CHEBI:28822 - icosanoic acid

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ChEBI Name icosanoic acid
ChEBI ID CHEBI:28822
Definition A C20 striaght-chain saturated fatty acid which forms a minor constituent of peanut (L. arachis) and corn oils. Used as an organic thin film in the production of liquid crystals for a wide variety of technical applications.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:2798, CHEBI:24763
Supplier Information ChemicalBook:CB1300110, eMolecules:3716409
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Carbon monoxide (chemical formula CO) is a poisonous, flammable gas that is colorless, odorless, tasteless, and slightly less dense than air. Carbon monoxide consists of one carbon atom and one oxygen atom connected by a triple bond. It is the simplest carbon oxide. In coordination complexes, the carbon monoxide ligand is called carbonyl. It is a key ingredient in many processes in industrial chemistry. The most common source of carbon monoxide is the partial combustion of carbon-containing compounds. Numerous environmental and biological sources generate carbon monoxide. In industry, carbon monoxide is important in the production of many compounds, including drugs, fragrances, and fuels. Indoors CO is one of the most acutely toxic contaminants affecting indoor air quality. CO may be emitted from tobacco smoke and generated from malfunctioning fuel burning stoves (wood, kerosene, natural gas, propane) and fuel burning heating systems (wood, oil, natural gas) and from blocked flues connected to these appliances. Carbon monoxide poisoning is the most common type of fatal air poisoning in many countries. Carbon monoxide has important biological roles across phylogenetic kingdoms. It is produced by many organisms, including humans. In mammalian physiology, carbon monoxide is a classical example of hormesis where low concentrations serve as an endogenous neurotransmitter (gasotransmitter) and high concentrations are toxic resulting in carbon monoxide poisoning. It is isoelectronic with both cyanide anion CN− and molecular nitrogen N2.
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Formula C20H40O2
Net Charge 0
Average Mass 312.53040
Monoisotopic Mass 312.30283
InChI 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)
InChIKey VKOBVWXKNCXXDE-UHFFFAOYSA-N
SMILES CCCCCCCCCCCCCCCCCCCC(O)=O
Roles Classification
Chemical Role(s): Bronsted acid
A molecular entity capable of donating a hydron to an acceptor (Bronsted base).
(via oxoacid )
Biological Role(s): plant metabolite
Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
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ChEBI Ontology
Outgoing icosanoic acid (CHEBI:28822) has role plant metabolite (CHEBI:76924)
icosanoic acid (CHEBI:28822) is a long-chain fatty acid (CHEBI:15904)
icosanoic acid (CHEBI:28822) is a straight-chain saturated fatty acid (CHEBI:39418)
