Livestock Metabolome Database: Showing metabocard for Linoleic acid (LMDB00210)

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-07-13 19:44:47 UTC

Update Date

2016-09-23 18:44:55 UTC

Lmdb

LMDB00210

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Linoleic acid

Description

Linoleic acid is a doubly unsaturated fatty acid, also known as an omega-6 fatty acid, occurring widely in plant glycosides. In this particular polyunsaturated fatty acid (PUFA), the first double bond is located between the sixth and seventh carbon atom from the methyl end of the fatty acid (n-6). Linoleic acid is an essential fatty acid in animal nutrition because it cannot be synthesized by animals. It is used in the biosynthesis of prostaglandins (via arachidonic acid) and cell membranes. (From Stedman, 26th ed).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(9Z,12Z)-Octadecadienoic acid	ChEBI
(Z,Z)-9,12-Octadecadienoic acid	ChEBI
9-cis,12-cis-Octadecadienoic acid	ChEBI
9Z,12Z-Octadecadienoic acid	ChEBI
Acide cis-linoleique	ChEBI
Acide linoleique	ChEBI
Acido linoleico	ChEBI
all-cis-9,12-Octadecadienoic acid	ChEBI
C18:2 9C, 12C Omega6 todos cis-9,12-octadienoico	ChEBI
C18:2, N-6,9 all-cis	ChEBI
cis,cis-9,12-Octadecadienoic acid	ChEBI
cis,cis-Linoleic acid	ChEBI
cis-Delta(9,12)-Octadecadienoic acid	ChEBI
LA	ChEBI
Linolic acid	ChEBI
9-cis,12-cis-Octadecadienoate	Kegg
(9Z,12Z)-Octadecadienoate	Generator
(Z,Z)-9,12-Octadecadienoate	Generator
9Z,12Z-Octadecadienoate	Generator
all-cis-9,12-Octadecadienoate	Generator
cis,cis-9,12-Octadecadienoate	Generator
cis,cis-Linoleate	Generator
cis-delta(9,12)-Octadecadienoate	Generator
cis-Δ(9,12)-octadecadienoate	Generator
cis-Δ(9,12)-octadecadienoic acid	Generator
Linolate	Generator
Linoleate	Generator
(9Z,12Z)-9,12-Octadecadienoate	HMDB
(9Z,12Z)-9,12-Octadecadienoic acid	HMDB
9-cis,12-cis-Linoleate	HMDB
9-cis,12-cis-Linoleic acid	HMDB
9Z,12Z-Linoleate	HMDB
9Z,12Z-Linoleic acid	HMDB
cis-9,cis-12-Octadecadienoate	HMDB
cis-9,cis-12-Octadecadienoic acid	HMDB
cis-D9,12-Octadecadienoate	HMDB
cis-D9,12-Octadecadienoic acid	HMDB
Emersol 315	HMDB
Extra linoleic 90	HMDB
Polylin 515	HMDB
Unifac 6550	HMDB
Acid, 9,12-octadecadienoic	HMDB
Linoelaidic acid	HMDB
Linoleic acid, (e,e)-isomer	HMDB
Linoleic acid, (Z,Z)-isomer	HMDB
Linoleic acid, (Z,Z)-isomer, 14C-labeled	HMDB
Linoleic acid, ammonium salt, (Z,Z)-isomer	HMDB
Linoleic acid, potassium salt, (Z,Z)-isomer	HMDB
9 trans,12 trans Octadecadienoic acid	HMDB
9-trans,12-trans-Octadecadienoic acid	HMDB
Linoleic acid, sodium salt, (e,e)-isomer	HMDB
Linoleic acid, sodium salt, (Z,Z)-isomer	HMDB
trans,trans-9,12-Octadecadienoic acid	HMDB
9,12-Octadecadienoic acid	HMDB
Linoelaidic acid, (e,Z)-isomer	HMDB
Linoleic acid, calcium salt, (Z,Z)-isomer	HMDB
Linolelaidic acid	HMDB
9,12 Octadecadienoic acid	HMDB
Linoleic acid, (Z,e)-isomer	HMDB
FA(18:2(9Z,12Z))	HMDB

Chemical Formula

C₁₈H₃₂O₂

Average Molecular Weight

280.4455

Monoisotopic Molecular Weight

280.240230268

IUPAC Name

(9Z,12Z)-octadeca-9,12-dienoic acid

Traditional Name

linoleic

CAS Registry Number

60-33-3

SMILES

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

InChI Identifier

InChI=1S/C18H32O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h6-7,9-10H,2-5,8,11-17H2,1H3,(H,19,20)/b7-6-,10-9-

