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Showing NP-Card for N-Acryloylglycine (NP0000433)

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Record Information
Version2.0
Created at2006-01-27 11:06:50 UTC
Updated at2020-11-24 22:15:27 UTC
NP-MRD IDNP0000433
Secondary Accession NumbersNone
Natural Product Identification
Common NameN-Acryloylglycine
DescriptionN-Acryloylglycine is an acyl glycine. Acyl glycines are normally minor metabolites of fatty acids. However, the excretion of certain acyl glycines is increased in several inborn errors of metabolism. In certain cases the measurement of these metabolites in body fluids can be used to diagnose disorders associated with mitochondrial fatty acid beta-oxidation. Acyl glycines are produced through the action of glycine N-acyltransferase (EC 2.3.1.13) Which is an enzyme that catalyzes the chemical reaction:. Acyl-CoA + glycine < -- > CoA + N-acylglycine. N-Acryloylglycine is an acylglycines found in normal human biofluids (PMID 7364920 ; 912020; 7438429).
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0000433 (N-Acryloylglycine)


  Mrv1652305271900222D          

  9  8  0  0  0  0            999 V2000
   14.2086  -15.3770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4941  -15.7895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3507  -15.3770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7797  -15.3770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6363  -15.7895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0652  -15.7895    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.7797  -14.5520    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.9218  -15.3770    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.6363  -16.6145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  4  1  0  0  0  0
  3  6  1  0  0  0  0
  3  5  1  0  0  0  0
  4  7  2  0  0  0  0
  4  6  1  0  0  0  0
  5  8  1  0  0  0  0
  5  9  2  0  0  0  0
M  END
Download

3D MOL for NP0000433 (N-Acryloylglycine)

HMDB0001843
     RDKit          3D
N-Acryloylglycine
 16 15  0  0  0  0  0  0  0  0999 V2000
    2.7746    0.4911   -0.8233 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1568    0.8209    0.2890 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8368    0.3052    0.5959 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3162    0.6851    1.7061 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0959   -0.5752   -0.2339 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2187   -1.0259    0.1785 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1403    0.1320    0.3551 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7522    1.2888    0.1553 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4388   -0.1525    0.7501 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3377   -0.1715   -1.5558 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7798    0.9123   -1.0088 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6548    1.4953    0.9867 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5283   -0.8698   -1.1206 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1148   -1.5045    1.1844 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6342   -1.7852   -0.4862 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1817   -0.0460    0.0687 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  1 10  1  0
  1 11  1  0
  2 12  1  0
  5 13  1  0
  6 14  1  0
  6 15  1  0
  9 16  1  0
M  END
Download

3D SDF for NP0000433 (N-Acryloylglycine)


  Mrv1652305271900222D          

  9  8  0  0  0  0            999 V2000
   14.2086  -15.3770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4941  -15.7895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3507  -15.3770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7797  -15.3770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6363  -15.7895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0652  -15.7895    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.7797  -14.5520    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.9218  -15.3770    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.6363  -16.6145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  4  1  0  0  0  0
  3  6  1  0  0  0  0
  3  5  1  0  0  0  0
  4  7  2  0  0  0  0
  4  6  1  0  0  0  0
  5  8  1  0  0  0  0
  5  9  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0000433

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC(=O)CNC(=O)C=C

> <INCHI_IDENTIFIER>
InChI=1S/C5H7NO3/c1-2-4(7)6-3-5(8)9/h2H,1,3H2,(H,6,7)(H,8,9)

> <INCHI_KEY>
LZCXCXDOGAEFQX-UHFFFAOYSA-N

> <FORMULA>
C5H7NO3

> <MOLECULAR_WEIGHT>
129.114

> <EXACT_MASS>
129.042593095

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
16

> <JCHEM_AVERAGE_POLARIZABILITY>
11.919920160797718

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-(prop-2-enamido)acetic acid

> <ALOGPS_LOGP>
-0.28

> <JCHEM_LOGP>
-0.572335947

> <ALOGPS_LOGS>
-0.31

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
15.62688099323789

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.839946980922358

> <JCHEM_PKA_STRONGEST_BASIC>
-0.6265124656156366

> <JCHEM_POLAR_SURFACE_AREA>
66.4

> <JCHEM_REFRACTIVITY>
30.094900000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.36e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
N-acryloylglycine

