Cannabis Compound Database: Showing Compound Card for Oleic acid (CDB006166)

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Identification Taxonomy Ontology Physical properties Spectra Protein target Pathways Concentrations Links References enzymes (11)transporters (1) Show 13 proteins XML

Record Information

Version

1.0

Created at

2020-03-18 23:22:17 UTC

Updated at

2020-12-07 19:06:57 UTC

CannabisDB ID

CDB006166

Secondary Accession Numbers

Not Available

Cannabis Compound Identification

Common Name

Oleic acid

Description

Oleic acid, also known as oleate, belongs to the class of organic compounds known as long-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms. Oleic acid is a very hydrophobic molecule, practically insoluble in water, and relatively neutral. In chemical terms, oleic acid is classified as a monounsaturated omega-9 fatty acid. It has the formula CH3(CH2)7CH=CH(CH2)7COOH. The term "oleic" means related to, or derived from, oil or olive, the plant oil that is predominantly composed of oleic acid. Oleic acid is the most widely distributed and abundant fatty acid in nature. It occurs naturally in various animal and vegetable fats and oils. Fatty acids such as oleic acid occur primarily esters (not as free acids), mostly in the form of triglycerides, which are the greasy materials in many natural oils. Oleic acid is an odorless, colourless oil, although commercial samples may be yellowish. Oleic acid is particularly abundant in plant oils e.g. olive oil (about 80%), almond oil (about 80%) 59–75% of pecan oil, 61% of canola oil, 36–67% of peanut oil, 60% of macadamia oil, 20–80% of sunflower oil, 15–20% of grape seed oil, 40% of sesame oil and 14% of poppyseed oil. Oleic acid is also a constituent of cannabis plant and cannabis smoke. It is volatilized during the combustion of cannabis ( Ref:DOI ). Oleic acid is the most abundant fatty acid in human adipose tissue and the second most abundant in human tissues overall, following palmitic acid. Oleic acid is used in the manufacturing of surfactants, soaps, plasticizers and as an emulsifying agent in foods, lotions, cosmetics and pharmaceuticals. Oleic acid may be responsible for the hypotensive (blood pressure reducing) effects of olive oil . Altered levels of oleic acid have been found to be associated with isovaleric acidemia, which is an inborn error of metabolism.

Structure

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

Synonyms

Value	Source
(9Z)-Octadecenoic acid	ChEBI
(Z)-Octadec-9-enoic acid	ChEBI
18:1 N-9	ChEBI
18:1DElta9cis	ChEBI
C18:1 N-9	ChEBI
cis-9-Octadecenoic acid	ChEBI
cis-Delta(9)-Octadecenoic acid	ChEBI
cis-Oleic acid	ChEBI
FA 18:1	ChEBI
Octadec-9-enoic acid	ChEBI
Oelsaeure	ChEBI
Oleate	ChEBI
(9Z)-Octadecenoate	Generator
(Z)-Octadec-9-enoate	Generator
cis-9-Octadecenoate	Generator
cis-delta(9)-Octadecenoate	Generator
cis-Δ(9)-octadecenoate	Generator
cis-Δ(9)-octadecenoic acid	Generator
cis-Oleate	Generator
Octadec-9-enoate	Generator
(9Z)-9-Octadecenoate	HMDB
(9Z)-9-Octadecenoic acid	HMDB
(Z)-9-Octadecanoate	HMDB
(Z)-9-Octadecanoic acid	HMDB
9,10-Octadecenoate	HMDB
9,10-Octadecenoic acid	HMDB
9-(Z)-Octadecenoate	HMDB
9-(Z)-Octadecenoic acid	HMDB
9-Octadecenoate	HMDB
9-Octadecenoic acid	HMDB
Century CD fatty acid	HMDB
cis-Octadec-9-enoate	HMDB
cis-Octadec-9-enoic acid	HMDB
Distoline	HMDB
Emersol 210	HMDB
Emersol 211	HMDB
Emersol 213	HMDB
Emersol 220 white oleate	HMDB
Emersol 220 white oleic acid	HMDB
Emersol 221 low titer white oleate	HMDB
Emersol 221 low titer white oleic acid	HMDB
Emersol 233LL	HMDB
Emersol 6321	HMDB
Emersol 6333 NF	HMDB
Emersol 7021	HMDB
Glycon ro	HMDB
Glycon wo	HMDB
Groco 2	HMDB
Groco 4	HMDB
Groco 5l	HMDB
Groco 6	HMDB
Industrene 104	HMDB
Industrene 105	HMDB
Industrene 205	HMDB
Industrene 206	HMDB
L'acide oleique	HMDB
Metaupon	HMDB
Oelsauere	HMDB
Oleic acid extra pure	HMDB
Oleinate	HMDB
Oleinic acid	HMDB
Pamolyn	HMDB
Pamolyn 100	HMDB
Pamolyn 100 FG	HMDB
Pamolyn 100 FGK	HMDB
Pamolyn 125	HMDB
Priolene 6900	HMDB
Red oil	HMDB
Tego-oleic 130	HMDB
Vopcolene 27	HMDB
Wecoline oo	HMDB
Z-9-Octadecenoate	HMDB
Z-9-Octadecenoic acid	HMDB
Acid, 9-octadecenoic	HMDB
Acid, oleic	HMDB
9 Octadecenoic acid	HMDB
Acid, cis-9-octadecenoic	HMDB
cis 9 Octadecenoic acid	HMDB
FA(18:1(9Z))	HMDB
FA(18:1n9)	HMDB