InChI Key

OYHQOLUKZRVURQ-HZJYTTRNSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as lineolic acids and derivatives. These are derivatives of lineolic acid. Lineolic acid is a polyunsaturated omega-6 18 carbon long fatty acid, with two CC double bonds at the 9- and 12-positions.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Lineolic acids and derivatives

Direct Parent

Lineolic acids and derivatives

Alternative Parents

Substituents

Octadecanoid
Long-chain fatty acid
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

omega-6 fatty acid (CHEBI:17351 )
octadecadienoic acid (CHEBI:17351 )
Unsaturated fatty acids (C01595 )
Polyunsaturated fatty acids (C01595 )
Unsaturated fatty acids (LMFA01030120 )

Ontology

Status

Detected and Quantified

Origin

Not Available

Biofunction

Not Available

Application

Not Available

Cellular locations

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	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	7.06	ALOGPS
logP	6.42	ChemAxon
logS	-6.3	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	14	ChemAxon
Refractivity	88.52 m³·mol⁻¹	ChemAxon
Polarizability	35.86 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	View
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (1 TMS)	splash10-000t-7900000000-b6ee03c4800464c37471	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (1 TMS)	splash10-00vi-9300000000-c92dac639ced59eb5dbe	Spectrum
GC-MS	GC-MS Spectrum - GC-MS (1 TMS)	splash10-003s-9700000000-77e67d7b1a161e6ecfa6	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-000t-7900000000-b6ee03c4800464c37471	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-00vi-9300000000-c92dac639ced59eb5dbe	Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-003s-9700000000-77e67d7b1a161e6ecfa6	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0007-9750000000-50d69948d56dd2ba6e42	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-0079-9631000000-cc93c24bbf14d81ae9b6	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-0f89-0190000000-2be9501b1d4a9fcbd1c0	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-0uk9-0790000000-7f6e35a591f977bc488e	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-0udi-0090000000-c56edc2bbf9d6752aec5	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - FAB-EBEB (JMS-HX/HX 110A, JEOL) , Negative	splash10-004i-0090000000-baf4579e26c6b393d391	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative	splash10-004i-0090000000-815c1682b2c59ba96f10	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative	splash10-004i-0090000000-3406b2b2d5756807e1cd	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative	splash10-004i-0090000000-2fb4975278fa4d118f43	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative	splash10-0a6r-9380000000-37f833673c248405c8ef	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative	splash10-0a4i-9200000000-7d34ed5900a17ffe3f9b	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF 10V, Negative	splash10-004i-0090010000-f8df6099e003402f2566	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF , Negative	splash10-004i-0091021000-0e44779958d5744d873b	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF 10V, Negative	splash10-004i-0091021000-0e44779958d5744d873b	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF 20V, Negative	splash10-004i-0091021000-0e44779958d5744d873b	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF 30V, Negative	splash10-004i-0091021000-0e44779958d5744d873b	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF 10V, Negative	splash10-004i-0090010000-f8df6099e003402f2566	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF , Negative	splash10-004i-0091021000-0e44779958d5744d873b	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF 10V, Negative	splash10-004i-0090000000-adbf36f0a17c33ac33f8	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF 20V, Negative	splash10-004i-0090000000-2747c83af78732eb6e16	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF 30V, Negative	splash10-004i-0090000000-a0415b1cb63b4562b40e	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03di-0090000000-8bdf8d54a29f73494242	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0239-4590000000-e5ee57553b064eae2efe	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00rf-9830000000-b26ba057a2b4d135b478	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-0090000000-f1e9e4b543f7d4f48bf8	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-01ti-0090000000-665523c6142ff4e39c96	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4l-9240000000-dca36a25ad7519d500c3	Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-015a-9200000000-a193c27810bedf93c498	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
2D NMR	[1H,13C] 2D NMR Spectrum	Not Available	Spectrum

Biological Properties

Cellular Locations

Not Available

Biofluid Locations and Tissue Locations

Follicular Fluid
Milk
Muscle
Oocyte
Oocyte (zona-intact oocytes)
Plasma
Ruminal Fluid
Serum

