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Showing metabocard for 2-Butenal (HMDB0034233)

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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2012-09-11 19:02:13 UTC
Update Date2023-02-21 17:24:03 UTC
HMDB IDHMDB0034233
Secondary Accession Numbers
  • HMDB34233
Metabolite Identification
Common Name2-Butenal
Description2-Butenal (CAS: 4170-30-3), also known as crotonaldehyde, belongs to the class of organic compounds known as enals. These are alpha,beta-unsaturated aldehydes of the general formula RC=C-CH=O in which the aldehydic C=O function is conjugated to a C=C triple bond at the alpha,beta position. The (E)-form of 2-butenal predominates (>95%). 2-Butenal can undergo polycondensation with phenols to synthesize phenolic resins. It is an eye, skin, and mucous membrane irritant. (E)-2-Butenal is found in fruits and vegetables (e.g. tomato juice, strawberry aroma).
Structure
Data?1677000243
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0034233 (2-Butenal)


  Mrv1652306172021122D          

  5  4  0  0  0  0            999 V2000
 9998.9586 9998.7723    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.2439 9999.1844    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.6740 9999.1844    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.5292 9998.7723    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.3874 9998.7723    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  3  1  0  0  0  0
  2  4  1  0  0  0  0
  3  5  2  0  0  0  0
M  END
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3D MOL for HMDB0034233 (2-Butenal)

HMDB0034233
     RDKit          3D
2-Butenal
 11 10  0  0  0  0  0  0  0  0999 V2000
   -1.7218   -0.0811    0.0483 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3144   -0.1066   -0.4312 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6723    0.1381    0.4334 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0318    0.0994   -0.0939 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0090    0.3199    0.6626 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0329   -1.1326    0.2228 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4094    0.3486   -0.6981 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8155    0.4995    0.9854 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1414   -0.3254   -1.4762 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4608    0.3532    1.4716 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2614   -0.1130   -1.1247 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  1  6  1  0
  1  7  1  0
  1  8  1  0
  2  9  1  0
  3 10  1  0
  4 11  1  0
M  END
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3D SDF for HMDB0034233 (2-Butenal)


  Mrv1652306172021122D          

  5  4  0  0  0  0            999 V2000
 9998.9586 9998.7723    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.2439 9999.1844    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.6740 9999.1844    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.5292 9998.7723    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.3874 9998.7723    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  3  1  0  0  0  0
  2  4  1  0  0  0  0
  3  5  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0034233

> <DATABASE_NAME>
hmdb

> <SMILES>
C\C=C\C=O

> <INCHI_IDENTIFIER>
InChI=1S/C4H6O/c1-2-3-4-5/h2-4H,1H3/b3-2+

> <INCHI_KEY>
MLUCVPSAIODCQM-NSCUHMNNSA-N

> <FORMULA>
C4H6O

> <MOLECULAR_WEIGHT>
70.0898

> <EXACT_MASS>
70.041864814

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
11

> <JCHEM_AVERAGE_POLARIZABILITY>
7.6305531877965045

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2E)-but-2-enal

> <JCHEM_LOGP>
0.7609660349999998

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.090822229263441

> <JCHEM_POLAR_SURFACE_AREA>
17.07

> <JCHEM_REFRACTIVITY>
22.0395

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
crotonaldehyde

> <JCHEM_VEBER_RULE>
1

$$$$
Download

3D-SDF for HMDB0034233 (2-Butenal)

HMDB0034233
     RDKit          3D
2-Butenal
 11 10  0  0  0  0  0  0  0  0999 V2000
   -1.7218   -0.0811    0.0483 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3144   -0.1066   -0.4312 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6723    0.1381    0.4334 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0318    0.0994   -0.0939 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0090    0.3199    0.6626 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0329   -1.1326    0.2228 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4094    0.3486   -0.6981 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8155    0.4995    0.9854 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1414   -0.3254   -1.4762 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4608    0.3532    1.4716 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2614   -0.1130   -1.1247 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  1  6  1  0
  1  7  1  0
  1  8  1  0
  2  9  1  0
  3 10  1  0
  4 11  1  0
M  END
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PDB for HMDB0034233 (2-Butenal)

