PMID: 27566579 ), by specifically targeting mTOR signaling pathways, including both mTORC1 and mTORC2 signaling, possibly providing a better therapeutic substitution for rapamycin in the treatment of NSCLC patients. It has anti-leishmanial activity (PMID: 29352826 ) and is an insecticide that inhibits aphids ( PMID: 24354171 )

Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

Not Available

Chemical Formula

C₁₅H₂₆O

Average Molecular Weight

222.37

Monoisotopic Molecular Weight

222.1984

IUPAC Name

2-[(3S,5S,8S)-3,8-dimethyl-1,2,3,4,5,6,7,8-octahydroazulen-5-yl]propan-2-ol

Traditional Name

2-[(3S,5S,8S)-3,8-dimethyl-1,2,3,4,5,6,7,8-octahydroazulen-5-yl]propan-2-ol

CAS Registry Number

489-86-1

SMILES

C[C@H]1CCC2=C1C[C@H](CC[C@@H]2C)C(C)(C)O

InChI Identifier

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

InChI Key

TWVJWDMOZJXUID-SRVKXCTJSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Sesquiterpenoids

Alternative Parents

Substituents

Sesquiterpenoid
Tertiary alcohol
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Alcohol
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

Not Available

Ontology

Role

Industrial application:

Pharmaceutical industry:

Antineoplastic agent:

Anticancer agent

Household products:

Pesticide:

Insecticide

Antimicrobial agent:

Antibacterial

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	92 °C	Wikipedia
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
logP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	4.48	ALOGPS
logP	3.42	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Acidic)	19.37	ChemAxon
pKa (Strongest Basic)	-0.89	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	20.23 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	69.24 m³·mol⁻¹	ChemAxon
Polarizability	27.67 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
GC-MS	Guaiol, non-derivatized, GC-MS Spectrum	splash10-0btc-7900000000-8740930d4a3e89faacce	Spectrum
Predicted GC-MS	Guaiol, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	Not Available	2020-06-30	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	Not Available	2020-06-30	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	Not Available	2020-06-30	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	Not Available	2020-06-30	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	Not Available	2020-06-30	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	Not Available	2020-06-30	View Spectrum