Chemical Formula

C₁₈H₃₄O₂

Average Molecular Weight

282.46

Monoisotopic Molecular Weight

282.2559

IUPAC Name

(9Z)-octadec-9-enoic acid

Traditional Name

oleic acid

CAS Registry Number

112-80-1

SMILES

CCCCCCCC\C=C/CCCCCCCC(O)=O

InChI Identifier

InChI=1S/C18H34O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h9-10H,2-8,11-17H2,1H3,(H,19,20)/b10-9-

InChI Key

ZQPPMHVWECSIRJ-KTKRTIGZSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as long-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acids and conjugates

Direct Parent

Long-chain fatty acids

Alternative Parents

Substituents

Long-chain fatty acid
Unsaturated fatty acid
Straight chain fatty acid
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

octadec-9-enoic acid (CHEBI:16196 )
Unsaturated fatty acids (C00712 )
Monounsaturated fatty acids (C00712 )
Unsaturated fatty acids (LMFA01030002 )

Ontology

Ingestion

Source:

Synthetic:

Personal care product

Biological:

Animal

Plant:

Biological location:

Role

Industrial application:

Biological role:

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	13.4 °C	Not Available
Boiling Point	360 °C	Wikipedia
Water Solubility	Not Available	Not Available
logP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	7.68	ALOGPS
logP	6.78	ChemAxon
logS	-6.4	ALOGPS
pKa (Strongest Acidic)	4.99	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	37.3 Å²	ChemAxon
Rotatable Bond Count	15	ChemAxon
Refractivity	87.4 m³·mol⁻¹	ChemAxon
Polarizability	37.09 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
EI-MS	Mass Spectrum (Electron Ionization)	splash10-052f-9100000000-350dc6d7ac541a3c5b67	2018-05-25	View Spectrum
GC-MS	Oleic acid, 1 TMS, GC-MS Spectrum	splash10-00vi-9500000000-cdb5366d3ece43c3e166	Spectrum
GC-MS	Oleic acid, 1 TMS, GC-MS Spectrum	splash10-00nb-5900000000-fc03835c9c8fddb27970	Spectrum
GC-MS	Oleic acid, non-derivatized, GC-MS Spectrum	splash10-052f-9100000000-7618883a87bd14687fd5	Spectrum
GC-MS	Oleic acid, non-derivatized, GC-MS Spectrum	splash10-00vi-9500000000-cdb5366d3ece43c3e166	Spectrum
GC-MS	Oleic acid, non-derivatized, GC-MS Spectrum	splash10-00nb-5900000000-fc03835c9c8fddb27970	Spectrum
Predicted GC-MS	Oleic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0f6x-9640000000-29b5681d79890854ef2b	Spectrum
Predicted GC-MS	Oleic acid, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0fe0-9431000000-1879934642ac672cb401	Spectrum
Predicted GC-MS	Oleic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Oleic acid, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-00ls-4790000000-d753b2905852ca2a8cbd	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-0apm-9100000000-8d5c8ecf0c7a7cc3ccf6	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-0aou-9000000000-64594906d693e8a08650	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, N/A (Annotated)	splash10-00l2-4790000000-aefa66e9f83fcb24ead6	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, N/A (Annotated)	splash10-0apm-9100000000-a71c58b95cb65487eeed	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, N/A (Annotated)	splash10-0aou-9000000000-5889cbe3dd606123df50	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - FAB-EBEB (JMS-HX/HX 110A, JEOL) , Negative	splash10-001i-0090000000-89531b488fbe899c09e6	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - EI-B (Unknown) , Positive	splash10-052f-9100000000-de078efada08e691dbb8	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-TOF 10V, Negative	