Citreoviridin A (T3D3737)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesGene RegulationTargets (15)XML
Targets (15)
Record Information
Version2.0
Creation Date2010-05-06 14:52:05 UTC
Update Date2014-12-24 20:26:28 UTC
Accession NumberT3D3737
Identification
Common NameCitreoviridin A
ClassSmall Molecule
DescriptionCitreoviridin A is a metabolite of Penicillium citreo-viride, Penicillium toxicarium, Penicillium ochrosalmoneum and Aspergillus terreus. It is isolated from mouldy rice. Toxin formerly responsible for epidemic-like occurrences of cardiac beriberi in East Asia Citreoviridin A belongs to the family of Pyranones and Derivatives. These are compounds containing a pyran ring which bears a ketone.
Compound Type
  • Ester
  • Ether
  • Food Toxin
  • Fungal Toxin
  • Metabolite
  • Mycotoxin
  • Natural Compound
  • Organic Compound
Chemical Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
Synonym
Citreoviridin a
Citreoviridine
Citreoviridine a
Chemical FormulaC23H30O6
Average Molecular Mass402.481 g/mol
Monoisotopic Mass402.204 g/mol
CAS Registry Number25425-12-1
IUPAC Name6-[(1E,3E,5E,7E)-8-(3,4-dihydroxy-2,4,5-trimethyloxolan-2-yl)-7-methylocta-1,3,5,7-tetraen-1-yl]-4-methoxy-5-methyl-2H-pyran-2-one
Traditional Name6-[(1E,3E,5E,7E)-8-(3,4-dihydroxy-2,4,5-trimethyloxolan-2-yl)-7-methylocta-1,3,5,7-tetraen-1-yl]-4-methoxy-5-methylpyran-2-one
SMILES[H]/C(=C(/[H])\C(\[H])=C(/[H])C1=C(C)C(OC)=CC(=O)O1)/C(/[H])=C(\[H])/C(/C)=C(\[H])C1(C)OC(C)C(C)(O)C1O
InChI IdentifierInChI=1/C23H30O6/c1-15(14-22(4)21(25)23(5,26)17(3)29-22)11-9-7-8-10-12-18-16(2)19(27-6)13-20(24)28-18/h7-14,17,21,25-26H,1-6H3/b8-7+,11-9+,12-10+,15-14+
InChI KeyInChIKey=JLSVDPQAIKFBTO-USJRQALFNA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as pyranones and derivatives. Pyranones and derivatives are compounds containing a pyran ring which bears a ketone.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassPyrans
Sub ClassPyranones and derivatives
Direct ParentPyranones and derivatives
Alternative Parents
Substituents
  • Alkyl aryl ether
  • Pyranone
  • Heteroaromatic compound
  • Vinylogous ester
  • Tetrahydrofuran
  • Tertiary alcohol
  • 1,2-diol
  • Lactone
  • Secondary alcohol
  • Dialkyl ether
  • Ether
  • Oxacycle
  • Alcohol
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organic oxide
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Membrane
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting Point107 - 111°C
Boiling PointNot Available
SolubilityNot Available
LogPNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.0094 g/LALOGPS
logP3.89ALOGPS
logP2.46ChemAxon
logS-4.6ALOGPS
pKa (Strongest Acidic)12.6ChemAxon
pKa (Strongest Basic)-3.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area85.22 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity118.01 m³·mol⁻¹ChemAxon
Polarizability45.46 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0397800000-0f9771cfe7cb0f49d20b2016-08-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0zfs-0693100000-23553164c96a08dc98892016-08-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0uxu-9730000000-6504eb2eeea870dfbee42016-08-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-2116900000-70772f3c9c6f3fd5a55c2016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0f6x-6309400000-71c410220beebeb86e262016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-006y-9243000000-cf75b7ceb40a5bbec1802016-08-03View Spectrum
Toxicity Profile
Route of ExposureOral, dermal, inhalation, and parenteral (contaminated drugs). (7)
Mechanism of ToxicityCitreoviridin inhibits both membrane-bound and soluble mitochondrial ATPases. In particular, it inhibits synaptosomal Na+/K+-ATPase, altering synaptic transmission, and binds to the beta subunit of F1-ATPAse. As a result it has been shown to inhibit mitochondrial energy-linked reactions such as ADP-stimulated respiration, ATP-driven reduction of NAD + by succinate, and ATP-driven NAD transhydrogenase. 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, interfering with the secretion of endogenous metabolites, drugs, and xenobiotics including themselves. This results in increased cellular accumulation of toxic compounds causing nephro- and hepatotoxicity. (1, 2, 4, 5, 6)
MetabolismNot Available
