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Showing metabocard for Enbucrilate (HMDB0249472)

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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2021-09-11 03:59:07 UTC
Update Date2021-09-26 23:00:23 UTC
HMDB IDHMDB0249472
Secondary Accession NumbersNone
Metabolite Identification
Common NameEnbucrilate
DescriptionEnbucrilate, also known as histoacryl or enbucrilic acid, belongs to the class of organic compounds known as cyanoacrylates. These are organonitrogen compounds containing an acrylic acid ester, which carries a nitrile group. They have the general structure ROC(=O)C(=C)C#N, where R is an organic group. The binding of cyanide to this cytochrome prevents transport of electrons from cytochrome c oxidase to oxygen. Tissues that mainly depend on aerobic respiration, such as the central nervous system and the heart, are particularly affected. Enbucrilate is an extremely weak basic (essentially neutral) compound (based on its pKa). Enbucrilate is a potentially toxic compound. Cyanide binds to the ferric ion of methemoglobin to form inactive cyanmethemoglobin. Oxygen therapy can also be administered. Organic nitriles decompose into cyanide ions both in vivo and in vitro. This compound has been identified in human blood as reported by (PMID: 31557052 ). Enbucrilate is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Enbucrilate is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0249472 (Enbucrilate)

  Mrv0541 02241204362D          

 11 10  0  0  0  0            999 V2000
    2.9980   -2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7125   -2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4270   -2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1414   -2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8559   -2.5559    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5704   -2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5704   -1.3184    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2849   -2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2849   -3.3809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9993   -2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7138   -1.7309    0.0000 N   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  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
 10 11  3  0  0  0  0
M  END
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3D MOL for HMDB0249472 (Enbucrilate)

HMDB0249472
     RDKit          3D
Enbucrilate
 22 21  0  0  0  0  0  0  0  0999 V2000
    3.3371    1.3252   -0.3567 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4032    0.0878    0.1043 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7107   -0.5190    0.3271 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7435   -1.0016    0.5235 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1882   -0.6469    0.3814 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2570   -1.8101    0.8148 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9655   -0.0647    0.1675 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2497   -0.7472    0.4252 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3687    0.2162    0.0690 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7327   -0.4338    0.3153 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7841    0.5867   -0.0623 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3977    1.7932   -0.5287 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2419    1.8567   -0.5572 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2913   -1.6546   -0.2103 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3305   -1.0922    1.4690 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3401    0.4344   -1.0182 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3332    1.1266    0.7007 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8717   -1.3035   -0.3624 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8487   -0.7254    1.3737 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6707    0.5238    0.6128 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3547    1.5981    0.0231 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0686    0.4502   -1.1327 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  3  0
  2  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
  1 12  1  0
  1 13  1  0
  8 14  1  0
  8 15  1  0
  9 16  1  0
  9 17  1  0
 10 18  1  0
 10 19  1  0
 11 20  1  0
 11 21  1  0
 11 22  1  0
M  END
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3D SDF for HMDB0249472 (Enbucrilate)

  Mrv0541 02241204362D          

 11 10  0  0  0  0            999 V2000
    2.9980   -2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7125   -2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4270   -2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1414   -2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8559   -2.5559    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5704   -2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5704   -1.3184    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2849   -2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2849   -3.3809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9993   -2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7138   -1.7309    0.0000 N   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  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
 10 11  3  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0249472

> <DATABASE_NAME>
hmdb

> <SMILES>
CCCCOC(=O)C(=C)C#N

> <INCHI_IDENTIFIER>
InChI=1S/C8H11NO2/c1-3-4-5-11-8(10)7(2)6-9/h2-5H2,1H3

> <INCHI_KEY>
JJJFUHOGVZWXNQ-UHFFFAOYSA-N

> <FORMULA>
C8H11NO2

> <MOLECULAR_WEIGHT>
153.1784

> <EXACT_MASS>
153.078978601

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
16.404551454195584

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
butyl 2-cyanoprop-2-enoate

> <ALOGPS_LOGP>
1.76

> <JCHEM_LOGP>
2.0479323183333333

> <ALOGPS_LOGS>
-2.08

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-7.18905839280526

> <JCHEM_POLAR_SURFACE_AREA>
50.09

> <JCHEM_REFRACTIVITY>
40.98770000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.27e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
butyl cyanoacrylate

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for HMDB0249472 (Enbucrilate)

HMDB0249472
     RDKit          3D
Enbucrilate
 22 21  0  0  0  0  0  0  0  0999 V2000
    3.3371    1.3252   -0.3567 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4032    0.0878    0.1043 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7107   -0.5190    0.3271 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7435   -1.0016    0.5235 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1882   -0.6469    0.3814 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2570   -1.8101    0.8148 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9655   -0.0647    0.1675 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2497   -0.7472    0.4252 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3687    0.2162    0.0690 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7327   -0.4338    0.3153 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7841    0.5867   -0.0623 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3977    1.7932   -0.5287 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2419    1.8567   -0.5572 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2913   -1.6546   -0.2103 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3305   -1.0922    1.4690 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3401    0.4344   -1.0182 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3332    1.1266    0.7007 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8717   -1.3035   -0.3624 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8487   -0.7254    1.3737 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6707    0.5238    0.6128 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3547    1.5981    0.0231 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0686    0.4502   -1.1327 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  3  0
  2  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
  1 12  1  0
  1 13  1  0
  8 14  1  0
  8 15  1  0
  9 16  1  0
  9 17  1  0
 10 18  1  0
 10 19  1  0
 11 20  1  0
 11 21  1  0
 11 22  1  0
M  END
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PDB for HMDB0249472 (Enbucrilate)

