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Record Information
Version2.0
Creation Date2009-11-10 22:01:10 UTC
Update Date2014-12-24 20:26:12 UTC
Accession NumberT3D3597
Identification
Common NameCitrinin
ClassSmall Molecule
DescriptionCitrinin is a mycotoxin originally isolated from Penicillium citrinum. It has since been found to be produced by a variety of other fungi which are used in the production of human foods such as grain, cheese, sake and red pigments. Citrinin is also produced by a variety of other fungi including Aspergillus niveus, Aspergillus ochraceus, Aspergillus oryzae, Aspergillus terreus, Monascus ruber, Monascus purpureus, and Penicillium camemberti. It is usually found together with another nephrotoxic mycotoxin, ochratoxin A (OTA). (14, 2). It causes mycotoxic nephropathy in livestock and has been implicated as a cause of Balkan nephropathy and yellow rice fever in humans.
Compound Type
  • Ester
  • Ether
  • Food Toxin
  • Fungal Toxin
  • Industrial/Workplace Toxin
  • Lachrymator
  • Metabolite
  • Mycotoxin
  • Natural Compound
  • Organic Compound
Chemical Structure
Thumb
Synonyms
Synonym
(3R,4S)-4,6-dihydro-8-hydroxy-3,4,5-trimethyl-6-oxo-3H-2-benzopyran-7-carboxylic acid
(3R,4S)-8-hydroxy-3,4,5-trimethyl-6-oxo-4,6-dihydro-3H-isochromene-7-carboxylic acid
(3R-trans)-4,6-dihydro-8-hydroxy-3,4,5-trimethyl-6-oxo-3H-2-benzopyran-7-carboxylic acid
Antimycin
Citriain
Chemical FormulaC13H14O5
Average Molecular Mass250.247 g/mol
Monoisotopic Mass250.084 g/mol
CAS Registry Number518-75-2
IUPAC Name(3R,4S)-8-hydroxy-3,4,5-trimethyl-6-oxo-4,6-dihydro-3H-2-benzopyran-7-carboxylic acid
Traditional Nameantimycin
SMILES[H][C@]1(C)OC=C2C(O)=C(C(O)=O)C(=O)C(C)=C2[C@]1([H])C
InChI IdentifierInChI=1S/C13H14O5/c1-5-7(3)18-4-8-9(5)6(2)11(14)10(12(8)15)13(16)17/h4-5,7,15H,1-3H3,(H,16,17)/t5-,7-/m1/s1
InChI KeyInChIKey=CQIUKKVOEOPUDV-IYSWYEEDSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as benzopyrans. These are organic compounds containing a benzene ring fused to a pyran ring. Pyran a six-membered heterocyclic, non-aromatic ring, made up of five carbon atoms and one oxygen atom and containing two double bonds.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassBenzopyrans
Sub ClassNot Available
Direct ParentBenzopyrans
Alternative Parents
Substituents
  • Benzopyran
  • Vinylogous acid
  • Cyclic ketone
  • Ketone
  • Oxacycle
  • Monocarboxylic acid or derivatives
  • Enol
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Cytoplasm
  • Extracellular
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological Roles
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceLemon-yellow needles. Solution changes color with change in pH, from lemon-yellow at pH 4.6 to cherry-red at pH 9.9. (5)
Experimental Properties
PropertyValue
Melting Point178.5°C
Boiling PointNot Available
SolubilityNot Available
LogPNot Available
Predicted Properties
PropertyValueSource
Water Solubility1.16 mg/mLALOGPS
logP1.23ALOGPS
logP0.81ChemAxon
logS-2.3ALOGPS
pKa (Strongest Acidic)3.55ChemAxon
pKa (Strongest Basic)-4.8ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area83.83 Å2ChemAxon
Rotatable Bond Count1ChemAxon
Refractivity65.25 m3·mol-1ChemAxon
Polarizability25.01 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MSsplash10-07ii-1950000000-bf6353469eb59dfd035eView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS)splash10-004i-3409000000-998272da21093d63d473View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qToF , Positivesplash10-001i-0290000000-19d08795fea7c80d6d85View in MoNA
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-001i-0290000000-19d08795fea7c80d6d85View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0090000000-448b730e55729839783fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0pc0-1390000000-b2d7bec5177df13bf6b2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udi-9400000000-8c38a7814bc7b5aa2429View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4j-0090000000-cca6d7a143b768fc5b3dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-0390000000-4f2f5c7982385791b46fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-015j-3910000000-b3cbc912af168ecaeb68View in MoNA
Toxicity Profile
Route of ExposureOral, dermal, inhalation, and parenteral (contaminated drugs). (4)
