Livestock Metabolome Database: Showing metabocard for Arachidonic acid (LMDB00294)

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

Record Information

Version

1.0

Creation Date

2016-07-13 19:46:40 UTC

Update Date

2016-09-23 18:45:05 UTC

Lmdb

LMDB00294

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Arachidonic acid

Description

Arachidonic acid is a polyunsaturated, essential fatty acid. It is found in animal and animal fat as well as in the liver, brain, and glandular organs, and is a constituent of animal phosphatides. It is formed by the synthesis from dietary linoleic acid. Arachidonic acid mediates inflammation and the functioning of several organs and systems either directly or upon its conversion into eicosanoids. Arachidonic acid in cell membrane phospholipids is the substrate for the synthesis of a range of biologically active compounds (eicosanoids) including prostaglandins, thromboxanes, and leukotrienes. These compounds can act as mediators in their own right and can also act as regulators of other processes, such as platelet aggregation, blood clotting, smooth muscle contraction, leukocyte chemotaxis, inflammatory cytokine production, and immune function. Arachidonic acid can be metabolized by cytochrome p450 (CYP450) enzymes to 5,6-, 8,9-, 11,12-, and 14,15-epoxyeicosatrienoic acids (EETs), their corresponding dihydroxyeicosa-trienoic acids (DHETs), and 20-hydroxyeicosatetraenoic acid (20-HETE). The production of kidney CYP450 arachidonic acid metabolites is altered in diabetes, pregnancy, hepatorenal syndrome, and in various models of hypertension, and it is likely that changes in this system contribute to the abnormalities in renal function that are associated with many of these conditions. Phospholipase A2 (PLA2) catalyzes the hydrolysis of the sn-2 position of membrane glycerophospholipids to liberate arachidonic acid (PMID: 12736897 , 12736897 , 12700820 , 12570747 , 12432908 ).

Structure

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

Synonyms

Value	Source
(5Z,8Z,11Z,14Z)-5,8,11,14-Icosatetraenoic acid	ChEBI
(5Z,8Z,11Z,14Z)-Icosatetraenoic acid	ChEBI
AA	ChEBI
all-cis-5,8,11,14-Eicosatetraenoic acid	ChEBI
ARA	ChEBI
Arachidonate	ChEBI
Arachidonsaeure	ChEBI
cis-5,8,11,14-Eicosatetraenoic acid	ChEBI
cis-Delta(5,8,11,14)-Eicosatetraenoic acid	ChEBI
5Z,8Z,11Z,14Z-Eicosatetraenoic acid	Kegg
(5Z,8Z,11Z,14Z)-Icosa-5,8,11,14-tetraenoic acid	Kegg
(5Z,8Z,11Z,14Z)-5,8,11,14-Icosatetraenoate	Generator
(5Z,8Z,11Z,14Z)-Icosatetraenoate	Generator
all-cis-5,8,11,14-Eicosatetraenoate	Generator
cis-5,8,11,14-Eicosatetraenoate	Generator
cis-delta(5,8,11,14)-Eicosatetraenoate	Generator
cis-Δ(5,8,11,14)-eicosatetraenoate	Generator
cis-Δ(5,8,11,14)-eicosatetraenoic acid	Generator
5Z,8Z,11Z,14Z-Eicosatetraenoate	Generator
(5Z,8Z,11Z,14Z)-Icosa-5,8,11,14-tetraenoate	Generator
(all-Z)-5,8,11,14-Eicosatetraenoate	HMDB
(all-Z)-5,8,11,14-Eicosatetraenoic acid	HMDB
5,8,11,14-all-cis-Eicosatetraenoate	HMDB
5,8,11,14-all-cis-Eicosatetraenoic acid	HMDB
5,8,11,14-Eicosatetraenoate	HMDB
5,8,11,14-Eicosatetraenoic acid	HMDB
5-cis,8-cis,11-cis,14-cis-Eicosatetraenoate	HMDB
5-cis,8-cis,11-cis,14-cis-Eicosatetraenoic acid	HMDB
cis-D5,8,11,14-Eicosatetraenoate	HMDB
cis-D5,8,11,14-Eicosatetraenoic acid	HMDB
Immunocytophyte	HMDB
Arachidonate, sodium	HMDB
Arachidonic acid, (all-Z)-isomer, 3H-labeled	HMDB
Arachidonic acid, ammonium salt, (all-Z)-isomer	HMDB
Arachidonic acid, cerium salt, (all-Z)-isomer	HMDB
Arachidonic acid, sodium salt	HMDB
Arachidonic acid, sodium salt, (all-Z)-isomer	HMDB
Vitamin F	HMDB
Arachidonic acid, cesium salt, (all-Z)-isomer	HMDB
Arachidonic acid, lithium salt, (all-Z)-isomer	HMDB
Arachidonic acid, potassium salt, (all-Z)-isomer	HMDB
Sodium arachidonate	HMDB
Arachidonic acid, (all-Z)-isomer, 1-(14)C-labeled	HMDB
Arachidonic acid, zinc salt, (all-Z)-isomer	HMDB
FA(20:4(5Z,8Z,11Z,14Z))	HMDB
FA(20:4n6)	HMDB

Chemical Formula

C₂₀H₃₂O₂

Average Molecular Weight

304.4669

Monoisotopic Molecular Weight

304.240230268

IUPAC Name

(5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoic acid

Traditional Name

arachidonic acid

CAS Registry Number

506-32-1

SMILES

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

InChI Identifier

InChI=1S/C20H32O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20(21)22/h6-7,9-10,12-13,15-16H,2-5,8,11,14,17-19H2,1H3,(H,21,22)/b7-6-,10-9-,13-12-,16-15-

