Bovine Metabolome Database: Showing metabocard for Oleic acid (BMDB0000207)

Identification Taxonomy Physical properties Pathways Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-09-30 22:26:42 UTC

Update Date

2020-06-04 22:58:57 UTC

BMDB ID

BMDB0000207

Secondary Accession Numbers

BMDB00207

Metabolite Identification

Common Name

Oleic acid

Description

Oleic acid, also known as pamolyn or 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 exists as a liquid, very hydrophobic, practically insoluble (in water), and relatively neutral molecule. Oleic acid exists in all living species, ranging from bacteria to humans. Oleic acid is a potentially toxic compound. Oleic acid has been found to be associated with several diseases known as colorectal cancer, schizophrenia, gestational diabetes, and lung cancer; also oleic acid has been linked to the inborn metabolic disorders including isovaleric acidemia.

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
cis 9 Octadecenoic acid	MeSH
9 Octadecenoic acid	MeSH
9-Octadecenoic acid	MeSH
(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
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	MeSH, HMDB
Acid, oleic	MeSH, HMDB
Acid, cis-9-octadecenoic	MeSH, HMDB
FA(18:1(9Z))	HMDB
FA(18:1n9)	HMDB

Chemical Formula

C₁₈H₃₄O₂

Average Molecular Weight

282.4614

Monoisotopic Molecular Weight

282.255880332

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

Status

Detected and Quantified

Origin

Endogenous

Exogenous

Biofunction

Not Available

Application

Not Available

Cellular locations

Adiposome
Cell membrane
Cytoplasm
Membrane

Physical Properties

State

Liquid

Experimental Properties

Property	Value	Reference
Melting Point	13.4 °C	Not Available
Boiling Point	Not Available	Not Available
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	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (1 TMS)	splash10-00vi-9500000000-cdb5366d3ece43c3e166	View in MoNA
GC-MS	GC-MS Spectrum - GC-MS (1 TMS)	splash10-00nb-5900000000-fc03835c9c8fddb27970	View in MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-052f-9100000000-7618883a87bd14687fd5	View in MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-00vi-9500000000-cdb5366d3ece43c3e166	View in MoNA
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-00nb-5900000000-fc03835c9c8fddb27970	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0f6x-9640000000-29b5681d79890854ef2b	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-0fe0-9431000000-1879934642ac672cb401	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	View in JSpectraViewer
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-00ls-4790000000-d753b2905852ca2a8cbd	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-0apm-9100000000-8d5c8ecf0c7a7cc3ccf6	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-0aou-9000000000-64594906d693e8a08650	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, N/A (Annotated)	splash10-00l2-4790000000-aefa66e9f83fcb24ead6	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, N/A (Annotated)	splash10-0apm-9100000000-a71c58b95cb65487eeed	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, N/A (Annotated)	splash10-0aou-9000000000-5889cbe3dd606123df50	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - FAB-EBEB (JMS-HX/HX 110A, JEOL) , Negative	splash10-001i-0090000000-89531b488fbe899c09e6	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - EI-B (Unknown) , Positive	splash10-052f-9100000000-de078efada08e691dbb8	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF 10V, Negative	splash10-004i-0092000000-b8aabbdc61f9b89ac359	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF 20V, Negative	splash10-004i-0092000000-b8aabbdc61f9b89ac359	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF 30V, Negative	splash10-004i-0092000000-b8aabbdc61f9b89ac359	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF , Negative	splash10-004i-0092000000-b8aabbdc61f9b89ac359	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF 10V, Negative	splash10-001i-0090000000-92096c6b229762c5295f	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF 20V, Negative	splash10-001i-0090000000-5fe8495a19b387bf702c	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF 30V, Negative	splash10-001i-0090000000-5d40399b1c736b476445	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF , Negative	splash10-001i-0090000000-45785aeb659bd8a09240	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF 10V, Negative	splash10-001i-0091000000-3946ac7663105c7c2700	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-IT , negative	splash10-001i-0090000000-ce1372cb3b5e84122349	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-TOF , negative	splash10-001i-0090000000-92096c6b229762c5295f	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00lr-0090000000-755e8d1537818580a2fd	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00y0-4690000000-ca39c5846217fe093227	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0596-9830000000-fcb2923d448d11c54559	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-001i-0090000000-e809fd7222cf63431b77	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-001r-1090000000-9c340e3d19cbe7013ccd	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4l-9230000000-6e517cda629fcd4df07d	View in MoNA
MS	Mass Spectrum (Electron Ionization)	splash10-052f-9100000000-350dc6d7ac541a3c5b67	View in MoNA
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CDCl₃, experimental)	Not Available	View in JSpectraViewer
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, CDCl₃, experimental)	Not Available	View in JSpectraViewer