Mechanism of ToxicityCitrinin produces proximal tubular necrosis, but only after transport into proximal tubular cells. It utilizes the organic anion transporter for entry into the cells, a transporter probably important physiologically for moving metabolic substrates into cells. Citrinin is also cytotoxic and increases formation of reactive oxygen species by stimulating the production of superoxide anion in the respiratory chain. It further potentiates this oxidative stress by modifying antioxidative enzymatic defences by inhibiting GSSG-reductase and transhydrogenase. Citrinin also alters mitochondrial function and permeability, decreasing Ca2+ accumulation in the matrix by inhibiting its influx and increasing its efflux. This is thought to induce apoptosis through the release of cytochrome c from the mitochondria, which is known to activate apoptosis-regulating caspases 3, 6, 7, and 9. Citrinin inhibits respiration by interfering with the NADH oxidase and NADH cytochrome c reductase involved with complex I of the respiratory chain. Mycotoxins are often able to enter the liver and kidney by human organic anion transporters (hOATs) and human organic cation transporters (hOCTs). They can also inhibit uptake of anions and cations by these transporters, interefering with the secretion of endogenous metabolites, drugs, and xenobiotics including themselves. This results in increased cellular accumulation of toxic compounds causing nephro- and hepatotoxicity. (6, 1, 2, 3)
MetabolismThe major urinary metabolite of CTN is dihydrocitrinone. (2)
Toxicity ValuesLD50: 112 mg/kg (Oral, Mouse) (7) LD50: 50 mg/kg (Oral, Rat) (2) LD50: 67 mg/kg (Subcutaneous, Rat) (2)
Lethal DoseNot Available
Carcinogenicity (IARC Classification)3, not classifiable as to its carcinogenicity to humans. (13)
Uses/SourcesCitrinin is a mycotoxin originally isolated from Penicillium citrinum. It has since been found to be produced by a variety of other fungi which are used in the production of human foods such as grain, cheese, sake and red pigments. Citrinin is also produced by a variety of other fungi including Aspergillus niveus, Aspergillus ochraceus, Aspergillus oryzae, Aspergillus terreus, Monascus ruber, Monascus purpureus, and Penicillium camemberti. (14)
Minimum Risk LevelNot Available
Health EffectsCitrinin acts as a nephrotoxin. It causes mycotoxic nephropathy in livestock and has been implicated as a cause of Balkan nephropathy and yellow rice fever in humans. Though the kidney is the major target organ of citrinin toxicity, other target organs such as liver and bone marrow have also been reported. (14, 2)
SymptomsIrritation of the eyes, skin, or respiratory tract, depending on the route of exposure. May produce an allergic hypersensitivity dermatitis or asthma with bronchospasm and wheezing with chronic exposure. (8)
TreatmentIn case of oral exposure, consider gastric lavage and/or activated charcoal. Immediate dilution with milk or water may be of benefit in caustic or irritant chemical ingestions. In case of inhalation, consider moving patient to frsh air. Maintain ventilation, and oxygenation. In case of eye or skin contact, consider decontamination of the exposed region. (8)
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB41857
PubChem Compound ID219203
ChEMBL IDCHEMBL510139
ChemSpider ID10222475
KEGG IDC16765
UniProt IDNot Available
OMIM ID
ChEBI ID48707
BioCyc IDNot Available
CTD IDNot Available
Stitch IDNot Available
PDB IDNot Available
ACToR IDNot Available
Wikipedia LinkCitrinin
References
Synthesis ReferenceNot Available
MSDST3D3597.pdf
General References
  1. Chagas GM, Oliveira BM, Campello AP, Kluppel ML: Mechanism of citrinin-induced dysfunction of mitochondria. II. Effect on respiration, enzyme activities, and membrane potential of liver mitochondria. Cell Biochem Funct. 1992 Sep;10(3):209-16. [1330354 ]
  2. Flajs D, Peraica M: Toxicological properties of citrinin. Arh Hig Rada Toksikol. 2009 Dec;60(4):457-64. doi: 10.2478/10004-1254-60-2009-1992. [20061247 ]
  3. Tachampa K, Takeda M, Khamdang S, Noshiro-Kofuji R, Tsuda M, Jariyawat S, Fukutomi T, Sophasan S, Anzai N, Endou H: Interactions of organic anion transporters and organic cation transporters with mycotoxins. J Pharmacol Sci. 2008 Mar;106(3):435-43. Epub 2008 Mar 5. [18319568 ]
  4. Peraica M, Domijan AM: Contamination of food with mycotoxins and human health. Arh Hig Rada Toksikol. 2001 Mar;52(1):23-35. [11370295 ]
  5. Rodero L, Mellado E, Rodriguez AC, Salve A, Guelfand L, Cahn P, Cuenca-Estrella M, Davel G, Rodriguez-Tudela JL: G484S amino acid substitution in lanosterol 14-alpha demethylase (ERG11) is related to fluconazole resistance in a recurrent Cryptococcus neoformans clinical isolate. Antimicrob Agents Chemother. 2003 Nov;47(11):3653-6. [14576140 ]
  6. Ribeiro MA, Paula CR: Up-regulation of ERG11 gene among fluconazole-resistant Candida albicans generated in vitro: is there any clinical implication? Diagn Microbiol Infect Dis. 2007 Jan;57(1):71-5. Epub 2006 Jul 11. [16839736 ]
  7. Kelley RI, Kratz LE, Glaser RL, Netzloff ML, Wolf LM, Jabs EW: Abnormal sterol metabolism in a patient with Antley-Bixler syndrome and ambiguous genitalia. Am J Med Genet. 2002 Jun 15;110(2):95-102. [12116245 ]
  8. Grond S, Sablotzki A: Clinical pharmacology of tramadol. Clin Pharmacokinet. 2004;43(13):879-923. [15509185 ]
  9. Rumack BH POISINDEX(R) Information System Micromedex, Inc., Englewood, CO, 2010; CCIS Volume 143, edition expires Feb, 2010. Hall AH & Rumack BH (Eds): TOMES(R) Information System Micromedex, Inc., Englewood, CO, 2010; CCIS Volume 143, edition expires Feb, 2010.
