Tmic
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Record Information
Version2.0
Creation Date2014-09-11 05:17:50 UTC
Update Date2014-12-24 20:26:57 UTC
Accession NumberT3D4816
Identification
Common NameSalicylic acid
ClassSmall Molecule
DescriptionA compound obtained from the bark of the white willow and wintergreen leaves, and also prepared synthetically. It has bacteriostatic, fungicidal, and keratolytic actions. Its salts, the salicylates, are used as analgesics.
Compound Type
  • Anti-Infective Agent
  • Antifungal Agent
  • Drug
  • Ester
  • Food Toxin
  • Household Toxin
  • Keratolytic Agent
  • Metabolite
  • Natural Compound
  • Organic Compound
  • Plant Toxin
  • Synthetic Compound
Chemical Structure
Thumb
Synonyms
Synonym
2-Carboxyphenol
2-Hydroxybenzenecarboxylate
2-Hydroxybenzenecarboxylic acid
2-Hydroxybenzoate
2-Hydroxybenzoic acid
Advanced Pain Relief Callus Removers
Advanced Pain Relief Corn Removers
Clear away Wart Remover
Compound W
Dr. Scholl'S Callus Removers
Dr. Scholl'S Corn Removers
Dr. Scholl'S Wart Remover Kit
Duofil Wart Remover
Duoplant
Freezone
Ionil
Ionil Plus
Ionil Plus shampoo
K 537
K 557
Keralyt
O-Carboxyphenol
O-Hydroxybenzoate
O-Hydroxybenzoic acid
Phenol-2-carboxylate
Phenol-2-carboxylic acid
Psoriacid-S-Stift
Retarder W
Rutranex
Salicylate
Salicylic acid collodion
Salicylic acid Soap
Saligel
Salonil
Stri-Dex
Stridex
Trans-Ver-Sal
Chemical FormulaC7H6O3
Average Molecular Mass138.121 g/mol
Monoisotopic Mass138.032 g/mol
CAS Registry Number69-72-7
IUPAC Name2-hydroxybenzoic acid
Traditional Namesalicylic
SMILESOC(=O)C1=CC=CC=C1O
InChI IdentifierInChI=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
Description 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
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Vinylogous acid
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Cytoplasm
  • Extracellular
Biofluid LocationsNot Available
Tissue Locations
  • Liver
  • Skin
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting Point158°C
Boiling Point211°C at 2.00E+01 mm Hg
Solubility2240 mg/L (at 25°C)
LogP2.26
Predicted Properties
PropertyValueSource
Water Solubility11.3 g/LALOGPS
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 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity35.3 m³·mol⁻¹ChemAxon
Polarizability12.81 ųChemAxon
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
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-00du-9700000000-e1e2ee6b61d86c596403View in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-014i-3890000000-62eae168a9d7ab3ada6fView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-014i-2960000000-1b6b46cbb2b643b71448View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0079-8900000000-e8ee46d81fcc1ce3766eView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-006x-8950000000-9ed3a56f2b2654ba281fView in MoNA
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
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF , Negativesplash10-002b-0496100000-97708001d2a6d031beffView in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-002b-0496100000-97708001d2a6d031beffView in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF , Negativesplash10-002b-0496100000-97708001d2a6d031beffView in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-000i-0900000000-f88c693bac9b89416a52View in MoNA
LC-MS/MSLC-MS/MS Spectrum - DI-ESI-qTof , Positivesplash10-00di-0900000000-2aeace8112266d938c2bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-0006-9400000000-b0fb5458dfa73429b976View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-0006-9400000000-b0fb5458dfa73429b976View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-0006-9100000000-237ee14e8af5262c0dabView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-0006-9000000000-3ec5d7a9114e37b8af2aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-0006-9000000000-d8fdab29114453b10280View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-0006-9000000000-4a337e3639c9f42a9000View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-2900000000-23d1cf43d4dedc979389View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0076-8900000000-f8b39b175209523386d0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udi-9000000000-549ee40f4c3d2a965b2dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000l-6900000000-06bd3bf75f92d507fd8dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-9100000000-fd107d170618784f2f1fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-3fc7a3b941f5e3e4f7ddView in MoNA
MSMass Spectrum (Electron Ionization)splash10-00du-9600000000-6d4a0ff2d48d814b5c54View in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,1H] 2D NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicitySalicylic acid directly and irreversibly inhibits the activity of both types of cyclo-oxygenases (COX-1 and COX-2) to decrease the formation of precursors of prostaglandins and thromboxanes from arachidonic acid. Salicylate may competitively inhibit prostaglandin formation. Salicylate's antirheumatic (nonsteroidal anti-inflammatory) actions are a result of its analgesic and anti-inflammatory mechanisms. Salicylic acid is a key ingredient in many skin-care products for the treatment of acne, psoriasis, calluses, corns, keratosis pilaris, and warts. It works by causing the cells of the epidermis to slough off more readily, preventing pores from clogging up, and allowing room for new cell growth. Because of its effect on skin cells, salicylic acid is used in several shampoos used to treat dandruff. Salicylic acid is also used as an active ingredient in gels which remove verrucas (plantar warts). Salicylic acid inhibits the oxidation of uridine-5-diphosphoglucose (UDPG) competitively with nicotinamide adenosine dinucleotide (NAD) and noncompetitively with UDPG. It also competitively inhibits the transferring of glucuronyl group of uridine-5-phosphoglucuronic acid (UDPGA) to the phenolic acceptor. The wound-healing retardation action of salicylates is probably due mainly to its inhibitory action on mucopolysaccharide synthesis.
MetabolismNot Available
Toxicity ValuesOral rat LD50: 891 mg/kg. Inhalation rat LC50: > 900 mg/m3/1hr. Irritation: skin rabbit: 500 mg/24H mild. Eye rabbit: 100 mg severe.
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesKey additive in many skin-care products for the treatment of acne, psoriasis, callouses, corns, keratosis pilaris and warts.
Minimum Risk LevelNot Available
Health EffectsInvestigated as a mutagen and reproductive effector.
SymptomsNot Available
TreatmentNot Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
DrugBank IDDB00936
HMDB IDHMDB01895
PubChem Compound ID338
ChEMBL IDCHEMBL424
ChemSpider ID331
KEGG IDC00805
UniProt IDNot Available
OMIM ID
ChEBI ID16914
BioCyc IDNot Available
CTD IDNot Available
Stitch IDNot Available
PDB IDSAL
ACToR IDNot Available
Wikipedia LinkSalicyclic_acid
References
Synthesis Reference

