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