Toxicity ValuesLD50: 3.6 mg/kg (Subcutaneous, rat) (1) LD50: 7.5 mg/kg (Intraperitoneal, Mouse) (1) LD50: 29 mg/kg (Oral, Mouse) (1)
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesCitreoviridin is a mycotoxin that has been isolated in Peniciilium citreo-viride, P. ochrosalmoneum, and P. pulvullorum. It can be found in contaminated rice grains, as well as corn infested by Eupenicillium ochrosalmoneurn. (1)
Minimum Risk LevelNot Available
Health EffectsCitreoviridin selectively inhibits motor nerve cells in the medulla oblongata and accumulates in the grey matter and brain stem. This can cause central nervous system depression leading to respiratory and cardiovascular failures and death. (1, 3, 4)
SymptomsSymptoms of citreoviridin exposure include progressive paralysis, vomiting, convulsions, and gradual respiratory disorder. (1)
TreatmentNot Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB30868
PubChem Compound IDNot Available
ChEMBL IDNot Available
ChemSpider IDNot Available
KEGG IDNot Available
UniProt IDNot Available
OMIM ID
ChEBI IDNot Available
BioCyc IDNot Available
CTD IDNot Available
Stitch IDNot Available
PDB IDNot Available
ACToR IDNot Available
Wikipedia LinkNot Available
References
Synthesis ReferenceNot Available
MSDST3D3737.pdf
General References
  1. Ueno Y: The toxicology of mycotoxins. Crit Rev Toxicol. 1985;14(2):99-132. [3158480 ]
  2. Linnett PE, Mitchell AD, Osselton MD, Mulheirn LJ, Beechey RB: Citreoviridin, a specific inhibitor of the mitochondiral adenosine triphosphatase. Biochem J. 1978 Mar 15;170(3):503-10. [148274 ]
  3. Nishie K, Cole RJ, Dorner JW: Toxicity of citreoviridin. Res Commun Chem Pathol Pharmacol. 1988 Jan;59(1):31-52. [3258434 ]
  4. Datta SC, Ghosh JJ: Effect of citreoviridin, a mycotoxin from Penicillium citreoviride, on kinetic constants of acetylcholinesterase and ATPase in synaptosomes and microsomes from rat brain. Toxicon. 1981;19(4):555-62. [6460346 ]
  5. Gause EM, Buck MA, Douglas MG: Binding of citreoviridin to the beta subunit of the yeast F1-ATPase. J Biol Chem. 1981 Jan 25;256(2):557-9. [6450205 ]
  6. 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 ]
  7. Peraica M, Domijan AM: Contamination of food with mycotoxins and human health. Arh Hig Rada Toksikol. 2001 Mar;52(1):23-35. [11370295 ]
  8. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.
Gene Regulation
Up-Regulated GenesNot Available
Down-Regulated GenesNot Available

Targets

Target Details
1. ATP synthase subunit beta, mitochondrial
General Function:
Transporter activity
Specific Function:
Mitochondrial membrane ATP synthase (F(1)F(0) ATP synthase or Complex V) produces ATP from ADP in the presence of a proton gradient across the membrane which is generated by electron transport complexes of the respiratory chain. F-type ATPases consist of two structural domains, F(1) - containing the extramembraneous catalytic core, and F(0) - containing the membrane proton channel, linked together by a central stalk and a peripheral stalk. During catalysis, ATP synthesis in the catalytic domain of F(1) is coupled via a rotary mechanism of the central stalk subunits to proton translocation. Subunits alpha and beta form the catalytic core in F(1). Rotation of the central stalk against the surrounding alpha(3)beta(3) subunits leads to hydrolysis of ATP in three separate catalytic sites on the beta subunits.
Gene Name:
ATP5B
Uniprot ID:
P06576
Molecular Weight:
56559.42 Da
References
  1. Linnett PE, Mitchell AD, Osselton MD, Mulheirn LJ, Beechey RB: Citreoviridin, a specific inhibitor of the mitochondiral adenosine triphosphatase. Biochem J. 1978 Mar 15;170(3):503-10. [148274 ]
  2. Gause EM, Buck MA, Douglas MG: Binding of citreoviridin to the beta subunit of the yeast F1-ATPase. J Biol Chem. 1981 Jan 25;256(2):557-9. [6450205 ]
Target Details
2. Sodium/potassium-transporting ATPase subunit alpha-1
General Function:
Steroid hormone binding
Specific Function:
This is the catalytic component of the active enzyme, which catalyzes the hydrolysis of ATP coupled with the exchange of sodium and potassium ions across the plasma membrane. This action creates the electrochemical gradient of sodium and potassium ions, providing the energy for active transport of various nutrients.
