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Showing NP-Card for Maleamic acid (NP0002746)

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Record Information
Version1.0
Created at2020-11-23 19:39:23 UTC
Updated at2024-05-04 00:30:58 UTC
NP-MRD IDNP0002746
Secondary Accession NumbersNone
Natural Product Identification
Common NameMaleamic acid
Provided ByBMRBBMRB logo
DescriptionMaleamate, also known as maleamic acid or maleic monoamide, belongs to the class of organic compounds known as straight chain fatty acids. These are fatty acids with a straight aliphatic chain. Maleamic acid is found in Pogostemon cablin and Trypanosoma brucei. It was first documented in 2000 (PMID: 10742217). Based on a literature review a significant number of articles have been published on Maleamate (PMID: 17984079) (PMID: 22530095) (PMID: 31433182) (PMID: 30646534).
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0002746 (Maleamic acid)


     RDKit          2D

 13 12  0  0  0  0  0  0  0  0999 V2000
    2.6787    0.5166    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1836    0.3961    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3317    1.6307    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5403   -0.9590    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9549   -1.0794    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8068    0.1552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1635    1.5103    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3019    0.0347    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3220    1.8716    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5306   -0.7181    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3922   -2.1936    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5981   -2.4345    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1538    1.2694    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  1  9  1  0
  1 10  1  0
  4 11  1  0
  5 12  1  0
  8 13  1  0
M  END
Download

3D MOL for NP0002746 (Maleamic acid)

NP0002746
     RDKit          3D

 13 12  0  0  0  0  0  0  0  0999 V2000
   -2.0437    0.9045   -1.2203 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9983    0.4859   -0.5162 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8832    1.0336    0.7294 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1371   -0.4555   -1.1098 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9191   -0.9767   -0.5916 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4502   -0.7088    0.7116 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5204   -1.3092    1.0943 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9112    0.1494    1.6122 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6827    1.5990   -0.7876 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7137    0.9808    1.3381 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3767   -0.7994   -2.1366 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5220   -1.7294   -1.1914 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5126    0.8257    2.0677 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
  1  9  1  0
  3 10  1  0
  4 11  1  0
  5 12  1  0
  8 13  1  0
M  END
Download

3D SDF for NP0002746 (Maleamic acid)


     RDKit          2D

 13 12  0  0  0  0  0  0  0  0999 V2000
    2.6787    0.5166    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1836    0.3961    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3317    1.6307    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5403   -0.9590    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9549   -1.0794    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8068    0.1552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1635    1.5103    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3019    0.0347    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3220    1.8716    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5306   -0.7181    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3922   -2.1936    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5981   -2.4345    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1538    1.2694    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  1  9  1  0
  1 10  1  0
  4 11  1  0
  5 12  1  0
  8 13  1  0
M  END
> <DATABASE_ID>
NP0002746

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]\C(=C(/[H])C(O)=O)C(O)=N

> <INCHI_IDENTIFIER>
InChI=1S/C4H5NO3/c5-3(6)1-2-4(7)8/h1-2H,(H2,5,6)(H,7,8)/b2-1-

> <INCHI_KEY>
FSQQTNAZHBEJLS-UPHRSURJSA-N

> <FORMULA>
C4H5NO3

> <MOLECULAR_WEIGHT>
115.0874

> <EXACT_MASS>
115.026943031

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
13

> <JCHEM_AVERAGE_POLARIZABILITY>
9.668393532090775

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2Z)-3-(C-hydroxycarbonimidoyl)prop-2-enoic acid

> <ALOGPS_LOGP>
-0.75

> <JCHEM_LOGP>
-2.675896473407056

> <ALOGPS_LOGS>
-1.54

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
4.776953093682594

> <JCHEM_PKA_STRONGEST_ACIDIC>
-0.24780042692509774

> <JCHEM_PKA_STRONGEST_BASIC>
12.299095938550568

> <JCHEM_POLAR_SURFACE_AREA>
81.38

> <JCHEM_REFRACTIVITY>
37.3658

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.29e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
maleic monoamide

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for NP0002746 (Maleamic acid)

