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Showing metabocard for Bucrilate (HMDB0249423)

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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2021-09-11 03:56:03 UTC
Update Date2021-09-26 23:00:18 UTC
HMDB IDHMDB0249423
Secondary Accession NumbersNone
Metabolite Identification
Common NameBucrilate
DescriptionBucrilate, also known as bucrilic 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. Based on a literature review very few articles have been published on Bucrilate. This compound has been identified in human blood as reported by (PMID: 31557052 ). Bucrilate is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Bucrilate 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 HMDB0249423 (Bucrilate)


  Mrv1652309112105562D          

 11 10  0  0  0  0            999 V2000
    1.0461   -1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7605   -1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7605   -2.6664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750   -1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1895   -1.8414    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9039   -1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9039   -0.6039    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6184   -1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6184   -2.6664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3329   -1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0474   -1.0164    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
  2  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
Download

3D MOL for HMDB0249423 (Bucrilate)

HMDB0249423
     RDKit          3D
Bucrilate
 22 21  0  0  0  0  0  0  0  0999 V2000
    3.0411   -1.5588   -0.7351 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8184   -0.6302    0.1789 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7695   -0.3746    1.2163 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5619   -0.1749    2.0547 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.5924    0.1507    0.1410 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3700    1.0427    1.0121 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6116   -0.0193   -0.8193 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5878    0.7031   -0.9038 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4606    0.5386    0.3386 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7287    1.3483    0.1612 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8695   -0.9261    0.3797 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9497   -2.1450   -0.7158 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3373   -1.7684   -1.5267 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1193    0.3496   -1.8114 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4292    1.7965   -1.0375 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9381    0.8450    1.2396 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5393    0.9650    0.8241 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5349    2.4343    0.3214 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1279    1.2498   -0.8760 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9182   -1.5057    0.5532 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1825   -1.1885   -0.6520 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6160   -1.1322    1.1473 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
  9 11  1  0
  1 12  1  0
  1 13  1  0
  8 14  1  0
  8 15  1  0
  9 16  1  0
 10 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 HMDB0249423 (Bucrilate)


  Mrv1652309112105562D          

 11 10  0  0  0  0            999 V2000
    1.0461   -1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7605   -1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7605   -2.6664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750   -1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1895   -1.8414    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9039   -1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9039   -0.6039    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6184   -1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6184   -2.6664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3329   -1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0474   -1.0164    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
  2  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>
HMDB0249423

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(C)COC(=O)C(=C)C#N

> <INCHI_IDENTIFIER>
InChI=1S/C8H11NO2/c1-6(2)5-11-8(10)7(3)4-9/h6H,3,5H2,1-2H3

> <INCHI_KEY>
QRWOVIRDHQJFDB-UHFFFAOYSA-N

> <FORMULA>
C8H11NO2

> <MOLECULAR_WEIGHT>
153.181

> <EXACT_MASS>
153.078978598

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
22

> <JCHEM_AVERAGE_POLARIZABILITY>
16.16273823655567

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-methylpropyl 2-cyanoprop-2-enoate

> <ALOGPS_LOGP>
1.78

> <JCHEM_LOGP>
1.9683364796666667

> <ALOGPS_LOGS>
-2.03

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-7.189566002720282

> <JCHEM_POLAR_SURFACE_AREA>
50.09

> <JCHEM_REFRACTIVITY>
40.85830000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.44e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
isobutyl 2 cyanoacrylate

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for HMDB0249423 (Bucrilate)

HMDB0249423
     RDKit          3D
Bucrilate
 22 21  0  0  0  0  0  0  0  0999 V2000
    3.0411   -1.5588   -0.7351 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8184   -0.6302    0.1789 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7695   -0.3746    1.2163 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5619   -0.1749    2.0547 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.5924    0.1507    0.1410 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3700    1.0427    1.0121 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6116   -0.0193   -0.8193 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5878    0.7031   -0.9038 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4606    0.5386    0.3386 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7287    1.3483    0.1612 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8695   -0.9261    0.3797 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9497   -2.1450   -0.7158 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3373   -1.7684   -1.5267 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1193    0.3496   -1.8114 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4292    1.7965   -1.0375 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9381    0.8450    1.2396 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5393    0.9650    0.8241 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5349    2.4343    0.3214 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1279    1.2498   -0.8760 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9182   -1.5057    0.5532 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1825   -1.1885   -0.6520 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6160   -1.1322    1.1473 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
  9 11  1  0
  1 12  1  0
  1 13  1  0
  8 14  1  0
  8 15  1  0
  9 16  1  0
 10 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 HMDB0249423 (Bucrilate)

HEADER    PROTEIN                                 11-SEP-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-SEP-21         0                                  
HETATM    1  C   UNK     0       1.953  -2.667   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.286  -3.437   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.286  -4.977   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.620  -2.667   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       5.954  -3.437   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       7.287  -2.667   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       7.287  -1.127   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       8.621  -3.437   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.621  -4.977   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.955  -2.667   0.000  0.00  0.00           C+0
HETATM   11  N   UNK     0      11.288  -1.897   0.000  0.00  0.00           N+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    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 HMDB0249423 (Bucrilate)