splash10-004i-0092000000-b8aabbdc61f9b89ac359	2017-08-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-TOF 20V, Negative	splash10-004i-0092000000-b8aabbdc61f9b89ac359	2017-08-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-TOF 30V, Negative	splash10-004i-0092000000-b8aabbdc61f9b89ac359	2017-08-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-TOF , Negative	splash10-004i-0092000000-b8aabbdc61f9b89ac359	2017-08-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-TOF 10V, Negative	splash10-001i-0090000000-92096c6b229762c5295f	2017-09-12	View Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-TOF 20V, Negative	splash10-001i-0090000000-5fe8495a19b387bf702c	2017-09-12	View Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-TOF 30V, Negative	splash10-001i-0090000000-5d40399b1c736b476445	2017-09-12	View Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-TOF , Negative	splash10-001i-0090000000-45785aeb659bd8a09240	2017-09-12	View Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-TOF 10V, Negative	splash10-001i-0091000000-3946ac7663105c7c2700	2017-09-12	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-IT , negative	splash10-001i-0090000000-ce1372cb3b5e84122349	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-TOF , negative	splash10-001i-0090000000-92096c6b229762c5295f	2017-09-14	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00lr-0090000000-755e8d1537818580a2fd	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00y0-4690000000-ca39c5846217fe093227	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0596-9830000000-fcb2923d448d11c54559	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-001i-0090000000-e809fd7222cf63431b77	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-001r-1090000000-9c340e3d19cbe7013ccd	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4l-9230000000-6e517cda629fcd4df07d	2016-09-12	View Spectrum

NMR

Type	Description		View
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CDCl₃, experimental)		Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, CDCl₃, experimental)		Spectrum

Pathways

Not Available

Protein Targets

Enzymes

Protein Name	Gene Name	Locus	Uniprot ID	Details
Fatty acid synthase	FASN	17q25	P49327	details
Bile acid-CoA:amino acid N-acyltransferase	BAAT	9q22.3	Q14032	details
Cytosolic acyl coenzyme A thioester hydrolase	ACOT7	1p36	O00154	details
Acyl-coenzyme A thioesterase 2, mitochondrial	ACOT2	14q24.3	P49753	details
Acyl-coenzyme A thioesterase 4	ACOT4	14q24.3	Q8N9L9	details
Acyl-coenzyme A thioesterase 8	ACOT8	20q13.12	O14734	details
Fatty-acid amide hydrolase 1	FAAH	1p35-p34	O00519	details
2-acylglycerol O-acyltransferase 2	MOGAT2	11q13.5	Q3SYC2	details
Fatty-acid amide hydrolase 2	FAAH2	Xp11.21	Q6GMR7	details
Acyl-coenzyme A thioesterase 1	ACOT1	14q24.3	Q86TX2	details
S-acyl fatty acid synthase thioesterase, medium chain	OLAH	10p13	Q9NV23	details

Transporters

Protein Name	Gene Name	Locus	Uniprot ID	Details
Fatty acid synthase	FASN	17q25	P49327	details

Metal Bindings

Protein Name	Gene Name	Locus	Uniprot ID	Details
Fatty acid synthase	FASN	17q25	P49327	details

Receptors

Not Available

Transcriptional Factors

Not Available

Concentrations Data

Not Available

External Links

HMDB ID

HMDB0000207

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

Oleic_acid

METLIN ID

190

PubChem Compound

445639

PDB ID

Not Available

ChEBI ID

16196

References

General References

Not Available

Only showing the first 10 proteins. There are 13 proteins in total.

