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Record Information
Version3.6
Creation Date2006-03-08 13:57:48 UTC
Update Date2016-02-11 01:05:04 UTC
HMDB IDHMDB01895
Secondary Accession NumbersNone
Metabolite Identification
Common NameSalicylic acid
DescriptionSalicylic acid is a colorless, crystalline organic carboxylic acid. Salicylic acid is toxic if ingested in large quantities, but in small quantities is used as a food preservative and antiseptic in toothpaste. It is also the key additive in many skin-care products for the treatment of acne, psoriasis, callouses, corns, keratosis pilaris and warts. The carboxyl group (COOH) can react with alcohols, forming several useful esters. The name derives from the latin word for the willow tree (Salix), from whose bark it can be obtained. --Wikipedia.
Structure
Thumb
Synonyms
ValueSource
2-CarboxyphenolChEBI
2-HYDROXYBENZOIC ACIDChEBI
O-CarboxyphenolChEBI
O-Hydroxybenzoic acidChEBI
SalicylateGenerator
2-HYDROXYBENZOateGenerator
O-HydroxybenzoateGenerator
2-HydroxybenzenecarboxylateHMDB
2-Hydroxybenzenecarboxylic acidHMDB
Advanced pain relief callus removersHMDB
Advanced pain relief corn removersHMDB
Clear away wart removerHMDB
Compound WHMDB
Dr. scholl's callus removersHMDB
Dr. scholl's corn removersHMDB
Dr. scholl's wart remover kitHMDB
Duofil wart removerHMDB
DuoplantHMDB
FreezoneHMDB
IonilHMDB
Ionil plusHMDB
K 537HMDB
K 557HMDB
Phenol-2-carboxylateHMDB
Phenol-2-carboxylic acidHMDB
Psoriacid-S-stiftHMDB
Retarder WHMDB
RutranexHMDB
Salicylic acid collodionHMDB
Salicylic acid soapHMDB
SaligelHMDB
SalonilHMDB
Stri-dexHMDB
trans-Ver-salHMDB
Chemical FormulaC7H6O3
Average Molecular Weight138.1207
Monoisotopic Molecular Weight138.031694058
IUPAC Name2-hydroxybenzoic acid
Traditional Namesalicylic
CAS Registry Number69-72-7
SMILES
OC(=O)C1=CC=CC=C1O
InChI Identifier
InChI=1S/C7H6O3/c8-6-4-2-1-3-5(6)7(9)10/h1-4,8H,(H,9,10)
InChI KeyInChIKey=YGSDEFSMJLZEOE-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as salicylic acids. These are ortho-hydroxylated benzoic acids.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassBenzoic acids and derivatives
Direct ParentSalicylic acids
Alternative Parents
Substituents
  • Salicylic acid
  • Benzoic acid
  • Benzoyl
  • Phenol
  • Vinylogous acid
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
StatusDetected and Quantified
Origin
  • Drug
BiofunctionNot Available
ApplicationNot Available
Cellular locationsNot Available
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point158 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility2.24 mg/mL at 25 °CNot Available
LogP2.26HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
Water Solubility11.3 mg/mLALOGPS
logP1.96ALOGPS
logP1.98ChemAxon
logS-1.1ALOGPS
pKa (Strongest Acidic)2.79ChemAxon
pKa (Strongest Basic)-6.3ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area57.53 Å2ChemAxon
Rotatable Bond Count1ChemAxon
Refractivity35.3 m3·mol-1ChemAxon
Polarizability12.81 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-014i-3890000000-62eae168a9d7ab3ada6fView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MSNot Available
