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Showing metabocard for Diketene (HMDB0251360)

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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2021-09-11 08:41:51 UTC
Update Date2022-09-22 17:44:22 UTC
HMDB IDHMDB0251360
Secondary Accession NumbersNone
Metabolite Identification
Common NameDiketene
DescriptionDiketene belongs to the class of organic compounds known as beta propiolactones. These are organic compounds containing a four-member lactone (a cyclic ester). Diketene is an extremely weak basic (essentially neutral) compound (based on its pKa). Exemplary for the synthesis of arylides by the reaction of diketenes with aromatic amines is:Aromatic diazonium coupling with arylides to form azo dyes, such as Pigment Yellow 74:The industrial synthesis of the sweetener acesulfam-K is based on the reaction of diketene with sulfamic acid and cyclization by SO3. Besides the rosin resins with about 60% share of world consumption, long chain diketenes called alkylketene dimers (AKD) are with 16% share the most important synthetic paper sizes, they are usually used in concentrations of 0.15%, meaning 1.5 kg solid AKD/t paper. Diketene is a member of the oxetane family. Certain diketenes with two aliphatic chains, such as alkyl ketene dimers (AKDs), are used industrially to improve hydrophobicity in paper. The latter are used in the manufacture of dyestuffs and pigments. An example is the reaction with 2-aminoindane:Diketene is an important industrial intermediate used for the production of acetoacetate esters and amides as well as substituted 1-phenyl-3-methylpyrazolones. It is formed by dimerization of ketene, H2CCO (IUPAC name: ethenone). For example pyrazolones are formed from substituted phenylhydrazines, they were used as analgetics but are now largely obsolete. It is used as a reagent in organic chemistry. This compound has been identified in human blood as reported by (PMID: 31557052 ). Diketene is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Diketene 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 HMDB0251360 (Diketene)


  Mrv1572004191603522D          

  6  6  0  0  0  0            999 V2000
    0.4125    1.8209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9959    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4125    0.9959    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4125   -0.1709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4125   -0.9959    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1709    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  2  0  0  0  0
  3  2  1  0  0  0  0
  4  2  1  0  0  0  0
  5  4  2  0  0  0  0
  6  3  1  0  0  0  0
  6  4  1  0  0  0  0
M  END
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3D MOL for HMDB0251360 (Diketene)

HMDB0251360
     RDKit          3D
Diketene
 10 10  0  0  0  0  0  0  0  0999 V2000
    1.5007   -0.7043   -0.4428 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3232   -0.1673   -0.3443 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8261   -0.2018    0.5766 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9930    1.1523    0.0347 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4658    2.2209    0.4226 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3857    0.7196   -1.1173 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9321   -1.4040    0.2639 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1545   -0.4710   -1.2821 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6596   -0.8620    0.2388 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5802   -0.2823    1.6499 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  6  2  1  0
  1  7  1  0
  1  8  1  0
  3  9  1  0
  3 10  1  0
M  END
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3D SDF for HMDB0251360 (Diketene)


  Mrv1572004191603522D          

  6  6  0  0  0  0            999 V2000
    0.4125    1.8209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9959    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4125    0.9959    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4125   -0.1709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4125   -0.9959    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1709    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  2  0  0  0  0
  3  2  1  0  0  0  0
  4  2  1  0  0  0  0
  5  4  2  0  0  0  0
  6  3  1  0  0  0  0
  6  4  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0251360

> <DATABASE_NAME>
hmdb

> <SMILES>
C=C1CC(=O)O1

> <INCHI_IDENTIFIER>
InChI=1S/C4H4O2/c1-3-2-4(5)6-3/h1-2H2

> <INCHI_KEY>
WASQWSOJHCZDFK-UHFFFAOYSA-N

> <FORMULA>
C4H4O2

> <MOLECULAR_WEIGHT>
84.074

> <EXACT_MASS>
84.021129369

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
10

> <JCHEM_AVERAGE_POLARIZABILITY>
7.649806696770913

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
4-methylideneoxetan-2-one

> <ALOGPS_LOGP>
0.30

> <JCHEM_LOGP>
0.08109592266666657

> <ALOGPS_LOGS>
0.44

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
19.771314652002136

> <JCHEM_PKA_STRONGEST_BASIC>
-7.243169251577513

> <JCHEM_POLAR_SURFACE_AREA>
26.3

> <JCHEM_REFRACTIVITY>
20.315800000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.33e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
diketene

> <JCHEM_VEBER_RULE>
1

$$$$
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3D-SDF for HMDB0251360 (Diketene)

HMDB0251360
     RDKit          3D
Diketene
 10 10  0  0  0  0  0  0  0  0999 V2000
    1.5007   -0.7043   -0.4428 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3232   -0.1673   -0.3443 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8261   -0.2018    0.5766 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9930    1.1523    0.0347 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4658    2.2209    0.4226 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3857    0.7196   -1.1173 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9321   -1.4040    0.2639 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1545   -0.4710   -1.2821 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6596   -0.8620    0.2388 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5802   -0.2823    1.6499 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  6  2  1  0
  1  7  1  0
  1  8  1  0
  3  9  1  0
  3 10  1  0
M  END
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PDB for HMDB0251360 (Diketene)

HEADER    PROTEIN                                 19-APR-16   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-APR-16         0                                  
HETATM    1  C   UNK     0       0.770   3.399   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.859   0.770   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.770   1.859   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.770  -0.319   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       0.770  -1.859   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0      -0.319   0.770   0.000  0.00  0.00           O+0
CONECT    1    3                                                            
CONECT    2    3    4                                                       
CONECT    3    1    2    6                                                  
CONECT    4    2    5    6                                                  
CONECT    5    4                                                            
CONECT    6    3    4                                                       
MASTER        0    0    0    0    0    0    0    0    6    0   12    0
END
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3D PDB for HMDB0251360 (Diketene)