NMR

Not Available

Pathways

Not Available

Protein Targets

Enzymes

Not Available

Transporters

Not Available

Metal Bindings

Not Available

Receptors

Not Available

Transcriptional Factors

Not Available

Concentrations Data

Cannabis Cultivar	Status	Value	Reference	Details
8-Ball Kush	Detected and Quantified	1.439 mg/g dry wt	PMID: 30036388	details
9 Lb Hammer	Detected and Quantified	0.100 mg/g dry wt	PMID: 30036388	details
9 Lb Hammer	Detected and Quantified	0.1 mg/g dry wt	PMID: 30036388	details
Adonis	Detected and Quantified	0.081 mg/g dry wt	PMID: 30036388	details
Alien Sour Apple	Detected and Quantified	0.079 mg/g dry wt	PMID: 30036388	details
Black Boss	Detected and Quantified	0.573 mg/g dry wt	PMID: 30036388	details
Blue Dream	Detected and Quantified	0.138 mg/g dry wt	PMID: 30036388	details
Blue Dream	Detected and Quantified	0.154 mg/g dry wt	PMID: 30036388	details
Blue Dream	Detected and Quantified	0.897 mg/g dry wt	PMID: 30036388	details
Blue Dream	Detected and Quantified	0.917 mg/g dry wt	PMID: 30036388	details
Bob Marley	Detected and Quantified	0.521 mg/g dry wt	PMID: 30036388	details
Chemdawg	Detected and Quantified	0.099 mg/g dry wt	PMID: 30036388	details
Chemdawg #4	Detected and Quantified	0.080 mg/g dry wt	PMID: 30036388	details
Chemdawg #4	Detected and Quantified	0.100 mg/g dry wt	PMID: 30036388	details
Chemdawg #4	Detected and Quantified	0.08 mg/g dry wt	PMID: 30036388	details
Chemdawg #4	Detected and Quantified	0.1 mg/g dry wt	PMID: 30036388	details
Cookies and Cream	Detected and Quantified	0.056 mg/g dry wt	PMID: 30036388	details
Dairy Queen	Detected and Quantified	0.314 mg/g dry wt	PMID: 30036388	details
Dark Shadow Haze	Detected and Quantified	0.116 mg/g dry wt	PMID: 30036388	details
FLO	Detected and Quantified	0.054 mg/g dry wt	PMID: 30036388	details
Goji OG	Detected and Quantified	0.753 mg/g dry wt	PMID: 30036388	details
Golden Cobra	Detected and Quantified	0.218 mg/g dry wt	PMID: 30036388	details
Golden Sage	Detected and Quantified	0.063 mg/g dry wt	PMID: 30036388	details
Gorilla Glue	Detected and Quantified	0.143 mg/g dry wt	PMID: 30036388	details
Gorilla Glue #4	Detected and Quantified	0.093 mg/g dry wt	PMID: 30036388	details
Grape Stomper	Detected and Quantified	0.075 mg/g dry wt	PMID: 30036388	details
Grizzly Kush	Detected and Quantified	0.071 mg/g dry wt	PMID: 30036388	details
Hash Plant	Detected and Quantified	0.660 mg/g dry wt	PMID: 30036388	details
Hash Plant	Detected and Quantified	0.900 mg/g dry wt	PMID: 30036388	details
Hash Plant	Detected and Quantified	0.66 mg/g dry wt	PMID: 30036388	details
Hash Plant	Detected and Quantified	0.9 mg/g dry wt	PMID: 30036388	details
Hemlock	Detected and Quantified	0.066 mg/g dry wt	PMID: 30036388	details
Jabberwocky	Detected and Quantified	1.143 mg/g dry wt	PMID: 30036388	details
Jabberwocky	Detected and Quantified	1.425 mg/g dry wt	PMID: 30036388	details
Jack Herer	Detected and Quantified	0.569 mg/g dry wt	PMID: 30036388	details
Kandy Kush	Detected and Quantified	0.143 mg/g dry wt	PMID: 30036388	details
Kush Puppy	Detected and Quantified	0.662 mg/g dry wt	PMID: 30036388	details
La Choco	Detected and Quantified	0.961 mg/g dry wt	PMID: 30036388	details
Lemon Balm	Detected and Quantified	0.909 mg/g dry wt	PMID: 30036388	details
Lemon Goji	Detected and Quantified	0.124 mg/g dry wt	PMID: 30036388	details
Lemon OG	Detected and Quantified	0.099 mg/g dry wt	PMID: 30036388	details
Lemon Sherbet	Detected and Quantified	0.629 mg/g dry wt	PMID: 30036388	details
Lemon Skunk	Detected and Quantified	0.062 mg/g dry wt	PMID: 30036388	details
Lemon Skunk	Detected and Quantified	0.189 mg/g dry wt	PMID: 30036388	details
Liberty Haze	Detected and Quantified	0.164 mg/g dry wt	PMID: 30036388	details
Lohan	Detected and Quantified	0.057 mg/g dry wt	PMID: 30036388	details
Lucky Charms	Detected and Quantified	0.206 mg/g dry wt	PMID: 30036388	details
Maui Haze	Detected and Quantified	0.089 mg/g dry wt	PMID: 30036388	details
Moby Dick	Detected and Quantified	0.406 mg/g dry wt	PMID: 30036388	details
Moonshine Ghost Trane Haze	Detected and Quantified	0.815 mg/g dry wt	PMID: 30036388	details
Nightmare Cookie	Detected and Quantified	0.265 mg/g dry wt	PMID: 30036388	details
Orange Skunk	Detected and Quantified	0.873 mg/g dry wt	PMID: 30036388	details
Pineapple Skunk	Detected and Quantified	1.544 mg/g dry wt	PMID: 30036388	details
Pipe Dream	Detected and Quantified	0.825 mg/g dry wt	PMID: 30036388	details
Platinum Delight	Detected and Quantified	0.171 mg/g dry wt	PMID: 30036388	details
Purple Eclipse	Detected and Quantified	0.206 mg/g dry wt	PMID: 30036388	details
Rocket Fuel	Detected and Quantified	1.271 mg/g dry wt	PMID: 30036388	details
Rollex OG	Detected and Quantified	0.177 mg/g dry wt	PMID: 30036388	details
Rosetta Stone	Detected and Quantified	0.140 mg/g dry wt	PMID: 30036388	details
Rosetta Stone	Detected and Quantified	0.14 mg/g dry wt	PMID: 30036388	details
Sensi Star	Detected and Quantified	0.37 mg/g dry wt	David S. Wishart,...	details
Sensi Star (Pure Indica)	Detected and Quantified	0.30 +/- 0.01 mg/g dry wt	David S. Wishart,...	details
Skunk Haze	Detected and Quantified	0.246 mg/g dry wt	PMID: 30036388	details
Skywalker OG	Detected and Quantified	1.184 mg/g dry wt	PMID: 30036388	details
Spectrum	Detected and Quantified	0.915 mg/g dry wt	PMID: 30036388	details
Star Bud	Detected and Quantified	0.063 mg/g dry wt	PMID: 30036388	details
Star Killer	Detected and Quantified	0.141 mg/g dry wt	PMID: 30036388	details
Strawberry Fields	Detected and Quantified	0.088 mg/g dry wt	PMID: 30036388	details
Strawberry Fields	Detected and Quantified	0.108 mg/g dry wt	PMID: 30036388	details
Sunset Sherbet	Detected and Quantified	0.130 mg/g dry wt	PMID: 30036388	details
Sunset Sherbet	Detected and Quantified	0.190 mg/g dry wt	PMID: 30036388	details
Sunset Sherbet	Detected and Quantified	0.13 mg/g dry wt	PMID: 30036388	details
Sunset Sherbet	Detected and Quantified	0.19 mg/g dry wt	PMID: 30036388	details
Tangerine Dream	Detected and Quantified	0.140 mg/g dry wt	PMID: 30036388	details
Tangerine Dream	Detected and Quantified	0.56 mg/g dry wt	David S. Wishart,...	details
Tangerine Dream	Detected and Quantified	0.14 mg/g dry wt	PMID: 30036388	details
Tangerine Dream (Sativa dominant)	Detected and Quantified	0.49 +/- 0.02 mg/g dry wt	David S. Wishart,...	details
The Sauce	Detected and Quantified	0.264 mg/g dry wt	PMID: 30036388	details
Venom OG	Detected and Quantified	0.170 mg/g dry wt	PMID: 30036388	details
Venom OG	Detected and Quantified	0.17 mg/g dry wt	PMID: 30036388	details
White Widow	Detected and Quantified	0.805 mg/g dry wt	PMID: 30036388	details
Wonder Woman	Detected and Quantified	0.644 mg/g dry wt	PMID: 30036388	details

