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Showing NP-Card for Dimethyl maleate (NP0333286)

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Record Information
Version2.0
Created at2024-05-21 21:49:00 UTC
Updated at2024-09-03 04:21:50 UTC
NP-MRD IDNP0333286
Natural Product DOIhttps://doi.org/10.57994/2637
Secondary Accession NumbersNone
Natural Product Identification
Common NameDimethyl maleate
DescriptionDimethyl fumarate, also known as methyl maleic acid or BG 12 compound, belongs to the class of organic compounds known as fatty acid esters. These are carboxylic ester derivatives of a fatty acid. Due to the geometry of the starting ester, the Diels-Alder product will have a trans configuration. Dimethyl fumarate is an extremely weak basic (essentially neutral) compound (based on its pKa). ; Dimethyl fumarate is used to treat psoriasis. Dimethyl fumarate is an ester and an?. -Unsaturated electrophilic compound, undergoing reactions typical to them. It is a lipophilic, highly mobile molecule in human tissue. However, as an , -unsaturated ester, dimethyl fumarate reacts rapidly with the detoxifying agent glutathione by Michael addition. Dimethyl maleate was first documented in 2011 (PMID: 21772304). It is also a diene acceptor in the ordinary Diels-Alder reaction, where the reactivity of its vinylidenic bond is enchanced by the two electron-withdrawing ester groups (PMID: 24700785).
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0333286 (Dimethyl maleate)


  Mrv0541 05061305502D          

 10  9  0  0  0  0            999 V2000
    2.4750   -1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6500   -1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    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
    0.8250   -1.4289    0.0000 O   0  0  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
    2.0625   -0.7145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2375   -0.7145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  4  3  2  0  0  0  0
  5  3  1  0  0  0  0
  6  4  1  0  0  0  0
  7  5  2  0  0  0  0
  8  6  2  0  0  0  0
  9  1  1  0  0  0  0
  9  5  1  0  0  0  0
 10  2  1  0  0  0  0
 10  6  1  0  0  0  0
M  END
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3D MOL for NP0333286 (Dimethyl maleate)

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3D SDF for NP0333286 (Dimethyl maleate)

  Mrv0541 05061305502D          

 10  9  0  0  0  0            999 V2000
    2.4750   -1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6500   -1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    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
    0.8250   -1.4289    0.0000 O   0  0  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
    2.0625   -0.7145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2375   -0.7145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  4  3  2  0  0  0  0
  5  3  1  0  0  0  0
  6  4  1  0  0  0  0
  7  5  2  0  0  0  0
  8  6  2  0  0  0  0
  9  1  1  0  0  0  0
  9  5  1  0  0  0  0
 10  2  1  0  0  0  0
 10  6  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0333286

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C6H8O4/c1-9-5(7)3-4-6(8)10-2/h3-4H,1-2H3/b4-3-

> <INCHI_KEY>
LDCRTTXIJACKKU-ARJAWSKDSA-N

> <FORMULA>
C6H8O4

> <MOLECULAR_WEIGHT>
144.1253

> <EXACT_MASS>
144.042258744

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
13.168837047620139

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
1,4-dimethyl (2Z)-but-2-enedioate

> <ALOGPS_LOGP>
0.45

> <JCHEM_LOGP>
0.7175404473333331

> <ALOGPS_LOGS>
-1.05

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-6.5267283323427785

> <JCHEM_POLAR_SURFACE_AREA>
52.60000000000001

> <JCHEM_REFRACTIVITY>
34.1452

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.29e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
dimethyl maleate

> <JCHEM_VEBER_RULE>
0

$$$$

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3D-SDF for NP0333286 (Dimethyl maleate)
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PDB for NP0333286 (Dimethyl maleate)
HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0       4.620  -2.667   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -3.080  -2.667   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.540   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.310  -1.334   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.770  -1.334   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       1.540  -2.667   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0       0.000  -2.667   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0       3.850  -1.334   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0      -2.310  -1.334   0.000  0.00  0.00           O+0
CONECT    1    9                                                            
CONECT    2   10                                                            
CONECT    3    4    5                                                       
CONECT    4    3    6                                                       
CONECT    5    3    7    9                                                  
CONECT    6    4    8   10                                                  
CONECT    7    5                                                            
CONECT    8    6                                                            
CONECT    9    1    5                                                       
CONECT   10    2    6                                                       
MASTER        0    0    0    0    0    0    0    0   10    0   18    0
END

