Showing NP-Card for ethyl maleate (NP0303707)

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Record Information
Version2.0
Created at2022-09-10 18:17:30 UTC
Updated at2022-09-10 18:17:31 UTC
NP-MRD IDNP0303707
Secondary Accession NumbersNone
Natural Product Identification
Common Nameethyl maleate
DescriptionEthyl hydrogen fumarate, also known as monoethyl fumarate or potassium ethyl fumarate, belongs to the class of organic compounds known as fatty acid esters. These are carboxylic ester derivatives of a fatty acid. ethyl maleate is found in Vaccinium macrocarpon. Ethyl hydrogen fumarate is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0303707 (ethyl maleate)

  Mrv0541 05061311412D          

 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
    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  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
   -1.2375   -0.7145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  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  5  1  0  0  0  0
  9  6  2  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 NP0303707 (ethyl maleate)

     RDKit          3D

 18 17  0  0  0  0  0  0  0  0999 V2000
    2.5472    0.8005    0.2966 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3567    1.1855   -0.5237 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2291    0.3620   -0.2984 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1500   -0.9546   -0.4885 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2153   -1.5396   -0.9242 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9605   -1.8182   -0.2752 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1290   -1.4132    0.1641 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5116   -0.0879    0.5031 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7353    0.0580    0.9176 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7896    1.0524    0.4591 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2395    0.5372    1.3274 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1890    0.0288   -0.1775 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2104    1.7082    0.3857 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6324    1.0589   -1.6117 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1558    2.2441   -0.3766 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8541   -2.9207   -0.4895 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9070   -2.2328    0.2784 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0383    1.9314    0.0328 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  2  0
  7  8  1  0
  8 10  1  0
  8  9  2  0
  1 11  1  0
  1 12  1  0
  1 13  1  0
  2 14  1  0
  2 15  1  0
  6 16  1  0
  7 17  1  0
 10 18  1  0
M  END
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3D SDF for NP0303707 (ethyl maleate)

  Mrv0541 05061311412D          

 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
    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  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
   -1.2375   -0.7145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  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  5  1  0  0  0  0
  9  6  2  0  0  0  0
 10  2  1  0  0  0  0
 10  6  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0303707

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C6H8O4/c1-2-10-6(9)4-3-5(7)8/h3-4H,2H2,1H3,(H,7,8)/b4-3-

> <INCHI_KEY>
XLYMOEINVGRTEX-ARJAWSKDSA-N

> <FORMULA>
C6H8O4

> <MOLECULAR_WEIGHT>
144.1253

> <EXACT_MASS>
144.042258744

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
13.422244569061608

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2Z)-4-ethoxy-4-oxobut-2-enoic acid

> <ALOGPS_LOGP>
0.86

> <JCHEM_LOGP>
0.6951210126666666

> <ALOGPS_LOGS>
-0.76

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.0787403645946103

> <JCHEM_PKA_STRONGEST_BASIC>
-6.834751266595363

> <JCHEM_POLAR_SURFACE_AREA>
63.599999999999994

> <JCHEM_REFRACTIVITY>
34.1247

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.52e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2Z)-4-ethoxy-4-oxobut-2-enoic acid

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for NP0303707 (ethyl maleate)

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PDB for NP0303707 (ethyl 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       3.850  -1.334   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0       1.540  -2.667   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0       0.000  -2.667   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    2                                                            
CONECT    2    1   10                                                       
CONECT    3    4    5                                                       
CONECT    4    3    6                                                       
CONECT    5    3    7    8                                                  
CONECT    6    4    9   10                                                  
CONECT    7    5                                                            
CONECT    8    5                                                            
CONECT    9    6                                                            
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 NP0303707 (ethyl maleate)
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SMILES for NP0303707 (ethyl maleate)
CCOC(=O)\C=C/C(O)=O
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INCHI for NP0303707 (ethyl maleate)
InChI=1S/C6H8O4/c1-2-10-6(9)4-3-5(7)8/h3-4H,2H2,1H3,(H,7,8)/b4-3-
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View in JSmol
Synonyms
ValueSource
Ethyl hydrogen fumaric acidGenerator
(2E)-4-Ethoxy-4-oxo-2-butenoic acidHMDB
2-Butenedioic acid (e)-, monoethyl esterHMDB
Fumaric acid monoethyl esterHMDB
Monoethyl fumarateHMDB
Potassium ethyl fumarateHMDB
Ethyl hydrogen maleateMeSH
Diethyl maleateMeSH
Diethyl maleic acid diesterMeSH
Ethyl maleateMeSH
Maleic acid diethyl esterMeSH
Maleic acid, ethyl esterMeSH
DiethylmaleateMeSH
Monoethyl maleateMeSH
Chemical FormulaC6H8O4
Average Mass144.1253 Da
Monoisotopic Mass144.04226 Da
IUPAC Name(2Z)-4-ethoxy-4-oxobut-2-enoic acid
Traditional Name(2Z)-4-ethoxy-4-oxobut-2-enoic acid
CAS Registry NumberNot Available
SMILES
CCOC(=O)\C=C/C(O)=O
InChI Identifier
InChI=1S/C6H8O4/c1-2-10-6(9)4-3-5(7)8/h3-4H,2H2,1H3,(H,7,8)/b4-3-
InChI KeyXLYMOEINVGRTEX-ARJAWSKDSA-N
Experimental Spectra
Not Available
Predicted Spectra
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Vaccinium macrocarponLOTUS Database
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
    • 

  • Unsaturated fatty acid
    • 

  • Dicarboxylic acid or derivatives
    • 

  • Alpha,beta-unsaturated carboxylic ester
    • 

  • Enoate ester
    • 

  • Carboxylic acid ester
    • 

  • Carboxylic acid
    • 

  • Carboxylic acid derivative
    • 

  • Organic oxygen compound
    • 

  • Organic oxide
    • 

  • Hydrocarbon derivative
    • 

  • Organooxygen compound
    • 

  • Carbonyl group
    • 

  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
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
logP0.86ALOGPS
logP0.7ChemAxon
logS-0.76ALOGPS
pKa (Strongest Acidic)3.08ChemAxon
pKa (Strongest Basic)-6.8ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area63.6 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity34.12 m³·mol⁻¹ChemAxon
Polarizability13.42 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0040207  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB019919  
KNApSAcK IDNot Available
Chemspider ID4510650  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5354457  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. LOTUS database [Link]