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

92245464

PDB ID

Not Available

ChEBI ID

Not Available

References

General References

Buhaescu I, Izzedine H: Mevalonate pathway: a review of clinical and therapeutical implications. Clin Biochem. 2007 Jun;40(9-10):575-84. doi: 10.1016/j.clinbiochem.2007.03.016. Epub 2007 Mar 31. [PubMed:17467679 ]
Yang X, Zhu J, Wu J, Huang N, Cui Z, Luo Y, Sun F, Pan Q, Li Y, Yang Q: (-)-Guaiol regulates autophagic cell death depending on mTOR signaling in NSCLC. Cancer Biol Ther. 2018 Aug 3;19(8):706-714. doi: 10.1080/15384047.2018.1451277. Epub 2018 Apr 19. [PubMed:29611762 ]
Kamal BS, Kamal F, Lantela DE: Cannabis and the Anxiety of Fragmentation-A Systems Approach for Finding an Anxiolytic Cannabis Chemotype. Front Neurosci. 2018 Oct 22;12:730. doi: 10.3389/fnins.2018.00730. eCollection 2018. [PubMed:30405331 ]
Yang Q, Wu J, Luo Y, Huang N, Zhen N, Zhou Y, Sun F, Li Z, Pan Q, Li Y: (-)-Guaiol regulates RAD51 stability via autophagy to induce cell apoptosis in non-small cell lung cancer. Oncotarget. 2016 Sep 20;7(38):62585-62597. doi: 10.18632/oncotarget.11540. [PubMed:27566579 ]
Garcia MCF, Soares DC, Santana RC, Saraiva EM, Siani AC, Ramos MFS, Danelli MDGM, Souto-Padron TC, Pinto-da-Silva LH: The in vitro antileishmanial activity of essential oil from Aloysia gratissima and guaiol, its major sesquiterpene against Leishmania amazonensis. Parasitology. 2018 Aug;145(9):1219-1227. doi: 10.1017/S0031182017002335. Epub 2018 Jan 21. [PubMed:29352826 ]
Liu T, Wang CJ, Xie HQ, Mu Q: Guaiol--a naturally occurring insecticidal sesquiterpene. Nat Prod Commun. 2013 Oct;8(10):1353-4. [PubMed:24354171 ]

Showing Compound Card for Guaiol (CDB000079)

Structure for CDB000079 (Guaiol)