CIT

CITRIC ACID

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is present as a standalone ligand in 1,447 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	vet_approved 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 monohydrate 2-Hydroxytricarballylic acid Citric acid,anhydrous 3-carboxy-3-hydroxypentane-1,5-dioic acid Citric acid monoglyceride Acidum citricum Citric acid Anhydrous citric acid Citronensäure ácido cítrico 2-hydroxy-1,2,3-propanetricarboxyic acid Citric acid, anhydrous
Brand Names	Up and Up Antacid and Pain Relief Alka-seltzer Flavoured - Evt Premier Value Antacid and Pain Relief Medicine Blood Pack Unit Cpd Rite Aid Antacid and Pain Relief Citrasate C2125 Haemonetics Anticoagulant Citrate Phosphate Double Dextrose Solution (CP2D) IDkit HP ONE Lytren Rhs Liq Hemosate Ultra Hs3150 Hemosate Ultra Hs0125 Anticoagulant Citrate Dextrose Solution USP (acd) Formula B Citrasate C1150 Publix Fast Relief Effervescent KID-CLEAN Epiguard (Herbage Basis germ Growth InhibitsSolution) Haemonetics Additive Solution Formula 3 (AS-3) Leukotrap WB System Av-1000 HEB Extra Strength Effervescent Antacid and Pain Relief Signature Care Effervescent Antacid and Pain Relief ACD Blood-Pack Units (PL 146 Plastic) Care One Original Antacid and Pain Relief Hemosate Ultra Hs4125 Pain Relief Fast Relief Sterile Cord Blood Collection Unit Nutricel Additive System - CP2D Effervescent Pain Relief Fast Relief Fast Relief Hand Washing Alka Seltzer ADSOL Red Cell Preservation Solution System in Plastic Container (PL 146 Plastic) Citrasate C1125 Dr. Juans Santo Remedio PARA LA ACIDEZ DG Health Effervescent Antacid and Pain Relief Haemonetics Anticoagulant Citrate Dextrose Solution Cpd/adsol Picot Plus Effervescent Alka-Seltzer Lemon Lime Clenpiq 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 Pico-salax Citric Buffered Normal Saline Equaline Effervescent Antacid and Pain Relief Alka Seltzer Original Anticoagulant Cit Phos Dex Adenine Sol USP Sal de Uvas Picot Potassium Citrate-Citric Acid Hemasate Ultra Hs4125 Hemasate Ultra Hs3125 Cloon Stick Whitening Lemon Peel Enl Medique Medi Seltzer Hemasate Ultra Hs1150 Oral Citrate Solution Additive Formula 3 Family Care Effervescent Antacid and Pain Relief Equate Effervescent Antacid and Pain Relief Sodium Citrate and Citric Acid Picodan Fluad Tetra CPDA-1 Blood Collection System Cytra-K Crystals Hemosate Ultra Hs1125 Citrasate C10125 Tricitrates Anticoagulant Citrate Phosphate Dextrose (CPD) Blood-Pack Units in PL 146 Plastic Phexxi Potassium Citrate Citric Acid Crystals Adsol Red Cell Preservation Cytra 3 Urologic Solution G Lytren Effervescent Pain Relief Alka-Seltzer Heartburn Relief Lemon Lime Alka-Seltzer HEARTBURN Alka-Seltzer Heartburn Alka-seltzer Flavoured Sodium Citrate-Citric Acid As 3 Urologic G for Irrigation All-Natural Pen Spray Prepopik Citracid-50 Equate Extra Strength Effervescent Antacid and Pain Relief CVS Health Antacid and Pain Reliever Iypoly Oracit Potassium Citrate and Citric Acid Zee-Seltzer Antacid and Pain Reliever BioShield 99 Acd A Neutra-seltzer Oral Purgative B100 Virtrate-3 Hemasate Ultra Hs2125 Drug Mart Effervescent Pain Relief Clayr TERUFLEX Blood Bag System with Diversion Blood Sampling Arm Anticoagulant Citrate Phosphate Dextrose (CPD) AND OPTISOL (AS-5) Red Cell Preservative Citrasate C0125 HyVee Health Effervescent Antacid and Pain Relief Puralor Kroger Effervescent Antacid and Pain Relief Hemasate Ultra Hs1125 Quality Choice Extra Strength Effervescent Antacid and Pain Relief Bromo Seltzer TERUFLEX Blood Bag System Anticoagulant Citrate Phosphate Dextrose (CPD) AND OPTISOL Red Cell