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Showing NP-Card for Maleic acid (NP0000368)

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Record Information
Version2.0
Created at2005-11-16 15:48:42 UTC
Updated at2021-10-07 20:42:10 UTC
NP-MRD IDNP0000368
Secondary Accession NumbersNone
Natural Product Identification
Common NameMaleic acid
DescriptionMaleic acid is a dicarboxylic acid, a molecule with two carboxyl groups. It consists of an ethylene group flanked by two carboxylic acid groups. Maleic acid is the cis isomer of butenedioic acid, whereas fumaric acid is the trans isomer. The cis isomer is the less stable one of the two; the difference in heat of combustion is 22.7 KJ/mol. The physical properties of maleic acid are very different from that of fumaric acid. Maleic acid is soluble in water whereas fumaric acid is not and the melting point of maleic acid (130 - 131 oC) is also much lower than that of fumaric acid (287 oC). Maleic acid is converted into maleic anhydride by dehydration, to malic acid by hydration, and to succinic acid by hydrogenation. Maleic acid is used in making polyesters for fibre-reinforced laminated moldings and paint vehicles. More specifically it is used in the manufacture of phthalic-type alkyd and polyester resins, surface coatings, copolymers, plasticizers, lubricant additives and agricultural chemicals. It is also found in adhesives and sealants and as a preservative for oils and fats. In the natural world, maleic acid has been identified in ginseng, pineapple, cacao plants, sour cherries and corn. A large number of microbes are able to convert maleic acid to D-malate using the enzyme maleate hydratase (PMID: 1444397 ).
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0000368 (Maleic acid)


  Mrv1652305271900202D          

  8  7  0  0  0  0            999 V2000
10000.3928 9999.3865    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.5678 9999.3865    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.8529 9999.7980    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.1382 9999.3865    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9998.852910000.6234    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10001.1083 9999.7980    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.8217 9999.3865    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10001.108310000.6234    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  6  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  3  5  2  0  0  0  0
  6  7  1  0  0  0  0
  6  8  2  0  0  0  0
M  END
Download

3D MOL for NP0000368 (Maleic acid)

HMDB0000176
     RDKit          3D
Maleic acid
 12 11  0  0  0  0  0  0  0  0999 V2000
    1.2932   -0.8164   -1.3800 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4817    0.0123   -0.4966 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8283    0.3986   -0.3335 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5510    0.6485    0.3942 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7385    0.4793    0.4610 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4643   -0.4198   -0.3946 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9553   -1.1230   -1.2766 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8802   -0.4971   -0.2006 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4399   -0.1199    0.2473 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9409    1.3974    1.1492 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2728    1.0808    1.2349 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2240   -1.0407    0.5953 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  3  9  1  0
  4 10  1  0
  5 11  1  0
  8 12  1  0
M  END
Download

3D SDF for NP0000368 (Maleic acid)


  Mrv1652305271900202D          

  8  7  0  0  0  0            999 V2000
10000.3928 9999.3865    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.5678 9999.3865    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.8529 9999.7980    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.1382 9999.3865    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9998.852910000.6234    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10001.1083 9999.7980    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.8217 9999.3865    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10001.108310000.6234    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  6  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  3  5  2  0  0  0  0
  6  7  1  0  0  0  0
  6  8  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0000368

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC(=O)\C=C/C(O)=O

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

> <INCHI_KEY>
VZCYOOQTPOCHFL-UPHRSURJSA-N

> <FORMULA>
C4H4O4

> <MOLECULAR_WEIGHT>
116.0722

> <EXACT_MASS>
116.010958616

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
12

> <JCHEM_AVERAGE_POLARIZABILITY>
9.194281482540934

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2Z)-but-2-enedioic acid

> <ALOGPS_LOGP>
0.21

> <JCHEM_LOGP>
-0.040914331333333324

> <ALOGPS_LOGS>
-0.68

> <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>
74.6

> <JCHEM_REFRACTIVITY>
24.607

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.41e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
maleic acid

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for NP0000368 (Maleic acid)

