Showing Compound Card for Myrtenol (CDB000718)

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IdentificationTaxonomyOntologyPhysical propertiesSpectraProtein targetPathwaysConcentrationsLinksReferencestransporters (6) Show 14 proteinsXML
Record Information
Version1.0
Created at2020-03-19 00:52:53 UTC
Updated at2020-12-07 19:07:42 UTC
CannabisDB IDCDB000718
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NameMyrtenol
DescriptionMyrtenol or 2-Pinen-10-ol, also known as pin-2-ene-10-ol, belongs to the class of organic compounds known as bicyclic monoterpenoids. These are monoterpenoids containing exactly 2 rings, which are fused to each other. Monoterpenoids are terpenes that contain 10 carbon atoms and are comprised of two isoprene units. The biosynthesis of monoterpenes is known to occur mainly through the methyl-eritritol-phosphate (MEP) pathway in the plastids (PMID: 7640522 ). Geranyl diphosphate (GPP) is a key intermediate in the biosynthesis of cyclic monoterpenes. GPP undergoes several cyclization reactions to yield a diverse number of cyclic arrangements. Myrtenol is considered to be an isoprenoid lipid molecule. Myrtenol is a very hydrophobic molecule, practically insoluble in water, and relatively neutral. Myrtenol can be used as a food additive or a food flavoring agent and can also be used in cosmetics. It is naturally present in mandarin peel oil, raspberry, blackberry, strawberry, ginger, hop oil, black tea, peppermint oil, pepper (Piper nigrum), myrtle leaf or berry, summer savoury (Satureja hortensis) and other spices or foodstuffs including hyssops, rosemaries, and spearmints. This could make, Myrtenol a potential biomarker for the consumption of these foods. Myrtenol has a woody, minty or medicinal aroma and has a cooling minty, campherous medicinal taste. Myrtenol (along with isopulegol, verbenol, and pinocarveol) are particularly potent modifiers of GABA(A) receptor function and this interaction may lead to certain sedative effects found in plants or plant oils that contain this compound (PMID: 24273211 ). Myrtenol is one of the terpenoids that present only in traces in cannabis plants (PMID: 6991645 ). There are more than 140 known terpenes in cannabis and the combination of these terepenoids produces the skunky, fruity odor characteristic of C. savita.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(+)-MyrtenolHMDB
(+)-Pin-2-ene-10-olHMDB
(1S)-(+)-MyrtenolHMDB
(1S)-2-Pinen-10-olHMDB
(1S)-6,6-dimethylbicyclo[3.1.1]Hept-2-ene-2-methanolHMDB
2-Pinen-10-ol, (1S,5R)-(+)- (8ci)HMDB
6,6-Dimethyl-(1S)-bicyclo(3.1.1)hept-2-ene-2-methanolHMDB
6,6-Dimethyl-(1S)-bicyclo[3.1.1]hept-2-ene-2-methanolHMDB
6,6-Dimethyl-(1S,5R)-bicyclo[3.1.1]hept-2-ene-2-methanolHMDB
Chemical FormulaC10H16O
Average Molecular Weight152.23
Monoisotopic Molecular Weight152.1201
IUPAC Name[(1S,5R)-6,6-dimethylbicyclo[3.1.1]hept-2-en-2-yl]methanol
Traditional Name[(1S,5R)-6,6-dimethylbicyclo[3.1.1]hept-2-en-2-yl]methanol
CAS Registry Number6712-78-3
SMILES
CC1(C)[C@H]2C[C@@H]1C(CO)=CC2
InChI Identifier
InChI=1S/C10H16O/c1-10(2)8-4-3-7(6-11)9(10)5-8/h3,8-9,11H,4-6H2,1-2H3/t8-,9-/m1/s1
InChI KeyRXBQNMWIQKOSCS-RKDXNWHRSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as bicyclic monoterpenoids. These are monoterpenoids containing exactly 2 rings, which are fused to each other.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassMonoterpenoids
Direct ParentBicyclic monoterpenoids
Alternative Parents
Substituents
  • Pinane monoterpenoid
  • Bicyclic monoterpenoid
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Primary alcohol
  • Organooxygen compound
  • Alcohol
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Biological location:

Source:

Role

Industrial application:

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
logPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP2.71ALOGPS
logP1.52ChemAxon
logS-2ALOGPS
pKa (Strongest Acidic)17.1ChemAxon
pKa (Strongest Basic)-1.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity46.5 m³·mol⁻¹ChemAxon
Polarizability18.12 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSMyrtenol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0fl0-4900000000-94dac4a63ebff6374246Spectrum
Predicted GC-MSMyrtenol, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00di-9420000000-ca6d4e365a12ebd1b2f3Spectrum
Predicted GC-MSMyrtenol, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udr-0900000000-b19ea4150917a6bafd942016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0900000000-aec595a21a1484e269cb2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00kr-0900000000-a4ed5627231523db689b2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0900000000-3c298e096851b5f5f3c62016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0uk9-0900000000-431fc5e7bd81c6899b0d2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00di-0900000000-13dd05855689717c22262016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0900000000-c373c9eea3cebf186f532021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0900000000-705283d393728bb3f1e32021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0udi-0900000000-1d76e4e74ba5204cba1a2021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0900000000-0dd01a232778d34915e72021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0900000000-90e520208520180a8a6f2021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-0900000000-2a50defe3cd69eac1ca42021-09-24View Spectrum
NMRNot Available
Pathways
Pathways
Protein Targets
EnzymesNot Available
Transporters
Protein NameGene NameLocusUniprot IDDetails
Gamma-aminobutyric acid receptor subunit alpha-1GABRA15q34-q35P14867 details
Gamma-aminobutyric acid receptor subunit alpha-2GABRA24p12P47869 details
Gamma-aminobutyric acid receptor subunit alpha-3GABRA3P34903 details
Gamma-aminobutyric acid receptor subunit alpha-4GABRA44p12P48169 details
Gamma-aminobutyric acid receptor subunit alpha-5GABRA515q11.2-q12P31644 details
Gamma-aminobutyric acid receptor subunit alpha-6GABRA65q34Q16445 details
Metal BindingsNot Available
Receptors
Protein NameGene NameLocusUniprot IDDetails
Gamma-aminobutyric acid receptor subunit alpha-1GABRA15q34-q35P14867 details
Gamma-aminobutyric acid receptor subunit alpha-2GABRA24p12P47869 details
Gamma-aminobutyric acid receptor subunit alpha-3GABRA3P34903 details
Gamma-aminobutyric acid receptor subunit alpha-4GABRA44p12P48169 details
Gamma-aminobutyric acid receptor subunit alpha-5GABRA515q11.2-q12P31644 details
Gamma-aminobutyric acid receptor subunit alpha-6GABRA65q34Q16445 details
Taste receptor type 1 member 3TAS1R31p36.33Q7RTX0 details
Taste receptor type 1 member 2TAS1R21p36.13Q8TE23 details
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDHMDB0035125
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB013760
KNApSAcK IDC00011041
Chemspider ID552247
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound636475
PDB IDNot Available
ChEBI IDNot Available
References
General References
  1. McGarvey DJ, Croteau R: Terpenoid metabolism. Plant Cell. 1995 Jul;7(7):1015-26. doi: 10.1105/tpc.7.7.1015. [PubMed:7640522 ]
  2. Kessler A, Sahin-Nadeem H, Lummis SC, Weigel I, Pischetsrieder M, Buettner A, Villmann C: GABA(A) receptor modulation by terpenoids from Sideritis extracts. Mol Nutr Food Res. 2014 Apr;58(4):851-62. doi: 10.1002/mnfr.201300420. Epub 2013 Nov 24. [PubMed:24273211 ]
  3. Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. [PubMed:6991645 ]

Only showing the first 10 proteins. There are 14 proteins in total.

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Transporters

Enzyme Details
1. Gamma-aminobutyric acid receptor subunit alpha-1
General function:
Involved in ion transport
Specific function:
GABA, the major inhibitory neurotransmitter in the vertebrate brain, mediates neuronal inhibition by binding to the GABA/benzodiazepine receptor and opening an integral chloride channel
Gene Name:
GABRA1
Uniprot ID:
P14867
Molecular weight:
51801.4
Enzyme Details
2. Gamma-aminobutyric acid receptor subunit alpha-2
General function:
Involved in ion transport
Specific function:
GABA, the major inhibitory neurotransmitter in the vertebrate brain, mediates neuronal inhibition by binding to the GABA/benzodiazepine receptor and opening an integral chloride channel
Gene Name:
GABRA2
Uniprot ID:
P47869
Molecular weight:
51325.9
Enzyme Details
3. Gamma-aminobutyric acid receptor subunit alpha-3
General function:
Involved in ion transport
Specific function:
GABA, the major inhibitory neurotransmitter in the vertebrate brain, mediates neuronal inhibition by binding to the GABA/benzodiazepine receptor and opening an integral chloride channel
Gene Name:
GABRA3
Uniprot ID:
P34903
Molecular weight:
55164.1
Enzyme Details
4. Gamma-aminobutyric acid receptor subunit alpha-4
General function:
Involved in ion transport
Specific function:
GABA, the major inhibitory neurotransmitter in the vertebrate brain, mediates neuronal inhibition by binding to the GABA/benzodiazepine receptor and opening an integral chloride channel
Gene Name:
GABRA4
Uniprot ID:
P48169
Molecular weight:
61622.6
Enzyme Details
5. Gamma-aminobutyric acid receptor subunit alpha-5
General function:
Involved in ion transport
Specific function:
GABA, the major inhibitory neurotransmitter in the vertebrate brain, mediates neuronal inhibition by binding to the GABA/benzodiazepine receptor and opening an integral chloride channel
Gene Name:
GABRA5
Uniprot ID:
P31644
Molecular weight:
52145.6
Enzyme Details
6. Gamma-aminobutyric acid receptor subunit alpha-6
General function:
Involved in ion transport
Specific function:
GABA, the major inhibitory neurotransmitter in the vertebrate brain, mediates neuronal inhibition by binding to the GABA/benzodiazepine receptor and opening an integral chloride channel
Gene Name:
GABRA6
Uniprot ID:
Q16445
Molecular weight:
51023.7

Only showing the first 10 proteins. There are 14 proteins in total.

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