CIT

CITRIC ACID

Created:	1999-07-08
Last modified:	2024-09-27

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1,471 entries where CIT is found as a standalone ligand13 entries where CIT is covalently linked to polymer or other heterogen groups

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

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Chemical Component Summary
Name	CITRIC ACID
Systematic Name (OpenEye OEToolkits)	2-hydroxypropane-1,2,3-tricarboxylic acid
Formula	C₆ H₈ O₇
Molecular Weight	192.124
Type	NON-POLYMER

Chemical Descriptors
Type	Program	Version	Descriptor
SMILES	ACDLabs	10.04	O=C(O)CC(O)(C(=O)O)CC(=O)O
SMILES	CACTVS	3.341	OC(=O)CC(O)(CC(O)=O)C(O)=O
SMILES	OpenEye OEToolkits	1.5.0	C(C(=O)O)C(CC(=O)O)(C(=O)O)O
Canonical SMILES	CACTVS	3.341	OC(=O)CC(O)(CC(O)=O)C(O)=O
Canonical SMILES	OpenEye OEToolkits	1.5.0	C(C(=O)O)C(CC(=O)O)(C(=O)O)O
InChI	InChI	1.03	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	InChI	1.03	KRKNYBCHXYNGOX-UHFFFAOYSA-N

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	Citric acid monoglyceride Acidum citricum 2-Hydroxytricarballylic acid 3-carboxy-3-hydroxypentane-1,5-dioic acid Citric acid,anhydrous 2-hydroxy-1,2,3-propanetricarboxyic acid Anhydrous citric acid Citronensäure ácido cítrico Citric acid, anhydrous Citric acid Citric acid monohydrate
Brand Names	Alka-Seltzer Original Picot Plus Effervescent Stop Hair Citric Acid Wipes Effervescent Pain Relief Sal De Uvas Picot ADSOL Red Cell Preservation Solution System in Plastic Container (PL 146 Plastic) KID-CLEAN Epiguard (Herbage Basis germ Growth InhibitsSolution) Phexxi Alka Seltzer Originial 1s Blister Pack Haemonetics Anticoagulant Citrate Dextrose Solution Iypoly Clenpiq Hemasate Ultra Hs1125 Citrasate C3125 CVS Health Extra Strength Antacid and Pain Reliever Effervescent Antacid and Pain Relief Urologic G for Irrigation Additive Formula 3 Sodium Picosulfate, Magnesium Oxide and Anhydrous Citric Acid Alka-seltzer Original Citrasate C2150 Vida Mia Pain Relief Effervescent Pain Relief Fast Relief Sodium Citrate-Citric Acid TopCare Effervescent Antacid and Pain Relief Hemosate Ultra Hs1125 Potassium Citrate and Citric Acid Kroger Effervescent Antacid and Pain Relief Cytra 3 B100 Dr. Juans Santo Remedio PARA LA ACIDEZ Clayr Sterile Cord Blood Collection Unit Lysol Simply Disinfectant All Purpose Cleaner Pain Relief Fast Relief Hemosate Ultra Hs3150 Virtrate-2 Quality Choice Extra Strength Effervescent Antacid and Pain Relief Top Value Effervescent Pain Relief Hemosate Ultra Hs1150 A-C-D Solution Neutra-seltzer Alka Seltzer Flavoured Haemonetics Anticoagulant Citrate Phosphate Double Dextrose Solution (CP2D) DG Health Effervescent Antacid and Pain Relief Signature Care Effervescent Antacid and Pain Relief 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 Walgreens Antacid Pain Relief Extra Strength Citric Buffered Normal Saline Urologic Solution G Picodan Citric Acid Anticoagulant Citrate Dextrose A Hemosate Ultra Hs2150 Smart Sense Effervescent Antacid and Pain Relief Lot Leader Extra Strength Effervescent Antacid and Pain Reliever All-Natural Pen Spray Anticoagulant Citrate Dextrose Solution USP (acd) Formula A Up and Up Antacid and Pain Relief Purilab Sterile Cord Blood Collection Unit (MSC127D) Pico-salax Alka-Seltzer HEARTBURN Alka-Seltzer XTRA STRENGTH Cytra-2 Quality Choice Effervescent Antacid and Pain Relief Surface Wipes Alka Seltzer Anticoagulant Citrate Phosphate Dextrose (CPD) Blood-Pack Units in PL 146 Plastic Oracit ACD Blood-Pack Units (PL 146 Plastic) Anticoagulant Solution Citrate Phosphate Dextrose (CPD) Sodium Citrate and Citric Acid Sterile Cord Blood Collection Unit (msc123d) CPD Solution CPDA-1 Blood Collection System Oral Citrate Solution Best Choice Effervescent Antacid Pain Relief Citrasate C3150 Alka-Seltzer Heartburn Relief Extra Strength Drug Mart Effervescent Pain Relief Haemonetics Additive Solution Formula 3 (AS-3) Good