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Showing metabocard for 2-Butenoylglycine (HMDB0341232)

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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2022-09-09 19:51:26 UTC
Update Date2022-09-22 18:34:42 UTC
HMDB IDHMDB0341232
Secondary Accession NumbersNone
Metabolite Identification
Common Name2-Butenoylglycine
Description2-{[(2E)-1-hydroxybut-2-en-1-ylidene]amino}acetic acid 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. 2-{[(2E)-1-hydroxybut-2-en-1-ylidene]amino}acetic acid is a moderately basic compound (based on its pKa).
Structure
Thumb
MOLSDFPDBSMILESInChI

MOL for HMDB0341232 (2-Butenoylglycine)


  Mrv1652308061607422D          

 12 11  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 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
    0.8250    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
    0.0000    0.0000    0.0000 N   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
   -1.6500   -1.4289    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6500    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750    0.0000    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    1.4289    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  3  2  2  0  0  0  0
  5  3  1  0  0  0  0
  6  4  1  0  0  0  0
  7  4  1  4  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  6  1  0  0  0  0
 11  2  1  0  0  0  0
 12  3  1  0  0  0  0
M  END
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3D MOL for HMDB0341232 (2-Butenoylglycine)

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3D SDF for HMDB0341232 (2-Butenoylglycine)

  Mrv1652308061607422D          

 12 11  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 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
    0.8250    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
    0.0000    0.0000    0.0000 N   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
   -1.6500   -1.4289    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6500    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750    0.0000    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    1.4289    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  3  2  2  0  0  0  0
  5  3  1  0  0  0  0
  6  4  1  0  0  0  0
  7  4  1  4  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  6  1  0  0  0  0
 11  2  1  0  0  0  0
 12  3  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0341232

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C6H9NO3/c1-2-3-5(8)7-4-6(9)10/h2-3H,4H2,1H3,(H,7,8)(H,9,10)/b3-2+

> <INCHI_KEY>
WWJXRJJBIVSSNF-NSCUHMNNSA-N

> <FORMULA>
C6H9NO3

> <MOLECULAR_WEIGHT>
143.142

> <EXACT_MASS>
143.058243154

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
19

> <JCHEM_AVERAGE_POLARIZABILITY>
14.08894187362974

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-{[(2E)-1-hydroxybut-2-en-1-ylidene]amino}acetic acid

> <ALOGPS_LOGP>
0.10

> <JCHEM_LOGP>
0.4996877738964812

> <ALOGPS_LOGS>
-1.51

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
6.532989298012905

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.024170202176396

> <JCHEM_PKA_STRONGEST_BASIC>
2.3185080177326562

> <JCHEM_POLAR_SURFACE_AREA>
69.89

> <JCHEM_REFRACTIVITY>
36.2901

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.39e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
{[(2E)-1-hydroxybut-2-en-1-ylidene]amino}acetic acid

> <JCHEM_VEBER_RULE>
0

$$$$

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3D-SDF for HMDB0341232 (2-Butenoylglycine)
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PDB for HMDB0341232 (2-Butenoylglycine)
HEADER    PROTEIN                                 06-AUG-16   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-AUG-16         0                                  
HETATM    1  C   UNK     0       4.620   2.667   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.850   1.334   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  C   UNK     0       1.540   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.310  -1.334   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0       0.000   0.000   0.000  0.00  0.00           N+0
HETATM    8  O   UNK     0       2.310  -1.334   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0      -3.080  -2.667   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0      -3.080   0.000   0.000  0.00  0.00           O+0
HETATM   11  H   UNK     0       4.620   0.000   0.000  0.00  0.00           H+0
HETATM   12  H   UNK     0       1.540   2.667   0.000  0.00  0.00           H+0
CONECT    1    2                                                            
CONECT    2    1    3   11                                                  
CONECT    3    2    5   12                                                  
CONECT    4    6    7                                                       
CONECT    5    3    7    8                                                  
CONECT    6    4    9   10                                                  
CONECT    7    4    5                                                       
CONECT    8    5                                                            
CONECT    9    6                                                            
CONECT   10    6                                                            
CONECT   11    2                                                            
CONECT   12    3                                                            
MASTER        0    0    0    0    0    0    0    0   12    0   22    0
END

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3D PDB for HMDB0341232 (2-Butenoylglycine)
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SMILES for HMDB0341232 (2-Butenoylglycine)
[H]\C(C)=C(\[H])C(O)=NCC(O)=O
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INCHI for HMDB0341232 (2-Butenoylglycine)
InChI=1S/C6H9NO3/c1-2-3-5(8)7-4-6(9)10/h2-3H,4H2,1H3,(H,7,8)(H,9,10)/b3-2+
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View in JSmolView Stereo Labels
Synonyms
ValueSource
2-{[(2E)-1-hydroxybut-2-en-1-ylidene]amino}acetateGenerator
Chemical FormulaC6H9NO3
Average Molecular Weight143.142
Monoisotopic Molecular Weight143.058243154
IUPAC Name2-{[(2E)-1-hydroxybut-2-en-1-ylidene]amino}acetic acid
Traditional Name{[(2E)-1-hydroxybut-2-en-1-ylidene]amino}acetic acid
CAS Registry NumberNot Available
SMILES
[H]\C(C)=C(\[H])C(O)=NCC(O)=O
InChI Identifier
InChI=1S/C6H9NO3/c1-2-3-5(8)7-4-6(9)10/h2-3H,4H2,1H3,(H,7,8)(H,9,10)/b3-2+
InChI KeyWWJXRJJBIVSSNF-NSCUHMNNSA-N
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
    • 

  • N-acyl-amine
    • 

  • 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
Ontology
Not AvailableNot Available
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
logP0.1ALOGPS
logP0.5ChemAxon
logS-1.5ALOGPS
pKa (Strongest Acidic)4.02ChemAxon
pKa (Strongest Basic)2.32ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area69.89 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity36.29 m³·mol⁻¹ChemAxon
Polarizability14.09 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties
Predicted Kovats Retention Indices
Not Available
Spectra
MS/MS Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Butenoylglycine  10V, Positive-QTOFsplash10-00fu-9500000000-d0d1f0896080107cedfc2019-02-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Butenoylglycine  20V, Positive-QTOFsplash10-05i0-9000000000-cb10e6eec029e5bd29f72019-02-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Butenoylglycine  40V, Positive-QTOFsplash10-0a6r-9000000000-1d235973bea206eaf20e2019-02-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Butenoylglycine  10V, Negative-QTOFsplash10-0006-2900000000-04d1a6da73c0d6d05a2f2019-02-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Butenoylglycine  20V, Negative-QTOFsplash10-006x-9500000000-d4a5e8021f72ba996f942019-02-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Butenoylglycine  40V, Negative-QTOFsplash10-006x-9000000000-e30a24c764179056d8092019-02-23Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
    • 

  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedCancer patients undergoing total body irradiation  details
UrineDetected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedCancer patients undergoing total body irradiation  details
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound6303498  
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Simon-Manso Y, Marupaka R, Yan X, Liang Y, Telu KH, Mirokhin Y, Stein SE: Mass Spectrometry Fingerprints of Small-Molecule Metabolites in Biofluids: Building a Spectral Library of Recurrent Spectra for Urine Analysis. Anal Chem. 2019 Sep 17;91(18):12021-12029. doi: 10.1021/acs.analchem.9b02977. Epub 2019 Aug 30. [PubMed:31424920  ]