CIT

CITRIC ACID

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is present as a standalone ligand in 1,470 entries

as a non-polymer is covalently linked to polymer or other heterogen groups 13 entries

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Chemical Component Summary
Name	CITRIC ACID
Identifiers	2-hydroxypropane-1,2,3-tricarboxylic acid
Formula	C₆ H₈ O₇
Molecular Weight	192.124
Type	NON-POLYMER
Isomeric SMILES	C(C(=O)O)C(CC(=O)O)(C(=O)O)O
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

Chemical Details
Formal Charge	0
Atom Count	21
Chiral Atom Count	0
Bond Count	20
Aromatic Bond Count	0

Drug Info: DrugBank

DrugBank ID	DB04272
Name	Citric acid
Groups	approved vet_approved nutraceutical
Description	A key intermediate in metabolism. It is an acid compound found in citrus fruits. The salts of citric acid (citrates) can be used as anticoagulants due to their calcium-chelating ability. Citric acid is one of the active ingredients in Phexxi, a non-hormonal contraceptive agent that was approved by the FDA on May 2020.[L14120] It is also used in combination with magnesium oxide to form magnesium citrate, an osmotic laxative.[L43832]
Synonyms	Acidum citricum Citric acid,anhydrous 3-carboxy-3-hydroxypentane-1,5-dioic acid Citric acid, anhydrous Citric acid monohydrate Citric acid Citric acid monoglyceride Anhydrous citric acid 2-Hydroxytricarballylic acid 2-hydroxy-1,2,3-propanetricarboxyic acid ácido cítrico Citronensäure
Brand Names	Sterile Cord Blood Collection Unit Sterile Cord Blood Collection Unit (MSC127D) Sodium Picosulfate, Magnesium Oxide and Anhydrous Citric Acid Rite Aid Antacid and Pain Relief Hemosate Ultra Hs2150 As 3 CVS Health Antacid and Pain Reliever Av100 Sterile Cord Blood Collection Unit (msc123d) Hemasate Ultra Hs3125 ACD Blood-Pack Units (PL 146 Plastic) Acd A Equaline Effervescent Antacid and Pain Relief Pall Sterile Cord Blood Collection Unit Smart Sense Effervescent Antacid and Pain Relief Dr. Juans Santo Remedio PARA LA ACIDEZ Additive Formula 3 Hand Washing Cytra-K Walgreens Effervescent Pain Relief Alka-Seltzer Anticoagulant Solution Citrate Phosphate Dextrose (CPD) Citrasate C2150 Cygzyme Potassium Citrate-Citric Acid Family Wellness Effervescent Antacid and Pain Relief Cloon Stick Surface Wipes Picodan Sanitize/Disinfect Wipes Citrasate C1125 Family Care Effervescent Antacid and Pain Relief Hemosate Ultra Hs1150 Sal De Uvas Picot All-Natural Pen Spray Effervescent Pain Relief Fast Relief Nutricel Additive System - CP2D Purilab Anticoagulant Citrate Dextrose Solution-A TERUFLEX Blood Bag System with Diversion Blood Sampling Arm Anticoagulant Citrate Phosphate Dextrose (CPD) AND OPTISOL (AS-5) Red Cell Preservative Effervescent Antacid and Pain Relief Alka-seltzer Flavoured - Evt EnLyte Av-1000 Haemonetics Anticoagulant Citrate Phosphate Double Dextrose Solution (CP2D) Zee-Seltzer Antacid and Pain Reliever Virtrate-K B100 BioShield 