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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2006-05-22 14:17:42 UTC
Update Date2018-01-04 03:30:40 UTC
HMDB IDHMDB0002212
Secondary Accession Numbers
  • HMDB02212
Metabolite Identification
Common NameArachidic acid
DescriptionArachidic acid also called eicosanoic acid is a saturated fatty acid found in peanut oil. It can be formed by the hydrogenation of arachidonic acid. It is practically insoluble in water and stable under ordinary conditions -- Wikipedia.
Structure
Thumb
Synonyms
ValueSource
Arachidinic acidChEBI
ArachinsaeureChEBI
C20:0ChEBI
CH3-[CH2]18-COOHChEBI
Eicosanoic acidChEBI
Eicosoic acidChEBI
Icosanoic acidChEBI
N-Eicosanoic acidChEBI
ArachidinateGenerator
ArachidateGenerator
EicosanoateGenerator
EicosoateGenerator
IcosanoateGenerator
N-EicosanoateGenerator
ArachateHMDB
Arachic acidHMDB
Arachidic acid, sodium saltMeSH
Arachidic acid, calcium saltMeSH
Zinc arachidateMeSH
Arachidic acid, magnesium saltMeSH
Arachidic acid, ammonium saltMeSH
Arachidic acid, barium saltMeSH
Arachidic acid, potassium saltMeSH
Chemical FormulaC20H40O2
Average Molecular Weight312.5304
Monoisotopic Molecular Weight312.302830524
IUPAC Nameicosanoic acid
Traditional Namearachidic acid
CAS Registry Number506-30-9
SMILES
CCCCCCCCCCCCCCCCCCCC(O)=O
InChI Identifier
InChI=1S/C20H40O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20(21)22/h2-19H2,1H3,(H,21,22)
InChI KeyVKOBVWXKNCXXDE-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as long-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms.
KingdomChemical entities
Super ClassOrganic compounds
ClassLipids and lipid-like molecules
Sub ClassFatty Acyls
Direct ParentLong-chain fatty acids
Alternative Parents
Substituents
  • Long-chain 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 FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Physiological effect

Health effect:

  Health condition:

Disposition

Biological Location:

  Subcellular:

  Biofluid and excreta:

  Cell and elements:

Source:

  Biological:

    Animal:

Route of exposure:

  Enteral:

Process

Naturally occurring process:

  Biological process:

    Cellular process:

    Chemical reaction:

    Biochemical process:

    Biochemical pathway:

Role

Indirect biological role:

Industrial application:

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point75.4 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP9.29SANGSTER (1993)
Predicted Properties
PropertyValueSource
Water Solubility5.0e-05 g/LALOGPS
logP8.53ALOGPS
logP8.03ChemAxon
logS-6.8ALOGPS
pKa (Strongest Acidic)4.95ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count18ChemAxon
Refractivity95.49 m³·mol⁻¹ChemAxon
Polarizability42.91 ųChemAxon
Number of Rings0ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-0159-0900000000-cc7f30812c4ef45583b1View in MoNA
GC-MSGC-MS Spectrum - GC-MS (1 TMS)splash10-0159-2901000000-7d146c5d993118307ce5View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0596-9100000000-53a544b7fbf2ee3b176aView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0159-0900000000-cc7f30812c4ef45583b1View in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0159-2901000000-7d146c5d993118307ce5View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-014i-1900000000-33733dae76fd89dc7394View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9450000000-ff95bd6be578f2c72ce9View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0109-9560000000-d2d19ad6d5ef54fdf90aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-03di-0029000000-273e657da59fa67385c2View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0a4i-9200000000-84b07a6d22109c441336View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0a4i-9100000000-9d6e321e2bf8cd1f20e4View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-03di-0009000000-d7e3408b3b2e854229b0View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-03di-0109000000-c0ed9d28e54855b40069View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-0a6r-0013493000-832a78a9cf97d74660eaView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-06vi-0012391000-e4dcf31aba99059fcf39View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-0a4i-0193000000-031626259c4a17016165View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-0a4i-0091000000-9389b44ea9cfe1afe40bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0092000000-c40a8544a31d253f26c6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0i01-2491000000-60bf2b9a6912f287f6f0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0zfu-8970000000-fd0569abd03da6142ee2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0092000000-c40a8544a31d253f26c6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0i01-2491000000-60bf2b9a6912f287f6f0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0zfu-8970000000-fd0569abd03da6142ee2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0049000000-54fd1cf54bdd386d406eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03xu-1095000000-2584a862e47ea0cb88f2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052f-9140000000-2caaff4da05fbcb0fdf7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0049000000-54fd1cf54bdd386d406eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03xu-1095000000-2584a862e47ea0cb88f2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052f-9140000000-2caaff4da05fbcb0fdf7View in MoNA
MSMass Spectrum (Electron Ionization)splash10-0596-9100000000-091619221e36a7a177ffView in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane (predicted from logP)
Biofluid Locations
  • Blood
  • Feces
Tissue LocationNot Available
PathwaysNot Available
NameSMPDB/PathwhizKEGG
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified12.8 +/- 3.2 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified9.6 +/- 6.3 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified6.4 +/- 3.2 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified3.2 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified9.599 +/- 6.399 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified9.599 +/- 3.200 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified6.399 +/- 3.200 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified3.200 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified11.743 +/- 6.655 uMAdult (>18 years old)FemaleNormal details
BloodDetected and Quantified0.238 +/- 0.002 uMAdult (>18 years old)BothNormal details
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected but not Quantified Adult (>18 years old)Both
Schizophrenia
details
FecesDetected but not Quantified Adult (>18 years old)BothColorectal Cancer details
Associated Disorders and Diseases
Disease References
Schizophrenia
  1. Al Awam K, Haussleiter IS, Dudley E, Donev R, Brune M, Juckel G, Thome J: Multiplatform metabolome and proteome profiling identifies serum metabolite and protein signatures as prospective biomarkers for schizophrenia. J Neural Transm (Vienna). 2015 Aug;122 Suppl 1:S111-22. doi: 10.1007/s00702-014-1224-0. Epub 2014 May 1. [PubMed:24789758 ]
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB002927
KNApSAcK IDC00001209
Chemspider ID10035
KEGG Compound IDC06425
BioCyc IDARACHIDIC_ACID
BiGG ID48230
Wikipedia LinkArachidic_acid
METLIN ID401
PubChem Compound10467
PDB IDDCR
ChEBI ID28822
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Dray F: Sensitivity and specificity of eicosanoid radioimmunoassays: new strategy. Br J Dermatol. 1983 Jul;109 Suppl 25:36-40. [PubMed:6860583 ]
  2. Onodera Y, Kawaguchi T, Itoh H: Fatty acid of cerebrospinal fluid in arrested hydrocephalus. Childs Brain. 1982;9(2):95-101. [PubMed:7094674 ]

Only showing the first 10 proteins. There are 71 proteins in total.