Biological Properties

Cellular Locations

Adiposome
Cell membrane
Cytoplasm
Membrane

Biospecimen Locations

Adipose Tissue
Blood
Epidermis
Intestine
Liver
Mammary Gland
Milk
Muscle
Oocyte
Pancreas
Placenta
Prostate Tissue
Ruminal Fluid
Semen
Skeletal Muscle

Pathways

Not Available

Name	SMPDB/Pathwhiz	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Adipose Tissue	Detected and Quantified	74191.38 nmol/g of tissue	Not Specified	Not Specified	Normal	C. Mapiye, T.D.Tu...	details
Adipose Tissue	Detected and Quantified	72947.31 nmol/g of tissue	Not Specified	Not Specified	Normal	C. Mapiye, T.D.Tu...	details
Adipose Tissue	Detected and Quantified	710540.98 nmol/g of tissue	Not Specified	Not Specified	Normal	C. Mapiye, T.D.Tu...	details
Adipose Tissue	Detected and Quantified	804930.87 nmol/g of tissue	Not Specified	Not Specified	Normal	C. Mapiye, T.D.Tu...	details
Adipose Tissue	Detected and Quantified	1047306.99 nmol/g of tissue	Not Specified	Not Specified	Normal	C. Mapiye, T.D.Tu...	details
Adipose Tissue	Detected and Quantified	1070050.28 nmol/g of tissue	Not Specified	Not Specified	Normal	C. Mapiye, T.D.Tu...	details
Adipose Tissue	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	PMID: 25093808	details
Adipose Tissue	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	PMID: 25093808	details
Adipose Tissue	Detected and Quantified	1242647.67 nmol/g of tissue	Not Specified	Not Specified	Normal	PMID: 24188642	details
Adipose Tissue	Detected and Quantified	1239461.39 nmol/g of tissue	Not Specified	Not Specified	Normal	PMID: 24188642	details
Adipose Tissue	Detected and Quantified	1289804.55 nmol/g of tissue	Not Specified	Not Specified	Normal	PMID: 24188642	details
Adipose Tissue	Detected and Quantified	1300531.68 nmol/g of tissue	Not Specified	Not Specified	Normal	PMID: 24188642	details
Adipose Tissue	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	PMID: 25093808	details
Adipose Tissue	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	PMID: 25093808	details
Adipose Tissue	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	PMID: 22274861	details
Adipose Tissue	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	PMID: 22274861	details
Adipose Tissue	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	PMID: 22274861	details
Adipose Tissue	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	PMID: 22274861	details
Epidermis	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Intestine	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Liver	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	PMID: 31873721	details
Liver	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	PMID: 31873721	details
Liver	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	PMID: 31867104	details
Mammary Gland	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	PMID: 31873721	details
Mammary Gland	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	PMID: 31873721	details
Milk	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	PMID: 11913692	details
Milk	Detected and Quantified	11.1 +/- 0.2 uM	Not Specified	Not Specified	Normal	PMID: 30994344	details
Milk	Detected and Quantified	21.1 +/- 0.4 uM	Not Specified	Not Specified	Normal	PMID: 30994344	details
Milk	Detected and Quantified	24 +/- 1 uM	Not Specified	Not Specified	Normal	PMID: 30994344	details
Milk	Detected and Quantified	32 +/- 2 uM	Not Specified	Not Specified	Normal	PMID: 30994344	details
Milk	Detected and Quantified	79.64 +/- 7.47 uM	Not Specified	Not Specified	Normal	Bashar Amer, Caro...	details
Milk	Detected and Quantified	87.11 +/- 9.30 uM	Not Specified	Not Specified	Normal	Bashar Amer, Caro...	details
Milk	Detected and Quantified	34.06 +/- 1.048 uM	Not Specified	Not Specified	Normal	Bashar Amer, Caro...	details
Milk	Detected and Quantified	5.76 +/- 0.52 uM	Not Specified	Not Specified	Normal	Bashar Amer, Caro...	details
Milk	Detected and Quantified	71.97 +/- 0.60 uM	Not Specified	Not Specified	Normal	Bashar Amer, Caro...	details
Milk	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Kurt J. Boudonck,...	details
Milk	Detected and Quantified	25384.0353 +/- 7080.624 uM	Not Specified	Not Specified	Normal	M. Ferrand et al....	details
Milk	Detected and Quantified	23790.895 +/- 6584.980 uM	Not Specified	Not Specified	Normal	M. Ferrand et al....	details
Milk	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Lawrence K. Cream...	details
Muscle	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	PMID: 23871026	details
Oocyte	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	PMID: 10793638	details
Pancreas	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Placenta	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Prostate Tissue	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Ruminal Fluid	Detected and Quantified	1.1 +/- 0.3 uM	Not Specified	Not Specified	Normal	Fozia Saleem, Sou...	details
Ruminal Fluid	Detected and Quantified	1.1 +/- 0.3 uM	Not Specified	Not Specified	Normal	Fozia Saleem, Sou...	details
Semen	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	PMID: 31533629	details
Skeletal Muscle	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Heat stress	PMID: 25913299	details

