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Showing metabocard for beta-propiolactone (HMDB0249149)

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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2021-09-11 03:38:30 UTC
Update Date2021-09-26 22:59:50 UTC
HMDB IDHMDB0249149
Secondary Accession NumbersNone
Metabolite Identification
Common Namebeta-propiolactone
DescriptionPropiolactone, also known as betaprone or propanolide, belongs to the class of organic compounds known as beta propiolactones. These are organic compounds containing a four-member lactone (a cyclic ester). Based on a literature review a significant number of articles have been published on Propiolactone. This compound has been identified in human blood as reported by (PMID: 31557052 ). Beta-propiolactone is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically beta-propiolactone 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 HMDB0249149 (beta-propiolactone)


  Mrv1572011271518022D          

  5  5  0  0  0  0            999 V2000
   -0.4124   -0.5834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9958    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4124    0.5834    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1709    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9958    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  4  1  0  0  0  0
  3  4  1  0  0  0  0
  2  3  1  0  0  0  0
  4  5  2  0  0  0  0
M  END
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3D MOL for HMDB0249149 (beta-propiolactone)

HMDB0249149
     RDKit          3D
beta-propiolactone
  9  9  0  0  0  0  0  0  0  0999 V2000
   -0.5505    2.2430    0.1162 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2929    1.0649   -0.1797 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7487    0.0775    0.1522 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4327   -0.8599   -0.0373 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8925    0.1201   -0.9832 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1658    0.1077    1.1583 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5408   -0.0690   -0.6054 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0801   -0.8535    0.8619 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2067   -1.8310   -0.4829 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  2  1  0
  3  6  1  0
  3  7  1  0
  4  8  1  0
  4  9  1  0
M  END
Download

3D SDF for HMDB0249149 (beta-propiolactone)


  Mrv1572011271518022D          

  5  5  0  0  0  0            999 V2000
   -0.4124   -0.5834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9958    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4124    0.5834    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1709    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9958    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  4  1  0  0  0  0
  3  4  1  0  0  0  0
  2  3  1  0  0  0  0
  4  5  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0249149

> <DATABASE_NAME>
hmdb

> <SMILES>
O=C1CCO1

> <INCHI_IDENTIFIER>
InChI=1S/C3H4O2/c4-3-1-2-5-3/h1-2H2

> <INCHI_KEY>
VEZXCJBBBCKRPI-UHFFFAOYSA-N

> <FORMULA>
C3H4O2

> <MOLECULAR_WEIGHT>
72.063

> <EXACT_MASS>
72.021129369

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
9

> <JCHEM_AVERAGE_POLARIZABILITY>
6.5457433799020786

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
oxetan-2-one

> <ALOGPS_LOGP>
-0.55

> <JCHEM_LOGP>
-0.13910989933333343

> <ALOGPS_LOGS>
0.78

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-7.059542213312479

> <JCHEM_POLAR_SURFACE_AREA>
26.3

> <JCHEM_REFRACTIVITY>
15.553099999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.36e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
β propiolactone

> <JCHEM_VEBER_RULE>
1

$$$$
Download

3D-SDF for HMDB0249149 (beta-propiolactone)

HMDB0249149
     RDKit          3D
beta-propiolactone
  9  9  0  0  0  0  0  0  0  0999 V2000
   -0.5505    2.2430    0.1162 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2929    1.0649   -0.1797 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7487    0.0775    0.1522 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4327   -0.8599   -0.0373 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8925    0.1201   -0.9832 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1658    0.1077    1.1583 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5408   -0.0690   -0.6054 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0801   -0.8535    0.8619 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2067   -1.8310   -0.4829 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  2  1  0
  3  6  1  0
  3  7  1  0
  4  8  1  0
  4  9  1  0
M  END
Download

PDB for HMDB0249149 (beta-propiolactone)

HEADER    PROTEIN                                 27-NOV-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-NOV-15         0                                  
HETATM    1  C   UNK     0      -0.770  -1.089   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.859   0.000   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      -0.770   1.089   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       0.319   0.000   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       1.859   0.000   0.000  0.00  0.00           O+0
CONECT    1    2    4                                                       
CONECT    2    1    3                                                       
CONECT    3    4    2                                                       
CONECT    4    1    3    5                                                  
CONECT    5    4                                                            
MASTER        0    0    0    0    0    0    0    0    5    0   10    0
END
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3D PDB for HMDB0249149 (beta-propiolactone)

COMPND    HMDB0249149
HETATM    1  O1  UNL     1      -0.551   2.243   0.116  1.00  0.00           O  
HETATM    2  C1  UNL     1      -0.293   1.065  -0.180  1.00  0.00           C  
HETATM    3  C2  UNL     1       0.749   0.078   0.152  1.00  0.00           C  
HETATM    4  C3  UNL     1      -0.433  -0.860  -0.037  1.00  0.00           C  
HETATM    5  O2  UNL     1      -0.893   0.120  -0.983  1.00  0.00           O  
HETATM    6  H1  UNL     1       1.166   0.108   1.158  1.00  0.00           H  
HETATM    7  H2  UNL     1       1.541  -0.069  -0.605  1.00  0.00           H  
HETATM    8  H3  UNL     1      -1.080  -0.853   0.862  1.00  0.00           H  
HETATM    9  H4  UNL     1      -0.207  -1.831  -0.483  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    5
CONECT    3    4    6    7
CONECT    4    5    8    9
END
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SMILES for HMDB0249149 (beta-propiolactone)

O=C1CCO1
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INCHI for HMDB0249149 (beta-propiolactone)