99 Stop Hair ACD Solution Modified Hemosate Ultra Hs2125 Citric Acid Alka-Seltzer Extra Strength Equate Extra Strength Effervescent Antacid and Pain Relief Lot Citrasate C3125 Hemosate Ultra Hs1125 Haemonetics Additive Solution Formula 3 (AS-3) Citrocarbonate Eff Pws Neutra-seltzer Cytra 3 Cytra-K Crystals Meijer Effervescent Antacid and Pain Relief Top Value Effervescent Pain Relief E-Z-gas II HEB Extra Strength Effervescent Antacid and Pain Relief Picot Plus Effervescent Alka-Seltzer HEARTBURN IMUFLEX WB-RP Blood Bag System with Integral Whole Blood Leukocyte Reduction Filter (Removing Platelets) with Diversion Blood Sampling Arm Anticoagulant Citrate Phosphate Dextrose (CPD) AND OPTISOL (AS-5) Red Cell Preservative Pain Relief Fast Relief Riga Purgative Lemon Flav Liq HyVee Health Effervescent Antacid and Pain Relief Bromo Seltzer Enl Potassium Citrate-Sodium Citrate-Citric Acid Surface Cleaner Green Fresh IMUFLEX WB-SP Blood Bag System with Integral Whole Blood Leukocyte Reduction Filter (Saving Platelets) with Diversion Blood Sampling Arm Anticoagulant Citrate Phosphate Dextrose (CPD) and OPTISOL (AS-5) Red Cell Preservative Bicaruvas Anticoagulant Citrate Dextrose (ACD-A) Anticoagulant Citrate Dextrose A Urologic Solution G Citrasate C4125 Freds Effervescent Antacid Pain Relief A-C-D Solution Phexxi Hemasate Ultra Hs0125 Hemosate Ultra Hs3150 Premier Value Antacid and Pain Relief Medicine Citracleen Publix Fast Relief Effervescent Whitening Lemon Peel Vida Mia Pain Relief Alka Seltzer Original Sterile Cord Blood Collection Unit (MSC128D) Potassium Citrate Citric Acid Crystals Alka Seltzer Originial 1s Blister Pack WinCo Foods Effervescent Antacid and Pain Relief Good Sense Effervescent Antacid and Pain Relief Adsol Red Cell Preservation Hemasate Ultra Hs4125 Alka-seltzer Flavoured Quality Choice Effervescent Antacid and Pain Relief Alka-Seltzer Gold Aquacetic-30 Sodium Citrate-Citric Acid Care One Original Antacid and Pain Relief Citrasate C3150 Anticoagulant Citrate Dextr Sol Formula A USP Effervescent Pain Relief Alka-Seltzer Heartburn Relief Extra Strength Cpda-1 Leucoflex CGP Cytra-2 Oral Citrate Solution Blood Pack Unit Cpd Additive Solution Formula 3 As-3 Citric Buffered Normal Saline TERUFLEX Blood Bag System Anticoagulant Citrate Phosphate Dextrose Adenine (CPDA-1) TERUFLEX Blood Bag System Anticoagulant Citrate Phosphate Dextrose (CPD) AND OPTISOL Red Cell Preservative Tricitrates Acd-A Virtrate-3 Reveos Select CPD/AS-5 Red Cell Preservative For Collection Of Blood Medique Medi Seltzer Citrasate C10125 Bt100s Disinfect Wipes KID-CLEAN Epiguard (Herbage Basis germ Growth InhibitsSolution) Lytren Leader Extra Strength Effervescent Antacid and Pain Reliever Alka Seltzer Flavoured Anticoagulant Citrate Dextrose Solution USP (acd) Formula B Citrasate C0125 Hemosate Ultra Hs0125 Alka-Seltzer XTRA STRENGTH Quality Choice Extra Strength Effervescent Antacid and Pain