HEADER    PROTEIN                                 17-JUN-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-JUN-20         0                                  
HETATM    1  C   UNK     0    8664.7238664.375   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    8663.3898665.144   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0    8666.0588665.144   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0    8662.0558664.375   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0    8667.3908664.375   0.000  0.00  0.00           O+0
CONECT    1    2    3                                                       
CONECT    2    1    4                                                       
CONECT    3    1    5                                                       
CONECT    4    2                                                            
CONECT    5    3                                                            
MASTER        0    0    0    0    0    0    0    0    5    0    8    0
END
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3D PDB for HMDB0034233 (2-Butenal)

COMPND    HMDB0034233
HETATM    1  C1  UNL     1      -1.722  -0.081   0.048  1.00  0.00           C  
HETATM    2  C2  UNL     1      -0.314  -0.107  -0.431  1.00  0.00           C  
HETATM    3  C3  UNL     1       0.672   0.138   0.433  1.00  0.00           C  
HETATM    4  C4  UNL     1       2.032   0.099  -0.094  1.00  0.00           C  
HETATM    5  O1  UNL     1       3.009   0.320   0.663  1.00  0.00           O  
HETATM    6  H1  UNL     1      -2.033  -1.133   0.223  1.00  0.00           H  
HETATM    7  H2  UNL     1      -2.409   0.349  -0.698  1.00  0.00           H  
HETATM    8  H3  UNL     1      -1.815   0.499   0.985  1.00  0.00           H  
HETATM    9  H4  UNL     1      -0.141  -0.325  -1.476  1.00  0.00           H  
HETATM   10  H5  UNL     1       0.461   0.353   1.472  1.00  0.00           H  
HETATM   11  H6  UNL     1       2.261  -0.113  -1.125  1.00  0.00           H  
CONECT    1    2    6    7    8
CONECT    2    3    3    9
CONECT    3    4   10
CONECT    4    5    5   11
END
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SMILES for HMDB0034233 (2-Butenal)

C\C=C\C=O
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INCHI for HMDB0034233 (2-Butenal)

