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Showing metabocard for 1,3-Butadiene (HMDB0041792)

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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-13 11:39:41 UTC
Update Date2022-03-07 02:57:12 UTC
HMDB IDHMDB0041792
Secondary Accession Numbers
  • HMDB41792
Metabolite Identification
Common Name1,3-Butadiene
Description1,3-Butadiene is a simple conjugated diene with the formula C4H6. It is an important industrial chemical used as a monomer in the production of synthetic rubber. When the word butadiene is used, most of the time it refers to 1,3-butadiene. 1,3-Butadiene is inconvenient for laboratory use because it is a flammable gas subject to polymerization on storage. 3-Butadiene cyclic sulfone (sulfolene) is a convenient solid storable source for 1,3-butadiene for many laboratory purposes when the generation of sulfur dioxide byproduct in the reaction mixture is not objectionable. Long-term exposure has been associated with cardiovascular disease, there is a consistent association with leukemia, and weaker association with other cancers. Most butadiene is polymerized to produce synthetic rubber. While polybutadiene itself is a very soft, almost liquid material, copolymers prepared from mixtures of butadiene with styrene and/or acrylonitrile, such as acrylonitrile butadiene styrene (ABS), acrylonitrile butadiene (NBR) and styrene-butadiene (SBR) are tough and elastic. SBR is the material most commonly used for the production of automobile tires. Smaller amounts of butadiene are used to make the nylon intermediate, adiponitrile, by the addition of a molecule of hydrogen cyanide to each of the double bonds in a process called hydrocyanation developed by DuPont. Other synthetic rubber materials such as chloroprene, and the solvent sulfolane are also manufactured from butadiene. Butadiene is used in the industrial production of 4-vinylcyclohexene via a Diels Alder dimerization reaction and the vinylcyclohexene is a common impurity found in butadiene upon storage. Cyclooctadiene and cyclododecatriene are produced via nickel- or titanium-catalyzed dimerization and trimerization reactions, respectively. Butadiene is also useful in the synthesis of cycloalkanes and cycloalkenes, as it reacts with double and triple carbon-carbon bonds through the Diels-Alder reaction. The name butadiene can also refer to the isomer, 1,2-butadiene, which is a cumulated diene. However, this allene is difficult to prepare and has no industrial significance. This diene is also not expected to act as a diene in a Diels-Alder reaction due to its structure. To effect a Diels-Alder reaction only a conjugated diene will suffice.
Structure
Data?1563863703
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0041792 (1,3-Butadiene)


  Mrv1652305261923522D          

  4  3  0  0  0  0            999 V2000
    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
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  2  0  0  0  0
  4  2  2  0  0  0  0
  4  3  1  0  0  0  0
M  END
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3D MOL for HMDB0041792 (1,3-Butadiene)

HMDB0041792
     RDKit          3D
1,3-Butadiene
 10  9  0  0  0  0  0  0  0  0999 V2000
   -1.4854   -0.4276   -0.8714 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6888    0.1958   -0.0364 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7038   -0.2102    0.0277 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4989    0.4167    0.8656 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1504   -1.2226   -1.5066 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5169   -0.1369   -0.9282 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0337    1.0027    0.6069 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0267   -1.0131   -0.6188 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5482    0.1846    0.9827 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0977    1.2104    1.4786 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  2  3
  1  5  1  0
  1  6  1  0
  2  7  1  0
  3  8  1  0
  4  9  1  0
  4 10  1  0
M  END
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3D SDF for HMDB0041792 (1,3-Butadiene)


  Mrv1652305261923522D          

  4  3  0  0  0  0            999 V2000
    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
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  2  0  0  0  0
  4  2  2  0  0  0  0
  4  3  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0041792