NP0002746
     RDKit          3D

 13 12  0  0  0  0  0  0  0  0999 V2000
   -2.0437    0.9045   -1.2203 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9983    0.4859   -0.5162 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8832    1.0336    0.7294 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1371   -0.4555   -1.1098 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9191   -0.9767   -0.5916 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4502   -0.7088    0.7116 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5204   -1.3092    1.0943 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9112    0.1494    1.6122 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6827    1.5990   -0.7876 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7137    0.9808    1.3381 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3767   -0.7994   -2.1366 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5220   -1.7294   -1.1914 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5126    0.8257    2.0677 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
  1  9  1  0
  3 10  1  0
  4 11  1  0
  5 12  1  0
  8 13  1  0
M  END
Download

PDB for NP0002746 (Maleamic acid)

HEADER    PROTEIN                                 06-MAY-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-20         0                                  
HETATM    1  C   UNK     0       1.540   0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.310  -1.334   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.770  -1.334   0.000  0.00  0.00           C+0
HETATM    5  N   UNK     0       3.850  -1.334   0.000  0.00  0.00           N+0
HETATM    6  O   UNK     0       1.540  -2.667   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0       0.000  -2.667   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0      -2.310  -1.334   0.000  0.00  0.00           O+0
HETATM    9  H   UNK     0       2.310   1.334   0.000  0.00  0.00           H+0
HETATM   10  H   UNK     0      -0.770   1.334   0.000  0.00  0.00           H+0
CONECT    1    2    3    9                                                  
CONECT    2    1    4   10                                                  
CONECT    3    1    5    6                                                  
CONECT    4    2    7    8                                                  
CONECT    5    3                                                            
CONECT    6    3                                                            
CONECT    7    4                                                            
CONECT    8    4                                                            
CONECT    9    1                                                            
CONECT   10    2                                                            
MASTER        0    0    0    0    0    0    0    0   10    0   18    0
END
Download

3D PDB for NP0002746 (Maleamic acid)

COMPND    NP0002746
HETATM    1  N1  UNL     1      -2.044   0.905  -1.220  1.00  0.00           N  
HETATM    2  C1  UNL     1      -0.998   0.486  -0.516  1.00  0.00           C  
HETATM    3  O1  UNL     1      -0.883   1.034   0.729  1.00  0.00           O  
HETATM    4  C2  UNL     1      -0.137  -0.456  -1.110  1.00  0.00           C  
HETATM    5  C3  UNL     1       0.919  -0.977  -0.592  1.00  0.00           C  
HETATM    6  C4  UNL     1       1.450  -0.709   0.712  1.00  0.00           C  
HETATM    7  O2  UNL     1       2.520  -1.309   1.094  1.00  0.00           O  
HETATM    8  O3  UNL     1       0.911   0.149   1.612  1.00  0.00           O  
HETATM    9  H1  UNL     1      -2.683   1.599  -0.788  1.00  0.00           H  
HETATM   10  H2  UNL     1      -1.714   0.981   1.338  1.00  0.00           H  
HETATM   11  H3  UNL     1      -0.377  -0.799  -2.137  1.00  0.00           H  
HETATM   12  H4  UNL     1       1.522  -1.729  -1.191  1.00  0.00           H  
HETATM   13  H5  UNL     1       1.513   0.826   2.068  1.00  0.00           H  
CONECT    1    2    2    9
CONECT    2    3    4
CONECT    3   10
CONECT    4    5    5   11
CONECT    5    6   12
CONECT    6    7    7    8
CONECT    8   13
END
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SMILES for NP0002746 (Maleamic acid)

[H]\C(=C(/[H])C(O)=O)C(O)=N
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INCHI for NP0002746 (Maleamic acid)