Concentrations

Biofluid	Status	Value	Condition	Species	Reference	Details
Follicular Fluid	Detected but not Quantified	Not Applicable	Not Available	Porcine	Warzych, E., Cies...	details
Milk	Detected but not Quantified	Not Applicable	Not Available	Bovine	11913692	details
Milk	Detected but not Quantified	Not Applicable	Not Available	Bovine	20855010	details
Milk	Detected but not Quantified	Not Applicable	Not Available	Bovine	11913692	details
Milk	Detected but not Quantified	Not Applicable	Not Available	Bovine	9718493	details
Milk	Detected but not Quantified	Not Applicable	Not Available	Bovine	11913692	details
Milk	Detected but not Quantified	Not Applicable	Not Available	Bovine	9718493	details
Milk	Detected but not Quantified	Not Applicable	Not Available	Bovine	11913692	details
Milk	Detected but not Quantified	Not Applicable	Not Available	Bovine	9718493	details
Milk	Detected but not Quantified	Not Applicable	Not Available	Bovine	5409465	details
Milk	Detected but not Quantified	Not Applicable	Not Available	Caprine	H. Steinshamn, R....	details
Milk	Detected but not Quantified	Not Applicable	Not Available	Caprine	H. Steinshamn, R....	details
Milk	Detected but not Quantified	Not Applicable	Not Available	Bovine	9718493	details
Milk	Detected but not Quantified	Not Applicable	Not Available	Caprine	H. Steinshamn, R....	details
Milk	Detected but not Quantified	Not Applicable	Not Available	Bovine	9718493	details
Milk	Detected but not Quantified	Not Applicable	Not Available	Caprine	H. Steinshamn, R....	details
Milk	Detected but not Quantified	Not Applicable	Not Available	Bovine	9718493	details
Milk	Detected but not Quantified	Not Applicable	Not Available	Bovine	9718493	details
Milk	Detected but not Quantified	Not Applicable	Not Available	Bovine	9718493	details
Milk	Detected but not Quantified	Not Applicable	Not Available	Bovine	9718493	details
Milk	Detected but not Quantified	Not Applicable	Not Available	Bovine	9718493	details
Milk	Detected but not Quantified	Not Applicable	Not Available	Bovine	9718493	details
Milk	Detected but not Quantified	Not Applicable	Not Available	Bovine	9718493	details
Milk	Detected but not Quantified	Not Applicable	Not Available	Bovine	1779072	details
Milk	Detected but not Quantified	Not Applicable	Not Available	Bovine	11913692	details
Milk	Detected but not Quantified	Not Applicable	Not Available	Bovine	11913692	details
Milk	Detected but not Quantified	Not Applicable	Not Available	Bovine	11913692	details
Milk	Detected but not Quantified	Not Applicable	Not Available	Bovine	11913692	details
Milk	Detected but not Quantified	Not Applicable	Not Available	Bovine	11913692	details
Milk	Detected but not Quantified	Not Applicable	Not Available	Bovine	11913692	details
Milk	Detected but not Quantified	Not Applicable	Not Available	Bovine	11913692	details
Milk	Detected and Quantified	6000 mg/kg	Not Available	Bovine	M.J. Abarghuei, Y...	details
Milk	Detected and Quantified	7400 mg/kg	Not Available	Bovine	M.J. Abarghuei, Y...	details
Milk	Detected and Quantified	7700 mg/kg	Not Available	Bovine	M.J. Abarghuei, Y...	details
Milk	Detected and Quantified	8100 mg/kg	Not Available	Bovine	M.J. Abarghuei, Y...	details
Milk	Detected but not Quantified	Not Applicable	Not Available	Ovine	Park, Y. W; Juáre...	details
Milk	Detected but not Quantified	Not Applicable	Not Available	Caprine	Park, Y. W; Juáre...	details
Milk	Detected but not Quantified	Not Applicable	Not Available	Bovine	Kurt J. Boudonck,...	details
Milk	Detected but not Quantified	Not Applicable	Not Available	Bovine	Lawrence K. Cream...	details
Milk	Detected and Quantified	2.5 mol/100 mol	Not Available	Bovine	1779072	details
Muscle	Detected but not Quantified	Not Applicable	Not Available	Bovine	23871026	details
Oocyte	Detected but not Quantified	Not Applicable	Not Available	Ovine	10793638	details
Oocyte (zona-intact oocytes)	Detected but not Quantified	Not Applicable	Not Available	Bovine	10793638	details
Oocyte (zona-intact oocytes)	Detected but not Quantified	Not Applicable	Not Available	Porcine	10793638	details
Oocyte (zona-intact oocytes)	Detected but not Quantified	Not Applicable	Not Available	Porcine	10793638	details
Plasma	Detected but not Quantified	Not Applicable	Not Available	Bovine	25913299	details
Plasma	Detected but not Quantified	Not Applicable	Not Available	Bovine	5409465	details
Plasma	Detected but not Quantified	Not Applicable	Not Available	Porcine	20231903	details
Ruminal Fluid	Detected and Quantified	3.5 +/- 2.6 uM	Not Available	Bovine	Saleem F, Bouatra...	details
Serum	Detected but not Quantified	Not Applicable	Not Available	Porcine	23255817	details
Serum	Detected but not Quantified	Not Applicable	Not Available	Porcine	22761248	details