Maleic acid

Identification

Generic Name
Maleic acid
DrugBank Accession Number
DB04299
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
Weight
Average: 116.0722
Monoisotopic: 116.010958616
Chemical Formula
C4H4O4
Synonyms
  • (Z)-2-butenedioic acid
  • (Z)-butenedioic acid
  • cis-1,2-ethylenedicarboxylic acid
  • cis-but-2-enedioic acid
  • cis-Butenedioic acid
  • Maleic acid
  • Toxilic acid

Pharmacology

Indication

Not Available

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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UAspartate aminotransferaseNot AvailableEscherichia coli (strain K12)
UTrypanothione reductaseNot AvailableTrypanosoma cruzi
UAspartate aminotransferaseNot AvailableThermus thermophilus (strain HB8 / ATCC 27634 / DSM 579)
UAromatic-amino-acid aminotransferaseNot AvailableParacoccus denitrificans
UAspartate aminotransferase, cytoplasmicNot AvailableHumans
Absorption

Not Available

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism
Not Available
Route of elimination

Not Available

Half-life

Not Available

Clearance

Not Available

Adverse Effects
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Toxicity

Not Available

Pathways
PathwayCategory
Adenylosuccinate Lyase DeficiencyDisease
PhenylketonuriaDisease
Xanthine Dehydrogenase Deficiency (Xanthinuria)Disease
Arginine: Glycine Amidinotransferase Deficiency (AGAT Deficiency)Disease
Creatine Deficiency, Guanidinoacetate Methyltransferase DeficiencyDisease
Hyperornithinemia with Gyrate Atrophy (HOGA)Disease
Xanthinuria Type IDisease
Mitochondrial DNA Depletion SyndromeDisease
Myoadenylate Deaminase DeficiencyDisease
The Oncogenic Action of FumarateDisease
The Oncogenic Action of L-2-Hydroxyglutarate in HydroxygluaricaciduriaDisease
Carbamoyl Phosphate Synthetase DeficiencyDisease
Argininosuccinic AciduriaDisease
Tyrosine MetabolismMetabolic
Arginine and Proline MetabolismMetabolic
Purine MetabolismMetabolic
Citric Acid CycleMetabolic
Guanidinoacetate Methyltransferase Deficiency (GAMT Deficiency)Disease
Purine Nucleoside Phosphorylase DeficiencyDisease
Tyrosinemia Type IDisease
Mitochondrial Electron Transport ChainMetabolic
Hyperprolinemia Type IIDisease
Hyperprolinemia Type IDisease
Lesch-Nyhan Syndrome (LNS)Disease
Gout or Kelley-Seegmiller SyndromeDisease
Tyrosinemia Type 3 (TYRO3)Disease
Mercaptopurine Action PathwayDrug action
Disulfiram Action PathwayDrug action
L-Arginine:Glycine Amidinotransferase DeficiencyDisease
Adenine Phosphoribosyltransferase Deficiency (APRT)Disease
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Not Available
Food Interactions
Not Available

Categories

Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as dicarboxylic acids and derivatives. These are organic compounds containing exactly two carboxylic acid groups.
Kingdom
Organic compounds
Super Class
Organic acids and derivatives
Class
Carboxylic acids and derivatives
Sub Class
Dicarboxylic acids and derivatives
Direct Parent
Dicarboxylic acids and derivatives
Alternative Parents
Unsaturated fatty acids / Carboxylic acids / Organic oxides / Hydrocarbon derivatives / Carbonyl compounds
Substituents
Aliphatic acyclic compound / Carbonyl group / Carboxylic acid / Dicarboxylic acid or derivatives / Fatty acid / Fatty acyl / Hydrocarbon derivative / Organic oxide / Organic oxygen compound / Organooxygen compound
Molecular Framework
Aliphatic acyclic compounds
External Descriptors
butenedioic acid (CHEBI:18300)
Affected organisms
Not Available

Chemical Identifiers

UNII
91XW058U2C
CAS number
110-16-7
InChI Key
VZCYOOQTPOCHFL-UPHRSURJSA-N
InChI
InChI=1S/C4H4O4/c5-3(6)1-2-4(7)8/h1-2H,(H,5,6)(H,7,8)/b2-1-
IUPAC Name
(2Z)-but-2-enedioic acid
SMILES
OC(=O)\C=C/C(O)=O

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.