HMDB0000176
     RDKit          3D
Maleic acid
 12 11  0  0  0  0  0  0  0  0999 V2000
    1.2932   -0.8164   -1.3800 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4817    0.0123   -0.4966 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8283    0.3986   -0.3335 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5510    0.6485    0.3942 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7385    0.4793    0.4610 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4643   -0.4198   -0.3946 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9553   -1.1230   -1.2766 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8802   -0.4971   -0.2006 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4399   -0.1199    0.2473 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9409    1.3974    1.1492 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2728    1.0808    1.2349 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2240   -1.0407    0.5953 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  3  9  1  0
  4 10  1  0
  5 11  1  0
  8 12  1  0
M  END
Download

PDB for NP0000368 (Maleic acid)

HEADER    PROTEIN                                 27-MAY-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-19         0                                  
HETATM    1  C   UNK     0    8667.4008665.521   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    8665.8608665.521   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0    8664.5258666.290   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0    8663.1918665.521   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0    8664.5258667.830   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0    8668.7358666.290   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0    8670.0678665.521   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0    8668.7358667.830   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3                                                            
CONECT    6    1    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6                                                            
MASTER        0    0    0    0    0    0    0    0    8    0   14    0
END
Download

3D PDB for NP0000368 (Maleic acid)

COMPND    HMDB0000176
HETATM    1  O1  UNL     1       1.293  -0.816  -1.380  1.00  0.00           O  
HETATM    2  C1  UNL     1       1.482   0.012  -0.497  1.00  0.00           C  
HETATM    3  O2  UNL     1       2.828   0.399  -0.334  1.00  0.00           O  
HETATM    4  C2  UNL     1       0.551   0.649   0.394  1.00  0.00           C  
HETATM    5  C3  UNL     1      -0.739   0.479   0.461  1.00  0.00           C  
HETATM    6  C4  UNL     1      -1.464  -0.420  -0.395  1.00  0.00           C  
HETATM    7  O3  UNL     1      -0.955  -1.123  -1.277  1.00  0.00           O  
HETATM    8  O4  UNL     1      -2.880  -0.497  -0.201  1.00  0.00           O  
HETATM    9  H1  UNL     1       3.440  -0.120   0.247  1.00  0.00           H  
HETATM   10  H2  UNL     1       0.941   1.397   1.149  1.00  0.00           H  
HETATM   11  H3  UNL     1      -1.273   1.081   1.235  1.00  0.00           H  
HETATM   12  H4  UNL     1      -3.224  -1.041   0.595  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    4
CONECT    3    9
CONECT    4    5    5   10
CONECT    5    6   11
CONECT    6    7    7    8
CONECT    8   12
END
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SMILES for NP0000368 (Maleic acid)

OC(=O)\C=C/C(O)=O
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INCHI for NP0000368 (Maleic acid)

