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Showing metabocard for Ethyl 2-cyanoacrylate (HMDB0252026)

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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2021-09-11 09:42:07 UTC
Update Date2021-09-26 23:04:22 UTC
HMDB IDHMDB0252026
Secondary Accession NumbersNone
Metabolite Identification
Common NameEthyl 2-cyanoacrylate
DescriptionEthyl cyanoacrylate 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. Ethyl cyanoacrylate is a chemical compound of cyanide. Cyanide is mainly metabolized into thiocyanate by either rhodanese or 3-mercaptopyruvate sulfur transferase. Ethyl cyanoacrylate is an extremely weak basic (essentially neutral) compound (based on its pKa). Ethyl cyanoacrylate is a potentially toxic compound. It complexes with the ferric iron atom in this enzyme. The binding of cyanide to this cytochrome prevents transport of electrons from cytochrome c oxidase to oxygen. Oxygen therapy can also be administered. This compound has been identified in human blood as reported by (PMID: 31557052 ). Ethyl 2-cyanoacrylate is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Ethyl 2-cyanoacrylate 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
Thumb
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0252026 (Ethyl 2-cyanoacrylate)


  Mrv0541 02241204362D          

  9  8  0  0  0  0            999 V2000
    1.7605   -1.8414    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
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  4  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
  8  9  3  0  0  0  0
M  END
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3D MOL for HMDB0252026 (Ethyl 2-cyanoacrylate)

HMDB0252026
     RDKit          3D
Ethyl 2-cyanoacrylate
 16 15  0  0  0  0  0  0  0  0999 V2000
   -2.1592    1.2674   -0.1718 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0605    0.0738    0.3577 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2049   -0.6504    0.8562 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1375   -1.2198    1.2673 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7455   -0.5408    0.4442 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6151   -1.6761    0.9425 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3946    0.1024   -0.0168 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6409   -0.5324    0.0890 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7421    0.3309   -0.4666 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1178    1.7386   -0.2454 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2892    1.7693   -0.5286 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5928   -1.5200   -0.4529 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8171   -0.7880    1.1462 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3554   -0.2582   -1.1617 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4139    0.6756    0.3543 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3728    1.2276   -0.9952 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
  1 10  1  0
  1 11  1  0
  8 12  1  0
  8 13  1  0
  9 14  1  0
  9 15  1  0
  9 16  1  0
M  END
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3D SDF for HMDB0252026 (Ethyl 2-cyanoacrylate)


  Mrv0541 02241204362D          

  9  8  0  0  0  0            999 V2000
    1.7605   -1.8414    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
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  4  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
  8  9  3  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0252026

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C6H7NO2/c1-3-9-6(8)5(2)4-7/h2-3H2,1H3

> <INCHI_KEY>
FGBJXOREULPLGL-UHFFFAOYSA-N

> <FORMULA>
C6H7NO2

> <MOLECULAR_WEIGHT>
125.1253

> <EXACT_MASS>
125.047678473

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
12.371771045335166

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
ethyl 2-cyanoprop-2-enoate

> <ALOGPS_LOGP>
1.05

> <JCHEM_LOGP>
1.0808412583333333

> <ALOGPS_LOGS>
-1.11

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-7.188517340895565

> <JCHEM_POLAR_SURFACE_AREA>
50.09

> <JCHEM_REFRACTIVITY>
31.8627

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.62e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
ethyl cyanoacrylate

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for HMDB0252026 (Ethyl 2-cyanoacrylate)

HMDB0252026
     RDKit          3D
Ethyl 2-cyanoacrylate
 16 15  0  0  0  0  0  0  0  0999 V2000
   -2.1592    1.2674   -0.1718 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0605    0.0738    0.3577 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2049   -0.6504    0.8562 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1375   -1.2198    1.2673 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7455   -0.5408    0.4442 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6151   -1.6761    0.9425 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3946    0.1024   -0.0168 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6409   -0.5324    0.0890 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7421    0.3309   -0.4666 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1178    1.7386   -0.2454 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2892    1.7693   -0.5286 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5928   -1.5200   -0.4529 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8171   -0.7880    1.1462 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3554   -0.2582   -1.1617 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4139    0.6756    0.3543 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3728    1.2276   -0.9952 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
  1 10  1  0
  1 11  1  0
  8 12  1  0
  8 13  1  0
  9 14  1  0
  9 15  1  0
  9 16  1  0
M  END
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PDB for HMDB0252026 (Ethyl 2-cyanoacrylate)

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       3.286  -3.437   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.620  -2.667   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       5.954  -3.437   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       7.287  -2.667   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       7.287  -1.127   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       8.621  -3.437   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.621  -4.977   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       9.955  -2.667   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0      11.288  -1.897   0.000  0.00  0.00           N+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9    8                                                            
MASTER        0    0    0    0    0    0    0    0    9    0   16    0
END
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3D PDB for HMDB0252026 (Ethyl 2-cyanoacrylate)