Howard Jones, Robert W. Houser, “Process for preparing 4-(2,4-difluorophenyl)-salicyclic acid.” U.S. Patent US4225730, issued August, 1972.

MSDSLink
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. 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 ]
  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. 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 ]
  8. 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 ]
  9. 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 ]
  10. 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 ]
  11. 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 ]
  12. 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 ]
  13. 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 ]
  14. 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 ]
  15. 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 ]
  16. 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 ]
  17. 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 ]
  18. 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 ]
  19. 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 ]
  20. 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 ]
  21. 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 ]
  22. 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 ]
Gene Regulation
Up-Regulated GenesNot Available
Down-Regulated GenesNot Available

Targets

General Function:
Prostaglandin-endoperoxide synthase activity
Specific Function:
Converts arachidonate to prostaglandin H2 (PGH2), a committed step in prostanoid synthesis. Involved in the constitutive production of prostanoids in particular in the stomach and platelets. In gastric epithelial cells, it is a key step in the generation of prostaglandins, such as prostaglandin E2 (PGE2), which plays an important role in cytoprotection. In platelets, it is involved in the generation of thromboxane A2 (TXA2), which promotes platelet activation and aggregation, vasoconstriction and proliferation of vascular smooth muscle cells.
Gene Name:
PTGS1
Uniprot ID:
P23219
Molecular Weight:
68685.82 Da
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:
Prostaglandin-endoperoxide synthase activity
Specific Function:
Converts arachidonate to prostaglandin H2 (PGH2), a committed step in prostanoid synthesis. Constitutively expressed in some tissues in physiological conditions, such as the endothelium, kidney and brain, and in pathological conditions, such as in cancer. PTGS2 is responsible for production of inflammatory prostaglandins. Up-regulation of PTGS2 is also associated with increased cell adhesion, phenotypic changes, resistance to apoptosis and tumor angiogenesis. In cancer cells, PTGS2 is a key step in the production of prostaglandin E2 (PGE2), which plays important roles in modulating motility, proliferation and resistance to apoptosis.
Gene Name:
PTGS2
Uniprot ID:
P35354
Molecular Weight:
68995.625 Da
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:
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase 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 Da
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:
Zinc ion binding
Specific Function:
Steroid hormone receptors are ligand-activated transcription factors that regulate eukaryotic gene expression and affect cellular proliferation and differentiation in target tissues. Transcription factor activity is modulated by bound coactivator and corepressor proteins. Transcription activation is down-regulated by NR0B2. Activated, but not phosphorylated, by HIPK3 and ZIPK/DAPK3.
Gene Name:
AR
Uniprot ID:
P10275
Molecular Weight:
98987.9 Da
Binding/Activity Constants
TypeValueAssay TypeAssay Source
AC501.06 uMATG_AR_TRANSAttagene
References
  1. Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]