InChI=1S/C4H4O4/c5-3(6)1-2-4(7)8/h1-2H,(H,5,6)(H,7,8)/b2-1-
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View in JSmol
Synonyms
ValueSource
(Z)-2-Butenedioic acidChEBI
(Z)-Butenedioic acidChEBI
cis-1,2-Ethylenedicarboxylic acidChEBI
cis-But-2-enedioic acidChEBI
cis-Butenedioic acidChEBI
H2MaleChEBI
Toxilic acidChEBI
MaleateKegg
(Z)-2-ButenedioateGenerator
(Z)-ButenedioateGenerator
cis-1,2-EthylenedicarboxylateGenerator
cis-But-2-enedioateGenerator
cis-ButenedioateGenerator
ToxilateGenerator
(2Z)-2-ButenedioateHMDB
(2Z)-2-Butenedioic acidHMDB
(2Z)-But-2-enedioateHMDB
(2Z)-But-2-enedioic acidHMDB
(2Z)-Butene-2-dioateHMDB
(2Z)-Butene-2-dioic acidHMDB
2-ButenedioateHMDB
2-Butenedioic acidHMDB
cis-2-ButenedioateHMDB
cis-2-Butenedioic acidHMDB
Kyselina maleinovaHMDB
MAEHMDB
Maleinic acidHMDB
Malenic acidHMDB
Malezid CMHMDB
Scotchbond multipurpose etchantHMDB
Maleic acid, disodium saltHMDB
Maleic acid, monocopper (2+) saltHMDB
Maleic acid, potassium saltHMDB
Maleic acid, sodium saltHMDB
Sodium maleateHMDB
Hydrogen maleateHMDB
Maleic acid, ammonium saltHMDB
Maleic acid, calcium saltHMDB
Maleic acid, iron saltHMDB
Maleic acid, neodymium saltHMDB
Maleic acid, dipotassium saltHMDB
Maleic acid, monoammonium saltHMDB
Maleic acid, monosodium saltHMDB
Chemical FormulaC4H4O4
Average Mass116.0722 Da
Monoisotopic Mass116.01096 Da
IUPAC Name(2Z)-but-2-enedioic acid
Traditional Namemaleic acid
CAS Registry Number110-16-7
SMILES
OC(=O)\C=C/C(O)=O
InChI Identifier
InChI=1S/C4H4O4/c5-3(6)1-2-4(7)8/h1-2H,(H,5,6)(H,7,8)/b2-1-
InChI KeyVZCYOOQTPOCHFL-UPHRSURJSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Agave americanaLOTUS Database
Arabidopsis thalianaKNApSAcK Database
Astragalus cibariusLOTUS Database
Chlamydomonas reinhardtiiLOTUS Database
Fasciola hepaticaLOTUS Database
Hibiscus sabbariffaFooDB
Homo sapiens (Urine)Animalia
Levisticum officinaleFooDB
Lotus corniculatusLOTUS Database
Mus musculusLOTUS Database
Populus tremulaLOTUS Database
Prunus cerasusFooDB
Salmonella entericaLOTUS Database
Theobroma cacaoFooDB
Zea mays L.FooDB
Chemical Taxonomy
Description 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
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point130.5 °CNot Available
Boiling Point355.00 to 356.00 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility441 mg/mL at 25 °CNot Available
LogP-0.48Sangster, J. (1993). LOGKOW- a Databank of Evaluated Octanol-Water Partition Coefficients. Sangster Research Laboratories, Montreal.
Predicted Properties
PropertyValueSource
Water Solubility24.1 g/LALOGPS
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 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity24.61 m³·mol⁻¹ChemAxon
Polarizability9.19 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0000176
DrugBank IDDB04299
Phenol Explorer Compound IDNot Available
FoodDB IDFDB008113
KNApSAcK IDC00007417
Chemspider ID392248
KEGG Compound IDC01384
BioCyc IDMALEATE
BiGG IDNot Available
Wikipedia LinkMaleic_acid
METLIN IDNot Available
PubChem Compound444266
PDB IDNot Available
ChEBI ID18300
Good Scents IDrw1256251
References
General References
  1. 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. [PubMed:12859262 ]
  2. 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. [PubMed:1495787 ]
  3. 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. [PubMed:16797943 ]
  4. 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. [PubMed:15835174 ]
  5. Gong Z, Lv Y, Huang Y, Zhang Z: Determination of ergometrine maleate by fluorescence detection. Luminescence. 2005 May-Jun;20(3):124-8. [PubMed:15924314 ]
  6. 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. [PubMed:9835798 ]
  7. Gallagher RM: Menstrual migraine and intermittent ergonovine therapy. Headache. 1989 Jun;29(6):366-7. [PubMed:2759844 ]
  8. 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. [PubMed:9872612 ]
  9. 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. [PubMed:12895502 ]
  10. 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. [PubMed:10965422 ]
  11. 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. [PubMed:7075967 ]
  12. 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. [PubMed:10024972 ]
  13. 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. [PubMed:10522050 ]
  14. 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. [PubMed:10635272 ]
  15. 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. [PubMed:16778650 ]
  16. 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. [PubMed:16043230 ]
  17. 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. [PubMed:7905382 ]
  18. 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. [PubMed:12450709 ]
  19. van der Werf MJ, van den Tweel WJ, Hartmans S: Screening for microorganisms producing D-malate from maleate. Appl Environ Microbiol. 1992 Sep;58(9):2854-60. doi: 10.1128/aem.58.9.2854-2860.1992. [PubMed:1444397 ]