Maleic Acid

Identification

Name
Maleic Acid
Accession Number
DB04299  (EXPT02106)
Type
Small Molecule
Groups
Experimental
Description
Not Available
Structure
Thumb
Synonyms
Not Available
Categories
UNII
91XW058U2C
CAS number
110-16-7
Weight
Average: 116.0722
Monoisotopic: 116.010958616
Chemical Formula
C4H4O4
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

Pharmacology

Indication
Not Available
Structured Indications
Not Available
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 AvailableHuman
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
Toxicity
Not Available
Affected organisms
Not Available
Pathways
PathwayCategory
Argininosuccinic AciduriaDisease
Tyrosine MetabolismMetabolic
Citric Acid CycleMetabolic
AICA-RibosiduriaDisease
Prolidase Deficiency (PD)Disease
Mercaptopurine Action PathwayDrug action
Thioguanine Action PathwayDrug action
Tyrosinemia, transient, of the newbornDisease
Xanthinuria type IDisease
Glutaminolysis and CancerDisease
Guanidinoacetate Methyltransferase Deficiency (GAMT Deficiency)Disease
Hyperprolinemia Type IIDisease
Arginine: Glycine Amidinotransferase Deficiency (AGAT Deficiency)Disease
Gout or Kelley-Seegmiller SyndromeDisease
Tyrosinemia Type 2 (or Richner-Hanhart syndrome)Disease
Tyrosinemia Type 3 (TYRO3)Disease
Azathioprine Action PathwayDrug action
Creatine deficiency, guanidinoacetate methyltransferase deficiencyDisease
Hyperornithinemia with gyrate atrophy (HOGA)Disease
Hyperornithinemia-hyperammonemia-homocitrullinuria [HHH-syndrome]Disease
L-arginine:glycine amidinotransferase deficiencyDisease
Xanthinuria type IIDisease
The oncogenic action of FumarateDisease
Adenylosuccinate Lyase DeficiencyDisease
HypoacetylaspartiaDisease
Molybdenum Cofactor DeficiencyDisease
Purine Nucleoside Phosphorylase DeficiencyDisease
Tyrosinemia Type IDisease
ArgininemiaDisease
Disulfiram Action PathwayDrug action
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not Available

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
External Links
Human Metabolome Database
HMDB00176
KEGG Compound
C01384
ChemSpider
392248
ChEBI
18300
ChEMBL
CHEMBL539648
HET
MAE
PDB Entries
1ahy / 1amr / 1aog / 1ari / 1asa / 1asb / 1asd / 1ase / 1asg / 1asm
show 21 more

Clinical Trials

Clinical Trials
Not Available

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
Water Solubility24.1 mg/mLALOGPS
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 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-MSNot Available
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
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
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
1H NMR Spectrum1D NMRNot Applicable
[1H,1H] 2D NMR Spectrum2D NMRNot Applicable
[1H,13C] 2D NMR Spectrum2D NMRNot Applicable

Taxonomy

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
Fatty acyl / Fatty acid / Unsaturated fatty acid / Dicarboxylic acid or derivatives / Carboxylic acid / Organic oxygen compound / Organic oxide / Hydrocarbon derivative / Organooxygen compound / Carbonyl group
Molecular Framework
Aliphatic acyclic compounds
External Descriptors
butenedioic acid (CHEBI:18300)

Targets

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. [PubMed:17139284]
  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. [PubMed:17016423]
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. [PubMed:17139284]
  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. [PubMed:17016423]
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. [PubMed:17139284]
  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. [PubMed:17016423]
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. [PubMed:17139284]
  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. [PubMed:17016423]
Kind
Protein
Organism
Human
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. [PubMed:10592235]

Drug created on June 13, 2005 07:24 / Updated on October 02, 2017 05:33