CHEBI:30769 - citric acid

ChEBI IDCHEBI:30769
ChEBI Namecitric acid
Stars
DefinitionA tricarboxylic acid that is propane-1,2,3-tricarboxylic acid bearing a hydroxy substituent at position 2. It is an important metabolite in the pathway of all aerobic organisms.
Secondary ChEBI IDsCHEBI:3727, CHEBI:23322, CHEBI:41523
Last Modified31 October 2024
SubmitterKirill Degtyarenko
DownloadsMolfile
FormulaC6H8O7
Net Charge0
Average Mass192.123
Monoisotopic Mass192.02700
SMILESO=C(O)CC(O)(CC(=O)O)C(=O)O
InChIInChI=1S/C6H8O7/c7-3(8)1-6(13,5(11)12)2-4(9)10/h13H,1-2H2,(H,7,8)(H,9,10)(H,11,12)
InChIKeyKRKNYBCHXYNGOX-UHFFFAOYSA-N
Wikipedia
Roles Classification
Chemical Roles:
calcium chelator  A chelator that is any compound containing a ligand (typically organic) which is able to form a bond to a central calcium atom at two or more points.
chelator  A ligand with two or more separate binding sites that can bind to a single metallic central atom, forming a chelate.
Bronsted acid  A molecular entity capable of donating a hydron to an acceptor (Brønsted base).
Biological Roles:
food acidity regulator  A food additive that is used to change or otherwise control the acidity or alkalinity of foods. They may be acids, bases, neutralising agents or buffering agents.
antimicrobial agent  A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.
fundamental metabolite  Any metabolite produced by all living cells.
Application:
food acidity regulator  A food additive that is used to change or otherwise control the acidity or alkalinity of foods. They may be acids, bases, neutralising agents or buffering agents.
ChEBI Ontology
Outgoing Relation(s)
citric acid (CHEBI:30769) has role antimicrobial agent (CHEBI:33281)
citric acid (CHEBI:30769) has role calcium chelator (CHEBI:232436)
citric acid (CHEBI:30769) has role chelator (CHEBI:38161)
citric acid (CHEBI:30769) has role food acidity regulator (CHEBI:64049)
citric acid (CHEBI:30769) has role fundamental metabolite (CHEBI:78675)
citric acid (CHEBI:30769) is a tricarboxylic acid (CHEBI:27093)
citric acid (CHEBI:30769) is conjugate acid of citrate anion (CHEBI:133748)
citric acid (CHEBI:30769) is conjugate acid of citrate(1−) (CHEBI:35804)
Incoming Relation(s)
(3S)-citryl-CoA (CHEBI:15459) has functional parent citric acid (CHEBI:30769)
Nα-citryl-Nε-acetyl-Nε-hydroxylysine (CHEBI:63801) has functional parent citric acid (CHEBI:30769)
2-[(L-alanin-3-ylcarbamoyl)methyl]-2-hydroxybutanedioate(2−) (CHEBI:142969) has functional parent citric acid (CHEBI:30769)
2-methylcitric acid (CHEBI:30835) has functional parent citric acid (CHEBI:30769)
iron(III) dicitrate(3−) (CHEBI:4991) has functional parent citric acid (CHEBI:30769)
rhizobactin 1021 (CHEBI:74252) has functional parent citric acid (CHEBI:30769)
schizokinen (CHEBI:84582) has functional parent citric acid (CHEBI:30769)
staphyloferrin A (CHEBI:84711) has functional parent citric acid (CHEBI:30769)
staphyloferrin B (CHEBI:134612) has functional parent citric acid (CHEBI:30769)
vibrioferrin (CHEBI:84585) has functional parent citric acid (CHEBI:30769)
β-citryl-Glu-Glu (CHEBI:90168) has functional parent citric acid (CHEBI:30769)
β-citrylglutamic acid (CHEBI:77065) has functional parent citric acid (CHEBI:30769)
Anaerocult™ (CHEBI:82659) has part citric acid (CHEBI:30769)
citrate anion (CHEBI:133748) is conjugate base of citric acid (CHEBI:30769)
citrate(1−) (CHEBI:35804) is conjugate base of citric acid (CHEBI:30769)
IUPAC Name 
2-hydroxypropane-1,2,3-tricarboxylic acid
Synonyms  Source
Citric acidKEGG COMPOUND
2-Hydroxy-1,2,3-propanetricarboxylic acidKEGG COMPOUND
2-Hydroxytricarballylic acidKEGG COMPOUND
CITRIC ACIDPDBeChem
H3citIUPAC
3-Carboxy-3-hydroxypentane-1,5-dioic acidHMDB
Manual XrefsDatabases
C00158KEGG COMPOUND
CITPDBeChem
Citric_AcidWikipedia
HMDB0000094HMDB
CITMetaCyc
DB04272DrugBank
D00037KEGG DRUG
C00007619KNApSAcK
666DrugCentral
1359BPDB
Registry NumbersSources
Gmelin:4240Gmelin
Reaxys:782061Reaxys
CAS:77-92-9KEGG COMPOUND
CAS:77-92-9ChemIDplus
CAS:77-92-9NIST Chemistry WebBook
Citations