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Enzymes

Enzyme Details

1. Fatty acid synthase

General function:: Involved in transferase activity
Specific function:: Fatty acid synthetase catalyzes the formation of long-chain fatty acids from acetyl-CoA, malonyl-CoA and NADPH. This multifunctional protein has 7 catalytic activities and an acyl carrier protein.
Gene Name:: FASN
Uniprot ID:: P49327
Molecular weight:: 273424.06

Enzyme Details

2. Bile acid-CoA:amino acid N-acyltransferase

General function:: Involved in thiolester hydrolase activity
Specific function:: Involved in bile acid metabolism. In liver hepatocytes catalyzes the second step in the conjugation of C24 bile acids (choloneates) to glycine and taurine before excretion into bile canaliculi. The major components of bile are cholic acid and chenodeoxycholic acid. In a first step the bile acids are converted to an acyl-CoA thioester, either in peroxisomes (primary bile acids deriving from the cholesterol pathway), or cytoplasmic at the endoplasmic reticulum (secondary bile acids). May catalyze the conjugation of primary or secondary bile acids, or both. The conjugation increases the detergent properties of bile acids in the intestine, which facilitates lipid and fat-soluble vitamin absorption. In turn, bile acids are deconjugated by bacteria in the intestine and are recycled back to the liver for reconjugation (secondary bile acids). May also act as an acyl-CoA thioesterase that regulates intracellular levels of free fatty acids. In vitro, catalyzes the hydrolysis of long- and very long-chain saturated acyl-CoAs to the free fatty acid and coenzyme A (CoASH), and conjugates glycine to these acyl-CoAs.
Gene Name:: BAAT
Uniprot ID:: Q14032
Molecular weight:: 46298.865

Enzyme Details

3. Cytosolic acyl coenzyme A thioester hydrolase

General function:: Lipid transport and metabolism
Specific function:: Acyl-CoA thioesterases are a group of enzymes that catalyze the hydrolysis of acyl-CoAs to the free fatty acid and coenzyme A (CoASH), providing the potential to regulate intracellular levels of acyl-CoAs, free fatty acids and CoASH. May play an important physiological function in brain. May play a regulatory role by modulating the cellular levels of fatty acyl-CoA ligands for certain transcription factors as well as the substrates for fatty acid metabolizing enzymes, contributing to lipid homeostasis. Has broad specificity, active towards fatty acyl-CoAs with chain-lengths of C8-C18. Has a maximal activity toward palmitoyl-CoA.
Gene Name:: ACOT7
Uniprot ID:: O00154
Molecular weight:: 40454.945

Enzyme Details

4. Acyl-coenzyme A thioesterase 2, mitochondrial

General function:: Involved in thiolester hydrolase activity
Specific function:: Acyl-CoA thioesterases are a group of enzymes that catalyze the hydrolysis of acyl-CoAs to the free fatty acid and coenzyme A (CoASH), providing the potential to regulate intracellular levels of acyl-CoAs, free fatty acids and CoASH. Displays high levels of activity on medium- and long chain acyl CoAs.
Gene Name:: ACOT2
Uniprot ID:: P49753
Molecular weight:: 53218.02

Enzyme Details

5. Acyl-coenzyme A thioesterase 4

General function:: Involved in thiolester hydrolase activity
Specific function:: Acyl-CoA thioesterases are a group of enzymes that catalyze the hydrolysis of acyl-CoAs to the free fatty acid and coenzyme A (CoASH), providing the potential to regulate intracellular levels of acyl-CoAs, free fatty acids and CoASH (By similarity). Succinyl-CoA thioesterase that also hydrolyzes long chain saturated and unsaturated monocarboxylic acyl-CoAs.
Gene Name:: ACOT4
Uniprot ID:: Q8N9L9
Molecular weight:: 46326.09

