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Identification
NameMaleic Acid
Accession NumberDB04299  (EXPT02106)
TypeSmall Molecule
GroupsExperimental
DescriptionNot Available
Structure
Thumb
SynonymsNot Available
External Identifiers Not Available
Approved Prescription ProductsNot Available
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International BrandsNot Available
Brand mixturesNot Available
SaltsNot Available
Categories
UNII91XW058U2C
CAS number110-16-7
WeightAverage: 116.0722
Monoisotopic: 116.010958616
Chemical FormulaC4H4O4
InChI KeyVZCYOOQTPOCHFL-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
Taxonomy
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.
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
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Pharmacology
IndicationNot Available
PharmacodynamicsNot Available
Mechanism of actionNot Available
Related Articles
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
MetabolismNot Available
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organismsNot Available
Pathways
PathwayCategorySMPDB ID
Adenylosuccinate Lyase DeficiencyDiseaseSMP00167
HypoacetylaspartiaDiseaseSMP00192
Molybdenum Cofactor DeficiencyDiseaseSMP00203
Purine Nucleoside Phosphorylase DeficiencyDiseaseSMP00210
Tyrosinemia Type IDiseaseSMP00218
ArgininemiaDiseaseSMP00357
Disulfiram Action PathwayDrug actionSMP00429
Adenine phosphoribosyltransferase deficiency (APRT)DiseaseSMP00535
Mitochondrial DNA depletion syndromeDiseaseSMP00536
Congenital lactic acidosisDiseaseSMP00546
Fumarase deficiencyDiseaseSMP00547
Mitochondrial complex II deficiencyDiseaseSMP00548
Pyruvate dehydrogenase deficiency (E2)DiseaseSMP00551
Argininosuccinic AciduriaDiseaseSMP00003
Tyrosine MetabolismMetabolicSMP00006
Citric Acid CycleMetabolicSMP00057
AICA-RibosiduriaDiseaseSMP00168
Prolidase Deficiency (PD)DiseaseSMP00207
Mercaptopurine Action PathwayDrug actionSMP00428
Thioguanine Action PathwayDrug actionSMP00430
Tyrosinemia, transient, of the newbornDiseaseSMP00494
Xanthinuria type IDiseaseSMP00512
Glutaminolysis and CancerDiseaseSMP02298
Guanidinoacetate Methyltransferase Deficiency (GAMT Deficiency)DiseaseSMP00188
Hyperprolinemia Type IIDiseaseSMP00360
Arginine: Glycine Amidinotransferase Deficiency (AGAT Deficiency)DiseaseSMP00362
Gout or Kelley-Seegmiller SyndromeDiseaseSMP00365
Tyrosinemia Type 2 (or Richner-Hanhart syndrome)DiseaseSMP00369
Tyrosinemia Type 3 (TYRO3)DiseaseSMP00370
Azathioprine Action PathwayDrug actionSMP00427
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
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 )
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point130.5 °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 FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)splash10-0002-0900000000-170a9d63d0cb31451c1dView in MoNA
GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-001j-5940000000-59e85bafafc1675e24adView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)splash10-00di-9200000000-77d8b2c7abcec2e3d5a1View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)splash10-00di-9200000000-8d8a8b14a723e0363227View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)splash10-0229-9700000000-061b31801a2ae4703fc5View in MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI RMU-6L) , Positivesplash10-0uxs-9000000000-d768b92d45a58ec32ec7View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-03di-2900000000-6bbe33cf398e663af0fcView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-00di-9100000000-550ee9efb3babd781bcaView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-00di-9000000000-18e922c569242e2111e7View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-00di-9000000000-f344fe84d76f2bf06f91View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-00fu-9000000000-6f90988f5d68f87b52d2View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-00di-9400000000-99bc7f4db87479b4122aView in MoNA
1D NMR1H NMR SpectrumNot Available
2D NMR[1H,1H] 2D NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot 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 ReferencesNot Available
External Links
ATC CodesNot Available
AHFS CodesNot Available
PDB Entries
FDA labelNot Available
MSDSNot Available
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available

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
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
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
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
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 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 a...
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. [PubMed:10592235 ]
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Drug created on June 13, 2005 07:24 / Updated on March 23, 2016 07:28