icosanoic acid (CHEBI:28822) is conjugate acid of icosanoate (CHEBI:32360)
Incoming α-D-Gal-(1→4)-β-D-Gal-(1→4)-β-D-Glc-(1↔1')-Cer(d18:1/20:0) (CHEBI:84692) has functional parent icosanoic acid (CHEBI:28822)
α-Neu5Ac-(2→3)-β-D-Gal-(1→3)-β-D-GalNAc-(1→4)-[α-Neu5Ac-(2→3)]-β-D-Gal-(1→4)-β-D-Glc-(1↔1')-Cer(d18:1/20:0) (CHEBI:84657) has functional parent icosanoic acid (CHEBI:28822)
α-Neu5Ac-(2→3)-β-D-Gal-(1→4)-β-D-Glc-(1↔1')-Cer(d18:1/20:0) (CHEBI:84676) has functional parent icosanoic acid (CHEBI:28822)
β-D-galactosyl-(1→4)-β-D-glucosyl-(1↔1)-N-eicosanoylsphingosine (CHEBI:84761) has functional parent icosanoic acid (CHEBI:28822)
β-D-galactosyl-(1↔1ʼ)-N-eicosanoylsphinganine (CHEBI:84704) has functional parent icosanoic acid (CHEBI:28822)
β-D-galactosyl-(1↔1ʼ)-N-icosanoyl-(4E,14Z)-sphingadienine (CHEBI:132455) has functional parent icosanoic acid (CHEBI:28822)
β-D-galactosyl-N-eicosanoylsphingosine (CHEBI:84722) has functional parent icosanoic acid (CHEBI:28822)
β-D-glucosyl-(1↔1ʼ)-N-eicosanoylsphinganine (CHEBI:84703) has functional parent icosanoic acid (CHEBI:28822)
β-D-glucosyl-(1↔1ʼ)-N-icosanoyl-(4E,14Z)-sphingadienine (CHEBI:132456) has functional parent icosanoic acid (CHEBI:28822)
β-D-glucosyl-N-eicosanoylsphingosine (CHEBI:84721) has functional parent icosanoic acid (CHEBI:28822)
(19R)-19-hydroxyicosanoic acid (CHEBI:79015) has functional parent icosanoic acid (CHEBI:28822)
(R)-icosanoylcarnitine (CHEBI:84645) has functional parent icosanoic acid (CHEBI:28822)
1-α-linolenoyl-2-icosanoyl-sn-glycerol (CHEBI:89241) has functional parent icosanoic acid (CHEBI:28822)
1-[(8Z,11Z,14Z,17Z)-icosatetraenoyl]-2-icosanoyl-sn-glycero-3-phospho-1D-myo-inositol (CHEBI:89244) has functional parent icosanoic acid (CHEBI:28822)
1-[(9Z)-octadecenoyl]-2-eicosanoyl-sn-glycero-3-phosphocholine (CHEBI:86172) has functional parent icosanoic acid (CHEBI:28822)
1-[(9Z,12Z)-octadecadienoyl]-2-icosanoyl-sn-glycerol (CHEBI:86985) has functional parent icosanoic acid (CHEBI:28822)
1-docosanoyl-2-eicosanoyl-sn-glycero-3-phosphocholine (CHEBI:86210) has functional parent icosanoic acid (CHEBI:28822)
1-eicosanoyl-2-[(11Z)-eicosenoyl]-sn-glycero-3-phosphocholine (CHEBI:86188) has functional parent icosanoic acid (CHEBI:28822)
1-eicosanoyl-2-[(11Z)-octadecenoyl]-sn-glycero-3-phosphocholine (CHEBI:86170) has functional parent icosanoic acid (CHEBI:28822)
1-eicosanoyl-2-[(11Z,14Z)-eicosadienoyl]-sn-glycero-3-phosphocholine (CHEBI:86199) has functional parent icosanoic acid (CHEBI:28822)
1-eicosanoyl-2-[(11Z,14Z,17Z)-eicosatrienoyl]-sn-glycero-3-phosphocholine (CHEBI:86416) has functional parent icosanoic acid (CHEBI:28822)
1-eicosanoyl-2-[(13Z)-docosenoyl]-sn-glycero-3-phosphocholine (CHEBI:86216) has functional parent icosanoic acid (CHEBI:28822)
1-eicosanoyl-2-[(4Z,7Z,10Z,13Z,16Z,19Z)-docosahexaenoyl]-sn-glycero-3-phosphocholine (CHEBI:86221) has functional parent icosanoic acid (CHEBI:28822)
