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Maleic acid (T3D4800)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesGene RegulationTargets (2)XML
Targets (2)
Record Information
Version2.0
Creation Date2014-09-11 05:17:11 UTC
Update Date2014-12-24 20:26:57 UTC
Accession NumberT3D4800
Identification
Common NameMaleic acid
ClassSmall Molecule
DescriptionMaleic acid is an industrial raw material for the production of glyoxylic acid by ozonolysis. Maleic acid is an organic compound which is a dicarboxylic acid (molecule with two carboxyl groups). The molecule consists of an ethylene group flanked by two carboxylic acid groups. Maleic acid is the cis isomer of butenedioic acid, whereas fumaric acid is the trans isomer. The cis isomer is the less stable one of the two; the difference in heat of combustion is 22.7 kJ/mol. The physical properties of maleic acid are very different from that of fumaric acid. Maleic acid is soluble in water whereas fumaric acid is not and the melting point of maleic acid (130 - 131 degree centigrade) is also much lower than that of fumaric acid (287 degree centigrade). Both properties of maleic acid can be explained on account of the intramolecular hydrogen bonding that takes place at the expense of intermolecular interactions. Maleic acid is converted into maleic anhydride by dehydration, to malic acid by hydration, and to succinic acid by hydrogenation. It reacts with thionyl chloride or phosphorus pentachloride to give the maleic acid chloride (it is not possible to isolate the mono acid chloride). Maleic acid is a reactant in many Diels-Alder reactions.
Compound Type
  • Food Toxin
  • Household Toxin
  • Industrial/Workplace Toxin
  • Metabolite
  • Natural Compound
  • Organic Compound
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
Synonym
(2Z)-2-Butenedioate
(2Z)-2-Butenedioic acid
(2Z)-but-2-enedioate
(2Z)-but-2-enedioic acid
(2Z)-Butene-2-dioate
(2Z)-Butene-2-dioic acid
(Z)-2-Butenedioate
(Z)-2-Butenedioic acid
(z)-butenedioate
(z)-butenedioic acid
2-Butenedioate
2-Butenedioic acid
cis-1,2-Ethylenedicarboxylic acid
cis-2-Butenedioate
cis-2-Butenedioic acid
cis-But-2-enedioate
cis-But-2-enedioic acid
Cis-butenedioate
Cis-butenedioic acid
H2male
Kyselina maleinova
MAE
Maleate
Maleinic acid
Malenic acid
Malezid CM
Scotchbond multipurpose etchant
Toxilic acid
Chemical FormulaC4H4O4
Average Molecular Mass116.072 g/mol
Monoisotopic Mass116.011 g/mol
CAS Registry Number110-16-7
IUPAC Name(2Z)-but-2-enedioic acid
Traditional Namemaleic acid
SMILES[H]\C(=C(/[H])C(O)=O)C(O)=O
InChI IdentifierInChI=1S/C4H4O4/c5-3(6)1-2-4(7)8/h1-2H,(H,5,6)(H,7,8)/b2-1-
InChI KeyInChIKey=VZCYOOQTPOCHFL-UPHRSURJSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as dicarboxylic acids and derivatives. These are organic compounds containing exactly two carboxylic acid groups.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassDicarboxylic acids and derivatives
Direct ParentDicarboxylic acids and derivatives
Alternative Parents
Substituents
  • Fatty acyl
  • Fatty acid
  • Unsaturated fatty acid
  • Dicarboxylic acid or derivatives
  • Carboxylic acid
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginEndogenous
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
Biofluid LocationsNot Available
Tissue Locations
  • Fibroblasts
  • Muscle
  • Neuron
  • Pancreas
  • Platelet
  • Prostate
  • Spleen
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting Point130.5°C
Boiling PointNot Available
Solubility4.41E+005 mg/L (at 25°C)
LogP-0.48
Predicted Properties
PropertyValueSource
Water Solubility24.1 g/LALOGPS
logP0.21ALOGPS
logP-0.041ChemAxon
logS-0.68ALOGPS
pKa (Strongest Acidic)3.05ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area74.6 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity24.61 m³·mol⁻¹ChemAxon
Polarizability9.19 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-0002-0900000000-170a9d63d0cb31451c1d2014-06-16View Spectrum
GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-001j-5940000000-59e85bafafc1675e24ad2014-06-16View Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0uxs-9000000000-d768b92d45a58ec32ec72017-09-12View Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-004i-9000000000-617284552377852c7c462017-09-12View Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0002-0910000000-15f30f525d5ea74dc9d42017-09-12View Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0002-0900000000-170a9d63d0cb31451c1d2017-09-12View Spectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-001j-5940000000-59e85bafafc1675e24ad2017-09-12View Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0002-0900000000-4b46518e6c4f0c6724f22017-09-12View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-01ba-9200000000-52f88e04bac0ff8cdf172017-08-28View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-00di-8920000000-06da44f348d0fe0358b32017-10-06View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, PositiveNot Available2021-11-05View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, PositiveNot Available2021-11-05View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_2_1) - 70eV, PositiveNot Available2021-11-05View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)splash10-00di-9200000000-77d8b2c7abcec2e3d5a12012-07-24View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)splash10-00di-9200000000-8d8a8b14a723e03632272012-07-24View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)splash10-0229-9700000000-061b31801a2ae4703fc52012-07-24View Spectrum
