Showing metabocard for maleate (MMDBc0056076)

Record Information
Version2.0
StatusDetected and Quantified
Creation Date2022-06-17 20:15:08 UTC
Update Date2025-10-07 16:09:32 UTC
Metabolite IDMMDBc0056076
Metabolite Identification
Common Namemaleate
DescriptionMaleate is a dicarboxylic acid derivative belonging to the chemical class of carboxylates. Its chemical structure features a double bond between two carbon atoms, each of which is attached to a carboxyl group (–COOH). Maleate plays a role in various chemical reactions, including 1,3-dipolar cycloaddition, where it reacts with chiral azomethine ylides to yield pyrrolidine cycloadducts, as noted in the literature (PMID:41034175 ). In pharmacological contexts, maleate salts, such as timolol maleate, are utilized in drug delivery systems for ocular treatments, demonstrating effects on intraocular pressure and drug concentration in target tissues (PMID:41049113 ). Additionally, maleate derivatives like chlorpheniramine maleate exhibit antiviral properties against SARS-CoV-2, highlighting their potential in therapeutic applications (PMID:40988968 ). Furthermore, maleate compounds are evaluated for their efficacy in treating malaria, as seen in studies comparing Arterolane maleate-Piperaquine phosphate with other antimalarial regimens (PMID:41033576 ). Overall, maleate's structural characteristics and its involvement in diverse chemical and biological pathways underscore its significance in both synthetic chemistry and pharmacology.
Structure
MOLSDFPDBSMILESInChI

MOL for #<Metabolite:0x00007fadc0097188>


  Mrv1652306172222152D          

 10  9  0  0  0  0            999 V2000
    0.8250    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625   -0.7145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250   -1.4289    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.4289    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2375   -0.7145    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    1.2375    0.7145    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125    0.7145    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0  0  0  0
  3  1  1  0  0  0  0
  4  2  1  0  0  0  0
  5  3  2  0  0  0  0
  6  3  1  0  0  0  0
  7  4  2  0  0  0  0
  8  4  1  0  0  0  0
  9  1  1  0  0  0  0
 10  2  1  0  0  0  0
M  CHG  2   6  -1   8  -1
M  END
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3D MOL for #<Metabolite:0x00007fadc0097188>

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3D SDF for #<Metabolite:0x00007fadc0097188>

  Mrv1652306172222152D          

 10  9  0  0  0  0            999 V2000
    0.8250    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625   -0.7145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250   -1.4289    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.4289    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2375   -0.7145    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    1.2375    0.7145    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125    0.7145    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0  0  0  0
  3  1  1  0  0  0  0
  4  2  1  0  0  0  0
  5  3  2  0  0  0  0
  6  3  1  0  0  0  0
  7  4  2  0  0  0  0
  8  4  1  0  0  0  0
  9  1  1  0  0  0  0
 10  2  1  0  0  0  0
M  CHG  2   6  -1   8  -1
M  END
> <DATABASE_ID>
MMDBc0056076

> <DATABASE_NAME>
MIME

> <SMILES>
[H]\C(=C(/[H])C([O-])=O)C([O-])=O

> <INCHI_IDENTIFIER>
InChI=1S/C4H4O4/c5-3(6)1-2-4(7)8/h1-2H,(H,5,6)(H,7,8)/p-2/b2-1-

> <INCHI_KEY>
VZCYOOQTPOCHFL-UPHRSURJSA-L

> <FORMULA>
C4H2O4

> <MOLECULAR_WEIGHT>
114.057

> <EXACT_MASS>
113.996405704

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
10

> <JCHEM_AVERAGE_POLARIZABILITY>
8.537274324422356

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
-2

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2Z)-but-2-enedioate

> <JCHEM_LOGP>
-0.040914331333333324

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
5.912485134930333

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.045732417201613

> <JCHEM_POLAR_SURFACE_AREA>
80.25999999999999

> <JCHEM_REFRACTIVITY>
46.2812

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
maleate

> <JCHEM_VEBER_RULE>
0

$$$$

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3D-SDF for #<Metabolite:0x00007fadc0097188>
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PDB for #<Metabolite:0x00007fadc0097188>
HEADER    PROTEIN                                 17-JUN-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-JUN-22         0                                  
HETATM    1  C   UNK     0       1.540   0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.310  -1.334   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.770  -1.334   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       3.850  -1.334   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0       1.540  -2.667   0.000  0.00  0.00           O-1
HETATM    7  O   UNK     0       0.000  -2.667   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0      -2.310  -1.334   0.000  0.00  0.00           O-1
HETATM    9  H   UNK     0       2.310   1.334   0.000  0.00  0.00           H+0
HETATM   10  H   UNK     0      -0.770   1.334   0.000  0.00  0.00           H+0
CONECT    1    2    3    9                                                  
CONECT    2    1    4   10                                                  
CONECT    3    1    5    6                                                  
CONECT    4    2    7    8                                                  
CONECT    5    3                                                            
CONECT    6    3                                                            
CONECT    7    4                                                            
CONECT    8    4                                                            
CONECT    9    1                                                            
CONECT   10    2                                                            
MASTER        0    0    0    0    0    0    0    0   10    0   18    0
END

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3D PDB for #<Metabolite:0x00007fadc0097188>
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SMILES for #<Metabolite:0x00007fadc0097188>
[H]\C(=C(/[H])C([O-])=O)C([O-])=O
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INCHI for #<Metabolite:0x00007fadc0097188>
InChI=1S/C4H4O4/c5-3(6)1-2-4(7)8/h1-2H,(H,5,6)(H,7,8)/p-2/b2-1-
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Synonyms
ValueSource
MaleChEBI
Maleic acidGenerator
Maleic acid, ammonium saltMeSH
Hydrogen maleateMeSH
Maleic acid, disodium saltMeSH
Maleic acid, monocopper (2+) saltMeSH
Maleic acid, potassium saltMeSH
Maleic acid, sodium saltMeSH
Sodium maleateMeSH
Maleic acid, calcium saltMeSH
Maleic acid, neodymium saltMeSH
Maleic acid, dipotassium saltMeSH
Maleic acid, iron saltMeSH
Maleic acid, monoammonium saltMeSH
Maleic acid, monosodium saltMeSH
Molecular FormulaC4H2O4
Average Mass114.057
Monoisotopic Mass113.996405704
IUPAC Name(2Z)-but-2-enedioate
Traditional Namemaleate
CAS Registry NumberNot Available
SMILES
[H]\C(=C(/[H])C([O-])=O)C([O-])=O
InChI Identifier
InChI=1S/C4H4O4/c5-3(6)1-2-4(7)8/h1-2H,(H,5,6)(H,7,8)/p-2/b2-1-
InChI KeyVZCYOOQTPOCHFL-UPHRSURJSA-L