1-eicosanoyl-2-[(7Z,10Z,13Z,16Z,19Z)-docosapentaenoyl]-sn-glycero-3-phosphocholine (CHEBI:86220) has functional parent icosanoic acid (CHEBI:28822)
1-eicosanoyl-2-[(9Z)-octadecenoyl]-sn-glycero-3-phosphocholine (CHEBI:86171) has functional parent icosanoic acid (CHEBI:28822)
1-eicosanoyl-2-docosanoyl-sn-glycero-3-phosphocholine (CHEBI:86211) has functional parent icosanoic acid (CHEBI:28822)
1-eicosanoyl-2-octadecanoyl-sn-glycero-3-phosphocholine (CHEBI:86166) has functional parent icosanoic acid (CHEBI:28822)
1-hexadecanoyl-2-icosanoyl-sn-glycero-3-phosphoethanolamine (CHEBI:134078) has functional parent icosanoic acid (CHEBI:28822)
1-hexadecyl-2-eicosanoyl-sn-glycero-3-phosphocholine (CHEBI:86240) has functional parent icosanoic acid (CHEBI:28822)
1-icosanoyl-2-[(5Z,8Z,11ZZ,14Z,17Z)-eicosapentaenoyl]-sn-glycerol (CHEBI:87225) has functional parent icosanoic acid (CHEBI:28822)
1-icosanoyl-2-arachidonoyl-sn-glycero-3-phosphate (CHEBI:77241) has functional parent icosanoic acid (CHEBI:28822)
1-icosanoyl-2-arachidonoyl-sn-glycero-3-phosphocholine (CHEBI:74970) has functional parent icosanoic acid (CHEBI:28822)
1-icosanoyl-2-arachidonoyl-sn-glycerol (CHEBI:87223) has functional parent icosanoic acid (CHEBI:28822)
1-icosanoyl-2-docosanoyl-sn-glycero-3-phospho-(1ʼ-sn-glycerol) (CHEBI:136386) has functional parent icosanoic acid (CHEBI:28822)
1-icosanoyl-2-hexadecanoyl-sn-glycero-3-phosphocholine (CHEBI:134227) has functional parent icosanoic acid (CHEBI:28822)
1-icosanoyl-2-oleoyl-sn-glycero-3-phosphate (CHEBI:74942) has functional parent icosanoic acid (CHEBI:28822)
1-icosanoyl-2-oleoyl-sn-glycerol (CHEBI:75470) has functional parent icosanoic acid (CHEBI:28822)
1-icosanoyl-2-palmitoyl-sn-glycero-3-phosphocholine (CHEBI:75294) has functional parent icosanoic acid (CHEBI:28822)
1-icosanoyl-2-tetradecanoyl-sn-glycero-3-phosphocholine (CHEBI:134231) has functional parent icosanoic acid (CHEBI:28822)
1-icosanoyl-sn-glycero-3-phosphate (CHEBI:74939) has functional parent icosanoic acid (CHEBI:28822)
1-icosanoyl-sn-glycero-3-phosphocholine (CHEBI:74968) has functional parent icosanoic acid (CHEBI:28822)
1-icosanoyl-sn-glycero-3-phosphoethanolamine (CHEBI:131690) has functional parent icosanoic acid (CHEBI:28822)
1-icosanoylglycerol (CHEBI:142495) has functional parent icosanoic acid (CHEBI:28822)
1-octadecanoyl-2-eicosanoyl-sn-glycero-3-phosphocholine (CHEBI:86167) has functional parent icosanoic acid (CHEBI:28822)
1-octadecyl-2-icosanoyl-sn-glycero-3-phosphocholine (CHEBI:74482) has functional parent icosanoic acid (CHEBI:28822)
1-oleoyl-2-icosanoyl-sn-glycero-3-phosphate (CHEBI:75134) has functional parent icosanoic acid (CHEBI:28822)
1-palmitoyl-2-icosanoyl-sn-glycero-3-phosphocholine (CHEBI:82943) has functional parent icosanoic acid (CHEBI:28822)
1-tetradecanoyl-2-icosanoyl-sn-glycero-3-phosphocholine (CHEBI:134218) has functional parent icosanoic acid (CHEBI:28822)
18-methylicosanoic acid (CHEBI:84877) has functional parent icosanoic acid (CHEBI:28822)
