Livestock Metabolome Database: Showing metabocard for Erucic acid (LMDB00378)

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

Record Information

Version

1.0

Creation Date

2016-07-13 19:48:30 UTC

Update Date

2016-09-23 18:45:18 UTC

Lmdb

LMDB00378

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Erucic acid

Description

Erucic acid is a monounsaturated omega-9 fatty acid found mainly in the Brassica family of plants such as canola, rapeseed, wallflower seed, mustard seed as well as Brussels spouts and broccoli. Some Brassica cultivars can have up to 40 to 50 percent of their oil recovered as erucic acid. Erucic acid is also known as cis-13-docosenoic acid. The trans isomer is known as brassidic acid. Erucic acid occurs in nature only along with bitter-tasting compounds. Erucic acid has many of the same uses as mineral oils but with the advantage that it is more readily bio-degradable. Its high tolerance to temperature makes it suitable for transmission oil. Its ability to polymerize and dry means it can be - and is - used as a binder for oil paints. Increased levels of eicosenoic acid (20:ln9) and erucic acid (22:1n9) have been found in the red blood cell membranes of autistic subjects with developmental regression (PMID: 16581239 ). Erucic acid is broken down long-chain acyl-coenzyme A (CoA) dehydrogenase, which is produced in the liver. This enzyme breaks this long chain fatty acid into shorter-chain fatty acids. animal infants have relatively low amounts of this enzyme and because of this, babies should not be given foods high in erucic acid.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(13Z)-13-Docosenoic acid	ChEBI
(13Z)-Docosenoic acid	ChEBI
(Z)-13-Docosenoic acid	ChEBI
(Z)-Docos-13-enoic acid	ChEBI
13-cis-Docosenoic acid	ChEBI
22:1Omega9	ChEBI
C22:1N-9	ChEBI
cis-13-Docosenoic acid	ChEBI
cis-Delta(13)-Docosenoic acid	ChEBI
cis-Eruic acid	ChEBI
Docos-13C-enoic acid	ChEBI
Erucasaeure	ChEBI
(13Z)-13-Docosenoate	Generator
(13Z)-Docosenoate	Generator
(Z)-13-Docosenoate	Generator
(Z)-Docos-13-enoate	Generator
13-cis-Docosenoate	Generator
cis-13-Docosenoate	Generator
cis-delta(13)-Docosenoate	Generator
cis-Δ(13)-docosenoate	Generator
cis-Δ(13)-docosenoic acid	Generator
cis-Eruate	Generator
Docos-13C-enoate	Generator
Erucate	Generator
13-Docosenoic acid	HMDB
Erucic acid, (Z)-isomer	HMDB
13-Docosenoate	HMDB
13-Docosenoic acid (acd/name 4.0)	HMDB
cis-Erucic acid	HMDB
delta 13-cis-Docosenoate	HMDB
delta 13-cis-Docosenoic acid	HMDB
Delta.13-cis-docosenoate	HMDB
Delta.13-cis-docosenoic acid	HMDB
Prifrac 2990	HMDB
(Z)-Erucic acid	HMDB
13(Z)-Docosenoic acid	HMDB
FA(22:1(13Z))	HMDB
FA(22:1n9)	HMDB
cis-13-Erucic acid	HMDB
delta13-cis-Docosenoic acid	HMDB
Δ13-cis-docosenoic acid	HMDB
Erucic acid	HMDB

Chemical Formula

C₂₂H₄₂O₂

Average Molecular Weight

338.5677

Monoisotopic Molecular Weight

338.318480588

IUPAC Name

(13Z)-docos-13-enoic acid

Traditional Name

erucic acid

CAS Registry Number

112-86-7

SMILES

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

InChI Identifier

InChI=1S/C22H42O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22(23)24/h9-10H,2-8,11-21H2,1H3,(H,23,24)/b10-9-

InChI Key

DPUOLQHDNGRHBS-KTKRTIGZSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as very long-chain fatty acids. These are fatty acids with an aliphatic tail that contains at least 22 carbon atoms.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acids and conjugates

Direct Parent

Very long-chain fatty acids

Alternative Parents

Substituents

Very 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

docosenoic acid (CHEBI:28792 )
Unsaturated fatty acids (C08316 )
Monounsaturated fatty acids (C08316 )
Unsaturated fatty acids (LMFA01030089 )

