CHEBI:30769 - citric acid

Main ChEBI Ontology Automatic Xrefs Reactions Pathways Models
ChEBI Name citric acid
ChEBI ID CHEBI:30769
Definition A 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.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:41523, CHEBI:3727, CHEBI:23322
Supplier Information No supplier information found for this compound.
Download Molfile XML SDF
Wikipedia License
In biochemistry, medicine, and related sciences, inositol generally refers to myo-inositol (formerly meso-inositol), the most important stereoisomer of the chemical compound cyclohexane-1,2,3,4,5,6-hexol. Its formula is C6H12O6; the molecule has a ring of six carbon atoms, each with an hydrogen atom and a hydroxyl group (–OH). In myo-inositol, two of the hydroxyls, neither adjacent nor opposite, lie above the respective hydrogens relative to the mean plane of the ring. The compound is a carbohydrate, specifically a sugar alcohol (as distinct from aldoses like glucose) with half the sweetness of sucrose (table sugar). It is one of the most ancient components of living beings with multiple functions in eukaryotes, including structural lipids and secondary messengers. A human kidney makes about two grams per day from glucose, but other tissues synthesize it too. The highest concentration is in the brain, where it plays an important role in making other neurotransmitters and some steroid hormones bind to their receptors. In other tissues, it mediates cell signal transduction in response to a variety of hormones, neurotransmitters, and growth factors and participates in osmoregulation. In most mammalian cells the concentrations of myo-inositol are 5 to 500 times greater inside cells than outside them. A 2023 meta-analysis found that inositol is a safe and effective treatment in the management of polycystic ovary syndrome (PCOS). However, there is only evidence of very low quality for its efficacy in increasing fertility for IVF in women with PCOS. The other naturally occurring stereoisomers of cyclohexane-1,2,3,4,5,6-hexol are scyllo-, muco-, D-chiro-, L-chiro-, and neo-inositol, although they occur in minimal quantities compared to myo-inositol. The other possible isomers are allo-, epi-, and cis-inositol.
Read full article at Wikipedia
Formula C6H8O7
Net Charge 0
Average Mass 192.123
Monoisotopic Mass 192.02700
InChI InChI=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)
InChIKey KRKNYBCHXYNGOX-UHFFFAOYSA-N
SMILES OC(=O)CC(O)(CC(O)=O)C(O)=O
Roles Classification
Chemical Role(s): chelator
A ligand with two or more separate binding sites that can bind to a single metallic central atom, forming a chelate.
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.
Bronsted acid
A molecular entity capable of donating a hydron to an acceptor (Bronsted base).
(via oxoacid )
Biological Role(s): 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(s): 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.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing 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 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)
(3S)-citryl-CoA (CHEBI:15459) 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)
Nα-citryl-Nε-acetyl-Nε-hydroxylysine (CHEBI:63801) 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)
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 Sources
2-Hydroxy-1,2,3-propanetricarboxylic acid KEGG COMPOUND
2-Hydroxytricarballylic acid KEGG COMPOUND
3-Carboxy-3-hydroxypentane-1,5-dioic acid HMDB
Citric acid KEGG COMPOUND
CITRIC ACID PDBeChem
Citronensäure ChEBI
E330 ChEBI
H3cit IUPAC
Manual Xrefs Databases
1359 BPDB
666 DrugCentral
C00007619 KNApSAcK
C00158 KEGG COMPOUND
CIT PDBeChem
CIT MetaCyc
Citric_Acid Wikipedia
D00037 KEGG DRUG
DB04272 DrugBank
HMDB0000094 HMDB
View more database links
Registry Numbers Types Sources
4240 Gmelin Registry Number Gmelin
77-92-9 CAS Registry Number KEGG COMPOUND
77-92-9 CAS Registry Number NIST Chemistry WebBook
77-92-9 CAS Registry Number ChemIDplus
782061 Reaxys Registry Number Reaxys
Citations Types Sources
11762832 PubMed citation Europe PMC
11782123 PubMed citation Europe PMC
11857437 PubMed citation Europe PMC
14537820 PubMed citation Europe PMC
15311880 PubMed citation Europe PMC
15934243 PubMed citation Europe PMC
16232627 PubMed citation Europe PMC
17190852 PubMed citation Europe PMC
17357118 PubMed citation Europe PMC
17604395 PubMed citation Europe PMC
18298573 PubMed citation Europe PMC
18960216 PubMed citation Europe PMC
19288211 PubMed citation Europe PMC
22115968 PubMed citation Europe PMC
22192423 PubMed citation Europe PMC
22264346 PubMed citation Europe PMC
22373571 PubMed citation Europe PMC
22509852 PubMed citation Europe PMC
Last Modified
31 October 2024