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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (6) Show 6 proteins XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2008-08-13 13:56:01 UTC

Update Date

2023-02-21 17:17:22 UTC

HMDB ID

HMDB0006853

Secondary Accession Numbers

HMDB0006945
HMDB06853
HMDB06945

Metabolite Identification

Common Name

3-Butyn-1-al

Description

3-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

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
3-Butynal	ChEBI
3-Butyn-1-al	ChEBI

Chemical Formula

C₄H₄O

Average Molecular Weight

68.074

Monoisotopic Molecular Weight

68.02621475

IUPAC Name

but-3-ynal

Traditional Name

3-butynal

CAS Registry Number

52844-23-2

SMILES

O=CCC#C

InChI Identifier

InChI=1S/C4H4O/c1-2-3-4-5/h1,4H,3H2

InChI Key

OGQNOIVDVXRWRE-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.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbonyl compounds

Direct Parent

Alpha-hydrogen aldehydes

Alternative Parents

Substituents

Alpha-hydrogen aldehyde
Acetylide
Organic oxide
Hydrocarbon derivative
Short-chain aldehyde
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

terminal acetylenic compound (CHEBI:28180 )
alpha-CH2-containing aldehyde (CHEBI:28180 )
butynal (CHEBI:28180 )

Ontology

Not Available

Endogenous (HMDB: HMDB0006853)

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.82 g/L	ALOGPS
logP	0.1	ALOGPS
logP	-0.044	ChemAxon
logS	-1.9	ALOGPS
pKa (Strongest Acidic)	16.16	ChemAxon
pKa (Strongest Basic)	-7.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	17.07 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	19.41 m³·mol⁻¹	ChemAxon
Polarizability	6.87 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	112.048	31661259
DarkChem	[M-H]-	106.458	31661259
DeepCCS	[M+H]+	120.535	30932474
DeepCCS	[M-H]-	118.64	30932474
DeepCCS	[M-2H]-	153.967	30932474
DeepCCS	[M+Na]+	128.254	30932474
AllCCS	[M+H]+	119.3	32859911
AllCCS	[M+H-H2O]+	114.6	32859911
AllCCS	[M+NH4]+	123.6	32859911
AllCCS	[M+Na]+	124.8	32859911
AllCCS	[M-H]-	128.6	32859911
AllCCS	[M+Na-2H]-	134.1	32859911
AllCCS	[M+HCOO]-	140.0	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
3-Butyn-1-al	O=CCC#C	1073.6	Standard polar	33892256
3-Butyn-1-al	O=CCC#C	554.0	Standard non polar	33892256
3-Butyn-1-al	O=CCC#C	559.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
3-Butyn-1-al,1TMS,isomer #1	C#CC=CO[Si](C)(C)C	849.6	Semi standard non polar	33892256
3-Butyn-1-al,1TMS,isomer #1	C#CC=CO[Si](C)(C)C	838.5	Standard non polar	33892256
3-Butyn-1-al,1TMS,isomer #1	C#CC=CO[Si](C)(C)C	1250.8	Standard polar	33892256
3-Butyn-1-al,1TBDMS,isomer #1	C#CC=CO[Si](C)(C)C(C)(C)C	1090.7	Semi standard non polar	33892256
3-Butyn-1-al,1TBDMS,isomer #1	C#CC=CO[Si](C)(C)C(C)(C)C	1049.3	Standard non polar	33892256
3-Butyn-1-al,1TBDMS,isomer #1	C#CC=CO[Si](C)(C)C(C)(C)C	1457.8	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Butyn-1-al GC-MS (Non-derivatized) - 70eV, Positive	splash10-014r-9000000000-186f1fb5c27c6570a238	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Butyn-1-al GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Butyn-1-al 10V, Positive-QTOF	splash10-014i-9000000000-3f8a0595110442e90c95	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Butyn-1-al 20V, Positive-QTOF	splash10-0gb9-9000000000-3141a032fcc3f7ab5406	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Butyn-1-al 40V, Positive-QTOF	splash10-0f79-9000000000-ff11baf148b374c0f461	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Butyn-1-al 10V, Negative-QTOF	splash10-014i-9000000000-8dc8ee15af63a3d28601	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Butyn-1-al 20V, Negative-QTOF	splash10-014i-9000000000-8c9ecd41d4f3b2ccc13a	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Butyn-1-al 40V, Negative-QTOF	splash10-0007-9000000000-b47afd1d3e3e95099819	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Butyn-1-al 10V, Positive-QTOF	splash10-0udr-9000000000-8ae3b5b04ac3c02f3245	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Butyn-1-al 20V, Positive-QTOF	splash10-0f79-9000000000-5aa02529ac413fa44225	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Butyn-1-al 40V, Positive-QTOF	splash10-0udi-9000000000-0fa5c1092e71e153d4bc	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Butyn-1-al 10V, Negative-QTOF	splash10-014i-9000000000-aa96dfa89323c18d10ff	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Butyn-1-al 20V, Negative-QTOF	splash10-014i-9000000000-973807a6f9673227cc01	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Butyn-1-al 40V, Negative-QTOF	splash10-00kp-9000000000-c96af77c20bd14c1f29a	2021-09-22	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-03	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB024119

KNApSAcK ID

Not Available

Chemspider ID

126119

KEGG Compound ID

C06145

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

142966

PDB ID

Not Available

ChEBI ID

28180

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Enzymes

Enzyme Details

1. 4-trimethylaminobutyraldehyde dehydrogenase

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

Enzyme Details

2. Alpha-aminoadipic semialdehyde dehydrogenase

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

Enzyme Details

3. Aldehyde dehydrogenase family 1 member A3

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

Enzyme Details

4. Aldehyde dehydrogenase, mitochondrial

General function:: Involved in oxidoreductase activity
Specific function:: Not Available
Gene Name:: ALDH2
Uniprot ID:: P05091
Molecular weight:: 56380.93

Enzyme Details

5. Fatty aldehyde dehydrogenase

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

Enzyme Details

6. Aldehyde dehydrogenase X, mitochondrial

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

Showing metabocard for 3-Butyn-1-al (HMDB0006853)

MOL for HMDB0006853 (3-Butyn-1-al)

3D MOL for HMDB0006853 (3-Butyn-1-al)

3D SDF for HMDB0006853 (3-Butyn-1-al)

3D-SDF for HMDB0006853 (3-Butyn-1-al)

PDB for HMDB0006853 (3-Butyn-1-al)

3D PDB for HMDB0006853 (3-Butyn-1-al)

SMILES for HMDB0006853 (3-Butyn-1-al)

INCHI for HMDB0006853 (3-Butyn-1-al)

Structure for HMDB0006853 (3-Butyn-1-al)

3D Structure for HMDB0006853 (3-Butyn-1-al)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra

Enzymes