Gene Name:
ATP1A1
Uniprot ID:
P05023
Molecular Weight:
112895.01 Da
References
  1. Linnett PE, Mitchell AD, Osselton MD, Mulheirn LJ, Beechey RB: Citreoviridin, a specific inhibitor of the mitochondiral adenosine triphosphatase. Biochem J. 1978 Mar 15;170(3):503-10. [148274 ]
  2. Datta SC, Ghosh JJ: Effect of citreoviridin, a mycotoxin from Penicillium citreoviride, on kinetic constants of acetylcholinesterase and ATPase in synaptosomes and microsomes from rat brain. Toxicon. 1981;19(4):555-62. [6460346 ]
Target Details
3. Sodium/potassium-transporting ATPase subunit alpha-2
General Function:
Steroid hormone binding
Specific Function:
This is the catalytic component of the active enzyme, which catalyzes the hydrolysis of ATP coupled with the exchange of sodium and potassium ions across the plasma membrane. This action creates the electrochemical gradient of sodium and potassium, providing the energy for active transport of various nutrients.
Gene Name:
ATP1A2
Uniprot ID:
P50993
Molecular Weight:
112264.385 Da
References
  1. Linnett PE, Mitchell AD, Osselton MD, Mulheirn LJ, Beechey RB: Citreoviridin, a specific inhibitor of the mitochondiral adenosine triphosphatase. Biochem J. 1978 Mar 15;170(3):503-10. [148274 ]
  2. Datta SC, Ghosh JJ: Effect of citreoviridin, a mycotoxin from Penicillium citreoviride, on kinetic constants of acetylcholinesterase and ATPase in synaptosomes and microsomes from rat brain. Toxicon. 1981;19(4):555-62. [6460346 ]
Target Details
4. Sodium/potassium-transporting ATPase subunit alpha-3
General Function:
Steroid hormone binding
Specific Function:
This is the catalytic component of the active enzyme, which catalyzes the hydrolysis of ATP coupled with the exchange of sodium and potassium ions across the plasma membrane. This action creates the electrochemical gradient of sodium and potassium ions, providing the energy for active transport of various nutrients.
Gene Name:
ATP1A3
Uniprot ID:
P13637
Molecular Weight:
111747.51 Da
References
  1. Linnett PE, Mitchell AD, Osselton MD, Mulheirn LJ, Beechey RB: Citreoviridin, a specific inhibitor of the mitochondiral adenosine triphosphatase. Biochem J. 1978 Mar 15;170(3):503-10. [148274 ]
  2. Datta SC, Ghosh JJ: Effect of citreoviridin, a mycotoxin from Penicillium citreoviride, on kinetic constants of acetylcholinesterase and ATPase in synaptosomes and microsomes from rat brain. Toxicon. 1981;19(4):555-62. [6460346 ]
Target Details
5. Sodium/potassium-transporting ATPase subunit alpha-4
General Function:
Sodium:potassium-exchanging atpase activity
Specific Function:
This is the catalytic component of the active enzyme, which catalyzes the hydrolysis of ATP coupled with the exchange of sodium and potassium ions across the plasma membrane. This action creates the electrochemical gradient of sodium and potassium ions, providing the energy for active transport of various nutrients. Plays a role in sperm motility.
Gene Name:
ATP1A4
Uniprot ID:
Q13733
Molecular Weight:
114165.44 Da
References
  1. Linnett PE, Mitchell AD, Osselton MD, Mulheirn LJ, Beechey RB: Citreoviridin, a specific inhibitor of the mitochondiral adenosine triphosphatase. Biochem J. 1978 Mar 15;170(3):503-10. [148274 ]
  2. Datta SC, Ghosh JJ: Effect of citreoviridin, a mycotoxin from Penicillium citreoviride, on kinetic constants of acetylcholinesterase and ATPase in synaptosomes and microsomes from rat brain. Toxicon. 1981;19(4):555-62. [6460346 ]
Target Details
6. Sodium/potassium-transporting ATPase subunit beta-1
General Function:
Sodium:potassium-exchanging atpase activity
Specific Function:
This is the non-catalytic component of the active enzyme, which catalyzes the hydrolysis of ATP coupled with the exchange of Na(+) and K(+) ions across the plasma membrane. The beta subunit regulates, through assembly of alpha/beta heterodimers, the number of sodium pumps transported to the plasma membrane.Involved in cell adhesion and establishing epithelial cell polarity.