InChI=1S/C4H6O/c1-2-3-4-5/h2-4H,1H3/b3-2+
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View in JSmolView Stereo Labels
Synonyms
ValueSource
(2E)-BUT-2-enalChEBI
(e)-CrotonaldehydeChEBI
1-FormylpropeneChEBI
Aldehyde crotoniqueChEBI
beta-MethylacroleinChEBI
CrotonalChEBI
Crotonic aldehydeChEBI
CrotylaldehydeChEBI
MethylpropenalChEBI
Propylene aldehydeChEBI
trans-2-ButenalChEBI
trans-2-ButenaldehydeChEBI
trans-But-2-enalChEBI
trans-CrotonaldehydeChEBI
b-MethylacroleinGenerator
Β-methylacroleinGenerator
2-Butenal, (e)-isomerHMDB
(2E)-2-ButenalHMDB
(e)-2-ButenalHMDB
(e)-But-2-en-1-alHMDB
2(e)-ButenalHMDB
2-ButenaldehydeHMDB
But-2-en-1-alHMDB
CrotonaldehydeHMDB
trans-2-Buten-1-alHMDB
trans-CrotonalHMDB
2-ButenalChEBI
Chemical FormulaC4H6O
Average Molecular Weight70.0898
Monoisotopic Molecular Weight70.041864814
IUPAC Name(2E)-but-2-enal
Traditional Namecrotonaldehyde
CAS Registry Number123-73-9
SMILES
C\C=C\C=O
InChI Identifier
InChI=1S/C4H6O/c1-2-3-4-5/h2-4H,1H3/b3-2+
InChI KeyMLUCVPSAIODCQM-NSCUHMNNSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as enals. These are an alpha,beta-unsaturated aldehyde of general formula RC=C-CH=O in which the aldehydic C=O function is conjugated to a C=C triple bond at the alpha,beta position.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbonyl compounds
Direct ParentEnals
Alternative Parents
Substituents
  • Enal
  • Organic oxide
  • Hydrocarbon derivative
  • Short-chain aldehyde
  • Aldehyde
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Physiological effect
Organoleptic effect
Disposition
Biological locationSource
ProcessNot Available
RoleNot Available
Physical Properties
StateLiquid
Experimental Molecular Properties
PropertyValueReference
Melting Point-69 °CNot Available
Boiling Point104.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility150 mg/mL at 2 °CNot Available
LogP0.771 (est)The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility66.5 g/LALOGPS
logP0.76ChemAxon
pKa (Strongest Basic)-4.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area17.07 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity22.04 m³·mol⁻¹ChemAxon
Polarizability7.63 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+120.32330932474
DeepCCS[M-H]-118.42830932474
DeepCCS[M-2H]-153.66830932474
DeepCCS[M+Na]+127.92230932474
AllCCS[M+H]+119.632859911
AllCCS[M+H-H2O]+114.932859911
AllCCS[M+NH4]+123.932859911
AllCCS[M+Na]+125.132859911
AllCCS[M-H]-131.032859911
AllCCS[M+Na-2H]-136.532859911
AllCCS[M+HCOO]-142.532859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
2-ButenalC\C=C\C=O992.5Standard polar33892256
2-ButenalC\C=C\C=O609.7Standard non polar33892256
2-ButenalC\C=C\C=O649.5Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 2-Butenal GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-009f-9000000000-2642f67411e427d975d42015-03-01Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Butenal 10V, Positive-QTOFsplash10-00di-9000000000-6dbc83fce56e9add9da32016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Butenal 20V, Positive-QTOFsplash10-0fk9-9000000000-a86154a67b4683d772042016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Butenal 40V, Positive-QTOFsplash10-0f6x-9000000000-a1a2541c4047f270e26a2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Butenal 10V, Negative-QTOFsplash10-014i-9000000000-48305ae30578976af73c2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Butenal 20V, Negative-QTOFsplash10-014i-9000000000-4de0dbfac937aa9c25182016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Butenal 40V, Negative-QTOFsplash10-0udl-9000000000-e5f565b9dcc3f2e465612016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Butenal 10V, Positive-QTOFsplash10-0uk9-9000000000-930b0e2bbb268b2857532021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Butenal 20V, Positive-QTOFsplash10-0udl-9000000000-b146ab174aebfe8f37a32021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Butenal 40V, Positive-QTOFsplash10-0udi-9000000000-c512574bc7b38df158d42021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Butenal 10V, Negative-QTOFsplash10-014i-9000000000-1fe3e74f4451b5653b932021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Butenal 20V, Negative-QTOFsplash10-014i-9000000000-6a804ed7b9cae4dbf0cd2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Butenal 40V, Negative-QTOFsplash10-0f6x-9000000000-6eca02e73c31ee64da5f2021-09-25Wishart LabView Spectrum

IR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)2023-02-04FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)2023-02-04FELIX labView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen Locations
  • Feces
  • Saliva
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Not SpecifiedNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Campylobacter jejuni infection		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Clostridium difficile infection		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Ulcerative Colitis		 details
Associated Disorders and Diseases
Disease References
Ulcerative colitis
  1. Garner CE, Smith S, de Lacy Costello B, White P, Spencer R, Probert CS, Ratcliffe NM: Volatile organic compounds from feces and their potential for diagnosis of gastrointestinal disease. FASEB J. 2007 Jun;21(8):1675-88. Epub 2007 Feb 21. [PubMed:17314143 ]
Associated OMIM IDsNone
DrugBank IDDB04381
Phenol Explorer Compound IDNot Available
FooDB IDFDB030138
KNApSAcK IDC00050435
Chemspider ID394562
KEGG Compound IDC19377
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkCrotonaldehyde
METLIN IDNot Available
PubChem Compound447466
PDB IDNot Available
ChEBI ID41607
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1311001
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Mori Y, Yamada S: Contribution of cation-pi interactions in iminium catalysis. Molecules. 2012 Feb 21;17(2):2161-8. doi: 10.3390/molecules17022161. [PubMed:22354192 ]
  2. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Enzymes

Enzyme Details
1. Aldehyde dehydrogenase, mitochondrial
General function:
Involved in oxidoreductase activity
Specific function:
Not Available
Gene Name:
ALDH2
Uniprot ID:
P05091
Molecular weight:
56380.93
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]