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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2008-08-13 13:56:01 UTC
Update Date2023-02-21 17:17:22 UTC
HMDB IDHMDB0006853
Secondary Accession Numbers
  • HMDB0006945
  • HMDB06853
  • HMDB06945
Metabolite Identification
Common Name3-Butyn-1-al
Description3-Butyn-1-al is an intermediate in Butanoate metabolism (KEGG ID C06145). It is the third to last step in the synthesis and degradation of ketone bodies and is converted from 3-Butyn-1-ol via the enzyme alcohol dehydrogenase (acceptor) [EC:1.1.99.8]. It is then converted to 3-Butynoate via the enzyme aldehyde dehydrogenase (NAD+) [EC:1.2.1.3].
Structure
Data?1676999842
Synonyms
ValueSource
3-ButynalChEBI
3-Butyn-1-alChEBI
Chemical FormulaC4H4O
Average Molecular Weight68.074
Monoisotopic Molecular Weight68.02621475
IUPAC Namebut-3-ynal
Traditional Name3-butynal
CAS Registry Number52844-23-2
SMILES
O=CCC#C
InChI Identifier
InChI=1S/C4H4O/c1-2-3-4-5/h1,4H,3H2
InChI KeyOGQNOIVDVXRWRE-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as alpha-hydrogen aldehydes. These are aldehydes with the general formula HC(H)(R)C(=O)H, where R is an organyl group.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbonyl compounds
Direct ParentAlpha-hydrogen aldehydes
Alternative Parents
Substituents
  • Alpha-hydrogen aldehyde
  • Acetylide
  • Organic oxide
  • Hydrocarbon derivative
  • Short-chain aldehyde
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
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
Water Solubility0.82 g/LALOGPS
logP0.1ALOGPS
logP-0.044ChemAxon
logS-1.9ALOGPS
pKa (Strongest Acidic)16.16ChemAxon
pKa (Strongest Basic)-7.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area17.07 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity19.41 m³·mol⁻¹ChemAxon
Polarizability6.87 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
DarkChem[M+H]+112.04831661259
DarkChem[M-H]-106.45831661259
DeepCCS[M+H]+120.53530932474
DeepCCS[M-H]-118.6430932474
DeepCCS[M-2H]-153.96730932474
DeepCCS[M+Na]+128.25430932474
AllCCS[M+H]+119.332859911
AllCCS[M+H-H2O]+114.632859911
AllCCS[M+NH4]+123.632859911
AllCCS[M+Na]+124.832859911
AllCCS[M-H]-128.632859911
AllCCS[M+Na-2H]-134.132859911
AllCCS[M+HCOO]-140.032859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
3-Butyn-1-alO=CCC#C1073.6Standard polar33892256
3-Butyn-1-alO=CCC#C554.0Standard non polar33892256
3-Butyn-1-alO=CCC#C559.9Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
3-Butyn-1-al,1TMS,isomer #1C#CC=CO[Si](C)(C)C849.6Semi standard non polar33892256
3-Butyn-1-al,1TMS,isomer #1C#CC=CO[Si](C)(C)C838.5Standard non polar33892256
3-Butyn-1-al,1TMS,isomer #1C#CC=CO[Si](C)(C)C1250.8Standard polar33892256
3-Butyn-1-al,1TBDMS,isomer #1C#CC=CO[Si](C)(C)C(C)(C)C1090.7Semi standard non polar33892256
3-Butyn-1-al,1TBDMS,isomer #1C#CC=CO[Si](C)(C)C(C)(C)C1049.3Standard non polar33892256
3-Butyn-1-al,1TBDMS,isomer #1C#CC=CO[Si](C)(C)C(C)(C)C1457.8Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 3-Butyn-1-al GC-MS (Non-derivatized) - 70eV, Positivesplash10-014r-9000000000-186f1fb5c27c6570a2382017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-Butyn-1-al 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 - 3-Butyn-1-al 10V, Positive-QTOFsplash10-014i-9000000000-3f8a0595110442e90c952017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Butyn-1-al 20V, Positive-QTOFsplash10-0gb9-9000000000-3141a032fcc3f7ab54062017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Butyn-1-al 40V, Positive-QTOFsplash10-0f79-9000000000-ff11baf148b374c0f4612017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Butyn-1-al 10V, Negative-QTOFsplash10-014i-9000000000-8dc8ee15af63a3d286012017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Butyn-1-al 20V, Negative-QTOFsplash10-014i-9000000000-8c9ecd41d4f3b2ccc13a2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Butyn-1-al 40V, Negative-QTOFsplash10-0007-9000000000-b47afd1d3e3e950998192017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Butyn-1-al 10V, Positive-QTOFsplash10-0udr-9000000000-8ae3b5b04ac3c02f32452021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Butyn-1-al 20V, Positive-QTOFsplash10-0f79-9000000000-5aa02529ac413fa442252021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Butyn-1-al 40V, Positive-QTOFsplash10-0udi-9000000000-0fa5c1092e71e153d4bc2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Butyn-1-al 10V, Negative-QTOFsplash10-014i-9000000000-aa96dfa89323c18d10ff2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Butyn-1-al 20V, Negative-QTOFsplash10-014i-9000000000-973807a6f9673227cc012021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Butyn-1-al 40V, Negative-QTOFsplash10-00kp-9000000000-c96af77c20bd14c1f29a2021-09-22Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum

IR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)2023-02-03FELIX 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 IDFDB024119
KNApSAcK IDNot Available
Chemspider ID126119
KEGG Compound IDC06145
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound142966
PDB IDNot Available
ChEBI ID28180
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 ReferencesNot Available

Enzymes

General function:
Involved in oxidoreductase activity
Specific function:
Converts gamma-trimethylaminobutyraldehyde into gamma-butyrobetaine. Catalyzes the irreversible oxidation of a broad range of aldehydes to the corresponding acids in an NAD-dependent reaction.
Gene Name:
ALDH9A1
Uniprot ID:
P49189
Molecular weight:
56291.485
General function:
Involved in oxidoreductase activity
Specific function:
Multifunctional enzyme mediating important protective effects. Metabolizes betaine aldehyde to betaine, an important cellular osmolyte and methyl donor. Protects cells from oxidative stress by metabolizing a number of lipid peroxidation-derived aldehydes. Involved in lysine catabolism.
Gene Name:
ALDH7A1
Uniprot ID:
P49419
Molecular weight:
58486.74
General function:
Involved in oxidoreductase activity
Specific function:
Recognizes as substrates free retinal and cellular retinol-binding protein-bound retinal. Seems to be the key enzyme in the formation of an RA gradient along the dorso-ventral axis during the early eye development and also in the development of the olfactory system (By similarity).
Gene Name:
ALDH1A3
Uniprot ID:
P47895
Molecular weight:
56107.995
General function:
Involved in oxidoreductase activity
Specific function:
Not Available
Gene Name:
ALDH2
Uniprot ID:
P05091
Molecular weight:
56380.93
General function:
Involved in oxidoreductase activity
Specific function:
Catalyzes the oxidation of long-chain aliphatic aldehydes to fatty acids. Active on a variety of saturated and unsaturated aliphatic aldehydes between 6 and 24 carbons in length. Responsible for conversion of the sphingosine 1-phosphate (S1P) degradation product hexadecenal to hexadecenoic acid.
Gene Name:
ALDH3A2
Uniprot ID:
P51648
Molecular weight:
54847.36
General function:
Involved in oxidoreductase activity
Specific function:
ALDHs play a major role in the detoxification of alcohol-derived acetaldehyde. They are involved in the metabolism of corticosteroids, biogenic amines, neurotransmitters, and lipid peroxidation.
Gene Name:
ALDH1B1
Uniprot ID:
P30837
Molecular weight:
57248.96