COMPND    HMDB0252026
HETATM    1  C1  UNL     1      -2.159   1.267  -0.172  1.00  0.00           C  
HETATM    2  C2  UNL     1      -2.061   0.074   0.358  1.00  0.00           C  
HETATM    3  C3  UNL     1      -3.205  -0.650   0.856  1.00  0.00           C  
HETATM    4  N1  UNL     1      -4.137  -1.220   1.267  1.00  0.00           N  
HETATM    5  C4  UNL     1      -0.746  -0.541   0.444  1.00  0.00           C  
HETATM    6  O1  UNL     1      -0.615  -1.676   0.942  1.00  0.00           O  
HETATM    7  O2  UNL     1       0.395   0.102  -0.017  1.00  0.00           O  
HETATM    8  C5  UNL     1       1.641  -0.532   0.089  1.00  0.00           C  
HETATM    9  C6  UNL     1       2.742   0.331  -0.467  1.00  0.00           C  
HETATM   10  H1  UNL     1      -3.118   1.739  -0.245  1.00  0.00           H  
HETATM   11  H2  UNL     1      -1.289   1.769  -0.529  1.00  0.00           H  
HETATM   12  H3  UNL     1       1.593  -1.520  -0.453  1.00  0.00           H  
HETATM   13  H4  UNL     1       1.817  -0.788   1.146  1.00  0.00           H  
HETATM   14  H5  UNL     1       3.355  -0.258  -1.162  1.00  0.00           H  
HETATM   15  H6  UNL     1       3.414   0.676   0.354  1.00  0.00           H  
HETATM   16  H7  UNL     1       2.373   1.228  -0.995  1.00  0.00           H  
CONECT    1    2    2   10   11
CONECT    2    3    5
CONECT    3    4    4    4
CONECT    5    6    6    7
CONECT    7    8
CONECT    8    9   12   13
CONECT    9   14   15   16
END
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SMILES for HMDB0252026 (Ethyl 2-cyanoacrylate)

CCOC(=O)C(=C)C#N
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INCHI for HMDB0252026 (Ethyl 2-cyanoacrylate)

InChI=1S/C6H7NO2/c1-3-9-6(8)5(2)4-7/h2-3H2,1H3
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View in JSmolView NMR AssignmentsView Stereo Labels
Synonyms
ValueSource
Ethyl cyanoacrylic acidGenerator
EpiglueMeSH
CyacrineMeSH
cyano-VeneerMeSH
Ethyl alpha-cyanoacrylateMeSH
Krazy glueMeSH
Ethyl-2-cyanoacrylateMeSH
Chemical FormulaC6H7NO2
Average Molecular Weight125.1253
Monoisotopic Molecular Weight125.047678473
IUPAC Nameethyl 2-cyanoprop-2-enoate
Traditional Nameethyl cyanoacrylate
CAS Registry NumberNot Available
SMILES
CCOC(=O)C(=C)C#N
InChI Identifier
InChI=1S/C6H7NO2/c1-3-9-6(8)5(2)4-7/h2-3H2,1H3
InChI KeyFGBJXOREULPLGL-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
logP1.05ALOGPS
logP1.08ChemAxon
logS-1.1ALOGPS
pKa (Strongest Basic)-7.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area50.09 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity31.86 m³·mol⁻¹ChemAxon
Polarizability12.37 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]+128.94730932474
DeepCCS[M-H]-126.7230932474
DeepCCS[M-2H]-163.17530932474
DeepCCS[M+Na]+137.82930932474
AllCCS[M+H]+129.432859911
AllCCS[M+H-H2O]+125.332859911
AllCCS[M+NH4]+133.332859911
AllCCS[M+Na]+134.432859911
AllCCS[M-H]-125.832859911
AllCCS[M+Na-2H]-128.532859911
AllCCS[M+HCOO]-131.632859911

Predicted Retention Times

Underivatized

Chromatographic MethodRetention TimeReference
Predicted by Siyang on May 30, 202213.3182 minutes33406817
Predicted by Siyang using ReTip algorithm on June 8, 20222.59 minutes32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid1680.5 seconds40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid493.0 seconds40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid171.2 seconds40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid319.6 seconds40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid117.7 seconds40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid434.7 seconds40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid575.7 seconds40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)341.5 seconds40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid988.9 seconds40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid362.8 seconds40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid1222.6 seconds40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid322.5 seconds40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid363.8 seconds40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate628.0 seconds40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA481.2 seconds40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water149.9 seconds40023050

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Ethyl 2-cyanoacrylateCCOC(=O)C(=C)C#N1496.2Standard polar33892256
Ethyl 2-cyanoacrylateCCOC(=O)C(=C)C#N956.2Standard non polar33892256
Ethyl 2-cyanoacrylateCCOC(=O)C(=C)C#N915.3Semi standard non polar33892256
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 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 LinkEthyl cyanoacrylate
METLIN IDNot Available
PubChem CompoundNot Available
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 ]