> <DATABASE_NAME>
hmdb

> <SMILES>
C=CC=C

> <INCHI_IDENTIFIER>
InChI=1S/C4H6/c1-3-4-2/h3-4H,1-2H2

> <INCHI_KEY>
KAKZBPTYRLMSJV-UHFFFAOYSA-N

> <FORMULA>
C4H6

> <MOLECULAR_WEIGHT>
54.0904

> <EXACT_MASS>
54.046950192

> <JCHEM_ACCEPTOR_COUNT>
0

> <JCHEM_ATOM_COUNT>
10

> <JCHEM_AVERAGE_POLARIZABILITY>
6.6958421237309125

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
buta-1,3-diene

> <ALOGPS_LOGP>
1.94

> <JCHEM_LOGP>
1.6340245899999997

> <ALOGPS_LOGS>
-1.74

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_POLAR_SURFACE_AREA>
0.0

> <JCHEM_REFRACTIVITY>
20.2944

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.79e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1,3-butadiene

> <JCHEM_VEBER_RULE>
1

$$$$
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3D-SDF for HMDB0041792 (1,3-Butadiene)

HMDB0041792
     RDKit          3D
1,3-Butadiene
 10  9  0  0  0  0  0  0  0  0999 V2000
   -1.4854   -0.4276   -0.8714 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6888    0.1958   -0.0364 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7038   -0.2102    0.0277 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4989    0.4167    0.8656 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1504   -1.2226   -1.5066 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5169   -0.1369   -0.9282 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0337    1.0027    0.6069 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0267   -1.0131   -0.6188 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5482    0.1846    0.9827 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0977    1.2104    1.4786 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  2  3
  1  5  1  0
  1  6  1  0
  2  7  1  0
  3  8  1  0
  4  9  1  0
  4 10  1  0
M  END
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PDB for HMDB0041792 (1,3-Butadiene)

HEADER    PROTEIN                                 26-MAY-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   26-MAY-19         0                                  
HETATM    1  C   UNK     0       2.310   1.334   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.770  -1.334   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.540   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
CONECT    1    3                                                            
CONECT    2    4                                                            
CONECT    3    1    4                                                       
CONECT    4    2    3                                                       
MASTER        0    0    0    0    0    0    0    0    4    0    6    0
END
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3D PDB for HMDB0041792 (1,3-Butadiene)

COMPND    HMDB0041792
HETATM    1  C1  UNL     1      -1.485  -0.428  -0.871  1.00  0.00           C  
HETATM    2  C2  UNL     1      -0.689   0.196  -0.036  1.00  0.00           C  
HETATM    3  C3  UNL     1       0.704  -0.210   0.028  1.00  0.00           C  
HETATM    4  C4  UNL     1       1.499   0.417   0.866  1.00  0.00           C  
HETATM    5  H1  UNL     1      -1.150  -1.223  -1.507  1.00  0.00           H  
HETATM    6  H2  UNL     1      -2.517  -0.137  -0.928  1.00  0.00           H  
HETATM    7  H3  UNL     1      -1.034   1.003   0.607  1.00  0.00           H  
HETATM    8  H4  UNL     1       1.027  -1.013  -0.619  1.00  0.00           H  
HETATM    9  H5  UNL     1       2.548   0.185   0.983  1.00  0.00           H  
HETATM   10  H6  UNL     1       1.098   1.210   1.479  1.00  0.00           H  
CONECT    1    2    2    5    6
CONECT    2    3    7
CONECT    3    4    4    8
CONECT    4    9   10
END
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SMILES for HMDB0041792 (1,3-Butadiene)

C=CC=C
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INCHI for HMDB0041792 (1,3-Butadiene)