Preservative WinCo Foods Effervescent Antacid and Pain Relief Alka Seltzer Evt Hemasate Ultra Hs3150 bdr Re-action natural low base skin refiner exfoliation essence Purilab Reveos Select CPD/AS-5 Red Cell Preservative For Collection Of Blood Bt100s Heparin Sodium In 5% Dextrose Injection, 25000unit/500ml Cpd Best Choice Effervescent Antacid Pain Relief Hemasate Ultra Hs2150 Smart Sense Effervescent Antacid and Pain Relief Good Sense Effervescent Antacid and Pain Relief Alka-Seltzer Extra Strength Top Value Effervescent Pain Relief Heparin Sodium In 0.9% Sodium Chloride Injection Potassium Citrate, Sodium Citrate, and Citric Acid Riga Purgative Lemon Flav Liq Effervescent Antacid and Pain Relief PramLyte Bicaruvas Surface Cleaner Cpd Adenine Cpda 1 Effervescent Pain Relief Fast Relief Anticoagulant Citrate Dextr Sol Formula A USP TERUFLEX Blood Bag System Anticoagulant Citrate Phosphate Dextrose Adenine (CPDA-1) Quality Choice Effervescent Antacid and Pain Relief Sterile Cord Blood Collection Unit (MSC127D) TERUFLEX Blood Bag System with Blood Sampling Arm Anticoagulant Citrate Phosphate Dextrose (CPD) AND OPTISOL (AS-5) Red Cell Preservative Alka-Seltzer Gold Disinfect Wipes Cpda-1 Lysol Simply Disinfectant All Purpose Cleaner Alka-Seltzer Original Leader Extra Strength Effervescent Antacid and Pain Reliever Anticoagulant Citrate Dextrose A ACD-A Sanitize/Disinfect Wipes Citracleen Leucoflex CGP Cytra-K W.skin Treemon Cleansing Water Family Wellness Effervescent Antacid and Pain Relief Hemosate Ultra Hs2125 Vida Mia Pain Relief Citric Acid MTL1 Leucoflex TopCare Effervescent Antacid and Pain Relief Citrasate C2150 Market Basket Effervescent Antacid and Pain Relief Citrasate C3150 Hand Sanitizer Hemasate Ultra Hs0125 Alka Seltzer Flavoured ACD Solution Modified Hemosate Ultra Hs2150 Sal De Uvas Picot Anticoagulant Citrate Dextrose Solution-A EnLyte Pall Sterile Cord Blood Collection Unit Citric Acid Wipes Alka Seltzer Originial 1s Blister Pack Anticoagulant Citrate Dextrose (ACD-A) Picoflo Anticoagulant Citrate Dextrose Solution USP (acd) Formula A 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 Potassium Citrate-Sodium Citrate-Citric Acid Acd-A Stop Hair Sterile Cord Blood Collection Unit (MSC128D) Hemosate Ultra Hs3125 Cygzyme CPD/ADSOL Red Cell Preservation Solution System (PL 2209) Hemosate Ultra Hs1150 A-C-D Solution Green Fresh Imuflex Wb-SP Blood Bag System With Integral Whole Blood Leukocyte Reduction Filter (saving Platelets) With Diversion Blood Sampling Arm Citrasate C3125 Av100 Alka-Seltzer XTRA STRENGTH Alka-seltzer Original Renacidin Surface Wipes Virtrate-K Anticoagulant Citrate Dextrose A Additive Solution Formula 3 As-3 Cytra-2 Sodium Picosulfate, Magnesium Oxide and Anhydrous Citric Acid Sterile Cord Blood Collection Unit (msc123d) Citrocarbonate Eff Pws CVS Health Extra Strength Antacid and Pain Reliever E-Z-gas II Freds Effervescent Antacid Pain Relief Virtrate-2 CPD Solution Walgreens Antacid Pain Relief Extra Strength Alka-Seltzer Lot Meijer Effervescent Antacid and Pain Relief Walgreens Effervescent Pain Relief Anticoagulant Solution Citrate Phosphate Dextrose (CPD) Leader Effervescent Antacid and Pain Relief Nature Clean Alka-Seltzer Heartburn Relief Extra Strength Citrasate C4125 Purg-odan Aquacetic-30
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 National Science Foundation (DBI-1832184), 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 R01GM133198.

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CIT

CITRIC ACID

Chemical Component Summary

Chemical Details

Drug Info: DrugBank

Drug Targets

Related Resource References