  10. Berndt W et al; Toxicol Pathol 26 (1): 52-7 (1998)
  11. O'Neil, M.J. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. 13th Edition, Whitehouse Station, NJ: Merck and Co., Inc., 2001., p. 406
  12. Lewis, R.J. Sax's Dangerous Properties of Industrial Materials. 9th ed. Volumes 1-3. New York, NY: Van Nostrand Reinhold, 1996., p. 884
  13. International Agency for Research on Cancer (2014). IARC Monographs on the Evaluation of Carcinogenic Risks to Humans. [Link]
  14. Wikipedia. Citrinin. Last Updated 1 April 2010. [Link]
Gene Regulation
Up-Regulated Genes
GeneGene SymbolGene IDInteractionChromosomeDetails
Down-Regulated Genes
GeneGene SymbolGene IDInteractionChromosomeDetails

Targets

General Function:
Sodium-independent organic anion transmembrane transporter activity
Specific Function:
Mediates saturable uptake of estrone sulfate, dehydroepiandrosterone sulfate and related compounds.
Gene Name:
SLC22A11
Uniprot ID:
Q9NSA0
Molecular Weight:
59970.945 Da
Binding/Activity Constants
TypeValueAssay TypeAssay Source
Inhibitory366.4 uMNot AvailableBindingDB 50344961
References
  1. Tachampa K, Takeda M, Khamdang S, Noshiro-Kofuji R, Tsuda M, Jariyawat S, Fukutomi T, Sophasan S, Anzai N, Endou H: Interactions of organic anion transporters and organic cation transporters with mycotoxins. J Pharmacol Sci. 2008 Mar;106(3):435-43. Epub 2008 Mar 5. [18319568 ]
  2. Babu E, Takeda M, Narikawa S, Kobayashi Y, Enomoto A, Tojo A, Cha SH, Sekine T, Sakthisekaran D, Endou H: Role of human organic anion transporter 4 in the transport of ochratoxin A. Biochim Biophys Acta. 2002 Jun 12;1590(1-3):64-75. [12063169 ]
General Function:
Sodium-independent organic anion transmembrane transporter activity
Specific Function:
Involved in the renal elimination of endogenous and exogenous organic anions. Functions as organic anion exchanger when the uptake of one molecule of organic anion is coupled with an efflux of one molecule of endogenous dicarboxylic acid (glutarate, ketoglutarate, etc). Mediates the sodium-independent uptake of 2,3-dimercapto-1-propanesulfonic acid (DMPS) (By similarity). Mediates the sodium-independent uptake of p-aminohippurate (PAH), ochratoxin (OTA), acyclovir (ACV), 3'-azido-3-'deoxythymidine (AZT), cimetidine (CMD), 2,4-dichloro-phenoxyacetate (2,4-D), hippurate (HA), indoleacetate (IA), indoxyl sulfate (IS) and 3-carboxy-4-methyl-5-propyl-2-furanpropionate (CMPF), cidofovir, adefovir, 9-(2-phosphonylmethoxyethyl) guanine (PMEG), 9-(2-phosphonylmethoxyethyl) diaminopurine (PMEDAP) and edaravone sulfate. PAH uptake is inhibited by p-chloromercuribenzenesulphonate (PCMBS), diethyl pyrocarbonate (DEPC), sulindac, diclofenac, carprofen, glutarate and okadaic acid (By similarity). PAH uptake is inhibited by benzothiazolylcysteine (BTC), S-chlorotrifluoroethylcysteine (CTFC), cysteine S-conjugates S-dichlorovinylcysteine (DCVC), furosemide, steviol, phorbol 12-myristate 13-acetate (PMA), calcium ionophore A23187, benzylpenicillin, furosemide, indomethacin, bumetamide, losartan, probenecid, phenol red, urate, and alpha-ketoglutarate.