Enzyme Details

6. Acyl-coenzyme A thioesterase 8

General function:: Involved in acyl-CoA thioesterase activity
Specific function:: Acyl-CoA thioesterases are a group of enzymes that catalyze the hydrolysis of acyl-CoAs to the free fatty acid and coenzyme A (CoASH), providing the potential to regulate intracellular levels of acyl-CoAs, free fatty acids and CoASH. May mediate Nef-induced down-regulation of CD4. Major thioesterase in peroxisomes. Competes with BAAT (Bile acid CoA: amino acid N-acyltransferase) for bile acid-CoA substrate (such as chenodeoxycholoyl-CoA). Shows a preference for medium-length fatty acyl-CoAs (By similarity). May be involved in the metabolic regulation of peroxisome proliferation.
Gene Name:: ACOT8
Uniprot ID:: O14734
Molecular weight:: 35914.02

Enzyme Details

7. Fatty-acid amide hydrolase 1

General function:: Involved in carbon-nitrogen ligase activity, with glutamine as amido-N-donor
Specific function:: Degrades bioactive fatty acid amides like oleamide, the endogenous cannabinoid, anandamide and myristic amide to their corresponding acids, thereby serving to terminate the signaling functions of these molecules. Hydrolyzes polyunsaturated substrate anandamide preferentially as compared to monounsaturated substrates.
Gene Name:: FAAH
Uniprot ID:: O00519
Molecular weight:: 63065.28

Enzyme Details

8. 2-acylglycerol O-acyltransferase 2

General function:: Involved in transferase activity, transferring acyl groups other than amino-acyl groups
Specific function:: Catalyzes the formation of diacylglycerol from 2-monoacylglycerol and fatty acyl-CoA. Has a preference toward monoacylglycerols containing unsaturated fatty acids in an order of C18:3 > C18:2 > C18:1 > C18:0. Plays a central role in absorption of dietary fat in the small intestine by catalyzing the resynthesis of triacylglycerol in enterocytes. May play a role in diet-induced obesity.
Gene Name:: MOGAT2
Uniprot ID:: Q3SYC2
Molecular weight:: 38195.285

Enzyme Details

9. Fatty-acid amide hydrolase 2

General function:: Involved in carbon-nitrogen ligase activity, with glutamine as amido-N-donor
Specific function:: Degrades bioactive fatty acid amides like oleamide, the endogenous cannabinoid, anandamide and myristic amide to their corresponding acids, thereby serving to terminate the signaling functions of these molecules. Hydrolyzes monounsaturated substrate anandamide preferentially as compared to polyunsaturated substrates.
Gene Name:: FAAH2
Uniprot ID:: Q6GMR7
Molecular weight:: 58303.115

Enzyme Details

10. Acyl-coenzyme A thioesterase 1

General function:: Involved in thiolester hydrolase activity
Specific function:: Acyl-CoA thioesterases are a group of enzymes that catalyze the hydrolysis of acyl-CoAs to the free fatty acid and coenzyme A (CoASH), providing the potential to regulate intracellular levels of acyl-CoAs, free fatty acids and CoASH. Active towards fatty acyl-CoA with chain-lengths of C12-C16 (By similarity).
Gene Name:: ACOT1
Uniprot ID:: Q86TX2
Molecular weight:: 46276.96

Transporters

Enzyme Details

1. Fatty acid synthase

General function:: Involved in transferase activity
Specific function:: Fatty acid synthetase catalyzes the formation of long-chain fatty acids from acetyl-CoA, malonyl-CoA and NADPH. This multifunctional protein has 7 catalytic activities and an acyl carrier protein.
Gene Name:: FASN
Uniprot ID:: P49327
Molecular weight:: 273424.06

Only showing the first 10 proteins. There are 13 proteins in total.

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Showing Compound Card for Oleic acid (CDB006166)

Structure for CDB006166 (Oleic acid)

Enzymes

Transporters