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for NP0000433 (N-Acryloylglycine)

HMDB0001843
     RDKit          3D
N-Acryloylglycine
 16 15  0  0  0  0  0  0  0  0999 V2000
    2.7746    0.4911   -0.8233 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1568    0.8209    0.2890 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8368    0.3052    0.5959 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3162    0.6851    1.7061 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0959   -0.5752   -0.2339 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2187   -1.0259    0.1785 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1403    0.1320    0.3551 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7522    1.2888    0.1553 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4388   -0.1525    0.7501 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3377   -0.1715   -1.5558 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7798    0.9123   -1.0088 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6548    1.4953    0.9867 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5283   -0.8698   -1.1206 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1148   -1.5045    1.1844 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6342   -1.7852   -0.4862 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1817   -0.0460    0.0687 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  1 10  1  0
  1 11  1  0
  2 12  1  0
  5 13  1  0
  6 14  1  0
  6 15  1  0
  9 16  1  0
M  END
Download

PDB for NP0000433 (N-Acryloylglycine)

HEADER    PROTEIN                                 27-MAY-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-19         0                                  
HETATM    1  C   UNK     0      26.523 -28.704   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      25.189 -29.474   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      21.188 -28.704   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      23.855 -28.704   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      19.854 -29.474   0.000  0.00  0.00           C+0
HETATM    6  N   UNK     0      22.522 -29.474   0.000  0.00  0.00           N+0
HETATM    7  O   UNK     0      23.855 -27.164   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0      18.521 -28.704   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0      19.854 -31.014   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    4                                                       
CONECT    3    6    5                                                       
CONECT    4    2    7    6                                                  
CONECT    5    3    8    9                                                  
CONECT    6    3    4                                                       
CONECT    7    4                                                            
CONECT    8    5                                                            
CONECT    9    5                                                            
MASTER        0    0    0    0    0    0    0    0    9    0   16    0
END
Download

3D PDB for NP0000433 (N-Acryloylglycine)

COMPND    HMDB0001843
HETATM    1  C1  UNL     1       2.775   0.491  -0.823  1.00  0.00           C  
HETATM    2  C2  UNL     1       2.157   0.821   0.289  1.00  0.00           C  
HETATM    3  C3  UNL     1       0.837   0.305   0.596  1.00  0.00           C  
HETATM    4  O1  UNL     1       0.316   0.685   1.706  1.00  0.00           O  
HETATM    5  N1  UNL     1       0.096  -0.575  -0.234  1.00  0.00           N  
HETATM    6  C4  UNL     1      -1.219  -1.026   0.178  1.00  0.00           C  
HETATM    7  C5  UNL     1      -2.140   0.132   0.355  1.00  0.00           C  
HETATM    8  O2  UNL     1      -1.752   1.289   0.155  1.00  0.00           O  
HETATM    9  O3  UNL     1      -3.439  -0.152   0.750  1.00  0.00           O  
HETATM   10  H1  UNL     1       2.338  -0.172  -1.556  1.00  0.00           H  
HETATM   11  H2  UNL     1       3.780   0.912  -1.009  1.00  0.00           H  
HETATM   12  H3  UNL     1       2.655   1.495   0.987  1.00  0.00           H  
HETATM   13  H4  UNL     1       0.528  -0.870  -1.121  1.00  0.00           H  
HETATM   14  H5  UNL     1      -1.115  -1.505   1.184  1.00  0.00           H  
HETATM   15  H6  UNL     1      -1.634  -1.785  -0.486  1.00  0.00           H  
HETATM   16  H7  UNL     1      -4.182  -0.046   0.069  1.00  0.00           H  
CONECT    1    2    2   10   11
CONECT    2    3   12
CONECT    3    4    4    5
CONECT    5    6   13
CONECT    6    7   14   15
CONECT    7    8    8    9
CONECT    9   16
END
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SMILES for NP0000433 (N-Acryloylglycine)

OC(=O)CNC(=O)C=C
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INCHI for NP0000433 (N-Acryloylglycine)