Gene Name:
SLC22A6
Uniprot ID:
Q4U2R8
Molecular Weight:
61815.78 Da
Binding/Activity Constants
TypeValueAssay TypeAssay Source
Inhibitory3080 uMNot AvailableBindingDB 50344961
References
  1. Tachampa K, Takeda M, Khamdang S, Noshiro-Kofuji R, Tsuda M, Jariyawat S, Fukutomi T, Sophasan S, Anzai N, Endou H: Interactions of organic anion transporters and organic cation transporters with mycotoxins. J Pharmacol Sci. 2008 Mar;106(3):435-43. Epub 2008 Mar 5. [18319568 ]
  2. Kouznetsova VL, Tsigelny IF, Nagle MA, Nigam SK: Elucidation of common pharmacophores from analysis of targeted metabolites transported by the multispecific drug transporter-Organic anion transporter1 (Oat1). Bioorg Med Chem. 2011 Jun 1;19(11):3320-40. doi: 10.1016/j.bmc.2011.04.045. Epub 2011 Apr 28. [21571536 ]
General Function:
Thiamine pyrophosphate binding
Specific Function:
The 2-oxoglutarate dehydrogenase complex catalyzes the overall conversion of 2-oxoglutarate to succinyl-CoA and CO(2). It contains multiple copies of three enzymatic components: 2-oxoglutarate dehydrogenase (E1), dihydrolipoamide succinyltransferase (E2) and lipoamide dehydrogenase (E3).
Gene Name:
OGDH
Uniprot ID:
Q02218
Molecular Weight:
115934.37 Da
References
  1. Chagas GM, Oliveira MA, Campello AP, Kluppel ML: Mechanism of citrinin-induced dysfunction of mitochondria. IV--Effect on Ca2+ transport. Cell Biochem Funct. 1995 Mar;13(1):53-9. [7720190 ]
General Function:
Glyceraldehyde oxidoreductase activity
Specific Function:
Catalyzes the NADPH-dependent reduction of a wide variety of carbonyl-containing compounds to their corresponding alcohols with a broad range of catalytic efficiencies.
Gene Name:
AKR1B1
Uniprot ID:
P15121
Molecular Weight:
35853.125 Da
References
  1. Deruiter J, Jacyno JM, Davis RA, Cutler HG: Studies on aldose reductase inhibitors from fungi. I. Citrinin and related benzopyran derivatives. J Enzyme Inhib. 1992;6(3):201-10. [1284957 ]
General Function:
Dihydrolipoyllysine-residue acetyltransferase activity
Specific Function:
The pyruvate dehydrogenase complex catalyzes the overall conversion of pyruvate to acetyl-CoA and CO(2), and thereby links the glycolytic pathway to the tricarboxylic cycle.
Gene Name:
DLAT
Uniprot ID:
P10515
Molecular Weight:
68996.03 Da
References
  1. Chagas GM, Oliveira MA, Campello AP, Kluppel ML: Mechanism of citrinin-induced dysfunction of mitochondria. IV--Effect on Ca2+ transport. Cell Biochem Funct. 1995 Mar;13(1):53-9. [7720190 ]
General Function:
Dihydrolipoyllysine-residue succinyltransferase activity
Specific Function:
The 2-oxoglutarate dehydrogenase complex catalyzes the overall conversion of 2-oxoglutarate to succinyl-CoA and CO(2). It contains multiple copies of 3 enzymatic components: 2-oxoglutarate dehydrogenase (E1), dihydrolipoamide succinyltransferase (E2) and lipoamide dehydrogenase (E3).
Gene Name:
DLST
Uniprot ID:
P36957
Molecular Weight:
48754.87 Da
References
  1. Chagas GM, Oliveira MA, Campello AP, Kluppel ML: Mechanism of citrinin-induced dysfunction of mitochondria. IV--Effect on Ca2+ transport. Cell Biochem Funct. 1995 Mar;13(1):53-9. [7720190 ]
General Function:
Nad+ binding
Specific Function:
Mitochondrial glutamate dehydrogenase that converts L-glutamate into alpha-ketoglutarate. Plays a key role in glutamine anaplerosis by producing alpha-ketoglutarate, an important intermediate in the tricarboxylic acid cycle. May be involved in learning and memory reactions by increasing the turnover of the excitatory neurotransmitter glutamate (By similarity).