Sense Effervescent Antacid and Pain Relief Imuflex Wb-SP Blood Bag System With Integral Whole Blood Leukocyte Reduction Filter (saving Platelets) With Diversion Blood Sampling Arm Anticoagulant Citrate Dextrose Solution-A Fluad Tetra Leader Effervescent Antacid and Pain Relief Acd A Sal de Uvas Picot HyVee Health Effervescent Antacid and Pain Relief Acd-A Citrocarbonate Eff Pws Cpd Adenine Cpda 1 Pall Sterile Cord Blood Collection Unit As 3 Citrasate C1125 TERUFLEX Blood Bag System Anticoagulant Citrate Phosphate Dextrose (CPD) AND OPTISOL Red Cell Preservative Reveos Select CPD/AS-5 Red Cell Preservative For Collection Of Blood Potassium Citrate, Sodium Citrate, and Citric Acid Hemasate Ultra Hs0125 W.skin Treemon Cleansing Water Freds Effervescent Antacid Pain Relief Sterile Cord Blood Collection Unit (MSC128D) PramLyte Alka-Seltzer Gold Anticoagulant Cit Phos Dex Adenine Sol USP Alka-seltzer Flavoured - Evt Adsol Red Cell Preservation Surface Cleaner Bt100s Virtrate-3 Rite Aid Antacid and Pain Relief Alka-Seltzer Lemon Lime Hemasate Ultra Hs3150 IDkit HP ONE Anticoagulant Citrate Dextrose Solution USP (acd) Formula B Citracid-50 Hemasate Ultra Hs1150 Leukotrap WB System Lytren Rhs Liq Family Care Effervescent Antacid and Pain Relief Sanitize/Disinfect Wipes Renacidin Hand Sanitizer Leucoflex CGP Alka Seltzer Evt Cloon Stick Cytra-K Care One Original Antacid and Pain Relief TERUFLEX Blood Bag System Anticoagulant Citrate Phosphate Dextrose Adenine (CPDA-1) Alka-Seltzer Heartburn Relief Lemon Lime Prepopik Hemasate Ultra Hs2150 Equaline Effervescent Antacid and Pain Relief Disinfect Wipes 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 Walgreens Effervescent Pain Relief Hemasate Ultra Hs3125 Puralor Lytren Additive Solution Formula 3 As-3 Cpd/adsol Alka-Seltzer Extra Strength Cpda-1 MTL1 Leucoflex TERUFLEX Blood Bag System with Blood Sampling Arm Anticoagulant Citrate Phosphate Dextrose (CPD) AND OPTISOL (AS-5) Red Cell Preservative Market Basket Effervescent Antacid and Pain Relief Tricitrates Bromo Seltzer Citracleen EnLyte Medique Medi Seltzer TERUFLEX Blood Bag System with Diversion Blood Sampling Arm Anticoagulant Citrate Phosphate Dextrose (CPD) AND OPTISOL (AS-5) Red Cell Preservative Enl Whitening Lemon Peel Cpd BioShield 99 Publix Fast Relief Effervescent Heparin Sodium In 5% Dextrose Injection, 25000unit/500ml Heparin Sodium In 0.9% Sodium Chloride Injection Aquacetic-30 Purg-odan Bicaruvas Equate Effervescent Antacid and Pain Relief Meijer Effervescent Antacid and Pain Relief Potassium Citrate Citric Acid Crystals Anticoagulant Citrate Dextr Sol Formula A USP Citrasate C10125 Nutricel Additive System - CP2D Anticoagulant Citrate Dextrose (ACD-A) Family Wellness Effervescent Antacid and Pain Relief Zee-Seltzer Antacid and Pain Reliever Alka-Seltzer Heartburn HEB Extra Strength Effervescent Antacid and Pain Relief bdr Re-action natural low base skin refiner exfoliation essence CVS Health Antacid and Pain Reliever E-Z-gas II Oral Purgative Citrasate C1150 Cygzyme ACD Solution Modified Potassium Citrate-Citric Acid Hemosate Ultra Hs0125 Virtrate-K Anticoagulant Citrate Dextrose A ACD-A Picoflo Cytra-K Crystals Alka Seltzer Original Equate Extra Strength Effervescent Antacid and Pain Relief WinCo Foods Effervescent Antacid and Pain Relief Blood Pack Unit Cpd Effervescent Pain Relief Fast Relief Fast Relief Potassium Citrate-Sodium Citrate-Citric Acid Hemasate Ultra Hs4125 Hemosate Ultra Hs3125 Citrasate C0125 Nature Clean Alka-Seltzer Av-1000 Premier Value Antacid and Pain Relief Medicine CPD/ADSOL Red Cell Preservation Solution System (PL 2209) Hemosate Ultra Hs2125 Green Fresh Alka-seltzer Flavoured Riga Purgative Lemon Flav Liq Citrasate C4125 Hand Washing Citrasate C2125 Av100 Hemasate Ultra Hs2125 Hemosate Ultra Hs4125
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	311, 19782904, 88113319
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