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI RMU-6L) , Positivesplash10-0uxs-9000000000-d768b92d45a58ec32ec72012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-03di-2900000000-6bbe33cf398e663af0fc2012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-00di-9100000000-550ee9efb3babd781bca2012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-00di-9000000000-18e922c569242e2111e72012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-00di-9000000000-f344fe84d76f2bf06f912012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-00fu-9000000000-6f90988f5d68f87b52d22012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-00di-9400000000-99bc7f4db87479b4122a2012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-03di-2900000000-6bbe33cf398e663af0fc2017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-00di-9100000000-550ee9efb3babd781bca2017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-00di-9000000000-18e922c569242e2111e72017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-00di-9000000000-f344fe84d76f2bf06f912017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-00fu-9000000000-6f90988f5d68f87b52d22017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-00di-9400000000-99bc7f4db87479b4122a2017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-00di-9000000000-31211857acba85ea77cd2021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-00di-9000000000-deb5cdbb73c1005a302e2021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-00di-9000000000-58cd192c368bc09a750e2021-09-20View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014j-9800000000-dbf34563376daeb2901f2017-07-26View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00xs-9200000000-113bf08cdc77707ed3ad2017-07-26View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00fr-9000000000-f32d7ec65e8649bc2b0a2017-07-26View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-2900000000-408d53a9fff7acc8ca232017-07-26View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-6900000000-f149e9e5a34e27dd4d4e2017-07-26View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0fxt-9000000000-cae5f71dc27daaf17d9e2017-07-26View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)Not Available2012-12-04View Spectrum
1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Not Available2021-09-29View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Not Available2021-09-29View Spectrum
1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)Not Available2021-09-29View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Not Available2021-09-29View Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)Not Available2021-09-29View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Not Available2021-09-29View Spectrum
1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)Not Available2021-09-29View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Not Available2021-09-29View Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)Not Available2021-09-29View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Not Available2021-09-29View Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)Not Available2021-09-29View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Not Available2021-09-29View Spectrum
1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)Not Available2021-09-29View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Not Available2021-09-29View Spectrum
1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)Not Available2021-09-29View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Not Available2021-09-29View Spectrum
1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)Not Available2021-09-29View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Not Available2021-09-29View Spectrum
1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)Not Available2021-09-29View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Not Available2021-09-29View Spectrum
2D NMR[1H, 1H]-TOCSY. Unexported temporarily by An Chi on Oct 15, 2021 until json or nmrML file is generated. 2D NMR Spectrum (experimental)Not Available2012-12-04View Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Not Available2012-12-05View Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesThis is an endogenously produced metabolite found in the human body. It is used in metabolic reactions, catabolic reactions or waste generation.
