CHEBI:29019 - nonanoic acid

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ChEBI Name nonanoic acid
ChEBI ID CHEBI:29019
Definition A C9 straight-chain saturated fatty acid which occurs naturally as esters of the oil of pelargonium. Has antifungal properties, and is also used as a herbicide as well as in the preparation of plasticisers and lacquers.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:7616, CHEBI:25861
Supplier Information ChemicalBook:CB1143564, eMolecules:27677745, eMolecules:535714, Selleckchem:Carbamazepine(Carbatrol), ZINC000000004785
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Carbamazepine, sold under the brand name Tegretol among others, is an anticonvulsant medication used in the treatment of epilepsy and neuropathic pain. It is used as an adjunctive treatment in schizophrenia along with other medications and as a second-line agent in bipolar disorder. Carbamazepine appears to work as well as phenytoin and valproate for focal and generalized seizures. It is not effective for absence or myoclonic seizures. Carbamazepine was discovered in 1953 by Swiss chemist Walter Schindler. It was first marketed in 1962. It is available as a generic medication. It is on the World Health Organization's List of Essential Medicines. In 2020, it was the 185th most commonly prescribed medication in the United States, with more than 2 million prescriptions. Photoswitchable analogues of carbamazepine have been developed to control its pharmacological activity locally and on demand using light (World Health Organization), with the purpose of reducing the adverse systemic effects of the drug. One of these light-regulated compounds (carbadiazocine, based on a bridged photopharmacology or azobenzene) has been shown to produce analgesia with noninvasive illumination in vivo in a rat model of neuropathic pain.
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Formula C9H18O2
Net Charge 0
Average Mass 158.23800
Monoisotopic Mass 158.13068
InChI InChI=1S/C9H18O2/c1-2-3-4-5-6-7-8-9(10)11/h2-8H2,1H3,(H,10,11)
InChIKey FBUKVWPVBMHYJY-UHFFFAOYSA-N
SMILES CCCCCCCCC(O)=O
Metabolite of Species Details
Tilia cordata (NCBI:txid172266) Found in bark (BTO:0001301). See: PubMed
Chlamydomonas reinhardtii (NCBI:txid3055) See: PubMed
Daphnia magna (NCBI:txid35525) See: Mixtures of similarly acting compounds in Daphnia magna: From gene to metabolite and beyondTine Vandenbrouck, Oliver A.H. Jones, Nathalie Dom, Julian L. Griffin, Wim De CoenEnvironment International 36 (2010) 254-268
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): Daphnia magna metabolite
A Daphnia metabolite produced by the species Daphnia magna.
algal metabolite
Any eukaryotic metabolite produced during a metabolic reaction in algae including unicellular organisms like chlorella and diatoms to multicellular organisms like giant kelps and brown algae.
plant metabolite
Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
Application(s): antifeedant
A substance that prevents pests from feeding.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing nonanoic acid (CHEBI:29019) has parent hydride nonane (CHEBI:32892)
nonanoic acid (CHEBI:29019) has role Daphnia magna metabolite (CHEBI:83056)
nonanoic acid (CHEBI:29019) has role algal metabolite (CHEBI:84735)
nonanoic acid (CHEBI:29019) has role antifeedant (CHEBI:22583)
nonanoic acid (CHEBI:29019) has role plant metabolite (CHEBI:76924)
