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Showing NP-Card for monomethyl fumarate (NP0166770)

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Record Information
Version2.0
Created at2022-09-03 02:12:33 UTC
Updated at2022-09-03 02:12:33 UTC
NP-MRD IDNP0166770
Secondary Accession NumbersNone
Natural Product Identification
Common Namemonomethyl fumarate
DescriptionMonomethyl fumarate, also known as bafiertam or fumarato de monometilo, belongs to the class of organic compounds known as fatty acid esters. These are carboxylic ester derivatives of a fatty acid. monomethyl fumarate is found in Fumaria indica, Maclura cochinchinensis, Rothmannia longiflora and Tagetes minuta. monomethyl fumarate was first documented in 2022 (PMID: 35944162). Based on a literature review a small amount of articles have been published on monomethyl fumarate (PMID: 35697980) (PMID: 35665831) (PMID: 35569547).
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0166770 (monomethyl fumarate)


  Mrv1652309032204122D          

  9  8  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
    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 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
    0.8250    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
   -0.4125   -0.7145    0.0000 C   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
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
M  END
Download

3D MOL for NP0166770 (monomethyl fumarate)

     RDKit          3D

 15 14  0  0  0  0  0  0  0  0999 V2000
    2.9555    0.2569   -0.0746 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5473    0.3550   -0.1622 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8355   -0.8153    0.1378 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4723   -1.8632    0.4607 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6214   -0.8496    0.0856 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3578    0.1867   -0.2382 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8259    0.1309   -0.2849 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3874   -0.9431   -0.0057 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5468    1.2641   -0.6354 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4141    0.2827   -1.0830 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2901   -0.6354    0.4763 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3391    1.1348    0.5174 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1107   -1.7752    0.3260 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8498    1.1137   -0.4783 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1541    2.1570   -0.3039 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  2  0
  6  7  1  0
  7  9  1  0
  7  8  2  0
  1 10  1  0
  1 11  1  0
  1 12  1  0
  5 13  1  0
  6 14  1  0
  9 15  1  0
M  END
Download

3D SDF for NP0166770 (monomethyl fumarate)


  Mrv1652309032204122D          

  9  8  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
    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 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
    0.8250    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
   -0.4125   -0.7145    0.0000 C   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
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0166770

> <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-NSCUHMNNSA-N

> <FORMULA>
C5H6O4

> <MOLECULAR_WEIGHT>
130.099

> <EXACT_MASS>
130.026608673

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
15

> <JCHEM_AVERAGE_POLARIZABILITY>
11.609336069315967

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2E)-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>
3.3100967529351544

> <JCHEM_PKA_STRONGEST_BASIC>
-6.827686541596253

> <JCHEM_POLAR_SURFACE_AREA>
63.60000000000001

> <JCHEM_REFRACTIVITY>
29.376099999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.01e+01 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for NP0166770 (monomethyl fumarate)

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PDB for NP0166770 (monomethyl fumarate)
HEADER    PROTEIN                                 03-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-SEP-22         0                                  
HETATM    1  C   UNK     0       4.620   2.667   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       3.850   1.334   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       2.310   1.334   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       1.540   2.667   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       1.540   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.770  -1.334   0.000  0.00  0.00           C+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    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7                                                            
MASTER        0    0    0    0    0    0    0    0    9    0   16    0
END

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3D PDB for NP0166770 (monomethyl fumarate)
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SMILES for NP0166770 (monomethyl fumarate)
COC(=O)\C=C\C(O)=O
Download
INCHI for NP0166770 (monomethyl 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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View in JSmol
Synonyms
ValueSource
(e)-4-Methoxy-4-oxobut-2-enoic acidChEBI
BafiertamChEBI
Fumarate de monomethyleChEBI
Fumarato de monometiloChEBI
Fumaric acid monomethyl esterChEBI
Methyl hydrogen fumarateChEBI
MMFChEBI
mono-Methyl fumarateChEBI
MonomethylfumarateChEBI
Monomethylis fumarasChEBI
(e)-4-Methoxy-4-oxobut-2-enoateGenerator
Fumaric acid de monomethyleGenerator
Fumarate monomethyl esterGenerator
Methyl hydrogen fumaric acidGenerator
mono-Methyl fumaric acidGenerator
Monomethylfumaric acidGenerator
Monomethyl fumaric acidGenerator
MethylhydrogenfumarateMeSH
Chemical FormulaC5H6O4
Average Mass130.0990 Da
Monoisotopic Mass130.02661 Da
IUPAC Name(2E)-4-methoxy-4-oxobut-2-enoic acid
Traditional Name(2E)-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-NSCUHMNNSA-N
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Fumaria indicaLOTUS Database
Maclura cochinchinensisLOTUS Database
Rothmannia longifloraLOTUS Database
Tagetes minutaLOTUS 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
    • 

  • 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)3.31ChemAxon
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
Polarizability11.61 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDC00057320  
Chemspider ID4520322  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkMonomethyl_fumarate  
METLIN IDNot Available
PubChem Compound5369209  
PDB IDNot Available
ChEBI ID167450  
Good Scents IDrw1475371  
References
General References
  1. Wang Z, Yamazaki S, Mikata Y, Oba M, Takashima H, Morimoto T, Ogawa A: Intramolecular Diels-Alder Reactions of alpha-Bromostyrene-Functionalized Unsaturated Carboxamides. J Org Chem. 2022 Aug 19;87(16):11148-11164. doi: 10.1021/acs.joc.2c01417. Epub  2022 Aug 9. [PubMed:35944162  ] 
  2. Rabe P, Gehmlich M, Peters A, Krumbholz P, Nordstrom A, Staubert C: Combining metabolic phenotype determination with metabolomics and transcriptional analyses to reveal pathways regulated by hydroxycarboxylic acid receptor 2. Discov Oncol. 2022 Jun 13;13(1):47. doi: 10.1007/s12672-022-00503-3. [PubMed:35697980  ] 
  3. de Souza AG, Lopes IS, Filho AJMC, Cavalcante TMB, Oliveira JVS, de Carvalho MAJ, de Lima KA, Juca PM, Mendonca SS, Mottin M, Andrade CH, de Sousa FCF, Macedo DS, de Franca Fonteles MM: Neuroprotective effects of dimethyl fumarate against depression-like behaviors via astrocytes and microglia modulation in mice: possible involvement of the HCAR2/Nrf2 signaling pathway. Naunyn Schmiedebergs Arch Pharmacol. 2022 Sep;395(9):1029-1045. doi:  10.1007/s00210-022-02247-x. Epub 2022 Jun 4. [PubMed:35665831  ] 
  4. Majkutewicz I: Dimethyl fumarate: A review of preclinical efficacy in models of neurodegenerative diseases. Eur J Pharmacol. 2022 Jul 5;926:175025. doi: 10.1016/j.ejphar.2022.175025. Epub  2022 May 13. [PubMed:35569547  ] 
  5. LOTUS database [Link]