InChI Key

YZXBAPSDXZZRGB-DOFZRALJSA-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

long-chain fatty acid (CHEBI:15843 )
omega-6 fatty acid (CHEBI:15843 )
icosa-5,8,11,14-tetraenoic acid (CHEBI:15843 )
Unsaturated fatty acids (C00219 )
Polyunsaturated fatty acids (C00219 )
Unsaturated fatty acids (LMFA01030001 )

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	6.8	ALOGPS
logP	6.59	ChemAxon
logS	-6.3	ALOGPS
pKa (Strongest Acidic)	4.82	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	99.95 m³·mol⁻¹	ChemAxon
Polarizability	37.2 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)	splash10-005c-9800000000-87c290971fc8a628fb23	Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-005c-9800000000-87c290971fc8a628fb23	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0006-6900000000-6870df266b6c73f2a4a1	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-7390000000-7004b9cd28a9b3d9c991	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-05i9-9252000000-475d13959ee8ce889646	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 - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative	splash10-0nmi-0913000000-95846e8d5e8afd29664b	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF 10V, Negative	splash10-005l-0902100000-6fc8730bd28daa779b66	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF 20V, Negative	splash10-005l-0902100000-6fc8730bd28daa779b66	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF , Negative	splash10-005l-0902100000-6fc8730bd28daa779b66	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF 10V, Negative	splash10-0udi-0009000000-4dd23c77f8e48c0ab9ec	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF 30V, Negative	splash10-0udi-0009000000-4dd23c77f8e48c0ab9ec	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF 10V, Negative	splash10-0udi-0009000000-6bd9d0477c122d3eed94	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF 20V, Negative	splash10-0udi-0009000000-510ea33e558fa238a1d2	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF , Negative	splash10-0udi-0009000000-73a6b21464acba15463c	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF 10V, Negative	splash10-0udi-0009000000-4dd23c77f8e48c0ab9ec	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF 30V, Negative	splash10-0udi-0049000000-102d050109d3c78b1a25	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-IT , negative	splash10-0a4i-0090000000-2fb9003e782ec3d05e20	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-0nmi-0913000000-95846e8d5e8afd29664b	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-TOF , negative	splash10-0udi-0009000000-6bd9d0477c122d3eed94	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-TOF , negative	splash10-0udi-0009000000-510ea33e558fa238a1d2	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-TOF , negative	splash10-0udi-0049000000-102d050109d3c78b1a25	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-0udi-0009000000-6bd9d0477c122d3eed94	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-0udi-0009000000-510ea33e558fa238a1d2	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 6V, Positive	splash10-0a4i-1934000000-3fb5938d1b4795217a97	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4r-1196000000-a42ea66033eb9771d36d	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4j-5691000000-2bc7b1ae5487233dfce8	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0007-7950000000-b15a8d382a4b3ad62d08	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-0029000000-28a9bbfed5fabd10c0c2	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0zfr-2079000000-3f6e64ef7522a793e9a9	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-9130000000-9c0c8bb5fc8e30bf53c7	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H 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
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	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	200 mg/kg	Not Available	Bovine	M.J. Abarghuei, Y...	details
Milk	Detected and Quantified	400 mg/kg	Not Available	Bovine	M.J. Abarghuei, Y...	details
Milk	Detected and Quantified	500 mg/kg	Not Available	Bovine	M.J. Abarghuei, Y...	details
Milk	Detected and Quantified	500 mg/kg	Not Available	Bovine	M.J. Abarghuei, Y...	details
Milk	Detected but not Quantified	Not Applicable	Not Available	Bovine	Kurt J. Boudonck,...	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	Porcine	20231903	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
Serum	Detected and Quantified	0.00367 +/- 0.000125 uM	Not Available	Porcine	19847666	details
Serum	Detected and Quantified	0.00302 +/- 0.000230 uM	Not Available	Porcine	19847666	details

External Links

DrugBank ID

DB04557

HMDB ID

HMDB0001043

FooDB ID

FDB011872

Phenol Explorer ID

Not Available

KNApSAcK ID

BiGG ID

BioCyc ID

METLIN ID

PDB ID

Not Available

Wikipedia Link

Chemspider ID

ChEBI ID

PubChem Compound ID

Kegg Compound ID

YMDB ID

Not Available

ECMDB ID

M2MDB004816

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Pompeia C, Lima T, Curi R: Arachidonic acid cytotoxicity: can arachidonic acid be a physiological mediator of cell death? Cell Biochem Funct. 2003 Jun;21(2):97-104. [12736897 ]
Calder PC: Long-chain n-3 fatty acids and inflammation: potential application in surgical and trauma patients. Braz J Med Biol Res. 2003 Apr;36(4):433-46. Epub 2003 Apr 8. [12700820 ]
Zhao X, Imig JD: Kidney CYP450 enzymes: biological actions beyond drug metabolism. Curr Drug Metab. 2003 Feb;4(1):73-84. [12570747 ]
Kudo I, Murakami M: Phospholipase A2 enzymes. Prostaglandins Other Lipid Mediat. 2002 Aug;68-69:3-58. [12432908 ]

Showing metabocard for Arachidonic acid (LMDB00294)

Structure for LMDB00294 (Arachidonic acid)