Showing NP-Card for Methyl hydrogen fumarate (NP0338328)

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Record Information
Version2.0
Created at2024-09-11 14:55:54 UTC
Updated at2024-09-11 14:55:55 UTC
NP-MRD IDNP0338328
Secondary Accession NumbersNone
Natural Product Identification
Common NameMethyl hydrogen fumarate
DescriptionMethyl hydrogen fumarate, also known as mono-methyl fumarate or fumaric acid, methyl ester, belongs to the class of organic compounds known as fatty acid esters. These are carboxylic ester derivatives of a fatty acid. Methyl hydrogen fumarate is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Outside of the human body, Methyl hydrogen fumarate has been detected, but not quantified in, herbs and spices. This could make methyl hydrogen fumarate a potential biomarker for the consumption of these foods.
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0338328 (Methyl hydrogen fumarate)

  Mrv0541 05061307222D          

  9  8  0  0  0  0            999 V2000
   -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
  3  2  2  0  0  0  0
  4  2  1  0  0  0  0
  5  3  1  0  0  0  0
  6  4  2  0  0  0  0
  7  4  1  0  0  0  0
  8  5  2  0  0  0  0
  9  1  1  0  0  0  0
  9  5  1  0  0  0  0
M  END
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3D MOL for NP0338328 (Methyl hydrogen fumarate)

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3D SDF for NP0338328 (Methyl hydrogen fumarate)
  Mrv0541 05061307222D          

  9  8  0  0  0  0            999 V2000
   -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
  3  2  2  0  0  0  0
  4  2  1  0  0  0  0
  5  3  1  0  0  0  0
  6  4  2  0  0  0  0
  7  4  1  0  0  0  0
  8  5  2  0  0  0  0
  9  1  1  0  0  0  0
  9  5  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0338328

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C5H6O4/c1-9-5(8)3-2-4(6)7/h2-3H,1H3,(H,6,7)/b3-2-

> <INCHI_KEY>
NKHAVTQWNUWKEO-IHWYPQMZSA-N

> <FORMULA>
C5H6O4

> <MOLECULAR_WEIGHT>
130.0987

> <EXACT_MASS>
130.02660868

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
11.30925812032949

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
0.39

> <JCHEM_LOGP>
0.338313058

> <ALOGPS_LOGS>
-0.51

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.9100967531093045

> <JCHEM_PKA_STRONGEST_BASIC>
-6.827686541770403

> <JCHEM_POLAR_SURFACE_AREA>
63.599999999999994

> <JCHEM_REFRACTIVITY>
29.3761

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.01e+01 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

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3D-SDF for NP0338328 (Methyl hydrogen fumarate)
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PDB for NP0338328 (Methyl hydrogen fumarate)
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      -3.080  -2.667   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.540   0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.310  -1.334   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.770  -1.334   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       3.850  -1.334   0.000  0.00  0.00           O+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      -2.310  -1.334   0.000  0.00  0.00           O+0
CONECT    1    9                                                            
CONECT    2    3    4                                                       
CONECT    3    2    5                                                       
CONECT    4    2    6    7                                                  
CONECT    5    3    8    9                                                  
CONECT    6    4                                                            
CONECT    7    4                                                            
CONECT    8    5                                                            
CONECT    9    1    5                                                       
MASTER        0    0    0    0    0    0    0    0    9    0   16    0
END

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3D PDB for NP0338328 (Methyl hydrogen fumarate)
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SMILES for NP0338328 (Methyl hydrogen fumarate)
COC(=O)\C=C/C(O)=O
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INCHI for NP0338328 (Methyl hydrogen fumarate)
InChI=1S/C5H6O4/c1-9-5(8)3-2-4(6)7/h2-3H,1H3,(H,6,7)/b3-2-
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Synonyms
ValueSource
Methyl hydrogen fumaric acidGenerator
(2E)-4-Methoxy-4-oxo-2-butenoic acidHMDB
2-Butenedioic acid (e)-, monomethyl esterHMDB
Fumaric acid monomethyl esterHMDB
Fumaric acid, methyl esterHMDB
Fumaric acid, monomethyl esterHMDB
mono-Methyl fumarateHMDB
Monomethyl fumarateHMDB
Chemical FormulaC5H6O4
Average Mass130.0987 Da
Monoisotopic Mass130.02661 Da
IUPAC Name(2Z)-4-methoxy-4-oxobut-2-enoic acid
Traditional Name(2Z)-4-methoxy-4-oxobut-2-enoic acid
CAS Registry NumberNot Available
SMILES
COC(=O)\C=C/C(O)=O
InChI Identifier
InChI=1S/C5H6O4/c1-9-5(8)3-2-4(6)7/h2-3H,1H3,(H,6,7)/b3-2-
InChI KeyNKHAVTQWNUWKEO-IHWYPQMZSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
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
    • 

  • Unsaturated fatty acid
    • 

  • Dicarboxylic acid or derivatives
    • 

  • Alpha,beta-unsaturated carboxylic ester
    • 

  • Enoate ester
    • 

  • Methyl 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
logP0.39ALOGPS
logP0.34ChemAxon
logS-0.51ALOGPS
pKa (Strongest Acidic)2.91ChemAxon
pKa (Strongest Basic)-6.8ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area63.6 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity29.38 m³·mol⁻¹ChemAxon
Polarizability11.31 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0033809  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB011972  
KNApSAcK IDNot Available
Chemspider ID4510649  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5354456  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References