CIT

CITRIC ACID

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

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1,516 entries where CIT is found as a standalone ligand11 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 data are sourced from datasets licensed under a Creative Common's Attribution-NonCommercial 4.0 International License

DrugBank ID	DB04272
Name	Citric acid
Groups	vet_approved nutraceutical 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	Citric acid,anhydrous 2-Hydroxytricarballylic acid Anhydrous citric acid 2-hydroxy-1,2,3-propanetricarboxyic acid 3-carboxy-3-hydroxypentane-1,5-dioic acid Citric acid monoglyceride Citric acid monohydrate Citric acid, anhydrous Acidum citricum ácido cítrico Citronensäure Citric acid
Brand Names	Citrasate C1125 Purilab Leader Effervescent Antacid and Pain Relief Teruflex Blood Bag System With Diversion Blood Sampling Arm 70 Ml Cpda-1 Blood Pack Unit Cpd Kroger Effervescent Antacid and Pain Relief Drug Mart Effervescent Pain Relief Reveos Select CPD/AS-5 Red Cell Preservative For Collection Of Blood PramLyte Top Value Effervescent Pain Relief Haemonetics Anticoagulant Citrate Phosphate Double Dextrose Solution (CP2D) Hemasate Ultra Hs2150 Picodan Green Fresh TopCare Effervescent Antacid and Pain Relief TERUFLEX Blood Bag System with Diversion Blood Sampling Arm Anticoagulant Citrate Phosphate Dextrose (CPD) AND OPTISOL (AS-5) Red Cell Preservative Alka Seltzer Original E-Z-gas II Alka Seltzer Originial 1s Blister Pack Alka-Seltzer Lemon Lime Haemonetics Anticoagulant Citrate Dextrose Solution Potassium Citrate Citric Acid Crystals Alka Seltzer Hemosate Ultra Hs0125 TERUFLEX Blood with Diversion Blood Sampling Arm Anticoagulant CPD with OPTISOL Red Cell Preservative for Collection of 450mL of Blood Urologic G for Irrigation Heparin Sodium In 5% Dextrose Injection, 25000unit/500ml Dr. Juans Santo Remedio PARA LA ACIDEZ Meijer Effervescent Antacid and Pain Relief Equate Extra Strength Effervescent Antacid and Pain Relief Walgreens Antacid Pain Relief Extra Strength Alka-seltzer Original Anticoagulant Citrate Dextrose A IDkit HP ONE Puralor Hand Sanitizer Cpd Heparin Sodium In 0.9% Sodium Chloride Injection Imuflex Wb-SP Blood Bag System With Integral Whole Blood Leukocyte Reduction Filter (saving Platelets) With Diversion Blood Sampling Arm Citrasate C1150 Effervescent Pain Relief Fast Relief Fast Relief Vida Mia Pain Relief Anticoagulant Citrate Dextrose Solution USP (acd) Formula A Bt100s Stop Hair Alka-Seltzer Gold As 3 Purg-odan Citrasate C0125 Picoflo Alka-Seltzer HEARTBURN Whitening Lemon Peel Oral Purgative Surface Wipes Publix Fast Relief Effervescent HyVee Health Effervescent Antacid and Pain Relief Citrasate C2125 Cytra 3 Hemasate Ultra Hs3150 Pico-salax Cpd Adenine Cpda 1 CPD Solution Family Wellness Effervescent Antacid and Pain Relief KID-CLEAN Epiguard (Herbage Basis germ Growth InhibitsSolution) PaxLyte Anticoagulant Solution Citrate Phosphate Dextrose (CPD) Riga Purgative Lemon Flav Liq Hemosate Ultra Hs3125 Av100 Sanitize/Disinfect Wipes Walgreens Effervescent Pain Relief Alka-Seltzer Extra Strength Sodium Citrate-Citric Acid Cpda-1 Citrasate C2150 Disinfect Wipes Potassium Citrate and Citric Acid TERUFLEX Blood Anticoagulant Citrate Phosphate Dextrose Adenine (CPDA-1) for Collection of 450mL of Blood Up and Up Antacid and Pain Relief Hemasate Ultra Hs1125 Neutra-seltzer Alka-Seltzer Original Hemasate Ultra Hs2125 Sterile Cord Blood Collection Unit Alka-Seltzer Heartburn Citracid-50 Hemosate Ultra Hs1150 Citrocarbonate Eff Pws Acd A Anticoagulant Citrate Dextrose A ACD-A Additive Formula 3 Leucoflex CGP HEB Extra Strength Effervescent Antacid and Pain Relief Zee-Seltzer Antacid and Pain Reliever Anticoagulant Cit Phos Dex Adenine Sol USP Medique Medi Seltzer CPDA-1 Blood Collection System bdr Re-action natural low base skin refiner exfoliation essence Effervescent Pain Relief Family Care Effervescent Antacid and Pain Relief Signature Care Effervescent Antacid and Pain Relief Citric Acid Wipes MTL1 Leucoflex TERUFLEX Blood Bag System with Diversion Blood Sampling Arm Anticoagulant CPD with OPTISOL Red Cell Preservative Solution for Collection of 500mL of Blood Sterile Cord Blood Collection Unit (MSC128D) Tricitrates W.skin Treemon Cleansing Water Quality Choice Effervescent Antacid and Pain Relief