External Links

HMDB ID

HMDB0000207

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB 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

Synthesis Reference

Hu, Sheng; Yuan, Ji-rong; Zhu, Jin; Yin, Ying-sui. Preparation of high-purity oleic acid by selective reaction. Yingyong Huagong (2005), 34(12), 748-750, 753.

Material Safety Data Sheet (MSDS)

Not Available

General References

Jensen RG: The composition of bovine milk lipids: January 1995 to December 2000. J Dairy Sci. 2002 Feb;85(2):295-350. doi: 10.3168/jds.S0022-0302(02)74079-4. [PubMed:11913692 ]
Colman E, Fokkink WB, Craninx M, Newbold JR, De Baets B, Fievez V: Effect of induction of subacute ruminal acidosis on milk fat profile and rumen parameters. J Dairy Sci. 2010 Oct;93(10):4759-73. doi: 10.3168/jds.2010-3158. [PubMed:20855010 ]
van Gastelen S, Antunes-Fernandes EC, Hettinga KA, Dijkstra J: Relationships between methane emission of Holstein Friesian dairy cows and fatty acids, volatile metabolites and non-volatile metabolites in milk. Animal. 2017 Sep;11(9):1539-1548. doi: 10.1017/S1751731117000295. Epub 2017 Feb 21. [PubMed:28219465 ]
Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals (2009). Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375?386. Metabolomics.
M. Ferrand, B. Huquet. S. Barbey, F. Barillet, F. Faucon, H. Larroque, O. Leray, J.M. Trommenschlager, M. Brochard (2011). M. Ferrand et al. Determination of fatty acid profile in cow's milk using mid-infrared spectrometry: Interest of applying a variable selection by genetic algorithms before a PLS regression. Chemometrics and Intelligent Laboratory Systems 106 (2011) 183?189. Chemometrics and Intelligent Laboratory Systems.
Lawrence K. Creamer, Alastair K.H. MacGibbon (1996). Lawrence K. Creamer, Alastair K.H. MacGibbon. Some recent advances in the basic chemistry of milk proteins and lipids. International Dairy J. (1996) 6(6):539-568 doi: 10.1016/0958-6946(96)85309-X. International Dairy Journal.

Showing metabocard for Oleic acid (BMDB0000207)

Structure for BMDB0000207 (Oleic acid)