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)splash10-059j-9600000000-54545731fceee84be340View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)splash10-00xu-9500000000-2f1c989b672669aaf083View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)splash10-0gb9-9000000000-a0049e982e8ecd7ab730View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-000i-0900000000-f1e71df6894bcc8dda74View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-0006-9200000000-f9fd317c182ec7ca90dcView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-0006-9000000000-2b17aea4ee0ddd6321cfView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-0006-9000000000-320b7cd879b61439cf42View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-0006-9000000000-7d1b96d60026076a7eccView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
MSMass Spectrum (Electron Ionization)splash10-00du-9600000000-6d4a0ff2d48d814b5c54View in MoNA
1D NMR1H NMR SpectrumNot Available
1D NMR1H NMR SpectrumNot Available
1D NMR13C NMR SpectrumNot Available
2D NMR[1H,1H] 2D NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
Biological Properties
Cellular LocationsNot Available
Biofluid Locations
  • Blood
  • Feces
  • Saliva
  • Urine
Tissue Location
  • Liver
  • Skin
Pathways
NameSMPDB LinkKEGG Link
Salicylic Acid Action PathwaySMP00709Not Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 428
  • Not Applicable
details
FecesDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
FecesDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
FecesDetected and Quantified1.303 +/- 0.145 nmol/g of fecesAdult (>18 years old)Both
Normal
details
FecesDetected and Quantified2.751 +/- 3.0408 nmol/g of fecesAdult (>18 years old)Both
Normal
details
FecesDetected and Quantified4.996 +/- 9.557 nmol/g of fecesAdult (>18 years old)Both
Normal
details
FecesDetected and Quantified6.661 +/- 7.312 nmol/g of fecesAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot ApplicableNot SpecifiedNot Specified
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Not SpecifiedNormal details
UrineDetected but not QuantifiedNot ApplicableAdult (>18 years old)BothNormal details
UrineDetected and Quantified1.1 umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected and Quantified57.701 +/- 18.398 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Normal
    • Mordechai, Hien, ...
details
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
UrineDetected but not QuantifiedNot ApplicableAdult (>18 years old)BothAutosomal dominant polycystic kidney disease (ADPKD) details
UrineDetected and Quantified53.022 +/- 27.201 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Eosinophilic esophagitis
    • Mordechai, Hien, ...
details
UrineDetected and Quantified0.15 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Gastroesophageal reflux disease
    • Mordechai, Hien, ...
details
Predicted Concentrations
BiofluidValueOriginal ageOriginal sexOriginal conditionComments
Blood0-7 uMAdult (>18 years old)BothNormalPredicted based on drug qualities
Blood0-4 umol/mmol creatinineAdult (>18 years old)BothNormalPredicted based on drug qualities
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00936
DrugBank Metabolite IDNot Available
Phenol Explorer Compound ID428
Phenol Explorer Metabolite ID428
FoodDB IDFDB000882
KNApSAcK IDC00000206
Chemspider ID331
KEGG Compound IDC00805
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkSalicylic acid
NuGOwiki LinkHMDB01895
Metagene LinkHMDB01895
METLIN ID616
PubChem Compound338
PDB IDSAL
ChEBI ID16914
References