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
DrugBank IDDB04299
HMDB IDHMDB00176
PubChem Compound ID444266
ChEMBL IDCHEMBL539648
ChemSpider ID392248
KEGG IDC01384
UniProt IDNot Available
OMIM ID
ChEBI ID18300
BioCyc IDNot Available
CTD IDNot Available
Stitch IDNot Available
PDB IDMAE
ACToR IDNot Available
Wikipedia LinkMaleic acid
References
Synthesis Reference

Yasuhisha Fukumoto, Noboru Moriyama, Takashi Itoi, “Maleic acid copolymer, production thereof and scale-preventing agent containing the same.” U.S. Patent US4589995, issued August, 1933.

MSDSLink
General References
  1. Kotikoski H, Oksala O, Vapaatalo H, Aine E: Aqueous humour flow after a single oral dose of isosorbide-5-mononitrate in healthy volunteers. Acta Ophthalmol Scand. 2003 Aug;81(4):355-60. [12859262 ]
  2. Herreras JM, Pastor JC, Calonge M, Asensio VM: Ocular surface alteration after long-term treatment with an antiglaucomatous drug. Ophthalmology. 1992 Jul;99(7):1082-8. [1495787 ]
  3. Klose T, Welzel PB, Werner C: Protein adsorption from flowing solutions on pure and maleic acid copolymer modified glass particles. Colloids Surf B Biointerfaces. 2006 Aug 1;51(1):1-9. Epub 2006 May 17. [16797943 ]
  4. Renner L, Pompe T, Salchert K, Werner C: Dynamic alterations of fibronectin layers on copolymer substrates with graded physicochemical characteristics. Langmuir. 2004 Mar 30;20(7):2928-33. [15835174 ]
  5. Gong Z, Lv Y, Huang Y, Zhang Z: Determination of ergometrine maleate by fluorescence detection. Luminescence. 2005 May-Jun;20(3):124-8. [15924314 ]
  6. Goes MF, Sinhoreti MA, Consani S, Silva MA: Morphological effect of the type, concentration and etching time of acid solutions on enamel and dentin surfaces. Braz Dent J. 1998;9(1):3-10. [9835798 ]
  7. Guneral F, Bachmann C: Age-related reference values for urinary organic acids in a healthy Turkish pediatric population. Clin Chem. 1994 Jun;40(6):862-6. [8087979 ]
  8. Gallagher RM: Menstrual migraine and intermittent ergonovine therapy. Headache. 1989 Jun;29(6):366-7. [2759844 ]
  9. Seki T, Wakabayashi M, Nakagawa T, Imamura M, Tamai T, Nishimura A, Yamashiki N, Okamura A, Inoue K: Hepatic infarction following percutaneous ethanol injection therapy for hepatocellular carcinoma. Eur J Gastroenterol Hepatol. 1998 Nov;10(11):915-8. [9872612 ]
  10. Snider BJ, Moss JL, Revilla FJ, Lee CS, Wheeler VC, Macdonald ME, Choi DW: Neocortical neurons cultured from mice with expanded CAG repeats in the huntingtin gene: unaltered vulnerability to excitotoxins and other insults. Neuroscience. 2003;120(3):617-25. [12895502 ]
  11. Lavit M, Saivin S, Boudra H, Michel F, Martin A, Cahiez G, Labaune JP, Chomard JM, Houin G: Determination of trimebutine and desmethyl-trimebutine in human plasma by HPLC. Arzneimittelforschung. 2000 Jul;50(7):640-4. [10965422 ]
  12. Strasser G, Grabner G: The influence of long-term treatment with timolol on human tear lysozyme albumin content. Graefes Arch Clin Exp Ophthalmol. 1982;218(2):93-5. [7075967 ]