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3D PDB for NP0333286 (Dimethyl maleate)
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SMILES for NP0333286 (Dimethyl maleate)
COC(=O)\C=C/C(=O)OC
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INCHI for NP0333286 (Dimethyl maleate)
InChI=1S/C6H8O4/c1-9-5(7)3-4-6(8)10-2/h3-4H,1-2H3/b4-3-
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Synonyms
ValueSource
2-Butenedioic acid (2Z)-, dimethyl esterChEBI
2-Butenedioic acid (Z)-, dimethyl esterChEBI
Dimethyl cis-ethylenedicarboxylateChEBI
Maleic acid, dimethyl esterChEBI
Methyl maleateChEBI
2-Butenedioate (2Z)-, dimethyl esterGenerator
2-Butenedioate (Z)-, dimethyl esterGenerator
Dimethyl cis-ethylenedicarboxylic acidGenerator
Maleate, dimethyl esterGenerator
Methyl maleic acidGenerator
Dimethyl fumaric acidGenerator
(e)-CH3OC(O)CH=chc(O)OCH3HMDB
1,2-Bis(methoxycarbonyl)-trans-ethyleneHMDB
2-Butenedioic acid (2E)-, 1,4-dimethyl esterHMDB
2-Butenedioic acid (2E)-, dimethyl esterHMDB
2-Butenedioic acid (e)-, dimethyl esterHMDB
2-Butenedioic acid, dimethyl esterHMDB
Allomaleic acid dimethyl esterHMDB
BG 12 CompoundHMDB
Boletic acid dimethyl esterHMDB
But-2-enedioic acid, dimethyl esterHMDB
Dimethyl (2E)-2-butenedioateHMDB
Dimethyl (2E)-but-2-enedioateHMDB
Dimethyl (e)-but-2-enedioateHMDB
Dimethyl but-2-enedioateHMDB
Dimethyl ester(2E)-2-butenedioic acidHMDB
Dimethyl ester(e)-2-butenedioic acidHMDB
Dimethyl trans-ethylenedicarboxylateHMDB
Dimethylester kyseliny fumaroveHMDB
DimethylfumarateHMDB
FumadermHMDB
Fumaric acid dimethyl esterHMDB
Fumaric acid, dimethyl esterHMDB
Fumaric acid, dimethyl ester (8ci)HMDB
Methyl fumarateHMDB
trans-1, 2-Ethylenedicarboxylic acid dimethyl esterHMDB
trans-1,2-Ethylenedicarboxylic acid dimethyl esterHMDB
trans-Butenedioic acid dimethyl esterHMDB
Dimethyl maleic acidGenerator
Chemical FormulaC6H8O4
Average Mass144.1253 Da
Monoisotopic Mass144.04226 Da
IUPAC Name1,4-dimethyl (2Z)-but-2-enedioate
Traditional Namedimethyl maleate
CAS Registry NumberNot Available
SMILES
COC(=O)\C=C/C(=O)OC
InChI Identifier
InChI=1S/C6H8O4/c1-9-5(7)3-4-6(8)10-2/h3-4H,1-2H3/b4-3-
InChI KeyLDCRTTXIJACKKU-ARJAWSKDSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 201 MHz, CD3OD, experimental)ztmnb@umsystem.eduSumner lab, University of MissouriZach Tretter2024-05-21View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, CD3OD, experimental)ztmnb@umsystem.eduSumner lab, University of MissouriZach Tretter2024-05-21View Spectrum
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
Chemical Shift Submissions
Not Available
Species
Species of OriginNot Available
Chemical Taxonomy
Description Belongs to the class of organic compounds known as fatty acid esters. These are carboxylic ester derivatives of a fatty acid.
KingdomOrganic compounds  
Super ClassLipids and lipid-like molecules  
ClassFatty Acyls  
Sub ClassFatty acid esters  
Direct ParentFatty acid esters  
Alternative Parents
Substituents
  • Fatty acid ester
    • 

  • Dicarboxylic acid or derivatives
    • 

  • Alpha,beta-unsaturated carboxylic ester
    • 

  • Enoate ester
    • 

  • Methyl ester
    • 

  • Carboxylic acid ester
    • 

  • Carboxylic acid derivative
    • 

  • Organic oxygen compound
    • 

  • Organic oxide
    • 

  • Hydrocarbon derivative
    • 

  • Organooxygen compound
    • 

  • Carbonyl group
    • 

  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP0.45ALOGPS
logP0.72ChemAxon
logS-1ALOGPS
pKa (Strongest Basic)-6.5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area52.6 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity34.15 m³·mol⁻¹ChemAxon
Polarizability13.17 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0031257  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB003290  
KNApSAcK IDNot Available
Chemspider ID4436352  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkDimethyl_maleate  
METLIN IDNot Available
PubChem Compound5271565  
PDB IDNot Available
ChEBI ID35460  
Good Scents IDNot Available
References
General References
  1. Chen X, Zhu X, Ding Y, Shen Y: Antifungal activity of tautomycin and related compounds against Sclerotinia sclerotiorum. J Antibiot (Tokyo). 2011 Aug;64(8):563-9. doi: 10.1038/ja.2011.55. Epub 2011 Jul  20. [PubMed:21772304  ] 
  2. Hopf H, Jones PG, Nicolescu A, Bicu E, Birsa LM, Belei D: A facile synthesis of Pechmann dyes. Chemistry. 2014 May 5;20(19):5565-8. doi: 10.1002/chem.201400329. Epub 2014 Apr  2. [PubMed:24700785  ]