InChI=1S/C4H5NO3/c5-3(6)1-2-4(7)8/h1-2H,(H2,5,6)(H,7,8)/b2-1-
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View in JSmol
Synonyms
ValueSource
(Z)-3-Carbamoyl acrylic acidChEBI
(Z)-4-Amino-4-oxo-2-butenoic acidChEBI
Maleic monoamideChEBI
Maleamic acidKegg
(Z)-3-Carbamoyl acrylateGenerator
(Z)-4-Amino-4-oxo-2-butenoateGenerator
MaleamateGenerator
Maleic acid monoamideMeSH
Chemical FormulaC4H5NO3
Average Mass115.0874 Da
Monoisotopic Mass115.02694 Da
IUPAC Name(2Z)-3-(C-hydroxycarbonimidoyl)prop-2-enoic acid
Traditional Namemaleic monoamide
CAS Registry NumberNot Available
SMILES
[H]\C(=C(/[H])C(O)=O)C(O)=N
InChI Identifier
InChI=1S/C4H5NO3/c5-3(6)1-2-4(7)8/h1-2H,(H2,5,6)(H,7,8)/b2-1-
InChI KeyFSQQTNAZHBEJLS-UPHRSURJSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
HSQC NMR[1H, 13C] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)bgnzk@missouri.eduMU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2024-05-02View Spectrum
HMBC NMR[1H, 13C] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)bgnzk@missouri.eduMU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2024-05-02View Spectrum
COSY NMR[1H, 1H] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)bgnzk@missouri.eduMU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2024-05-02View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, CD3OD, experimental)bgnzk@missouri.eduMU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2024-05-02View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, CD3OD, experimental)bgnzk@missouri.eduMU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2024-05-02View Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Not Available
Chemical Shift Submissions
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 600.133705802, CD3OD, simulated)bgnzk@missouri.eduSumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2024-05-02View Spectrum
Species
Species of Origin
Species NameSourceReference
Pogostemon cablinLOTUS Database
Triticum aestivumKNApSAcK Database
Trypanosoma bruceiLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as straight chain fatty acids. These are fatty acids with a straight aliphatic chain.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acids and conjugates
Direct ParentStraight chain fatty acids
Alternative ParentsNot Available
SubstituentsNot Available
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
logP-0.75ALOGPS
logP-2.7ChemAxon
logS-1.5ALOGPS
pKa (Strongest Acidic)-0.25ChemAxon
pKa (Strongest Basic)12.3ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area81.38 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity37.37 m³·mol⁻¹ChemAxon
Polarizability9.67 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 IDC00053453
Chemspider ID4444106
KEGG Compound IDC01596
BioCyc IDMALEAMATE
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI ID29045
Good Scents IDNot Available
References
General References
  1. Ulrich EL, Akutsu H, Doreleijers JF, Harano Y, Ioannidis YE, Lin J, Livny M, Mading S, Maziuk D, Miller Z, Nakatani E, Schulte CF, Tolmie DE, Kent Wenger R, Yao H, Markley JL: BioMagResBank. Nucleic Acids Res. 2008 Jan;36(Database issue):D402-8. doi: 10.1093/nar/gkm957. Epub 2007 Nov 4. [PubMed:17984079 ]
  2. McLaggan D, Rufino H, Jaspars M, Booth IR: Glutathione-dependent conversion of N-ethylmaleimide to the maleamic acid by Escherichia coli: an intracellular detoxification process. Appl Environ Microbiol. 2000 Apr;66(4):1393-9. doi: 10.1128/AEM.66.4.1393-1399.2000. [PubMed:10742217 ]
  3. Tang H, Yao Y, Wang L, Yu H, Ren Y, Wu G, Xu P: Genomic analysis of Pseudomonas putida: genes in a genome island are crucial for nicotine degradation. Sci Rep. 2012;2:377. doi: 10.1038/srep00377. Epub 2012 Apr 23. [PubMed:22530095 ]
  4. Ion BF, Meister PJ, Gauld JW: Multiscale Computational Study on the Catalytic Mechanism of the Nonmetallo Amidase Maleamate Amidohydrolase (NicF). J Phys Chem A. 2019 Sep 12;123(36):7710-7719. doi: 10.1021/acs.jpca.9b05914. Epub 2019 Sep 3. [PubMed:31433182 ]
  5. Diaz-Garcia D, Ardiles PR, Prashar S, Rodriguez-Dieguez A, Paez PL, Gomez-Ruiz S: Preparation and Study of the Antibacterial Applications and Oxidative Stress Induction of Copper Maleamate-Functionalized Mesoporous Silica Nanoparticles. Pharmaceutics. 2019 Jan 14;11(1). pii: pharmaceutics11010030. doi: 10.3390/pharmaceutics11010030. [PubMed:30646534 ]