InChI=1S/C5H7NO3/c1-2-4(7)6-3-5(8)9/h2H,1,3H2,(H,6,7)(H,8,9)
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View in JSmol
Synonyms
ValueSource
1-Aminopropenal acetic acidHMDB
N-(1-oxo-2-Propenyl)-glycineHMDB
N-Acryloyl-glycineHMDB
APAAHMDB
2-[(1-Hydroxyprop-2-en-1-ylidene)amino]acetateHMDB
Chemical FormulaC5H7NO3
Average Mass129.1140 Da
Monoisotopic Mass129.04259 Da
IUPAC Name2-(prop-2-enamido)acetic acid
Traditional NameN-acryloylglycine
CAS Registry Number24599-25-5
SMILES
OC(=O)CNC(=O)C=C
InChI Identifier
InChI=1S/C5H7NO3/c1-2-4(7)6-3-5(8)9/h2H,1,3H2,(H,6,7)(H,8,9)
InChI KeyLZCXCXDOGAEFQX-UHFFFAOYSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Anas platyrhynchosFooDB
AnatidaeFooDB
Anser anserFooDB
Bison bisonFooDB
Bos taurusFooDB
Bos taurus X Bison bisonFooDB
Bubalus bubalisFooDB
Capra aegagrus hircusFooDB
CervidaeFooDB
Cervus canadensisFooDB
ColumbaFooDB
ColumbidaeFooDB
Dromaius novaehollandiaeFooDB
Equus caballusFooDB
Gallus gallusFooDB
Lagopus mutaFooDB
LeporidaeFooDB
Lepus timidusFooDB
Melanitta fuscaFooDB
Meleagris gallopavoFooDB
Numida meleagrisFooDB
OdocoileusFooDB
OryctolagusFooDB
Ovis ariesFooDB
PhasianidaeFooDB
Phasianus colchicusFooDB
Struthio camelusFooDB
Sus scrofaFooDB
Sus scrofa domesticaFooDB
Chemical Taxonomy
Description Belongs to the class of organic compounds known as n-acyl-alpha amino acids. N-acyl-alpha amino acids are compounds containing an alpha amino acid which bears an acyl group at its terminal nitrogen atom.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentN-acyl-alpha amino acids
Alternative Parents
Substituents
  • N-acyl-alpha-amino acid
  • Acrylic acid or derivatives
  • Secondary carboxylic acid amide
  • Carboxamide group
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility63.6 g/LALOGPS
logP-0.28ALOGPS
logP-0.57ChemAxon
logS-0.31ALOGPS
pKa (Strongest Acidic)3.84ChemAxon
pKa (Strongest Basic)-0.63ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area66.4 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity30.09 m³·mol⁻¹ChemAxon
Polarizability11.92 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0001843
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB022703
KNApSAcK IDNot Available
Chemspider ID90657
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID6343
PubChem Compound100321
PDB IDNot Available
ChEBI ID165890
Good Scents IDNot Available
References
General References
  1. Shapoval O, Oleksa V, Slouf M, Lobaz V, Trhlikova O, Filipova M, Janouskova O, Engstova H, Pankrac J, Modry A, Herynek V, Jezek P, Sefc L, Horak D: Colloidally Stable P(DMA-AGME)-Ale-Coated Gd(Tb)F3:Tb(3+)(Gd(3+)),Yb(3+),Nd(3+) Nanoparticles as a Multimodal Contrast Agent for Down- and Upconversion Luminescence, Magnetic Resonance Imaging, and Computed Tomography. Nanomaterials (Basel). 2021 Jan 16;11(1). pii: nano11010230. doi: 10.3390/nano11010230. [PubMed:33467188 ]
  2. Khadsai S, Seeja N, Rutnakornpituk M, Vilaivan T, Nakkuntod M, Suwankitti W, Kielar F, Rutnakornpituk B: Selective enrichment of zein gene of maize from cereal products using magnetic support having pyrrolidinyl peptide nucleic acid probe. Food Chem. 2021 Feb 15;338:127812. doi: 10.1016/j.foodchem.2020.127812. Epub 2020 Aug 10. [PubMed:32861133 ]
  3. Oleksa V, Mackova H, Patsula V, Dydowiczova A, Janouskova O, Horak D: Doxorubicin-Conjugated Iron Oxide Nanoparticles: Surface Engineering and Biomedical Investigation. Chempluschem. 2020 Jun;85(6):1156-1163. doi: 10.1002/cplu.202000360. [PubMed:32496029 ]