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0       5.596  -4.771   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.930  -4.001   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.264  -4.771   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       9.597  -4.001   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      10.931  -4.771   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      12.265  -4.001   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      12.265  -2.461   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      13.598  -4.771   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      13.598  -6.311   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      14.932  -4.001   0.000  0.00  0.00           C+0
HETATM   11  N   UNK     0      16.266  -3.231   0.000  0.00  0.00           N+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10                                                            
MASTER        0    0    0    0    0    0    0    0   11    0   20    0
END
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3D PDB for HMDB0249472 (Enbucrilate)

COMPND    HMDB0249472
HETATM    1  C1  UNL     1       3.337   1.325  -0.357  1.00  0.00           C  
HETATM    2  C2  UNL     1       3.403   0.088   0.104  1.00  0.00           C  
HETATM    3  C3  UNL     1       4.711  -0.519   0.327  1.00  0.00           C  
HETATM    4  N1  UNL     1       5.744  -1.002   0.524  1.00  0.00           N  
HETATM    5  C4  UNL     1       2.188  -0.647   0.381  1.00  0.00           C  
HETATM    6  O1  UNL     1       2.257  -1.810   0.815  1.00  0.00           O  
HETATM    7  O2  UNL     1       0.965  -0.065   0.168  1.00  0.00           O  
HETATM    8  C5  UNL     1      -0.250  -0.747   0.425  1.00  0.00           C  
HETATM    9  C6  UNL     1      -1.369   0.216   0.069  1.00  0.00           C  
HETATM   10  C7  UNL     1      -2.733  -0.434   0.315  1.00  0.00           C  
HETATM   11  C8  UNL     1      -3.784   0.587  -0.062  1.00  0.00           C  
HETATM   12  H1  UNL     1       2.398   1.793  -0.529  1.00  0.00           H  
HETATM   13  H2  UNL     1       4.242   1.857  -0.557  1.00  0.00           H  
HETATM   14  H3  UNL     1      -0.291  -1.655  -0.210  1.00  0.00           H  
HETATM   15  H4  UNL     1      -0.330  -1.092   1.469  1.00  0.00           H  
HETATM   16  H5  UNL     1      -1.340   0.434  -1.018  1.00  0.00           H  
HETATM   17  H6  UNL     1      -1.333   1.127   0.701  1.00  0.00           H  
HETATM   18  H7  UNL     1      -2.872  -1.303  -0.362  1.00  0.00           H  
HETATM   19  H8  UNL     1      -2.849  -0.725   1.374  1.00  0.00           H  
HETATM   20  H9  UNL     1      -4.671   0.524   0.613  1.00  0.00           H  
HETATM   21  H10 UNL     1      -3.355   1.598   0.023  1.00  0.00           H  
HETATM   22  H11 UNL     1      -4.069   0.450  -1.133  1.00  0.00           H  
CONECT    1    2    2   12   13
CONECT    2    3    5
CONECT    3    4    4    4
CONECT    5    6    6    7
CONECT    7    8
CONECT    8    9   14   15
CONECT    9   10   16   17
CONECT   10   11   18   19
CONECT   11   20   21   22
END
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SMILES for HMDB0249472 (Enbucrilate)

CCCCOC(=O)C(=C)C#N
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INCHI for HMDB0249472 (Enbucrilate)

InChI=1S/C8H11NO2/c1-3-4-5-11-8(10)7(2)6-9/h2-5H2,1H3
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View in JSmolView Stereo Labels
Synonyms
Chemical FormulaC8H11NO2
Average Molecular Weight153.1784
Monoisotopic Molecular Weight153.078978601
IUPAC Namebutyl 2-cyanoprop-2-enoate
Traditional Namebutyl cyanoacrylate
CAS Registry NumberNot Available
SMILES
CCCCOC(=O)C(=C)C#N
InChI Identifier
InChI=1S/C8H11NO2/c1-3-4-5-11-8(10)7(2)6-9/h2-5H2,1H3
InChI KeyJJJFUHOGVZWXNQ-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as cyanoacrylates. These are organonitrogen compounds containing an acrylic acid ester, which carries a nitrile group. They have the general structure ROC(=O)C(=C)C#N, where R is an organic group.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassCarboxylic acid derivatives
Direct ParentCyanoacrylates
Alternative Parents
Substituents
  • Cyanoacrylic acid ester
  • Nitrile
  • Carbonitrile
  • Monocarboxylic acid or derivatives
  • 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
Physiological effectNot Available
Disposition
Biological locationSource
ProcessNot Available
RoleNot 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
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB12358
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDC13415
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkButyl cyanoacrylate
METLIN IDNot Available
PubChem Compound23087
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. Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]