Gene Name:
GLUD1
Uniprot ID:
P00367
Molecular Weight:
61397.315 Da
References
  1. Chagas GM, Oliveira BM, Campello AP, Kluppel ML: Mechanism of citrinin-induced dysfunction of mitochondria. II. Effect on respiration, enzyme activities, and membrane potential of liver mitochondria. Cell Biochem Funct. 1992 Sep;10(3):209-16. [1330354 ]
General Function:
Leucine binding
Specific Function:
Important for recycling the chief excitatory neurotransmitter, glutamate, during neurotransmission.
Gene Name:
GLUD2
Uniprot ID:
P49448
Molecular Weight:
61433.465 Da
References
  1. Chagas GM, Oliveira BM, Campello AP, Kluppel ML: Mechanism of citrinin-induced dysfunction of mitochondria. II. Effect on respiration, enzyme activities, and membrane potential of liver mitochondria. Cell Biochem Funct. 1992 Sep;10(3):209-16. [1330354 ]
General Function:
Nadp binding
Specific Function:
Maintains high levels of reduced glutathione in the cytosol.
Gene Name:
GSR
Uniprot ID:
P00390
Molecular Weight:
56256.565 Da
References
  1. Flajs D, Peraica M: Toxicological properties of citrinin. Arh Hig Rada Toksikol. 2009 Dec;60(4):457-64. doi: 10.2478/10004-1254-60-2009-1992. [20061247 ]
General Function:
Poly(a) rna binding
Specific Function:
Not Available
Gene Name:
MDH2
Uniprot ID:
P40926
Molecular Weight:
35502.935 Da
References
  1. Chagas GM, Oliveira BM, Campello AP, Kluppel ML: Mechanism of citrinin-induced dysfunction of mitochondria. II. Effect on respiration, enzyme activities, and membrane potential of liver mitochondria. Cell Biochem Funct. 1992 Sep;10(3):209-16. [1330354 ]
General Function:
Nadh dehydrogenase (ubiquinone) activity
Specific Function:
Core subunit of the mitochondrial membrane respiratory chain NADH dehydrogenase (Complex I) that is believed to belong to the minimal assembly required for catalysis. Complex I functions in the transfer of electrons from NADH to the respiratory chain. The immediate electron acceptor for the enzyme is believed to be ubiquinone (By similarity). This is the largest subunit of complex I and it is a component of the iron-sulfur (IP) fragment of the enzyme. It may form part of the active site crevice where NADH is oxidized.
Gene Name:
NDUFS1
Uniprot ID:
P28331
Molecular Weight:
79466.77 Da
References
  1. Chagas GM, Oliveira BM, Campello AP, Kluppel ML: Mechanism of citrinin-induced dysfunction of mitochondria. II. Effect on respiration, enzyme activities, and membrane potential of liver mitochondria. Cell Biochem Funct. 1992 Sep;10(3):209-16. [1330354 ]
General Function:
Nadh dehydrogenase (ubiquinone) activity
Specific Function:
Core subunit of the mitochondrial membrane respiratory chain NADH dehydrogenase (Complex I) that is believed to belong to the minimal assembly required for catalysis. Complex I functions in the transfer of electrons from NADH to the respiratory chain. The immediate electron acceptor for the enzyme is believed to be ubiquinone (By similarity).
Gene Name:
MT-ND1
Uniprot ID:
P03886
Molecular Weight:
35660.055 Da
References
  1. Chagas GM, Oliveira BM, Campello AP, Kluppel ML: Mechanism of citrinin-induced dysfunction of mitochondria. II. Effect on respiration, enzyme activities, and membrane potential of liver mitochondria. Cell Biochem Funct. 1992 Sep;10(3):209-16. [1330354 ]
General Function:
Nadh dehydrogenase (ubiquinone) activity
Specific Function:
Core subunit of the mitochondrial membrane respiratory chain NADH dehydrogenase (Complex I) that is believed to belong to the minimal assembly required for catalysis. Complex I functions in the transfer of electrons from NADH to the respiratory chain. The immediate electron acceptor for the enzyme is believed to be ubiquinone (By similarity).
Gene Name:
MT-ND2
Uniprot ID:
P03891
Molecular Weight:
38960.47 Da
References
  1. Chagas GM, Oliveira BM, Campello AP, Kluppel ML: Mechanism of citrinin-induced dysfunction of mitochondria. II. Effect on respiration, enzyme activities, and membrane potential of liver mitochondria. Cell Biochem Funct. 1992 Sep;10(3):209-16. [1330354 ]
General Function:
Nadh dehydrogenase (ubiquinone) activity
Specific Function:
Core subunit of the mitochondrial membrane respiratory chain NADH dehydrogenase (Complex I) that is believed to belong to the minimal assembly required for catalysis. Complex I functions in the transfer of electrons from NADH to the respiratory chain. The immediate electron acceptor for the enzyme is believed to be ubiquinone (By similarity).
