General Information

MaintermMALEIC ACID
CAS Reg.No.(or other ID)110-16-7
Regnum 175.105
175.300
175.320
176.170
177.1200
177.1390
177.2420

From www.fda.gov

Computed Descriptors

Download SDF
2D Structure
CID444266
IUPAC Name(Z)-but-2-enedioic acid
InChIInChI=1S/C4H4O4/c5-3(6)1-2-4(7)8/h1-2H,(H,5,6)(H,7,8)/b2-1-
InChI KeyVZCYOOQTPOCHFL-UPHRSURJSA-N
Canonical SMILESC(=CC(=O)O)C(=O)O
Molecular FormulaC4H4O4
Wikipediamaleic acid

From Pubchem


Computed Properties

Property Name Property Value
Molecular Weight116.072
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count4
Rotatable Bond Count2
Complexity119.0
CACTVS Substructure Key Fingerprint A A A D c Y B g O A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A G g A A C A A A C A C A g A A A C A A A A g C I A C D S C A A A A A A A A A A I C A A A A E A A B A A A A A A A E A A A A A A A E Y A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A = =
Topological Polar Surface Area74.6
Monoisotopic Mass116.011
Exact Mass116.011
Compound Is CanonicalizedTrue
Formal Charge0
Heavy Atom Count8
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count1
Undefined Bond Stereocenter Count0
Isotope Atom Count0
Covalently-Bonded Unit Count1

From Pubchem


Food Additives Biosynthesis/Degradation


ADMET Predicted Profile --- Classification

Model Result Probability
Absorption
Blood-Brain BarrierBBB+0.9017
Human Intestinal AbsorptionHIA+0.8740
Caco-2 PermeabilityCaco2-0.6728
P-glycoprotein SubstrateNon-substrate0.8006
P-glycoprotein InhibitorNon-inhibitor0.9850
Non-inhibitor0.9808
Renal Organic Cation TransporterNon-inhibitor0.9583
Distribution
Subcellular localizationMitochondria0.7863
Metabolism
CYP450 2C9 SubstrateNon-substrate0.8262
CYP450 2D6 SubstrateNon-substrate0.9397
CYP450 3A4 SubstrateNon-substrate0.8039
CYP450 1A2 InhibitorNon-inhibitor0.9659
CYP450 2C9 InhibitorNon-inhibitor0.9490
CYP450 2D6 InhibitorNon-inhibitor0.9606
CYP450 2C19 InhibitorNon-inhibitor0.9773
CYP450 3A4 InhibitorNon-inhibitor0.9554
CYP Inhibitory PromiscuityLow CYP Inhibitory Promiscuity0.9899
Excretion
Toxicity
Human Ether-a-go-go-Related Gene InhibitionWeak inhibitor0.9836
Non-inhibitor0.9891
AMES ToxicityNon AMES toxic0.9132
CarcinogensNon-carcinogens0.5130
Fish ToxicityHigh FHMT0.8398
Tetrahymena Pyriformis ToxicityLow TPT0.9808
Honey Bee ToxicityHigh HBT0.7308
BiodegradationReady biodegradable0.7561
Acute Oral ToxicityIII0.7762
Carcinogenicity (Three-class)Non-required0.7191

From admetSAR


ADMET Predicted Profile --- Regression

Model Value Unit
Absorption
Aqueous solubility-0.3321LogS
Caco-2 Permeability0.4098LogPapp, cm/s
Distribution
Metabolism
Excretion
Toxicity
Rat Acute Toxicity1.6871LD50, mol/kg
Fish Toxicity0.9694pLC50, mg/L
Tetrahymena Pyriformis Toxicity-0.6339pIGC50, ug/L

From admetSAR


Toxicity Profile

Route of ExposureNone
Mechanism of ToxicityNone
MetabolismNone
Toxicity ValuesNone
Lethal DoseNone
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Minimum Risk LevelNone
Health EffectsNone
TreatmentNone
Reference
  1. 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 ]
  2. 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 ]
  3. 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 ]
  4. 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 ]
  5. 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 ]
  6. 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 ]
  7. Gong Z, Lv Y, Huang Y, Zhang Z: Determination of ergometrine maleate by fluorescence detection. Luminescence. 2005 May-Jun;20(3):124-8.[15924314 ]
  8. 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 ]
  9. Gallagher RM: Menstrual migraine and intermittent ergonovine therapy. Headache. 1989 Jun;29(6):366-7.[2759844 ]
  10. 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 ]
  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 ]

From T3DB


Taxonomic Classification

KingdomOrganic compounds
SuperclassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
SubclassDicarboxylic acids and derivatives
Intermediate Tree NodesNot available
Direct ParentDicarboxylic acids and derivatives
Alternative Parents
Molecular FrameworkAliphatic acyclic compounds
SubstituentsFatty 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
DescriptionThis compound belongs to the class of organic compounds known as dicarboxylic acids and derivatives. These are organic compounds containing exactly two carboxylic acid groups.

From ClassyFire


Targets

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 ]
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
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 ]
General Function:
Pyridoxal phosphate binding
Gene Name:
aspC
Uniprot ID:
P00509
Molecular Weight:
43572.965 Da
General Function:
Trypanothione-disulfide reductase activity
Specific Function:
Trypanothione is the parasite analog of glutathione; this enzyme is the equivalent of glutathione reductase.
Gene Name:
TPR
Uniprot ID:
P28593
Molecular Weight:
53867.475 Da
General Function:
Pyridoxal phosphate binding
Gene Name:
aspC
Uniprot ID:
Q56232
Molecular Weight:
42050.62 Da
General Function:
Pyridoxal phosphate binding
Specific Function:
Shows activities toward both dicarboxylic and aromatic substrates.
Gene Name:
tyrB
Uniprot ID:
P95468
Molecular Weight:
42731.635 Da

From T3DB