Enzymes

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
General function:
Involved in phospholipase A2 activity
Specific function:
PA2 catalyzes the calcium-dependent hydrolysis of the 2-acyl groups in 3-sn-phosphoglycerides. This isozyme hydrolyzes more efficiently L-alpha-1-palmitoyl-2-oleoyl phosphatidylcholine than L-alpha-1-palmitoyl-2-arachidonyl phosphatidylcholine, L-alpha-1-palmitoyl-2-arachidonyl phosphatidylethanolamine, or L-alpha-1-stearoyl-2-arachidonyl phosphatidylinositol. May be involved in the production of lung surfactant, the remodeling or regulation of cardiac muscle.
Gene Name:
PLA2G5
Uniprot ID:
P39877
Molecular weight:
15674.065
General function:
Involved in phospholipase A2 activity
Specific function:
PA2 catalyzes the calcium-dependent hydrolysis of the 2-acyl groups in 3-sn-phosphoglycerides. Hydrolyzes phosphatidylglycerol versus phosphatidylcholine with a 15-fold preference.
Gene Name:
PLA2G2F
Uniprot ID:
Q9BZM2
Molecular weight:
23256.29
General function:
Involved in metabolic process
Specific function:
Selectively hydrolyzes arachidonyl phospholipids in the sn-2 position releasing arachidonic acid. Together with its lysophospholipid activity, it is implicated in the initiation of the inflammatory response.
Gene Name:
PLA2G4A
Uniprot ID:
P47712
Molecular weight:
85210.19
General function:
Involved in phospholipase A2 activity
Specific function:
PA2 catalyzes the calcium-dependent hydrolysis of the 2-acyl groups in 3-sn-phosphoglycerides.
Gene Name:
PLA2G1B
Uniprot ID:
P04054
Molecular weight:
16359.535
General function:
Involved in phospholipase A2 activity
Specific function:
PA2 catalyzes the calcium-dependent hydrolysis of the 2-acyl groups in 3-sn-phosphoglycerides. Has a powerful potency for releasing arachidonic acid from cell membrane phospholipids. Prefers phosphatidylethanolamine and phosphatidylcholine liposomes to those of phosphatidylserine.
Gene Name:
PLA2G10
Uniprot ID:
O15496
Molecular weight:
18153.04
General function:
Involved in sugar binding
Specific function:
Has lysophospholipase activity.
Gene Name:
LGALS13
Uniprot ID:
Q9UHV8
Molecular weight:
16118.44
General function:
Involved in phospholipase A2 activity
Specific function:
PA2 catalyzes the calcium-dependent hydrolysis of the 2-acyl groups in 3-sn-phosphoglycerides. Has a preference for arachidonic-containing phospholipids.
Gene Name:
PLA2G2E
Uniprot ID:
Q9NZK7
Molecular weight:
15988.525
General function:
Involved in phospholipase A2 activity
Specific function:
PA2 catalyzes the calcium-dependent hydrolysis of the 2-acyl groups in 3-sn-phosphoglycerides. Does not exhibit detectable activity toward sn-2-arachidonoyl- or linoleoyl-phosphatidylcholine or -phosphatidylethanolamine.
Gene Name:
PLA2G12A
Uniprot ID:
Q9BZM1
Molecular weight:
21066.99
General function:
Involved in metabolic process
Specific function:
Catalyzes the release of fatty acids from phospholipids. It has been implicated in normal phospholipid remodeling, nitric oxide-induced or vasopressin-induced arachidonic acid release and in leukotriene and prostaglandin production. May participate in fas mediated apoptosis and in regulating transmembrane ion flux in glucose-stimulated B-cells. Has a role in cardiolipin (CL) deacylation. Required for both speed and directionality of monocyte MCP1/CCL2-induced chemotaxis through regulation of F-actin polymerization at the pseudopods. Isoform ankyrin-iPLA2-1 and isoform ankyrin-iPLA2-2, which lack the catalytic domain, are probably involved in the negative regulation of iPLA2 activity.
Gene Name:
PLA2G6
Uniprot ID:
O60733
Molecular weight:
84092.635

Transporters

General function:
Lipid transport and metabolism
Specific function:
Involved in translocation of long-chain fatty acids (LFCA) across the plasma membrane. The LFCA import appears to be hormone-regulated in a tissue-specific manner. In adipocytes, but not myocytes, insulin induces a rapid translocation of FATP1 from intracellular compartments to the plasma membrane, paralleled by increased LFCA uptake. May act directly as a bona fide transporter, or alternatively, in a cytoplasmic or membrane- associated multimeric protein complex to trap and draw fatty acids towards accumulation. Plays a pivotal role in regulating available LFCA substrates from exogenous sources in tissues undergoing high levels of beta-oxidation or triglyceride synthesis. May be involved in regulation of cholesterol metabolism. Has acyl-CoA ligase activity for long-chain and very-long-chain fatty acids
Gene Name:
SLC27A1
Uniprot ID:
Q6PCB7
Molecular weight:
71107.5

Only showing the first 10 proteins. There are 71 proteins in total.