Gene Name:
MT-ND3
Uniprot ID:
P03897
Molecular Weight:
13185.87 Da
References
  1. Chagas GM, Oliveira BM, Campello AP, Kluppel ML: Mechanism of citrinin-induced dysfunction of mitochondria. II. Effect on respiration, enzyme activities, and membrane potential of liver mitochondria. Cell Biochem Funct. 1992 Sep;10(3):209-16. [1330354 ]
General Function:
Nadh dehydrogenase (ubiquinone) activity
Specific Function:
Core subunit of the mitochondrial membrane respiratory chain NADH dehydrogenase (Complex I) that is believed to belong to the minimal assembly required for catalysis. Complex I functions in the transfer of electrons from NADH to the respiratory chain. The immediate electron acceptor for the enzyme is believed to be ubiquinone (By similarity).
Gene Name:
MT-ND4
Uniprot ID:
P03905
Molecular Weight:
51580.26 Da
References
  1. Chagas GM, Oliveira BM, Campello AP, Kluppel ML: Mechanism of citrinin-induced dysfunction of mitochondria. II. Effect on respiration, enzyme activities, and membrane potential of liver mitochondria. Cell Biochem Funct. 1992 Sep;10(3):209-16. [1330354 ]
General Function:
Nadh dehydrogenase (ubiquinone) activity
Specific Function:
Core subunit of the mitochondrial membrane respiratory chain NADH dehydrogenase (Complex I) that is believed to belong to the minimal assembly required for catalysis. Complex I functions in the transfer of electrons from NADH to the respiratory chain. The immediate electron acceptor for the enzyme is believed to be ubiquinone (By similarity).
Gene Name:
MT-ND4L
Uniprot ID:
P03901
Molecular Weight:
10741.005 Da
References
  1. Chagas GM, Oliveira BM, Campello AP, Kluppel ML: Mechanism of citrinin-induced dysfunction of mitochondria. II. Effect on respiration, enzyme activities, and membrane potential of liver mitochondria. Cell Biochem Funct. 1992 Sep;10(3):209-16. [1330354 ]
General Function:
Nadh dehydrogenase (ubiquinone) activity
Specific Function:
Core subunit of the mitochondrial membrane respiratory chain NADH dehydrogenase (Complex I) that is believed to belong to the minimal assembly required for catalysis. Complex I functions in the transfer of electrons from NADH to the respiratory chain. The immediate electron acceptor for the enzyme is believed to be ubiquinone (By similarity).
Gene Name:
MT-ND5
Uniprot ID:
P03915
Molecular Weight:
67025.67 Da
References
  1. Chagas GM, Oliveira BM, Campello AP, Kluppel ML: Mechanism of citrinin-induced dysfunction of mitochondria. II. Effect on respiration, enzyme activities, and membrane potential of liver mitochondria. Cell Biochem Funct. 1992 Sep;10(3):209-16. [1330354 ]
General Function:
Nadh dehydrogenase (ubiquinone) activity
Specific Function:
Core subunit of the mitochondrial membrane respiratory chain NADH dehydrogenase (Complex I) that is believed to belong to the minimal assembly required for catalysis. Complex I functions in the transfer of electrons from NADH to the respiratory chain. The immediate electron acceptor for the enzyme is believed to be ubiquinone (By similarity).
Gene Name:
MT-ND6
Uniprot ID:
P03923
Molecular Weight:
18622.045 Da
References
  1. Chagas GM, Oliveira BM, Campello AP, Kluppel ML: Mechanism of citrinin-induced dysfunction of mitochondria. II. Effect on respiration, enzyme activities, and membrane potential of liver mitochondria. Cell Biochem Funct. 1992 Sep;10(3):209-16. [1330354 ]
General Function:
Protein heterodimerization activity
Specific Function:
This multifunctional protein catalyzes the formation, breakage and rearrangement of disulfide bonds. At the cell surface, seems to act as a reductase that cleaves disulfide bonds of proteins attached to the cell. May therefore cause structural modifications of exofacial proteins. Inside the cell, seems to form/rearrange disulfide bonds of nascent proteins. At high concentrations, functions as a chaperone that inhibits aggregation of misfolded proteins. At low concentrations, facilitates aggregation (anti-chaperone activity). May be involved with other chaperones in the structural modification of the TG precursor in hormone biogenesis. Also acts a structural subunit of various enzymes such as prolyl 4-hydroxylase and microsomal triacylglycerol transfer protein MTTP. Receptor for LGALS9; the interaction retains P4HB at the cell surface of Th2 T helper cells, increasing disulfide reductase activity at the plasma membrane, altering the plasma membrane redox state and enhancing cell migration (PubMed:21670307).