Synthesis ReferenceYin, Yingwu; Guo, Qingbin. Preparation of salicylic acid from phenol. Faming Zhuanli Shenqing Gongkai Shuomingshu (2005), 7pp.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Vane JR: Inhibition of prostaglandin synthesis as a mechanism of action for aspirin-like drugs. Nat New Biol. 1971 Jun 23;231(25):232-5. [5284360 ]
  2. Rutner M, Fitzek J, Jahnel-Kracht H, Otto J, Krause W: [Therapy of rheumatic disease with a hydroxyethylsalicylate gel. Results of 2 clinical studies of effectiveness and bioavailability] Fortschr Med. 1995 Mar 20;113(8):111-3. [7759034 ]
  3. Khan AZ, Aarons L: A note on the use of salicylate saliva concentration in clinical pharmacokinetic studies. J Pharm Pharmacol. 1989 Oct;41(10):710-1. [2575150 ]
  4. Vila MM, Tubino M, de Oliveira Neto G: Determination of salicylate in blood serum by flow injection with immobilized salicylate hydroxylase. J AOAC Int. 2001 Sep-Oct;84(5):1363-9. [11601455 ]
  5. Zaugg S, Zhang X, Sweedler J, Thormann W: Determination of salicylate, gentisic acid and salicyluric acid in human urine by capillary electrophoresis with laser-induced fluorescence detection. J Chromatogr B Biomed Sci Appl. 2001 Mar 5;752(1):17-31. [11254191 ]
  6. Berkovitch M, Uziel Y, Greenberg R, Chen-Levy Z, Arcusin M, Marcus O, Pinto O, Evans S, Matias A, Lahat E: False-high blood salicylate levels in neonates with hyperbilirubinemia. Ther Drug Monit. 2000 Dec;22(6):757-61. [11128247 ]
  7. Goussis OS, Theodoropoulos TJ: Dilantin and salicylate effects on hepatic thyroxine bio-availability and dialyzable thyroxine. Horm Metab Res. 1990 Jun;22(6):342-4. [2379917 ]
  8. Benfeldt E, Serup J, Menne T: Microdialysis vs. suction blister technique for in vivo sampling of pharmacokinetics in the human dermis. Acta Derm Venereol. 1999 Sep;79(5):338-42. [10494706 ]
  9. Ndovi TT, Choi L, Caffo B, Parsons T, Baker S, Zhao M, Rohde C, Hendrix CW: Quantitative assessment of seminal vesicle and prostate drug concentrations by use of a noninvasive method. Clin Pharmacol Ther. 2006 Aug;80(2):146-58. [16890576 ]
  10. Kocoshis SA, Wong CT: Sodium salicylate and bile acid-induced colonic secretion in the rat. Ann Clin Lab Sci. 1991 May-Jun;21(3):197-204. [2064304 ]
  11. Owen SG, Francis HW, Roberts MS: Disappearance kinetics of solutes from synovial fluid after intra-articular injection. Br J Clin Pharmacol. 1994 Oct;38(4):349-55. [7833225 ]
  12. Quaranta A, Portalatini P, Camporeale M, Sallustio V: Effects of salicylates on evoked otoacoustic emissions and remote masking in humans. Audiology. 1999 May-Jun;38(3):174-9. [10437688 ]
  13. Yoshida NH, Roberts MS: Prediction of cathodal iontophoretic transport of various anions across excised skin from different vehicles using conductivity measurements. J Pharm Pharmacol. 1995 Nov;47(11):883-90. [8708980 ]
  14. Alanko K, Stubb S, Salo OP, Reitamo S: Suction blister fluid histamine in fixed drug eruption. Acta Derm Venereol. 1992;72(2):89-91. [1350413 ]
  15. Singh P, Anliker M, Smith GA, Zavortink D, Maibach HI: Transdermal iontophoresis and solute penetration across excised human skin. J Pharm Sci. 1995 Nov;84(11):1342-6. [8587053 ]
  16. Hazouard E, Grimbert M, Jonville-Berra AP, De Toffol MC, Legras A: [Salicylism and glaucoma: reciprocal augmentation of the toxicity of acetazolamide and acetylsalicylic acid] J Fr Ophtalmol. 1999 Feb;22(1):73-5. [10221197 ]
  17. Schmook FP, Meingassner JG, Billich A: Comparison of human skin or epidermis models with human and animal skin in in-vitro percutaneous absorption. Int J Pharm. 2001 Mar 14;215(1-2):51-6. [11250091 ]