Relief Equate Effervescent Antacid and Pain Relief Hemasate Ultra Hs3150 Iypoly Leader Effervescent Antacid and Pain Relief Alka-Seltzer Heartburn Potassium Citrate, Sodium Citrate, and Citric Acid Drug Mart Effervescent Pain Relief Fluad Tetra Market Basket Effervescent Antacid and Pain Relief TERUFLEX Blood Bag System with Blood Sampling Arm Anticoagulant Citrate Phosphate Dextrose (CPD) AND OPTISOL (AS-5) Red Cell Preservative Oracit Anticoagulant Cit Phos Dex Adenine Sol USP Heparin Sodium In 5% Dextrose Injection, 25000unit/500ml Alka Seltzer Evt Hemasate Ultra Hs2125 Prepopik Sal de Uvas Picot Heparin Sodium In 0.9% Sodium Chloride Injection Kroger Effervescent Antacid and Pain Relief MTL1 Leucoflex Hemasate Ultra Hs1150 ADSOL Red Cell Preservation Solution System in Plastic Container (PL 146 Plastic) Leukotrap WB System Imuflex Wb-SP Blood Bag System With Integral Whole Blood Leukocyte Reduction Filter (saving Platelets) With Diversion Blood Sampling Arm Citric Acid Wipes CVS Health Extra Strength Antacid and Pain Reliever Citrasate C1150 Anticoagulant Citrate Dextrose Solution USP (acd) Formula A Cpd Potassium Citrate and Citric Acid Virtrate-2 Walgreens Antacid Pain Relief Extra Strength Anticoagulant Citrate Phosphate Dextrose (CPD) Blood-Pack Units in PL 146 Plastic Haemonetics Anticoagulant Citrate Dextrose Solution Signature Care Effervescent Antacid and Pain Relief Sodium Citrate and Citric Acid Cpd Adenine Cpda 1 Best Choice Effervescent Antacid Pain Relief Anticoagulant Citrate Dextrose A ACD-A Nature Clean Renacidin CPDA-1 Blood Collection System Clayr Purg-odan Urologic G for Irrigation W.skin Treemon Cleansing Water Puralor Hand Sanitizer DG Health Effervescent Antacid and Pain Relief Hemasate Ultra Hs2150 Oral Purgative Citrasate C2125 Alka-Seltzer Heartburn Relief Lemon Lime Hemosate Ultra Hs3125 Lytren Rhs Liq Alka-Seltzer Lemon Lime PramLyte Effervescent Pain Relief Fast Relief Fast Relief bdr Re-action natural low base skin refiner exfoliation essence Hemosate Ultra Hs4125 Picoflo Citracid-50 Hemasate Ultra Hs1125 Pico-salax Clenpiq CPD/ADSOL Red Cell Preservation Solution System (PL 2209) Alka-seltzer Original Alka-Seltzer Original TopCare Effervescent Antacid and Pain Relief Up and Up Antacid and Pain Relief IDkit HP ONE Cpd/adsol CPD Solution Lysol Simply Disinfectant All Purpose Cleaner Alka Seltzer
Categories	Acid Preparations Acidifying Activity Acids, Acyclic Alimentary Tract and Metabolism Calcium Chelating Activity Calcium Chelating Agents Calculi Dissolution Agent Chelating Agents Citrates Compounds used in a research, industrial, or household setting Decreased Coagulation Factor Activity Digestives, Incl. Enzymes Disinfectants (For Agents Used on Object) Hematologic Agents Organic Anion Transporting Polypeptide 2B1 Inhibitors Sequestering Agents Tricarboxylic Acids Urinary Acidifying Agents Urinary Alkalinisers
ATC-Code	A09AB04
CAS number	77-92-9