  13. Glazunova OO, Korepanova EA, Efimov VS, Smirnov AI, Vladimirov YuA: A synthetic polycation, a copolymer of 1-vinyl-3-methylimidazole iodide with maleic acid diethyl ester, increases passive ionic permeability in erythrocyte membranes modified by fatty acids. Membr Cell Biol. 1998;12(3):401-9. [10024972 ]
  14. Yoshida H, Onda M, Tajiri T, Uchida E, Arima Y, Mamada Y, Yamamoto K, Kaneko M, Terada Y, Kumazaki T: Experience with intraarterial infusion of styrene maleic acid neocarzinostatin (SMANCS)-lipiodol in pancreatic cancer. Hepatogastroenterology. 1999 Jul-Aug;46(28):2612-5. [10522050 ]
  15. Benderli Y, Gokce K, Buyukgokcesu S: In vitro shear bond strength of adhesive to normal and fluoridated enamel under various contaminated conditions. Quintessence Int. 1999 Aug;30(8):570-5. [10635272 ]
  16. Liu Y, Yanai R, Lu Y, Hirano S, Sagara T, Nishida T: Effects of antiglaucoma drugs on collagen gel contraction mediated by human corneal fibroblasts. J Glaucoma. 2006 Jun;15(3):255-9. [16778650 ]
  17. Dorr J, Roth K, Zurbuchen U, Deisz R, Bechmann I, Lehmann TN, Meier S, Nitsch R, Zipp F: Tumor-necrosis-factor-related apoptosis-inducing-ligand (TRAIL)-mediated death of neurons in living human brain tissue is inhibited by flupirtine-maleate. J Neuroimmunol. 2005 Oct;167(1-2):204-9. [16043230 ]
  18. Turcan RG, Hillbeck D, Hartley TE, Gilbert PJ, Coe RA, Troke JA, Vose CW: Disposition of [14C]velnacrine maleate in rats, dogs, and humans. Drug Metab Dispos. 1993 Nov-Dec;21(6):1037-47. [7905382 ]
  19. Chen CN, Huang GF, Guo MK, Lin CP: An in vitro study on restoring bond strength of a GIC to saliva contaminated enamel under unrinse condition. J Dent. 2002 Jul-Aug;30(5-6):189-94. [12450709 ]
  20. Daykin CA, Foxall PJ, Connor SC, Lindon JC, Nicholson JK: The comparison of plasma deproteinization methods for the detection of low-molecular-weight metabolites by (1)H nuclear magnetic resonance spectroscopy. Anal Biochem. 2002 May 15;304(2):220-30. [12009699 ]
Gene Regulation
Up-Regulated GenesNot Available
Down-Regulated GenesNot Available

Targets

Target Details
1. Aspartate aminotransferase, cytoplasmic
General Function:
Pyridoxal phosphate binding
Specific Function:
Biosynthesis of L-glutamate from L-aspartate or L-cysteine. Important regulator of levels of glutamate, the major excitatory neurotransmitter of the vertebrate central nervous system. Acts as a scavenger of glutamate in brain neuroprotection. The aspartate aminotransferase activity is involved in hepatic glucose synthesis during development and in adipocyte glyceroneogenesis. Using L-cysteine as substrate, regulates levels of mercaptopyruvate, an important source of hydrogen sulfide. Mercaptopyruvate is converted into H(2)S via the action of 3-mercaptopyruvate sulfurtransferase (3MST). Hydrogen sulfide is an important synaptic modulator and neuroprotectant in the brain.
Gene Name:
GOT1
Uniprot ID:
P17174
Molecular Weight:
46247.14 Da
References
  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [10592235 ]
Target Details
2. Androgen receptor
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
AC500.00132 uMTox21_AR_LUC_MDAKB2_AgonistTox21/NCGC
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 ]