  18. Pirola R, Bareggi SR, De Benedittis G: Determination of acetylsalicylic acid and salicylic acid in skin and plasma by high-performance liquid chromatography. J Chromatogr B Biomed Sci Appl. 1998 Feb 13;705(2):309-15. [9521569 ]
  19. Kunkel A, Watzig H: Pharmacokinetic investigations with direct injection of plasma samples: possible savings using capillary electrophoresis (CE). Arch Pharm (Weinheim). 1999 May;332(5):175-8. [10366903 ]
  20. Azaroual, Imbenotte M, Cartigny B, Lhermitte M, Vermeersch G: [Identification and quantification of exogenous metabolites in biological liquids with new development in NMR spectroscopy in one and two dimensions] Acta Clin Belg Suppl. 1999;1:97-100. [10216993 ]
  21. Baggott JE, Morgan SL, Ha T, Vaughn WH, Hine RJ: Inhibition of folate-dependent enzymes by non-steroidal anti-inflammatory drugs. Biochem J. 1992 Feb 15;282 ( Pt 1):197-202. [1540135 ]
  22. Flower R, Gryglewski R, Herbaczynska-Cedro K, Vane JR: Effects of anti-inflammatory drugs on prostaglandin biosynthesis. Nat New Biol. 1972 Jul 26;238(82):104-6. [4505422 ]

Enzymes

General function:
Involved in oxidoreductase activity
Specific function:
Converts progesterone to its inactive form, 20-alpha-dihydroxyprogesterone (20-alpha-OHP). In the liver and intestine, may have a role in the transport of bile. May have a role in monitoring the intrahepatic bile acid concentration. Has a low bile-binding ability. May play a role in myelin formation.
Gene Name:
AKR1C1
Uniprot ID:
Q04828
Molecular weight:
36788.02
References
  1. Dhagat U, Carbone V, Chung RP, Matsunaga T, Endo S, Hara A, El-Kabbani O: A salicylic acid-based analogue discovered from virtual screening as a potent inhibitor of human 20alpha-hydroxysteroid dehydrogenase. Med Chem. 2007 Nov;3(6):546-50. [18045204 ]
General function:
Involved in peroxidase activity
Specific function:
Mediates the formation of prostaglandins from arachidonate. May have a role as a major mediator of inflammation and/or a role for prostanoid signaling in activity-dependent plasticity.
Gene Name:
PTGS2
Uniprot ID:
P35354
Molecular weight:
68995.625
References
  1. Graham GG, Scott KF: Mechanisms of action of paracetamol and related analgesics. Inflammopharmacology. 2003;11(4):401-13. [15035793 ]
  2. Fiebich BL, Chrubasik S: Effects of an ethanolic salix extract on the release of selected inflammatory mediators in vitro. Phytomedicine. 2004 Feb;11(2-3):135-8. [15070163 ]
  3. Chae HJ, Chae SW, Reed JC, Kim HR: Salicylate regulates COX-2 expression through ERK and subsequent NF-kappaB activation in osteoblasts. Immunopharmacol Immunotoxicol. 2004 Feb;26(1):75-91. [15106733 ]
  4. Wu KK: Aspirin and other cyclooxygenase inhibitors: new therapeutic insights. Semin Vasc Med. 2003 May;3(2):107-12. [15199473 ]
  5. Elvira C, Gallardo A, Lacroix N, Schacht E, San Roman J: Incorporation of salicylic acid derivatives to hydrophilic copolymer systems with biomedical applications. J Mater Sci Mater Med. 2001 Jun;12(6):535-42. [15348270 ]
  6. Vane JR: Inhibition of prostaglandin synthesis as a mechanism of action for aspirin-like drugs. Nat New Biol. 1971 Jun 23;231(25):232-5. [5284360 ]
General function:
Involved in peroxidase activity
Specific function:
May play an important role in regulating or promoting cell proliferation in some normal and neoplastically transformed cells.