US4589995
General References
Not Available
Human Metabolome Database
HMDB0000176
KEGG Compound
C01384
PubChem Compound
444266
PubChem Substance
46508977
ChemSpider
392248
RxNav
1426330
ChEBI
18300
ChEMBL
CHEMBL539648
ZINC
ZINC000012358683
PDBe Ligand
MAE
Wikipedia
Maleic_acid
PDB Entries
1ahy / 1amr / 1aog / 1ari / 1asa / 1asb / 1asd / 1ase / 1asg / 1asm
show 27 more

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
Not AvailableCompletedPreventionApical Periodontitis / Irreversible Pulpitis (Toothache) / Periapical Abscess / Root canal infection1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)130.5 °CPhysProp
water solubility4.41E+005 mg/L (at 25 °C)YALKOWSKY,SH & DANNENFELSER,RM (1992)
logP-0.48SANGSTER (1994)
pKa1.83LIDE,DR (1996)
Predicted Properties
PropertyValueSource
logP-0.041Chemaxon
pKa (Strongest Acidic)2.85Chemaxon
Physiological Charge-2Chemaxon
Hydrogen Acceptor Count4Chemaxon
Hydrogen Donor Count2Chemaxon
Polar Surface Area74.6 Å2Chemaxon
Rotatable Bond Count2Chemaxon
Refractivity24.61 m3·mol-1Chemaxon
Polarizability9.19 Å3Chemaxon
Number of Rings0Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.874
Blood Brain Barrier+0.9017
Caco-2 permeable-0.6728
P-glycoprotein substrateNon-substrate0.8006
P-glycoprotein inhibitor INon-inhibitor0.985
P-glycoprotein inhibitor IINon-inhibitor0.9808
Renal organic cation transporterNon-inhibitor0.9583
CYP450 2C9 substrateNon-substrate0.8262
CYP450 2D6 substrateNon-substrate0.9397
CYP450 3A4 substrateNon-substrate0.8039
CYP450 1A2 substrateNon-inhibitor0.9659
CYP450 2C9 inhibitorNon-inhibitor0.949
CYP450 2D6 inhibitorNon-inhibitor0.9606
CYP450 2C19 inhibitorNon-inhibitor0.9773
CYP450 3A4 inhibitorNon-inhibitor0.9554
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9899
Ames testNon AMES toxic0.9132
CarcinogenicityNon-carcinogens0.513
BiodegradationReady biodegradable0.7561
Rat acute toxicity1.6871 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9836
hERG inhibition (predictor II)Non-inhibitor0.9891
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)GC-MSsplash10-0002-0900000000-170a9d63d0cb31451c1d
GC-MS Spectrum - GC-MS (2 TMS)GC-MSsplash10-001j-5940000000-59e85bafafc1675e24ad
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSsplash10-01ba-9200000000-52f88e04bac0ff8cdf17
GC-MS Spectrum - EI-BGC-MSsplash10-0uxs-9000000000-d768b92d45a58ec32ec7
GC-MS Spectrum - EI-BGC-MSsplash10-004i-9000000000-617284552377852c7c46
GC-MS Spectrum - EI-BGC-MSsplash10-0002-0910000000-15f30f525d5ea74dc9d4
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-0002-0900000000-170a9d63d0cb31451c1d
GC-MS Spectrum - GC-MSGC-MSsplash10-001j-5940000000-59e85bafafc1675e24ad
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-0002-0900000000-4b46518e6c4f0c6724f2
MS/MS Spectrum - Quattro_QQQ 10V, NegativeLC-MS/MSsplash10-00di-9200000000-77d8b2c7abcec2e3d5a1
MS/MS Spectrum - Quattro_QQQ 25V, NegativeLC-MS/MSsplash10-00di-9200000000-8d8a8b14a723e0363227
MS/MS Spectrum - Quattro_QQQ 40V, NegativeLC-MS/MSsplash10-0229-9700000000-061b31801a2ae4703fc5
MS/MS Spectrum - EI-B (HITACHI RMU-6L) , PositiveLC-MS/MSsplash10-0uxs-9000000000-d768b92d45a58ec32ec7
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, NegativeLC-MS/MSsplash10-03di-2900000000-6bbe33cf398e663af0fc
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, NegativeLC-MS/MSsplash10-00di-9100000000-550ee9efb3babd781bca
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, NegativeLC-MS/MSsplash10-00di-9000000000-18e922c569242e2111e7
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, NegativeLC-MS/MSsplash10-00di-9000000000-f344fe84d76f2bf06f91
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, NegativeLC-MS/MSsplash10-00fu-9000000000-6f90988f5d68f87b52d2
LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , NegativeLC-MS/MSsplash10-00di-9400000000-99bc7f4db87479b4122a
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-03di-2900000000-6bbe33cf398e663af0fc
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-00di-9100000000-550ee9efb3babd781bca
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-00di-9000000000-18e922c569242e2111e7
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-00di-9000000000-f344fe84d76f2bf06f91
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-00fu-9000000000-6f90988f5d68f87b52d2
LC-MS/MS Spectrum - LC-ESI-QTOF , negativeLC-MS/MSsplash10-00di-9400000000-99bc7f4db87479b4122a
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-0a4j-9000000000-009840dd422003d0937c
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-00di-9100000000-a349e9f97e69a8322827
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0a4l-9000000000-f652e15d4540c8bff9a7
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-00di-9000000000-c50c7c715c52a1dc3b9d
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0a4i-9000000000-30d91bd428846399c543
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-00di-9000000000-a81f28655278c8dd8c3c
1H NMR Spectrum1D NMRNot Applicable
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
[1H,1H] 2D NMR Spectrum2D NMRNot Applicable
[1H,13C] 2D NMR Spectrum2D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-118.2695784
predicted
DarkChem Lite v0.1.0
[M-H]-118.2961784
predicted
DarkChem Lite v0.1.0
[M-H]-118.2592784
predicted
DarkChem Lite v0.1.0
[M-H]-115.80617
predicted
DeepCCS 1.0 (2019)
[M+H]+119.198715
predicted
DeepCCS 1.0 (2019)
[M+Na]+127.760895
predicted
DeepCCS 1.0 (2019)