nonanoic acid (CHEBI:29019) is a medium-chain fatty acid (CHEBI:59554)
nonanoic acid (CHEBI:29019) is a straight-chain saturated fatty acid (CHEBI:39418)
nonanoic acid (CHEBI:29019) is conjugate acid of nonanoate (CHEBI:32361)
Incoming γ-nonanolactone (CHEBI:10575) has functional parent nonanoic acid (CHEBI:29019)
(8R)-8-hydroxynonanoic acid (CHEBI:78839) has functional parent nonanoic acid (CHEBI:29019)
(R)-2-hydroxynonanoic acid (CHEBI:55538) has functional parent nonanoic acid (CHEBI:29019)
1-nonanoyl-2-pentadecanoyl-sn-glycero-3-phosphocholine (CHEBI:86281) has functional parent nonanoic acid (CHEBI:29019)
1-octadecanoyl-2-nonanoyl-sn-glycero-3-phosphocholine (CHEBI:138214) has functional parent nonanoic acid (CHEBI:29019)
2-hydroxynonanoic acid (CHEBI:73753) has functional parent nonanoic acid (CHEBI:29019)
2-oxononanoic acid (CHEBI:55523) has functional parent nonanoic acid (CHEBI:29019)
7,8-diaminononanoic acid (CHEBI:2247) has functional parent nonanoic acid (CHEBI:29019)
8-amino-7-oxononanoic acid (CHEBI:15830) has functional parent nonanoic acid (CHEBI:29019)
9-(methylsulfinyl)nonamide (CHEBI:91157) has functional parent nonanoic acid (CHEBI:29019)
9-(methylsulfinyl)nonanoic acid (CHEBI:91156) has functional parent nonanoic acid (CHEBI:29019)
9-aminononanoic acid (CHEBI:73740) has functional parent nonanoic acid (CHEBI:29019)
9-hydroxynonanoic acid (CHEBI:79121) has functional parent nonanoic acid (CHEBI:29019)
9-oxononanoic acid (CHEBI:78700) has functional parent nonanoic acid (CHEBI:29019)
N-nonanoylglycine (CHEBI:74439) has functional parent nonanoic acid (CHEBI:29019)
ethyl nonanoate (CHEBI:87501) has functional parent nonanoic acid (CHEBI:29019)
hexadecafluorononanoic acid (CHEBI:38398) has functional parent nonanoic acid (CHEBI:29019)
methyl nonanoate (CHEBI:44499) has functional parent nonanoic acid (CHEBI:29019)
nonanal (CHEBI:84268) has functional parent nonanoic acid (CHEBI:29019)
nonanoyl-CoA (CHEBI:27770) has functional parent nonanoic acid (CHEBI:29019)
perfluorononanoic acid (CHEBI:38397) has functional parent nonanoic acid (CHEBI:29019)
trimethylsilyl nonanoate (CHEBI:145975) has functional parent nonanoic acid (CHEBI:29019)
nonanoate (CHEBI:32361) is conjugate base of nonanoic acid (CHEBI:29019)
nonanoyl group (CHEBI:25580) is substituent group from nonanoic acid (CHEBI:29019)
IUPAC Name
nonanoic acid
Synonyms Sources
1-nonanoic acid ChEBI
1-octanecarboxylic acid ChEBI
CH3‒[CH2]7‒COOH IUPAC
n-nonanoic acid NIST Chemistry WebBook
n-nonanoic acid ChEBI
Nonanoate KEGG COMPOUND
Nonanoic acid KEGG COMPOUND
Nonansäure ChEBI
nonoic acid NIST Chemistry WebBook
nonylic acid NIST Chemistry WebBook
pelargic acid ChEBI
pelargon ChEBI
Pelargonic acid KEGG COMPOUND
Pelargonsäure ChEBI
pergonic acid ChEBI
Manual Xrefs Databases
1327 BPDB
C00030829 KNApSAcK
C01601 KEGG COMPOUND
CPD-8505 MetaCyc
LMFA01010009 LIPID MAPS
Nonanoic_acid Wikipedia
View more database links
Registry Numbers Types Sources
112-05-0 CAS Registry Number KEGG COMPOUND
112-05-0 CAS Registry Number ChemIDplus
112-05-0 CAS Registry Number NIST Chemistry WebBook
1752351 Reaxys Registry Number Reaxys
185341 Gmelin Registry Number Gmelin
Citations Types Sources
11413921 PubMed citation Europe PMC
16124228 PubMed citation Europe PMC
19274268 PubMed citation Europe PMC
20673187 PubMed citation Europe PMC
Last Modified
10 March 2020