Gene Name:
PTGS1
Uniprot ID:
P23219
Molecular weight:
68685.82
References
  1. Moon C, Ahn M, Jee Y, Heo S, Kim S, Kim H, Sim KB, Koh CS, Shin YG, Shin T: Sodium salicylate-induced amelioration of experimental autoimmune encephalomyelitis in Lewis rats is associated with the suppression of inducible nitric oxide synthase and cyclooxygenases. Neurosci Lett. 2004 Feb 12;356(2):123-6. [14746879 ]
  2. Graham GG, Scott KF: Mechanisms of action of paracetamol and related analgesics. Inflammopharmacology. 2003;11(4):401-13. [15035793 ]
  3. Sun R, Carlson NG, Hemmert AC, Kishore BK: P2Y2 receptor-mediated release of prostaglandin E2 by IMCD is altered in hydrated and dehydrated rats: relevance to AVP-independent regulation of IMCD function. Am J Physiol Renal Physiol. 2005 Sep;289(3):F585-92. Epub 2005 Apr 19. [15840771 ]
  4. Celik G, Pasaoglu G, Bavbek S, Abadoglu O, Dursun B, Mungan D, Misirligil Z: Tolerability of selective cyclooxygenase inhibitor, celecoxib, in patients with analgesic intolerance. J Asthma. 2005 Mar;42(2):127-31. [15871445 ]
  5. Liu X, Lee TL, Wong PT: Cyclooxygenase-1 inhibition shortens the duration of diazepam-induced loss of righting reflex in mice. Anesth Analg. 2006 Jan;102(1):135-40. [16368818 ]
  6. Vane JR: Inhibition of prostaglandin synthesis as a mechanism of action for aspirin-like drugs. Nat New Biol. 1971 Jun 23;231(25):232-5. [5284360 ]
  7. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [11752352 ]
General function:
Involved in monooxygenase activity
Specific function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. This enzyme contributes to the wide pharmacokinetics variability of the metabolism of drugs such as S-warfarin, diclofenac, phenytoin, tolbutamide and losartan.
Gene Name:
CYP2C9
Uniprot ID:
P11712
Molecular weight:
55627.365
References
  1. Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [19515014 ]
General function:
Involved in ligand-gated sodium channel activity
Specific function:
Cation channel with high affinity for sodium, which is gated by extracellular protons and inhibited by the diuretic amiloride. Also permeable for Ca(2+), Li(+) and K(+). Generates a biphasic current with a fast inactivating and a slow sustained phase. Mediates glutamate-independent Ca(2+) entry into neurons upon acidosis. This Ca(2+) overloading is toxic for cortical neurons and may be in part responsible for ischemic brain injury. Heteromeric channel assembly seems to modulate channel properties. Functions as a postsynaptic proton receptor that influences intracellular Ca(2+) concentration and calmodulin-dependent protein kinase II phosphorylation and thereby the density of dendritic spines. Modulates activity in the circuits underlying innate fear
Gene Name:
ACCN2
Uniprot ID:
P78348
Molecular weight:
59908.9
General function:
Involved in ligand-gated sodium channel activity
Specific function:
Cation channel with high affinity for sodium, which is gated by extracellular protons and inhibited by the diuretic amiloride. Generates a biphasic current with a fast inactivating and a slow sustained phase. In sensory neurons is proposed to mediate the pain induced by acidosis that occurs in ischemic, damaged or inflamed tissue. May be involved in hyperalgesia. May play a role in mechanoreception. Heteromeric channel assembly seems to modulate channel properties
Gene Name:
ACCN3
Uniprot ID:
Q9UHC3
Molecular weight:
58904.7

Transporters

General function:
Involved in transmembrane transport
Specific function:
Proton-linked monocarboxylate transporter. Catalyzes the rapid transport across the plasma membrane of many monocarboxylates such as lactate, pyruvate, branched-chain oxo acids derived from leucine, valine and isoleucine, and the ketone bodies acetoacetate, beta-hydroxybutyrate and acetate
Gene Name:
SLC16A1
