CHEBI:48131 - azelaic acid

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ChEBI Name azelaic acid
ChEBI ID CHEBI:48131
Definition An α,ω-dicarboxylic acid that is heptane substituted at positions 1 and 7 by carboxy groups.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:40912, CHEBI:2949
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Formula C9H16O4
Net Charge 0
Average Mass 188.22094
Monoisotopic Mass 188.105
InChI InChI=1S/C9H16O4/c10-8(11)6-4-2-1-3-5-7-9(12)13/h1-7H2,(H,10,11)(H,12,13)
InChIKey BDJRBEYXGGNYIS-UHFFFAOYSA-N
SMILES OC(=O)CCCCCCCC(O)=O
Metabolite of Species Details
Carthamus oxyacantha (NCBI:txid122010) Found in aerial part (BTO:0001658). Crude ethanolic extract of aerial parts See: PubMed
Homo sapiens (NCBI:txid9606) See: DOI
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): antibacterial agent
A substance that kills or slows the growth of bacteria.
plant metabolite
Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
Application(s): antineoplastic agent
A substance that inhibits or prevents the proliferation of neoplasms.
dermatologic drug
A drug used to treat or prevent skin disorders or for the routine care of skin.
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ChEBI Ontology
Outgoing azelaic acid (CHEBI:48131) has role antibacterial agent (CHEBI:33282)
azelaic acid (CHEBI:48131) has role antineoplastic agent (CHEBI:35610)
azelaic acid (CHEBI:48131) has role dermatologic drug (CHEBI:50177)
azelaic acid (CHEBI:48131) has role plant metabolite (CHEBI:76924)
azelaic acid (CHEBI:48131) is a α,ω-dicarboxylic acid (CHEBI:28383)
azelaic acid (CHEBI:48131) is conjugate acid of azelaate (CHEBI:132955)
azelaic acid (CHEBI:48131) is conjugate acid of azelaate(2−) (CHEBI:78208)
Incoming 1-O-hexadecyl-2-(8-carboxyoctanoyl)-sn-glycero-3-phosphocholine (CHEBI:138940) has functional parent azelaic acid (CHEBI:48131)
1-azelaoyl-sn-glycero-3-phosphocholine (CHEBI:91219) has functional parent azelaic acid (CHEBI:48131)
1-palmitoyl-2-azelaoyl-sn-glycero-3-phosphocholine (CHEBI:61817) has functional parent azelaic acid (CHEBI:48131)
2-azelaoyl-sn-glycero-3-phosphocholine (CHEBI:91220) has functional parent azelaic acid (CHEBI:48131)
azelaate (CHEBI:132955) is conjugate base of azelaic acid (CHEBI:48131)
azelaate(2−) (CHEBI:78208) is conjugate base of azelaic acid (CHEBI:48131)
IUPAC Name
nonanedioic acid
Synonyms Sources
1,7-dicarboxyheptane NIST Chemistry WebBook
1,7-Heptanedicarboxylic acid KEGG COMPOUND
1,9-nonanedioic acid ChemIDplus
acide azélaïque ChemIDplus
acidum azelaicum ChemIDplus
anchoic acid NIST Chemistry WebBook
Azelaic acid KEGG COMPOUND
AZELAIC ACID PDBeChem
Azelainsäure ChEBI
lepargylic acid ChemIDplus
n-nonanedioic acid NIST Chemistry WebBook
Nonandisäure ChEBI
Nonanedioic acid KEGG COMPOUND
Brand Names Sources
Azelex DrugBank
Finacea DrugBank
Skinoren DrugBank
Database Links Databases
270 DrugCentral
AZ1 PDBeChem
Azelaic_Acid Wikipedia
C08261 KEGG COMPOUND
CPD0-1265 MetaCyc
D03034 KEGG DRUG
DB00548 DrugBank
HMDB0000784 HMDB
LMFA01170054 LIPID MAPS
View more database links
Registry Numbers Types Sources
1101094 Beilstein Registry Number ChemIDplus
1101094 Reaxys Registry Number Reaxys
123-99-9 CAS Registry Number KEGG COMPOUND
123-99-9 CAS Registry Number ChemIDplus
123-99-9 CAS Registry Number NIST Chemistry WebBook
261342 Gmelin Registry Number Gmelin
Citations Waiting for Citations Types Sources
22770225 PubMed citation Europe PMC
24280644 PubMed citation Europe PMC
28600633 PubMed citation Europe PMC
Last Modified
07 November 2017
General Comment
2014-03-11 Azelaic acid is often found in samples of human urine probably as a result of dietary intake.