Drug Targets

Name	Target Sequence	Pharmacological Action	Actions
Metallo-beta-lactamase type 2	MELPNIMHPVAKLSTALAAALMLSGCMPGEIRPTIGQQMETGDQRFGDLV...	unknown	inhibitor
Aldose reductase	MASRLLLNNGAKMPILGLGTWKSPPGQVTEAVKVAIDVGYRHIDCAHVYQ...	unknown	inhibitor
Isocitrate dehydrogenase [NADP]	MAQGEKITVSNGVLNVPNNPIIPFIEGDGTGPDIWNAASKVLEAAVEKAY...	unknown	substrate,inhibitor
Beta-lactamase	MKLWFSTLKLKKAAAVLLFSCVALAGCANNQTNASQPAEKNEKTEMKDDF...	unknown	weak inhibitor
Beta-lactamase 2	MKKNTLLKVGLCVGLLGTIQFVSTISSVQASQKVEKTVIKNETGTISISQ...	unknown
Citrate synthase, mitochondrial	MALLTAAARLLGTKNASCLVLAARHASASSTNLKDILADLIPKEQARIKT...	unknown
Proto-oncogene tyrosine-protein kinase Src	MGSNKSKPKDASQRRRSLEPAENVHGAGGGAFPASQTPSKPASADGHRGP...	unknown
Ribonuclease pancreatic	MALEKSLVRLLLLVLILLVLGWVQPSLGKESRAKKFQRQHMDSDSSPSSS...	unknown
Eosinophil cationic protein	MVPKLFTSQICLLLLLGLMGVEGSLHARPPQFTRAQWFAIQHISLNPPRC...	unknown
Fumarate hydratase class II	MNTVRSEKDSMGAIDVPADKLWGAQTQRSLEHFRISTEKMPTSLIHALAL...	unknown	inhibitor
6-phosphogluconolactonase	MEKTVIYLLEDGYVDFVVEKIRTKMEKLLEEKDKIFVVLAGGRTPLPVYE...	unknown
L-amino-acid oxidase	MAPLALHLLVLVPILLSLVASQDWKAERSQDPFEKCMQDPDYEQLLKVVT...	unknown
Carboxy-terminal domain RNA polymerase II polypeptide A small phosphatase 1	MDSSAVITQISKEEARGPLRGKGDQKSAASQKPRSRGILHSLFCCVCRDD...	unknown
Cytochrome c peroxidase	DNLMERANSMFEPIPKYPPVIDGNELTQAKVELGKMEFFEPRLSSSHLIS...	unknown
Hepatocyte growth factor-regulated tyrosine kinase substrate	MGRGSGTFERLLDKATSQLLLETDWESILQICDLIRQGDTQAKYAVNSIK...	unknown
Invasin	MVFQPISEFLLIRNAGMSMYFNKIISFNIISRIVICIFLICGMFMAGASE...	unknown
Intron-associated endonuclease 1	MKSGIYQIKNTLNNKVYVGSAKDFEKRWKRHFKDLEKGCHSSIKLQRSFN...	unknown
Short tail fiber protein	MSNNTYQHVSNESRYVKFDPTDTNFPPEITDVQAAIAAISPAGVNGVPDA...	unknown
Malate dehydrogenase, mitochondrial	MLSALARPASAALRRSFSTSAQNNAKVAVLGASGGIGQPLSLLLKNSPLV...	unknown
N5-carboxyaminoimidazole ribonucleotide mutase	MSETAPLPSASSALEDKAASAPVVGIIMGSQSDWETMRHADALLTELEIP...	unknown
50S ribosomal protein L4	MAQVDLLNVKGEKVGTLEISDFVFNIDPNYDVMWRYVDMQLSNRRAGTAS...	unknown
Carboxypeptidase B	MLALLVLVTVALASAHHGGEHFEGEKVFRVNVEDENHINIIRELASTTQI...	unknown
Hexon protein	MATPSMMPQWSYMHISGQDASEYLSPGLVQFARATETYFSLNNKFRNPTV...	unknown
Riboflavin biosynthesis protein RibF	MVVSIGVFDGVHIGHQKVLRTMKEIAFFRKDDSLIYTISYPPEYFLPDFP...	unknown
Beta-fructosidase	MFKPNYHFFPITGWMNDPNGLIFWKGKYHMFYQYNPRKPEWGNICWGHAV...	unknown
Putative stringent starvation protein A	MAVAANKRSVMTLFSGPTDIFSHQVRIVLAEKGVSVEIEQVEADNLPQDL...	unknown
Citrate synthase	MEVARGLEGVLFTESRMCYIDGQQGKLYYYGIPIQELAEKSSFEETTFLL...	unknown
RNA 3'-terminal phosphate cyclase	MKRMIALDGAQGEGGGQILRSALSLSMITGQPFTITSIRAGRAKPGLLRQ...	unknown
U6 snRNA-associated Sm-like protein LSm6	MSLRKQTPSDFLKQIIGRPVVVKLNSGVDYRGVLACLDGYMNIALEQTEE...	unknown
Pleckstrin homology domain-containing family A member 1	MPYVDRQNRICGFLDIEENENSGKFLRRYFILDTREDSFVWYMDNPQNLP...	unknown
Fe(3+)-binding periplasmic protein	MKLRISSLGPVALLASSMMLAFGAQAASADQGIVIYNAQHENLVKSWVDG...	unknown
Signal recognition particle receptor FtsY	MGLFDFLKKGLQKTKETFFGRVVKLLKGKKLDDETREELEELLIQADVGV...	unknown