Hemasate Ultra Hs0125 Acd-A Equaline Effervescent Antacid and Pain Relief Anticoagulant Citrate Dextrose Solution-A Prepopik Clenpiq Lytren Alka-seltzer Flavoured CPD/ADSOL Red Cell Preservation Solution System (PL 2209) Citrasate C3125 Hemosate Ultra Hs4125 Oral Citrate Solution Citracleen 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-Citric Acid Anticoagulant Citrate Phosphate Dextrose (CPD) Blood-Pack Units in PL 146 Plastic Aquacetic-30 Picot Plus Effervescent Hemosate Ultra Hs2150 Quality Choice Extra Strength Effervescent Antacid and Pain Relief Alka-Seltzer Heartburn Relief Extra Strength Lytren Rhs Liq Freds Effervescent Antacid Pain Relief Potassium Citrate-Sodium Citrate-Citric Acid Alka-Seltzer XTRA STRENGTH Virtrate-2 Clayr Effervescent Antacid and Pain Relief ACD Solution Modified Bicaruvas Sal De Uvas Picot Hemasate Ultra Hs4125 Additive Solution Formula 3 As-3 Phexxi Cygzyme Sterile Cord Blood Collection Unit (MSC127D) DG Health Effervescent Antacid and Pain Relief Potassium Citrate, Sodium Citrate, and Citric Acid Best Choice Effervescent Antacid Pain Relief Hemosate Ultra Hs2125 Cytra-2 Alka-Seltzer Hemosate Ultra Hs1125 Citrasate C4125 Care One Original Antacid and Pain Relief Alka-seltzer Flavoured - Evt Sodium Picosulfate, Magnesium Oxide and Anhydrous Citric Acid Fluad Tetra TERUFLEX BLOOD with Diversion Blood Sampling Arm 70 mL CPDA-1 Virtrate-K Urologic Solution G Nutricel Additive System - CP2D Iypoly Pall Sterile Cord Blood Collection Unit Renacidin Leukotrap WB System Surface Cleaner Alka Seltzer Evt 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 Leader Extra Strength Effervescent Antacid and Pain Reliever ACD Blood-Pack Units (PL 146 Plastic) TERUFLEX Blood Bag System with Blood Sampling Arm Anticoagulant Citrate Phosphate Dextrose (CPD) AND OPTISOL (AS-5) Red Cell Preservative Phexx Oracit Sterile Cord Blood Collection Unit (msc123d) Anticoagulant Citrate Dextrose Solution USP (acd) Formula B Citrasate C3150 BioShield 99 Alka Seltzer Flavoured Enl Virtrate-3 A-C-D Solution Cytra-K Crystals Hemasate Ultra Hs3125 Anticoagulant Citrate Dextrose (ACD-A) WinCo Foods Effervescent Antacid and Pain Relief Lysol Simply Disinfectant All Purpose Cleaner Smart Sense Effervescent Antacid and Pain Relief TERUFLEX Blood Bag System Anticoagulant Citrate Phosphate Dextrose Adenine (CPDA-1) Av-1000 Hemosate Ultra Hs3150 Effervescent Pain Relief Fast Relief CVS Health Antacid and Pain Reliever Rite Aid Antacid and Pain Relief Sal de Uvas Picot Equate Effervescent Antacid and Pain Relief Anticoagulant Citrate Dextr Sol Formula A USP B100 Hand Washing Cytra-K ADSOL Red Cell Preservation Solution System in Plastic Container (PL 146 Plastic) Cloon Stick IMUFLEX WB-RP 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 for collection of 500mL of Blood Good Sense Effervescent Antacid and Pain Relief TERUFLEX Blood Bag System Anticoagulant Citrate Phosphate Dextrose (CPD) AND OPTISOL Red Cell Preservative Haemonetics Additive Solution Formula 3 (AS-3) Citric Buffered Normal Saline Hemasate Ultra Hs1150 All-Natural Pen Spray Nature Clean Citrasate C10125 Premier Value Antacid and Pain Relief Medicine Market Basket Effervescent Antacid and Pain Relief Lot Citric Acid Pain Relief Fast Relief Alka-Seltzer Heartburn Relief Lemon Lime EnLyte Cpd/adsol CVS Health Extra Strength Antacid and Pain Reliever Adsol Red Cell Preservation Bromo Seltzer Sodium Citrate and Citric Acid
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

DrugBank data are sourced from datasets licensed under a Creative Common's Attribution-NonCommercial 4.0 International License

Name	Target Sequence	Pharmacological Action	Actions
Metallo-beta-lactamase type 2	MELPNIMHPVAKLSTALAAALMLSGCMPGEIRPTIGQQMETGDQRFGDLV...	unknown	inhibitor
Lanosterol 14-alpha demethylase	MAIVETVIDGINYFLSLSVTQQISILLGVPFVYNLVWQYLYSLRKDRAPL...	unknown	binder
Transient receptor potential cation channel subfamily V member 4	MADSSEGPRAGPGEVAELPGDESGTPGGEAFPLSSLANLFEGEDGSLSPS...	unknown	activator
Aldo-keto reductase family 1 member B1	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 gp12	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	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
2-methylcitrate 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, 311, 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