2-hydroxyarachidic acid (CHEBI:76992) has functional parent icosanoic acid (CHEBI:28822)
2-icosanoyl-sn-glycero-3-phosphoethanolamine (CHEBI:131691) has functional parent icosanoic acid (CHEBI:28822)
20-hydroxyicosanoic acid (CHEBI:79190) has functional parent icosanoic acid (CHEBI:28822)
3-hydroxyicosanoic acid (CHEBI:52347) has functional parent icosanoic acid (CHEBI:28822)
3-oxoicosanoic acid (CHEBI:52350) has functional parent icosanoic acid (CHEBI:28822)
N-(icosanoyl)-tetradecasphing-4-enine-1-phosphoethanolamine (CHEBI:86518) has functional parent icosanoic acid (CHEBI:28822)
N-(icosanoyl)ethanolamine (CHEBI:85253) has functional parent icosanoic acid (CHEBI:28822)
N-eicosanoylsphinganine (CHEBI:67027) has functional parent icosanoic acid (CHEBI:28822)
N-icosanoyl-(4E,14Z)-sphinga-4,14-dienine (CHEBI:134549) has functional parent icosanoic acid (CHEBI:28822)
N-icosanoyl-1-oleoyl-sn-glycero-3-phosphoethanolamine (CHEBI:85667) has functional parent icosanoic acid (CHEBI:28822)
N-icosanoyl-14-methylhexadecasphinganine (CHEBI:131543) has functional parent icosanoic acid (CHEBI:28822)
N-icosanoyl-sn-glycero-3-phosphoethanolamine (CHEBI:85669) has functional parent icosanoic acid (CHEBI:28822)
N-icosanoylglycine (CHEBI:87606) has functional parent icosanoic acid (CHEBI:28822)
N-icosanoylsphingosine (CHEBI:72962) has functional parent icosanoic acid (CHEBI:28822)
N-icosanoylsphingosine 1-phosphate (CHEBI:73140) has functional parent icosanoic acid (CHEBI:28822)
N-icosanoylsphingosine-1-phosphocholine (CHEBI:83359) has functional parent icosanoic acid (CHEBI:28822)
N-icosanoyltaurine (CHEBI:132480) has functional parent icosanoic acid (CHEBI:28822)
ethyl arachidate (CHEBI:84859) has functional parent icosanoic acid (CHEBI:28822)
(11Z,14Z)-icosadienoic acid (CHEBI:73731) has parent hydride icosanoic acid (CHEBI:28822)
icosanoate (CHEBI:32360) is conjugate base of icosanoic acid (CHEBI:28822)
icosanoyl group (CHEBI:22614) is substituent group from icosanoic acid (CHEBI:28822)
IUPAC Name
icosanoic acid
Synonyms Sources
arachic acid NIST Chemistry WebBook
arachidic acid NIST Chemistry WebBook
Arachidic acid KEGG COMPOUND
arachidinic acid ChEBI
Arachinsäure ChEBI
C20:0 ChEBI
CH3‒[CH2]18‒COOH IUPAC
eicosanoic acid KEGG COMPOUND
icosanoic acid KEGG COMPOUND
n-eicosanoic acid NIST Chemistry WebBook
Manual Xrefs Databases
Arachidic_acid Wikipedia
ARACHIDIC_ACID MetaCyc
C00001209 KNApSAcK
C06425 KEGG COMPOUND
CN102352348 Patent
DCR PDBeChem
HMDB0002212 HMDB
LMFA01010020 LIPID MAPS
WO2013000382 Patent
View more database links
Registry Numbers Types Sources
1788211 Reaxys Registry Number Reaxys
506-30-9 CAS Registry Number KEGG COMPOUND
506-30-9 CAS Registry Number ChemIDplus
506-30-9 CAS Registry Number NIST Chemistry WebBook
854866 Gmelin Registry Number Gmelin
Citations Types Sources
17279692 PubMed citation Europe PMC
18036601 PubMed citation Europe PMC
19908738 PubMed citation Europe PMC
Last Modified
06 November 2018