Nicotinate-nucleotide adenylyltransferase	MKSLQALFGGTFDPVHYGHLKPVETLANLIGLTRVTIIPNNVPPHRPQPE...	unknown
N utilization substance protein B homolog	MKTPRRRMRLAVFKALFQHEFRRDEDLEQILEEILDETYDKKAKEDARRY...	unknown
Complement component C8 gamma chain	MLPPGTATLLTLLLAAGSLGQKPQRPRRPASPISTIQPKANFDAQQFAGT...	unknown
Ribonucleoside-diphosphate reductase subunit beta	MLTGKMKLIDRVSAINWNWLQDDKDAEVWDRLTGNFWLPEKVPVSNDLPS...	unknown
Glutamine synthetase 1	MTEKTPDDVFKLAKDEKVEYVDVRFCDLPGIMQHFTIPASAFDKSVFDDG...	unknown
Citrate synthase	MTEPTIHKGLAGVTADVTAISKVNSDTNSLLYRGYPVQELAAKCSFEQVA...	unknown
Prostaglandin F synthase	MALTQSLKLSNGVMMPVLGFGMWKLQDGNEAETATMWAIKSGYRHIDTAA...	unknown
Adenine phosphoribosyltransferase	MADSELQLVEQRIRSFPDFPTPGVVFRDISPVLKDPASFRAAIGLLARHL...	unknown
Glucose-1-phosphate thymidylyltransferase	MKRKGIILAGGSGTRLHPATLAISKQLLPVYDKPMIYYPLSTLMLAGIRE...	unknown
Glyoxalase family protein	MAKNKLLRMDNVSIVVESLDNAISFFEEIGLNLEGRANVEGEWAGRVTGL...	unknown
Laccase domain protein YfiH	MSKLIVPQWPQPKGVAACSSTRIGGVSLPPYDSLNLGAHCGDNPDHVEEN...	unknown
Ribose-5-phosphate isomerase A	MNQLEMKKLAAQAALQYVKADTIVGVGSGSTVNCFIEALGTIKDKIQGAV...	unknown
GMP synthase [glutamine-hydrolyzing]	MTENIHKHRILILDFGSQYTQLVARRVRELGVYCELWAWDVTEAQIRDFN...	unknown
Inosine triphosphate pyrophosphatase	MAASLVGKKIVFVTGNAKKLEEVVQILGDKFPCTLVAQKIDLPEYQGEPD...	unknown
Lysozyme	MKGKTAAGGGAICAIAVMITIVMGNGNVRTNQAGLELIGNAEGCRRDPYM...	unknown
Glycerol uptake operon antiterminator regulatory protein	MFKGIIAALWDMDSIGEIEPDVVFLLKSDILNLKFHLKILKDRGKTVFVD...	unknown
3-carboxy-cis,cis-muconate cycloisomerase	MTNQLFDAYFTAPAMREIFSDRGRLQGMLDFEAALARAEAAAGLVPHSAV...	unknown
Pyruvate decarboxylase	MSYTVGTYLAERLVQIGLKHHFAVAGDYNLVLLDNLLLNKNMEQVYCCNE...	unknown
Solute carrier organic anion transporter family member 2B1	MGPRIGPAGEVPQVPDKETKATMGTENTPGGKASPDPQDVRPSVFHNIKL...	unknown	inhibitor
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Drug Info/Drug Targets: DrugBank 3.0: a comprehensive resource for 'omics' research on drugs. Knox C, Law V, Jewison T, Liu P, Ly S, Frolkis A, Pon A, Banco K, Mak C, Neveu V, Djoumbou Y, Eisner R, Guo AC, Wishart DS. Nucleic Acids Res. 2011 Jan; 39 (Database issue):D1035-41. | PMID:21059682

Related Resource References

Resource Name	Reference
PubChem	88113319, 311, 19782904
ChEMBL	CHEMBL1261
ChEBI	CHEBI:30769
CCDC/CSD	CITARC01, CITRAC11, QIZTEB, KOVSOF, ZESMES, RUCFAX, CITRAC10, KIGKER, KIGKAN, MEBRUH, SIMXUK, CUYXUQ, CITARC, KOVDUW, HICZIF, EGUXAG, RUWGAS, XOBHIF, AMUBAM, LEWTAK, HICZIF01, QILWIU, RUCFEB, ICUFOE, KIGKER01, MIVHEF, IKEYOP, DAJYUM
COD	8100549, 2221193, 4501798, 7218809

RCSB PDB Core Operations are funded by the U.S. National Science Foundation (DBI-2321666), the US Department of Energy (DE-SC0019749), and the National Cancer Institute, National Institute of Allergy and Infectious Diseases, and National Institute of General Medical Sciences of the National Institutes of Health under grant R01GM157729.

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CIT

CITRIC ACID

Chemical Component Summary

Chemical Details

Drug Info: DrugBank

Drug Targets

Related Resource References