Uniprot ID:
P53985
Molecular weight:
53957.7
References
  1. Tamai I, Sai Y, Ono A, Kido Y, Yabuuchi H, Takanaga H, Satoh E, Ogihara T, Amano O, Izeki S, Tsuji A: Immunohistochemical and functional characterization of pH-dependent intestinal absorption of weak organic acids by the monocarboxylic acid transporter MCT1. J Pharm Pharmacol. 1999 Oct;51(10):1113-21. [10579682 ]
General function:
Involved in transporter activity
Specific function:
Mediates the Na(+)-independent transport of organic anions such as taurocholate, the prostaglandins PGD2, PGE1, PGE2, leukotriene C4, thromboxane B2 and iloprost
Gene Name:
SLCO2B1
Uniprot ID:
O94956
Molecular weight:
76697.9
References
  1. Satoh H, Yamashita F, Tsujimoto M, Murakami H, Koyabu N, Ohtani H, Sawada Y: Citrus juices inhibit the function of human organic anion-transporting polypeptide OATP-B. Drug Metab Dispos. 2005 Apr;33(4):518-23. Epub 2005 Jan 7. [15640378 ]
General function:
Involved in ATP binding
Specific function:
Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells
Gene Name:
ABCB1
Uniprot ID:
P08183
Molecular weight:
141477.3
References
  1. Faassen F, Vogel G, Spanings H, Vromans H: Caco-2 permeability, P-glycoprotein transport ratios and brain penetration of heterocyclic drugs. Int J Pharm. 2003 Sep 16;263(1-2):113-22. [12954186 ]
General function:
Involved in transporter activity
Specific function:
Mediates saturable uptake of estrone sulfate, dehydroepiandrosterone sulfate and related compounds
Gene Name:
SLC22A11
Uniprot ID:
Q9NSA0
Molecular weight:
59970.9
References
  1. Cha SH, Sekine T, Kusuhara H, Yu E, Kim JY, Kim DK, Sugiyama Y, Kanai Y, Endou H: Molecular cloning and characterization of multispecific organic anion transporter 4 expressed in the placenta. J Biol Chem. 2000 Feb 11;275(6):4507-12. [10660625 ]
General function:
Involved in ion 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). 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. 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:
61815.8
References
  1. Cihlar T, Ho ES: Fluorescence-based assay for the interaction of small molecules with the human renal organic anion transporter 1. Anal Biochem. 2000 Jul 15;283(1):49-55. [10929807 ]
  2. Takeda M, Khamdang S, Narikawa S, Kimura H, Hosoyamada M, Cha SH, Sekine T, Endou H: Characterization of methotrexate transport and its drug interactions with human organic anion transporters. J Pharmacol Exp Ther. 2002 Aug;302(2):666-71. [12130730 ]
  3. Race JE, Grassl SM, Williams WJ, Holtzman EJ: Molecular cloning and characterization of two novel human renal organic anion transporters (hOAT1 and hOAT3). Biochem Biophys Res Commun. 1999 Feb 16;255(2):508-14. [10049739 ]
  4. Uwai Y, Saito H, Inui K: Interaction between methotrexate and nonsteroidal anti-inflammatory drugs in organic anion transporter. Eur J Pharmacol. 2000 Dec 1;409(1):31-6. [11099697 ]
  5. Apiwattanakul N, Sekine T, Chairoungdua A, Kanai Y, Nakajima N, Sophasan S, Endou H: Transport properties of nonsteroidal anti-inflammatory drugs by organic anion transporter 1 expressed in Xenopus laevis oocytes. Mol Pharmacol. 1999 May;55(5):847-54. [10220563 ]
General function:
Involved in transmembrane transport
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:
60025.0
References
  1. Kobayashi Y, Ohshiro N, Shibusawa A, Sasaki T, Tokuyama S, Sekine T, Endou H, Yamamoto T: Isolation, characterization and differential gene expression of multispecific organic anion transporter 2 in mice. Mol Pharmacol. 2002 Jul;62(1):7-14. [12065749 ]
  2. Sekine T, Cha SH, Tsuda M, Apiwattanakul N, Nakajima N, Kanai Y, Endou H: Identification of multispecific organic anion transporter 2 expressed predominantly in the liver. FEBS Lett. 1998 Jun 12;429(2):179-82. [9650585 ]
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