Targets

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insights and accelerate drug research.
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Kind
Protein
Organism
Escherichia coli (strain K12)
Pharmacological action
Unknown
General Function
Pyridoxal phosphate binding
Specific Function
Not Available
Gene Name
aspC
Uniprot ID
P00509
Uniprot Name
Aspartate aminotransferase
Molecular Weight
43572.965 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [Article]
Kind
Protein
Organism
Trypanosoma cruzi
Pharmacological action
Unknown
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
Uniprot Name
Trypanothione reductase
Molecular Weight
53867.475 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [Article]
Kind
Protein
Organism
Thermus thermophilus (strain HB8 / ATCC 27634 / DSM 579)
Pharmacological action
Unknown
General Function
Pyridoxal phosphate binding
Specific Function
Not Available
Gene Name
aspC
Uniprot ID
Q56232
Uniprot Name
Aspartate aminotransferase
Molecular Weight
42050.62 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [Article]
Kind
Protein
Organism
Paracoccus denitrificans
Pharmacological action
Unknown
General Function
Pyridoxal phosphate binding
Specific Function
Shows activities toward both dicarboxylic and aromatic substrates.
Gene Name
tyrB
Uniprot ID
P95468
Uniprot Name
Aromatic-amino-acid aminotransferase
Molecular Weight
42731.635 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
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 sca...
Gene Name
GOT1
Uniprot ID
P17174
Uniprot Name
Aspartate aminotransferase, cytoplasmic
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. [Article]

Drug created at June 13, 2005 13:24 / Updated at February 24, 2021 23:07