Gene Name:
P4HB
Uniprot ID:
P07237
Molecular Weight:
57115.795 Da
References
  1. Flajs D, Peraica M: Toxicological properties of citrinin. Arh Hig Rada Toksikol. 2009 Dec;60(4):457-64. doi: 10.2478/10004-1254-60-2009-1992. [20061247 ]
General Function:
Pyruvate dehydrogenase activity
Specific Function:
The pyruvate dehydrogenase complex catalyzes the overall conversion of pyruvate to acetyl-CoA and CO(2), and thereby links the glycolytic pathway to the tricarboxylic cycle.
Gene Name:
PDHA1
Uniprot ID:
P08559
Molecular Weight:
43295.255 Da
References
  1. Chagas GM, Oliveira MA, Campello AP, Kluppel ML: Mechanism of citrinin-induced dysfunction of mitochondria. IV--Effect on Ca2+ transport. Cell Biochem Funct. 1995 Mar;13(1):53-9. [7720190 ]
General Function:
Pyruvate dehydrogenase (acetyl-transferring) activity
Specific Function:
The pyruvate dehydrogenase complex catalyzes the overall conversion of pyruvate to acetyl-CoA and CO(2), and thereby links the glycolytic pathway to the tricarboxylic cycle.
Gene Name:
PDHA2
Uniprot ID:
P29803
Molecular Weight:
42932.855 Da
References
  1. Chagas GM, Oliveira MA, Campello AP, Kluppel ML: Mechanism of citrinin-induced dysfunction of mitochondria. IV--Effect on Ca2+ transport. Cell Biochem Funct. 1995 Mar;13(1):53-9. [7720190 ]
General Function:
Pyruvate dehydrogenase activity
Specific Function:
The pyruvate dehydrogenase complex catalyzes the overall conversion of pyruvate to acetyl-CoA and CO(2), and thereby links the glycolytic pathway to the tricarboxylic cycle.
Gene Name:
PDHB
Uniprot ID:
P11177
Molecular Weight:
39233.1 Da
References
  1. Chagas GM, Oliveira MA, Campello AP, Kluppel ML: Mechanism of citrinin-induced dysfunction of mitochondria. IV--Effect on Ca2+ transport. Cell Biochem Funct. 1995 Mar;13(1):53-9. [7720190 ]
General Function:
Transferase activity, transferring acyl groups
Specific Function:
Required for anchoring dihydrolipoamide dehydrogenase (E3) to the dihydrolipoamide transacetylase (E2) core of the pyruvate dehydrogenase complexes of eukaryotes. This specific binding is essential for a functional PDH complex.
Gene Name:
PDHX
Uniprot ID:
O00330
Molecular Weight:
54121.76 Da
References
  1. Chagas GM, Oliveira MA, Campello AP, Kluppel ML: Mechanism of citrinin-induced dysfunction of mitochondria. IV--Effect on Ca2+ transport. Cell Biochem Funct. 1995 Mar;13(1):53-9. [7720190 ]
General Function:
Secondary active organic cation transmembrane transporter activity
Specific Function:
Translocates a broad array of organic cations with various structures and molecular weights including the model compounds 1-methyl-4-phenylpyridinium (MPP), tetraethylammonium (TEA), N-1-methylnicotinamide (NMN), 4-(4-(dimethylamino)styryl)-N-methylpyridinium (ASP), the endogenous compounds choline, guanidine, histamine, epinephrine, adrenaline, noradrenaline and dopamine, and the drugs quinine, and metformin. The transport of organic cations is inhibited by a broad array of compounds like tetramethylammonium (TMA), cocaine, lidocaine, NMDA receptor antagonists, atropine, prazosin, cimetidine, TEA and NMN, guanidine, cimetidine, choline, procainamide, quinine, tetrabutylammonium, and tetrapentylammonium. Translocates organic cations in an electrogenic and pH-independent manner. Translocates organic cations across the plasma membrane in both directions. Transports the polyamines spermine and spermidine. Transports pramipexole across the basolateral membrane of the proximal tubular epithelial cells. The choline transport is activated by MMTS. Regulated by various intracellular signaling pathways including inhibition by protein kinase A activation, and endogenously activation by the calmodulin complex, the calmodulin-dependent kinase II and LCK tyrosine kinase.
