Showing Compound Card for Methyl hexadecanoic acid (CDB000182)

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IdentificationTaxonomyOntologyPhysical propertiesSpectraProtein targetPathwaysConcentrationsLinksReferencestransporters (1) Show 3 proteinsXML
Record Information
Version1.0
Created at2020-03-18 23:27:49 UTC
Updated at2020-12-07 19:07:13 UTC
CannabisDB IDCDB000182
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NameMethyl hexadecanoic acid
DescriptionMethyl hexadecanoic acid, also known as palmitic acid methyl ester, belongs to the class of organic compounds known as fatty acid methyl esters. Fatty acid methyl esters are compounds containing a fatty acid that is esterified with a methyl group. They have the general structure RC(=O) OR', where R=fatty aliphatic tail or organyl group and R'=methyl group. Methyl hexadecanoic acid is very hydrophobic, practically insoluble in water, and relatively neutral. Methyl hexadecanoic acid has a fatty, oily, and waxy taste. Methyl hexadecanoic acid has been detected in cauliflowers, cloves, and evergreen blackberries. This could make methyl hexadecanoic acid a potential biomarker for the consumption of these foods. Methyl hexadecenoic acid is also found in cannabis plants (PMID:6991645 ) and in cannabis smoke ( Ref:DOI ). Methyl hexadecanoic acid is volatilized during the combustion of cannabis.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
Methyl hexadecanoateGenerator
Methyl palmitateHMDB
Methyl palmitic acidHMDB
Hexadecanoate methyl esterHMDB
Hexadecanoic acid methyl esterHMDB
Palmitic acid methyl esterHMDB
Methyl hexadecanoic acidGenerator
Chemical FormulaC17H34O2
Average Molecular Weight270.45
Monoisotopic Molecular Weight270.2559
IUPAC Namemethyl hexadecanoate
Traditional Namemethyl hexadecanoate
CAS Registry Number112-39-0
SMILES
CCCCCCCCCCCCCCCC(=O)OC
InChI Identifier
InChI=1S/C17H34O2/c1-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17(18)19-2/h3-16H2,1-2H3
InChI KeyFLIACVVOZYBSBS-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as fatty acid methyl esters. Fatty acid methyl esters are compounds containing a fatty acid that is esterified with a methyl group. They have the general structure RC(=O)OR', where R=fatty aliphatic tail or organyl group and R'=methyl group.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acid esters
Direct ParentFatty acid methyl esters
Alternative Parents
Substituents
  • Fatty acid methyl ester
  • Methyl ester
  • Carboxylic acid ester
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Role

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
logP7.41ALOGPS
logP6.4ChemAxon
logS-6.6ALOGPS
pKa (Strongest Basic)-7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area26.3 ŲChemAxon
Rotatable Bond Count15ChemAxon
Refractivity81.85 m³·mol⁻¹ChemAxon
Polarizability36.41 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
GC-MSMethyl hexadecanoic acid, non-derivatized, GC-MS Spectrumsplash10-000i-9410000000-06e342f68cdd631a32faSpectrum
GC-MSMethyl hexadecanoic acid, non-derivatized, GC-MS Spectrumsplash10-00di-0090000000-db5787e9b3eaac96f146Spectrum
GC-MSMethyl hexadecanoic acid, non-derivatized, GC-MS Spectrumsplash10-00dr-9100000000-683d8a1de530bbfa7510Spectrum
GC-MSMethyl hexadecanoic acid, non-derivatized, GC-MS Spectrumsplash10-05g3-9000000000-a2b255dd0fdd1efd2edcSpectrum
GC-MSMethyl hexadecanoic acid, non-derivatized, GC-MS Spectrumsplash10-05fr-9000000000-baccd6187fe64ba0fb81Spectrum
GC-MSMethyl hexadecanoic acid, non-derivatized, GC-MS Spectrumsplash10-000i-9400000000-6e386a4925d22e506f67Spectrum
Predicted GC-MSMethyl hexadecanoic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0540-5920000000-18adf3ceb15daf1890ffSpectrum
Predicted GC-MSMethyl hexadecanoic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Orbitrap 4V, positivesplash10-00di-0090000000-e3f1fb41bc39cf5c39802020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 7V, positivesplash10-00di-0190000000-837b670351375a88e3172020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 9V, positivesplash10-00di-5980000000-412d3cc4d2d44a8285472020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 12V, positivesplash10-0uyj-8910000000-abb13bbae38141c270672020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 15V, positivesplash10-0uej-9600000000-6d6061fa61e38f88aceb2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 18V, positivesplash10-0gbi-1910000000-3309cf3659c2c2662fe62020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 18V, positivesplash10-00di-9000000000-1501685b2e06c466d3b72020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 18V, positivesplash10-000i-9000000000-e103d05527cb343858562020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 18V, positivesplash10-0a4i-9000000000-cad0cc415c906a783cfc2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 18V, positivesplash10-0abc-5900000000-252b278e11ad05aaf4f52020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 18V, positivesplash10-01vt-1900000000-9e5b1071dde4e1224b3e2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 18V, positivesplash10-0a4i-5900000000-356dc1d8cd57cb9b88102020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 18V, positivesplash10-00di-3900000000-8c7e326caeaf4b57bbd02020-07-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00dr-0190000000-8d32a33ec60435ad40782016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00ds-6970000000-be7dcb63dde8bf429a3d2016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052f-9610000000-bb567c889e6285679c0d2016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0090000000-d0e2f55cef37f22099f32016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014r-1090000000-1b8c8aae3c8b029cfbd42016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052f-9240000000-4159ba9834de8d7f67c22016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00kr-0090000000-5b7592ccc42ad579e1ae2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014r-1090000000-dbc31b0134593f4464822021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9230000000-db97441651327b5034132021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-3290000000-bf26cd76362604fe9bd72021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0ab9-9320000000-09573567cce8839177352021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4l-9000000000-0dd6e755d6f048efee332021-09-22View Spectrum
NMRNot Available
Pathways
Pathways
Protein Targets
EnzymesNot Available
Transporters
Protein NameGene NameLocusUniprot IDDetails
Platelet glycoprotein 4CD367q11.2P16671 details
Metal BindingsNot Available
Receptors
Protein NameGene NameLocusUniprot IDDetails
Free fatty acid receptor 1FFAR119q13.1O14842 details
Free fatty acid receptor 4FFAR410q23.33Q5NUL3 details
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDHMDB0061859
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB003050
KNApSAcK IDC00030755
Chemspider IDNot Available
KEGG Compound IDC16995
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound8181
PDB IDNot Available
ChEBI IDNot Available
References
General References
  1. 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 ]

Transporters

Enzyme Details
1. Platelet glycoprotein 4
General function:
Not Available
Specific function:
Seems to have numerous potential physiological functions. Binds to collagen, thrombospondin, anionic phospholipids and oxidized LDL. May function as a cell adhesion molecule. Directly mediates cytoadherence of Plasmodium falciparum parasitized erythrocytes. Binds long chain fatty acids and may function in the transport and/or as a regulator of fatty acid transport
Gene Name:
CD36
Uniprot ID:
P16671
Molecular weight:
53054.0