COMPND    HMDB0249423
HETATM    1  C1  UNL     1       3.041  -1.559  -0.735  1.00  0.00           C  
HETATM    2  C2  UNL     1       2.818  -0.630   0.179  1.00  0.00           C  
HETATM    3  C3  UNL     1       3.770  -0.375   1.216  1.00  0.00           C  
HETATM    4  N1  UNL     1       4.562  -0.175   2.055  1.00  0.00           N  
HETATM    5  C4  UNL     1       1.592   0.151   0.141  1.00  0.00           C  
HETATM    6  O1  UNL     1       1.370   1.043   1.012  1.00  0.00           O  
HETATM    7  O2  UNL     1       0.612  -0.019  -0.819  1.00  0.00           O  
HETATM    8  C5  UNL     1      -0.588   0.703  -0.904  1.00  0.00           C  
HETATM    9  C6  UNL     1      -1.461   0.539   0.339  1.00  0.00           C  
HETATM   10  C7  UNL     1      -2.729   1.348   0.161  1.00  0.00           C  
HETATM   11  C8  UNL     1      -1.870  -0.926   0.380  1.00  0.00           C  
HETATM   12  H1  UNL     1       3.950  -2.145  -0.716  1.00  0.00           H  
HETATM   13  H2  UNL     1       2.337  -1.768  -1.527  1.00  0.00           H  
HETATM   14  H3  UNL     1      -1.119   0.350  -1.811  1.00  0.00           H  
HETATM   15  H4  UNL     1      -0.429   1.796  -1.038  1.00  0.00           H  
HETATM   16  H5  UNL     1      -0.938   0.845   1.240  1.00  0.00           H  
HETATM   17  H6  UNL     1      -3.539   0.965   0.824  1.00  0.00           H  
HETATM   18  H7  UNL     1      -2.535   2.434   0.321  1.00  0.00           H  
HETATM   19  H8  UNL     1      -3.128   1.250  -0.876  1.00  0.00           H  
HETATM   20  H9  UNL     1      -0.918  -1.506   0.553  1.00  0.00           H  
HETATM   21  H10 UNL     1      -2.183  -1.188  -0.652  1.00  0.00           H  
HETATM   22  H11 UNL     1      -2.616  -1.132   1.147  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   11   16
CONECT   10   17   18   19
CONECT   11   20   21   22
END
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SMILES for HMDB0249423 (Bucrilate)

CC(C)COC(=O)C(=C)C#N
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INCHI for HMDB0249423 (Bucrilate)

InChI=1S/C8H11NO2/c1-6(2)5-11-8(10)7(3)4-9/h6H,3,5H2,1-2H3
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View in JSmolView Stereo Labels
Synonyms
ValueSource
Bucrilic acidGenerator
BucrylateHMDB
Cyanoacrylate, isobutylHMDB
Isobutyl 2 cyanoacrylateHMDB
Isobutyl cyanoacrylateHMDB
Isobutyl alpha cyanoacrylateHMDB
Isobutyl alpha-cyanoacrylateHMDB
Isobutyl-2-cyanoacrylateHMDB
IsobutylcyanoacrylateHMDB
alpha-Cyanoacrylate, isobutylHMDB
Chemical FormulaC8H11NO2
Average Molecular Weight153.181
Monoisotopic Molecular Weight153.078978598
IUPAC Name2-methylpropyl 2-cyanoprop-2-enoate
Traditional Nameisobutyl 2 cyanoacrylate
CAS Registry NumberNot Available
SMILES
CC(C)COC(=O)C(=C)C#N
InChI Identifier
InChI=1S/C8H11NO2/c1-6(2)5-11-8(10)7(3)4-9/h6H,3,5H2,1-2H3
InChI KeyQRWOVIRDHQJFDB-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
PropertyValueSource
logP1.78ALOGPS
logP1.97ChemAxon
logS-2ALOGPS
pKa (Strongest Basic)-7.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area50.09 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity40.86 m³·mol⁻¹ChemAxon
Polarizability16.16 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+137.68630932474
DeepCCS[M-H]-135.16630932474
DeepCCS[M-2H]-171.83130932474
DeepCCS[M+Na]+146.85230932474
AllCCS[M+H]+134.632859911
AllCCS[M+H-H2O]+130.732859911
AllCCS[M+NH4]+138.232859911
AllCCS[M+Na]+139.332859911
AllCCS[M-H]-133.632859911
AllCCS[M+Na-2H]-135.632859911
AllCCS[M+HCOO]-137.932859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
BucrilateCC(C)COC(=O)C(=C)C#N1580.2Standard polar33892256
BucrilateCC(C)COC(=O)C(=C)C#N1077.6Standard non polar33892256
BucrilateCC(C)COC(=O)C(=C)C#N1098.3Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Bucrilate GC-MS (Non-derivatized) - 70eV, Positivesplash10-0f8c-9000000000-487f0177096af6df0f542021-09-23Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Bucrilate GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Bucrilate 10V, Positive-QTOFsplash10-0zgi-9300000000-7de312c22036540487022021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Bucrilate 20V, Positive-QTOFsplash10-0udi-9000000000-c6b158d3b0a6cf1deefb2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Bucrilate 40V, Positive-QTOFsplash10-0udi-9000000000-136c88bf536b181067c92021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Bucrilate 10V, Negative-QTOFsplash10-0udi-0900000000-e313e1b36d84291b434b2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Bucrilate 20V, Negative-QTOFsplash10-0udj-9200000000-74adbcf45ab7632342eb2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Bucrilate 40V, Negative-QTOFsplash10-0udi-9000000000-718882154b74313a520c2021-10-12Wishart LabView Spectrum
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 IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID13427
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound14046
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 ]