Gene Name:
ATP1B1
Uniprot ID:
P05026
Molecular Weight:
35061.07 Da
References
  1. Linnett PE, Mitchell AD, Osselton MD, Mulheirn LJ, Beechey RB: Citreoviridin, a specific inhibitor of the mitochondiral adenosine triphosphatase. Biochem J. 1978 Mar 15;170(3):503-10. [148274 ]
  2. Datta SC, Ghosh JJ: Effect of citreoviridin, a mycotoxin from Penicillium citreoviride, on kinetic constants of acetylcholinesterase and ATPase in synaptosomes and microsomes from rat brain. Toxicon. 1981;19(4):555-62. [6460346 ]
Target Details
7. Sodium/potassium-transporting ATPase subunit beta-2
General Function:
Sodium:potassium-exchanging atpase activity
Specific Function:
This is the non-catalytic component of the active enzyme, which catalyzes the hydrolysis of ATP coupled with the exchange of Na(+) and K(+) ions across the plasma membrane. The exact function of the beta-2 subunit is not known.Mediates cell adhesion of neurons and astrocytes, and promotes neurite outgrowth.
Gene Name:
ATP1B2
Uniprot ID:
P14415
Molecular Weight:
33366.925 Da
References
  1. Linnett PE, Mitchell AD, Osselton MD, Mulheirn LJ, Beechey RB: Citreoviridin, a specific inhibitor of the mitochondiral adenosine triphosphatase. Biochem J. 1978 Mar 15;170(3):503-10. [148274 ]
  2. Datta SC, Ghosh JJ: Effect of citreoviridin, a mycotoxin from Penicillium citreoviride, on kinetic constants of acetylcholinesterase and ATPase in synaptosomes and microsomes from rat brain. Toxicon. 1981;19(4):555-62. [6460346 ]
Target Details
8. Sodium/potassium-transporting ATPase subunit beta-3
General Function:
Sodium:potassium-exchanging atpase activity
Specific Function:
This is the non-catalytic component of the active enzyme, which catalyzes the hydrolysis of ATP coupled with the exchange of Na(+) and K(+) ions across the plasma membrane. The exact function of the beta-3 subunit is not known.
Gene Name:
ATP1B3
Uniprot ID:
P54709
Molecular Weight:
31512.34 Da
References
  1. Linnett PE, Mitchell AD, Osselton MD, Mulheirn LJ, Beechey RB: Citreoviridin, a specific inhibitor of the mitochondiral adenosine triphosphatase. Biochem J. 1978 Mar 15;170(3):503-10. [148274 ]
  2. Datta SC, Ghosh JJ: Effect of citreoviridin, a mycotoxin from Penicillium citreoviride, on kinetic constants of acetylcholinesterase and ATPase in synaptosomes and microsomes from rat brain. Toxicon. 1981;19(4):555-62. [6460346 ]
Target Details
9. Sodium/potassium-transporting ATPase subunit gamma
General Function:
Transporter activity
Specific Function:
May be involved in forming the receptor site for cardiac glycoside binding or may modulate the transport function of the sodium ATPase.
Gene Name:
FXYD2
Uniprot ID:
P54710
Molecular Weight:
7283.265 Da
References
  1. Linnett PE, Mitchell AD, Osselton MD, Mulheirn LJ, Beechey RB: Citreoviridin, a specific inhibitor of the mitochondiral adenosine triphosphatase. Biochem J. 1978 Mar 15;170(3):503-10. [148274 ]
  2. Datta SC, Ghosh JJ: Effect of citreoviridin, a mycotoxin from Penicillium citreoviride, on kinetic constants of acetylcholinesterase and ATPase in synaptosomes and microsomes from rat brain. Toxicon. 1981;19(4):555-62. [6460346 ]
Target Details
10. Solute carrier family 22 member 1
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 ]
Target Details
11. Solute carrier family 22 member 11
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
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 ]
Target Details
12. Solute carrier family 22 member 2
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 ]
Target Details
13. Solute carrier family 22 member 6
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
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 ]
Target Details
14. Solute carrier family 22 member 7
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 ]
Target Details
15. Solute carrier family 22 member 8
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 ]