Gene Name:
SLC22A1
Uniprot ID:
O15245
Molecular Weight:
61153.345 Da
References
  1. Tachampa K, Takeda M, Khamdang S, Noshiro-Kofuji R, Tsuda M, Jariyawat S, Fukutomi T, Sophasan S, Anzai N, Endou H: Interactions of organic anion transporters and organic cation transporters with mycotoxins. J Pharmacol Sci. 2008 Mar;106(3):435-43. Epub 2008 Mar 5. [18319568 ]
General Function:
Quaternary ammonium group transmembrane transporter activity
Specific Function:
Mediates tubular uptake of organic compounds from circulation. Mediates the influx of agmatine, dopamine, noradrenaline (norepinephrine), serotonin, choline, famotidine, ranitidine, histamin, creatinine, amantadine, memantine, acriflavine, 4-[4-(dimethylamino)-styryl]-N-methylpyridinium ASP, amiloride, metformin, N-1-methylnicotinamide (NMN), tetraethylammonium (TEA), 1-methyl-4-phenylpyridinium (MPP), cimetidine, cisplatin and oxaliplatin. Cisplatin may develop a nephrotoxic action. Transport of creatinine is inhibited by fluoroquinolones such as DX-619 and LVFX. This transporter is a major determinant of the anticancer activity of oxaliplatin and may contribute to antitumor specificity.
Gene Name:
SLC22A2
Uniprot ID:
O15244
Molecular Weight:
62579.99 Da
References
  1. Tachampa K, Takeda M, Khamdang S, Noshiro-Kofuji R, Tsuda M, Jariyawat S, Fukutomi T, Sophasan S, Anzai N, Endou H: Interactions of organic anion transporters and organic cation transporters with mycotoxins. J Pharmacol Sci. 2008 Mar;106(3):435-43. Epub 2008 Mar 5. [18319568 ]
General Function:
Sodium-independent organic anion transmembrane transporter activity
Specific Function:
Mediates sodium-independent multispecific organic anion transport. Transport of prostaglandin E2, prostaglandin F2, tetracycline, bumetanide, estrone sulfate, glutarate, dehydroepiandrosterone sulfate, allopurinol, 5-fluorouracil, paclitaxel, L-ascorbic acid, salicylate, ethotrexate, and alpha-ketoglutarate.
Gene Name:
SLC22A7
Uniprot ID:
Q9Y694
Molecular Weight:
60025.025 Da
References
  1. Tachampa K, Takeda M, Khamdang S, Noshiro-Kofuji R, Tsuda M, Jariyawat S, Fukutomi T, Sophasan S, Anzai N, Endou H: Interactions of organic anion transporters and organic cation transporters with mycotoxins. J Pharmacol Sci. 2008 Mar;106(3):435-43. Epub 2008 Mar 5. [18319568 ]
General Function:
Sodium-independent organic anion transmembrane transporter activity
Specific Function:
Plays an important role in the excretion/detoxification of endogenous and exogenous organic anions, especially from the brain and kidney. Involved in the transport basolateral of steviol, fexofenadine. Transports benzylpenicillin (PCG), estrone-3-sulfate (E1S), cimetidine (CMD), 2,4-dichloro-phenoxyacetate (2,4-D), p-amino-hippurate (PAH), acyclovir (ACV) and ochratoxin (OTA).
Gene Name:
SLC22A8
Uniprot ID:
Q8TCC7
Molecular Weight:
59855.585 Da
References
  1. Tachampa K, Takeda M, Khamdang S, Noshiro-Kofuji R, Tsuda M, Jariyawat S, Fukutomi T, Sophasan S, Anzai N, Endou H: Interactions of organic anion transporters and organic cation transporters with mycotoxins. J Pharmacol Sci. 2008 Mar;106(3):435-43. Epub 2008 Mar 5. [18319568 ]
General Function:
Temperature-gated cation channel activity
Specific Function:
Receptor-activated non-selective cation channel involved in detection of pain and possibly also in cold perception and inner ear function (PubMed:25389312, PubMed:25855297). Has a central role in the pain response to endogenous inflammatory mediators and to a diverse array of volatile irritants, such as mustard oil, cinnamaldehyde, garlic and acrolein, an irritant from tears gas and vehicule exhaust fumes (PubMed:25389312, PubMed:20547126). Is also activated by menthol (in vitro)(PubMed:25389312). Acts also as a ionotropic cannabinoid receptor by being activated by delta(9)-tetrahydrocannabinol (THC), the psychoactive component of marijuana (PubMed:25389312). May be a component for the mechanosensitive transduction channel of hair cells in inner ear, thereby participating in the perception of sounds. Probably operated by a phosphatidylinositol second messenger system (By similarity).
Gene Name:
TRPA1
Uniprot ID:
O75762
Molecular Weight:
127499.88 Da
References
  1. Nilius B, Prenen J, Owsianik G: Irritating channels: the case of TRPA1. J Physiol. 2011 Apr 1;589(Pt 7):1543-9. doi: 10.1113/jphysiol.2010.200717. Epub 2010 Nov 15. [21078588 ]