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	8.97	ALOGPS
logP	8.56	ChemAxon
logS	-7.2	ALOGPS
pKa (Strongest Acidic)	4.95	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	19	ChemAxon
Refractivity	105.81 m³·mol⁻¹	ChemAxon
Polarizability	45.6 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-MS (1 TMS)	splash10-00nb-6900000000-5e6160a7a5341d6f55de	Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-00nb-6900000000-5e6160a7a5341d6f55de	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9670000000-abb8d10b97d3c63c8480	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-0fmv-9452000000-be430773e3b82d00352d	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 (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, N/A (Annotated)	splash10-000i-0009000000-c637d7d9283da6dae58c	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, N/A (Annotated)	splash10-05ur-9100000000-4dfe9f552da0b8ea6e7c	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, N/A (Annotated)	splash10-0159-9000000000-867fce64ced7de3a289e	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - n/a 23V, negative	splash10-014i-0009000000-a67df2342edb038f0647	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 4V, positive	splash10-000i-0019000000-0026b53b7b328f5e5154	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 6V, positive	splash10-00dr-1119000000-fa6979100366edcb2892	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 8V, positive	splash10-0fki-5829000000-ff16fd0e5a988fe38fa4	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 20V, positive	splash10-0apj-9200000000-27116cd4b609b88b4005	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 27V, positive	splash10-0api-9100000000-0f82260b5b86e3b06b2a	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 33V, positive	splash10-0aor-9000000000-0a3061b18adfe4ddad07	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - n/a 23V, positive	splash10-00di-0129000000-fa49cfc1738521b925d3	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - n/a 23V, positive	splash10-000i-0290000000-b4f9a52c100defbf8a39	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - n/a 23V, positive	splash10-014i-0090000000-02a20bc6ce898cb3824c	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - n/a 23V, positive	splash10-07l5-0950000000-0ca01024ab3b5ad027ec	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - n/a 23V, positive	splash10-0udi-0319000000-7b31f345d0546a6c25ab	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 10V, positive	splash10-00di-2209000000-d03f3b30c822ce8c5e26	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 12V, positive	splash10-00di-9608000000-2fc5f27c0bd54f0c003a	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 14V, positive	splash10-059t-9502000000-8f68c9dbb8e1467805f7	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 16V, positive	splash10-05nb-9300000000-0701894bd7e9b3d37f40	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00di-0019000000-c06b5c8f2b9044af1c34	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00g3-5695000000-55896e489497235f6a67	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-004l-9880000000-69f41c34dca989e6c810	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-0019000000-cfb3c7afc93ecf28f3da	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00ku-1039000000-c2dd9360fea23806c313	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-052f-9131000000-393859815e6c1359d6df	Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0a5c-9300000000-53ce9b6b1bd7db601866	Spectrum
1D NMR	1H NMR Spectrum	Not Available	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

Milk
Oocyte
Oocyte (zona-intact oocytes)

Concentrations

Biofluid	Status	Value	Condition	Species	Reference	Details
Milk	Detected and Quantified	0 mg/kg	Not Available	Bovine	M.J. Abarghuei, Y...	details
Milk	Detected and Quantified	60 mg/kg	Not Available	Bovine	M.J. Abarghuei, Y...	details
Milk	Detected and Quantified	80 mg/kg	Not Available	Bovine	M.J. Abarghuei, Y...	details
Milk	Detected and Quantified	100 mg/kg	Not Available	Bovine	M.J. Abarghuei, Y...	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
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

External Links

DrugBank ID

Not Available

HMDB ID

HMDB0002068

FooDB ID

FDB004287

Phenol Explorer ID

Not Available

KNApSAcK ID

C00001217

BiGG ID

Not Available

BioCyc ID

CPD-14292

METLIN ID

6470

PDB ID

Not Available

Wikipedia Link

Chemspider ID

ChEBI ID

PubChem Compound ID

Kegg Compound ID

YMDB ID

Not Available

ECMDB ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Bu B, Ashwood P, Harvey D, King IB, Water JV, Jin LW: Fatty acid compositions of red blood cell phospholipids in children with autism. Prostaglandins Leukot Essent Fatty Acids. 2006 Apr;74(4):215-21. [16581239 ]

Showing metabocard for Erucic acid (LMDB00378)

Structure for LMDB00378 (Erucic acid)