InChI=1S/C4H6/c1-3-4-2/h3-4H,1-2H2
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View in JSmolView NMR AssignmentsView Stereo Labels
Synonyms
ValueSource
1,3-ButadienChEBI
alpha,gamma-ButadieneChEBI
BivinylChEBI
Buta-1,3-dienChEBI
CH2=ch-CH=ch2ChEBI
DivinylChEBI
VinylethyleneChEBI
a,g-ButadieneGenerator
Α,γ-butadieneGenerator
alpha,«gamma»-butadieneHMDB
BiethyleneHMDB
Buta-1,3-dieenHMDB
Buta-1,3-dieneHMDB
ButadieenHMDB
ButadienHMDB
ButadieneHMDB
CH22CH1CH2CH2HMDB
CH2=chch=ch2HMDB
ErythreneHMDB
PyrrolyleneHMDB
1,3-ButadieneChEBI
Chemical FormulaC4H6
Average Molecular Weight54.0904
Monoisotopic Molecular Weight54.046950192
IUPAC Namebuta-1,3-diene
Traditional Name1,3-butadiene
CAS Registry Number106-99-0
SMILES
C=CC=C
InChI Identifier
InChI=1S/C4H6/c1-3-4-2/h3-4H,1-2H2
InChI KeyKAKZBPTYRLMSJV-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as alkadienes. These are acyclic hydrocarbons that contain exactly two carbon-to-carbon double bonds.
KingdomOrganic compounds
Super ClassHydrocarbons
ClassUnsaturated hydrocarbons
Sub ClassOlefins
Direct ParentAlkadienes
Alternative Parents
Substituents
  • Alkadiene
  • Unsaturated aliphatic hydrocarbon
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
Biological location
ProcessNot Available
Role
Biological role
Physical Properties
StateLiquid
Experimental Molecular Properties
PropertyValueReference
Melting Point-108.9 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.74 mg/mL at 25 °CNot Available
LogP1.99Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.98 g/LALOGPS
logP1.94ALOGPS
logP1.63ChemAxon
logS-1.7ALOGPS
Physiological Charge0ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area0 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity20.29 m³·mol⁻¹ChemAxon
Polarizability6.7 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]+117.62730932474
DeepCCS[M-H]-115.73230932474
DeepCCS[M-2H]-151.07730932474
DeepCCS[M+Na]+125.48430932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
1,3-ButadieneC=CC=C523.3Standard polar33892256
1,3-ButadieneC=CC=C388.6Standard non polar33892256
1,3-ButadieneC=CC=C389.5Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - 1,3-Butadiene EI-B (Non-derivatized)splash10-0ufr-9000000000-cddbfceffd529008d5ec2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 1,3-Butadiene EI-B (Non-derivatized)splash10-0ufr-9000000000-cddbfceffd529008d5ec2018-05-18HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 1,3-Butadiene GC-MS (Non-derivatized) - 70eV, Positivesplash10-0udi-9000000000-e4f51ef2fbf933007d392017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 1,3-Butadiene GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-0udi-9000000000-cfc5558b93570d1d78c02014-09-20Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1,3-Butadiene 10V, Positive-QTOFsplash10-0a4i-9000000000-805abc61b7c8de6c57892016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1,3-Butadiene 20V, Positive-QTOFsplash10-0a4i-9000000000-805abc61b7c8de6c57892016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1,3-Butadiene 40V, Positive-QTOFsplash10-0a4i-9000000000-46aa55de9e12fa462b492016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1,3-Butadiene 10V, Negative-QTOFsplash10-0udi-9000000000-191296d0bc49a4a79c022016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1,3-Butadiene 20V, Negative-QTOFsplash10-0udi-9000000000-191296d0bc49a4a79c022016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1,3-Butadiene 40V, Negative-QTOFsplash10-0udi-9000000000-7031b766ca514dc531b42016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1,3-Butadiene 10V, Negative-QTOFsplash10-0udi-9000000000-0d737e29499be79402072021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1,3-Butadiene 20V, Negative-QTOFsplash10-0udi-9000000000-0d737e29499be79402072021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1,3-Butadiene 40V, Negative-QTOFsplash10-0udi-9000000000-0d737e29499be79402072021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1,3-Butadiene 10V, Positive-QTOFsplash10-0a4i-9000000000-1924391f943e092b44862021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1,3-Butadiene 20V, Positive-QTOFsplash10-0a4i-9000000000-c60974066ebc2547dd572021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1,3-Butadiene 40V, Positive-QTOFsplash10-0f79-9000000000-45337fddf4aab37b4ba02021-09-22Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
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 IDC00011553
Chemspider ID7557
KEGG Compound IDC16450
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia Link1,3-Butadiene
METLIN IDNot Available
PubChem Compound7845
PDB IDNot Available
ChEBI ID39478
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1146751
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Zhang ZC, Zhang X, Yu QY, Liu ZC, Xu CM, Gao JS, Zhuang J, Wang X: Pd cluster nanowires as highly efficient catalysts for selective hydrogenation reactions. Chemistry. 2012 Feb 27;18(9):2639-45. doi: 10.1002/chem.201102903. Epub 2012 Jan 26. [PubMed:22282407 ]