COMPND    HMDB0251360
HETATM    1  C1  UNL     1       1.501  -0.704  -0.443  1.00  0.00           C  
HETATM    2  C2  UNL     1       0.323  -0.167  -0.344  1.00  0.00           C  
HETATM    3  C3  UNL     1      -0.826  -0.202   0.577  1.00  0.00           C  
HETATM    4  C4  UNL     1      -0.993   1.152   0.035  1.00  0.00           C  
HETATM    5  O1  UNL     1      -1.466   2.221   0.423  1.00  0.00           O  
HETATM    6  O2  UNL     1      -0.386   0.720  -1.117  1.00  0.00           O  
HETATM    7  H1  UNL     1       1.932  -1.404   0.264  1.00  0.00           H  
HETATM    8  H2  UNL     1       2.154  -0.471  -1.282  1.00  0.00           H  
HETATM    9  H3  UNL     1      -1.660  -0.862   0.239  1.00  0.00           H  
HETATM   10  H4  UNL     1      -0.580  -0.282   1.650  1.00  0.00           H  
CONECT    1    2    2    7    8
CONECT    2    3    6
CONECT    3    4    9   10
CONECT    4    5    5    6
END
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SMILES for HMDB0251360 (Diketene)

C=C1CC(=O)O1
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INCHI for HMDB0251360 (Diketene)

InChI=1S/C4H4O2/c1-3-2-4(5)6-3/h1-2H2
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View in JSmolView Stereo Labels
Synonyms
ValueSource
DiketeneMeSH
Chemical FormulaC4H4O2
Average Molecular Weight84.074
Monoisotopic Molecular Weight84.021129369
IUPAC Name4-methylideneoxetan-2-one
Traditional Namediketene
CAS Registry NumberNot Available
SMILES
C=C1CC(=O)O1
InChI Identifier
InChI=1S/C4H4O2/c1-3-2-4(5)6-3/h1-2H2
InChI KeyWASQWSOJHCZDFK-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as beta propiolactones. These are organic compounds containing a four-member lactone (a cyclic ester).
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassLactones
Sub ClassBeta propiolactones
Direct ParentBeta propiolactones
Alternative Parents
Substituents
  • Enol ester
  • Beta_propiolactone
  • Oxetane
  • Carboxylic acid ester
  • Oxacycle
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic 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
logP0.3ALOGPS
logP0.081ChemAxon
logS0.44ALOGPS
pKa (Strongest Acidic)19.77ChemAxon
pKa (Strongest Basic)-7.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area26.3 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity20.32 m³·mol⁻¹ChemAxon
Polarizability7.65 ųChemAxon
Number of Rings1ChemAxon
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]+122.39230932474
DeepCCS[M-H]-120.49730932474
DeepCCS[M-2H]-155.97130932474
DeepCCS[M+Na]+130.37830932474
AllCCS[M+H]+117.932859911
AllCCS[M+H-H2O]+112.832859911
AllCCS[M+NH4]+122.732859911
AllCCS[M+Na]+124.032859911
AllCCS[M-H]-117.232859911
AllCCS[M+Na-2H]-120.932859911
AllCCS[M+HCOO]-124.932859911

Predicted Retention Times

Underivatized

Chromatographic MethodRetention TimeReference
Predicted by Siyang on May 30, 202210.3297 minutes33406817
Predicted by Siyang using ReTip algorithm on June 8, 20222.32 minutes32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid1229.4 seconds40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid405.3 seconds40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid144.3 seconds40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid290.1 seconds40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid80.6 seconds40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid354.1 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 Acid376.7 seconds40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)304.7 seconds40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid751.5 seconds40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid232.7 seconds40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid965.4 seconds40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid284.5 seconds40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid324.7 seconds40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate751.1 seconds40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA330.7 seconds40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water289.3 seconds40023050

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
DiketeneC=C1CC(=O)O11343.7Standard polar33892256
DiketeneC=C1CC(=O)O1768.3Standard non polar33892256
DiketeneC=C1CC(=O)O1724.3Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Diketene GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9000000000-a0b51be8c4a5da05ae102021-09-24Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Diketene 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 - Diketene 10V, Positive-QTOFsplash10-000l-9000000000-e84d30a418572a07dd4e2016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Diketene 20V, Positive-QTOFsplash10-000f-9000000000-9f1206781b7fc09ca6a82016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Diketene 40V, Positive-QTOFsplash10-0006-9000000000-b4111f95fb1545853ced2016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Diketene 10V, Negative-QTOFsplash10-0019-9000000000-678307ea28988ee069242016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Diketene 20V, Negative-QTOFsplash10-001i-9000000000-37891e47eb5b718d632a2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Diketene 40V, Negative-QTOFsplash10-000i-9000000000-d1b7b150dd9546f42ee62016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Diketene 10V, Positive-QTOFsplash10-052u-9000000000-57e758c2189e3335567f2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Diketene 20V, Positive-QTOFsplash10-000l-9000000000-9e2519856daa29a1c3f32021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Diketene 40V, Positive-QTOFsplash10-000i-9000000000-21c02445b456a081c2d92021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Diketene 10V, Negative-QTOFsplash10-001l-9000000000-536d7485294ddc2a817a2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Diketene 20V, Negative-QTOFsplash10-001l-9000000000-80c6408fa8b9dea0b4982021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Diketene 40V, Negative-QTOFsplash10-014l-9000000000-909b76bab47b65977dcf2021-10-12Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
UrineDetected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedCancer patients undergoing total body irradiation details
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 LinkDiketene
METLIN IDNot Available
PubChem Compound12661
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 ]