InChI=1S/C3H4O2/c4-3-1-2-5-3/h1-2H2
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View in JSmolView NMR AssignmentsView Stereo Labels
Synonyms
ValueSource
1,3-PropiolactoneChEBI
2-OxetanoneChEBI
3-Hydroxypropionic acid beta-lactoneChEBI
3-PropanolideChEBI
beta-Lactone hydracrylic acidChEBI
beta-Propanoic acid lactoneChEBI
beta-PropiolaktonChEBI
beta-PropionolactoneChEBI
BetapronChEBI
BetaproneChEBI
Hydracrylic acid beta-lactoneChEBI
PropanolideChEBI
PropiolactonaChEBI
PropiolactonumChEBI
beta-PropiolactoneKegg
3-Hydroxypropionate b-lactoneGenerator
3-Hydroxypropionate beta-lactoneGenerator
3-Hydroxypropionate β-lactoneGenerator
3-Hydroxypropionic acid b-lactoneGenerator
3-Hydroxypropionic acid β-lactoneGenerator
b-Lactone hydracrylateGenerator
b-Lactone hydracrylic acidGenerator
beta-Lactone hydracrylateGenerator
Β-lactone hydracrylateGenerator
Β-lactone hydracrylic acidGenerator
b-Propanoate lactoneGenerator
b-Propanoic acid lactoneGenerator
beta-Propanoate lactoneGenerator
Β-propanoate lactoneGenerator
Β-propanoic acid lactoneGenerator
b-PropiolaktonGenerator
Β-propiolaktonGenerator
b-PropionolactoneGenerator
Β-propionolactoneGenerator
Hydracrylate b-lactoneGenerator
Hydracrylate beta-lactoneGenerator
Hydracrylate β-lactoneGenerator
Hydracrylic acid b-lactoneGenerator
Hydracrylic acid β-lactoneGenerator
b-PropiolactoneGenerator
Β-propiolactoneGenerator
beta PropiolactoneMeSH
PropiolactoneChEBI
Chemical FormulaC3H4O2
Average Molecular Weight72.063
Monoisotopic Molecular Weight72.021129369
IUPAC Nameoxetan-2-one
Traditional Nameβ propiolactone
CAS Registry NumberNot Available
SMILES
O=C1CCO1
InChI Identifier
InChI=1S/C3H4O2/c4-3-1-2-5-3/h1-2H2
InChI KeyVEZXCJBBBCKRPI-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
  • 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 Descriptors
Ontology
Not AvailableNot 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
logP-0.55ALOGPS
logP-0.14ChemAxon
logS0.78ALOGPS
pKa (Strongest Basic)-7.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area26.3 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity15.55 m³·mol⁻¹ChemAxon
Polarizability6.55 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]+120.20630932474
DeepCCS[M-H]-118.3130932474
DeepCCS[M-2H]-153.92130932474
DeepCCS[M+Na]+128.33730932474
AllCCS[M+H]+116.132859911
AllCCS[M+H-H2O]+110.932859911
AllCCS[M+NH4]+121.032859911
AllCCS[M+Na]+122.532859911
AllCCS[M-H]-118.732859911
AllCCS[M+Na-2H]-123.232859911
AllCCS[M+HCOO]-128.232859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
beta-propiolactoneO=C1CCO11557.6Standard polar33892256
beta-propiolactoneO=C1CCO1713.4Standard non polar33892256
beta-propiolactoneO=C1CCO1700.1Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - beta-propiolactone GC-MS (Non-derivatized) - 70eV, Positivesplash10-004i-9000000000-efbfe1d770cd2e0e30fb2021-09-23Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - beta-propiolactone 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 - beta-propiolactone 10V, Positive-QTOFsplash10-00di-9000000000-da4e2fb7e1440fa41baf2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - beta-propiolactone 20V, Positive-QTOFsplash10-00di-9000000000-88bd8b2a15dc0e1909c82016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - beta-propiolactone 40V, Positive-QTOFsplash10-05bf-9000000000-5a4d7a94dcf7166278732016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - beta-propiolactone 10V, Negative-QTOFsplash10-004i-9000000000-d57433a13cb71eef88d22016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - beta-propiolactone 20V, Negative-QTOFsplash10-00di-9000000000-d401d3d7a4d064a938512016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - beta-propiolactone 40V, Negative-QTOFsplash10-004i-9000000000-066bffb2d7b5452affde2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - beta-propiolactone 10V, Positive-QTOFsplash10-00di-9000000000-21e1ba0881754226c8492021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - beta-propiolactone 20V, Positive-QTOFsplash10-0ab9-9000000000-45b4390078d1ed0290f72021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - beta-propiolactone 40V, Positive-QTOFsplash10-0a4i-9000000000-abfe152b665cab01877b2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - beta-propiolactone 10V, Negative-QTOFsplash10-00di-9000000000-85ee1d7f8db31720e3cf2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - beta-propiolactone 20V, Negative-QTOFsplash10-00di-9000000000-de0df988b2d4882f9cdb2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - beta-propiolactone 40V, Negative-QTOFsplash10-006x-9000000000-44751ed5df4cde96cfd52021-10-12Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-10-13Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-10-13Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-10-13Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-10-13Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-10-13Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-10-13Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-10-13Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-10-13Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-10-13Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-10-13Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-10-13Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-10-13Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-10-13Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-10-13Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-10-13Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-10-13Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-10-13Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-10-13Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-10-13Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-10-13Wishart 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 IDDB09348
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID2275
KEGG Compound IDC19297
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkPropiolactone
METLIN IDNot Available
PubChem Compound2365
PDB IDNot Available
ChEBI ID49073
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1223261
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 ]