Hmdb loader
You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.

Showing metabocard for Propynoic acid (HMDB0006804)

Jump To Section:
IdentificationTaxonomyOntologyPhysical propertiesSpectraBiological propertiesConcentrationsLinksReferencesenzymes (6) Show 6 proteinsXML
enzymes (6) Show 6 proteins
Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2008-08-12 13:25:57 UTC
Update Date2020-02-26 21:26:47 UTC
HMDB IDHMDB0006804
Secondary Accession Numbers
  • HMDB06804
Metabolite Identification
Common NamePropynoic acid
DescriptionPropynoic acid, also known as propiolic acid, is involved in propanoate metabolism and is interconverted into 2-propyn-1-al by mitochondrial aldehyde dehydrogenase. Propynoic acid is an unsaturated organic acid and it can be prepared by boiling acetylene dicarboxylic acid. It is chemically obtained by the action of alcoholic potash on dibromosuccinic acid, or its acid potassium salt with water. It forms silky crystals which melt at 6°C and boil at about 144°C with decomposition. It is soluble in water and possesses an odour resembling that of acetic acid. Exposure to sunlight converts it into trimesic acid (benzene-1,3,5-tricarboxylic acid). It undergoes bromination to give dibromoacrylic acid. With hydrogen chloride it forms chloroacrylic acid. Its ethyl ester condenses with hydrazine to form pyrazolone. Propynoic acid forms a characteristic explosive silver salt upon the addition of ammoniacal silver nitrate to its aqueous solution, and an amorphous precipitate which explodes upon warming with ammoniacal cuprous chloride. Its ethyl ester condenses with hydrazine to form pyrazolone (Wikipedia ).
Structure
Data?1582752407
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0006804 (Propynoic acid)


  Mrv0541 02231220522D          

  5  4  0  0  0  0            999 V2000
   13.4106   -9.5367    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6969   -9.9467    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1282   -9.9467    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.4106   -8.7091    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.9832  -10.3606    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  1  0  0  0  0
  1  4  2  0  0  0  0
  2  5  3  0  0  0  0
M  END
Download

3D MOL for HMDB0006804 (Propynoic acid)

HMDB0006804
     RDKit          3D
Propynoic acid
  7  6  0  0  0  0  0  0  0  0999 V2000
    1.8318    0.1398   -0.1321 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6513   -0.1533   -0.1922 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7444   -0.4790   -0.2766 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1493   -1.5852    0.1574 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6810    0.3818   -0.8225 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8584    0.4059   -0.0873 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7668    1.2900   -0.4101 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  3  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  1  6  1  0
  5  7  1  0
M  END
Download

3D SDF for HMDB0006804 (Propynoic acid)


  Mrv0541 02231220522D          

  5  4  0  0  0  0            999 V2000
   13.4106   -9.5367    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6969   -9.9467    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1282   -9.9467    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.4106   -8.7091    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.9832  -10.3606    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  1  0  0  0  0
  1  4  2  0  0  0  0
  2  5  3  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0006804

> <DATABASE_NAME>
hmdb

> <SMILES>
OC(=O)C#C

> <INCHI_IDENTIFIER>
InChI=1S/C3H2O2/c1-2-3(4)5/h1H,(H,4,5)

> <INCHI_KEY>
UORVCLMRJXCDCP-UHFFFAOYSA-N

> <FORMULA>
C3H2O2

> <MOLECULAR_WEIGHT>
70.0468

> <EXACT_MASS>
70.005479308

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
5.795843695723499

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
prop-2-ynoic acid

> <ALOGPS_LOGP>
0.03

> <JCHEM_LOGP>
0.18196973299999997

> <ALOGPS_LOGS>
-1.72

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.9903685717786654

> <JCHEM_POLAR_SURFACE_AREA>
37.3

> <JCHEM_REFRACTIVITY>
15.783999999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.32e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
propiolic acid

> <JCHEM_VEBER_RULE>
1

$$$$
Download

3D-SDF for HMDB0006804 (Propynoic acid)

HMDB0006804
     RDKit          3D
Propynoic acid
  7  6  0  0  0  0  0  0  0  0999 V2000
    1.8318    0.1398   -0.1321 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6513   -0.1533   -0.1922 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7444   -0.4790   -0.2766 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1493   -1.5852    0.1574 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6810    0.3818   -0.8225 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8584    0.4059   -0.0873 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7668    1.2900   -0.4101 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  3  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  1  6  1  0
  5  7  1  0
M  END
Download

PDB for HMDB0006804 (Propynoic acid)

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  C   UNK     0      25.033 -17.802   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      23.701 -18.567   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      26.373 -18.567   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      25.033 -16.257   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      22.369 -19.340   0.000  0.00  0.00           C+0
CONECT    1    2    3    4                                                  
CONECT    2    1    5                                                       
CONECT    3    1                                                            
CONECT    4    1                                                            
CONECT    5    2                                                            
MASTER        0    0    0    0    0    0    0    0    5    0    8    0
END
Download

3D PDB for HMDB0006804 (Propynoic acid)

COMPND    HMDB0006804
HETATM    1  C1  UNL     1       1.832   0.140  -0.132  1.00  0.00           C  
HETATM    2  C2  UNL     1       0.651  -0.153  -0.192  1.00  0.00           C  
HETATM    3  C3  UNL     1      -0.744  -0.479  -0.277  1.00  0.00           C  
HETATM    4  O1  UNL     1      -1.149  -1.585   0.157  1.00  0.00           O  
HETATM    5  O2  UNL     1      -1.681   0.382  -0.822  1.00  0.00           O  
HETATM    6  H1  UNL     1       2.858   0.406  -0.087  1.00  0.00           H  
HETATM    7  H2  UNL     1      -1.767   1.290  -0.410  1.00  0.00           H  
CONECT    1    2    2    2    6
CONECT    2    3
CONECT    3    4    4    5
CONECT    5    7
END
Download

SMILES for HMDB0006804 (Propynoic acid)

OC(=O)C#C
Download

INCHI for HMDB0006804 (Propynoic acid)

InChI=1S/C3H2O2/c1-2-3(4)5/h1H,(H,4,5)
Download
View in JSmolView NMR AssignmentsView Stereo Labels
Synonyms
ValueSource
2-Propynoic acidChEBI
Acetylenecarboxylic acidChEBI
Acetylenic acidChEBI
CarboxyacetyleneChEBI
HC#ccoohChEBI
Propargylic acidChEBI
Propinic acidChEBI
PropinsaeureChEBI
Propiolic acidChEBI
PropiolsaeureChEBI
AcetylenemonocarboxylateKegg
2-PropynoateGenerator
AcetylenecarboxylateGenerator
AcetylenateGenerator
PropargylateGenerator
PropinateGenerator
PropiolateGenerator
Acetylenemonocarboxylic acidGenerator
PropynoateGenerator
Propiolic acid, monosodium saltHMDB
Chemical FormulaC3H2O2
Average Molecular Weight70.0468
Monoisotopic Molecular Weight70.005479308
IUPAC Nameprop-2-ynoic acid
Traditional Namepropiolic acid
CAS Registry Number471-25-0
SMILES
OC(=O)C#C
InChI Identifier
InChI=1S/C3H2O2/c1-2-3(4)5/h1H,(H,4,5)
InChI KeyUORVCLMRJXCDCP-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as carboxylic acids. Carboxylic acids are compounds containing a carboxylic acid group with the formula -C(=O)OH.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassCarboxylic acids
Direct ParentCarboxylic acids
Alternative Parents
Substituents
  • Acetylide
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Disposition

Source

Route of exposure

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 Solubility1.32 g/LALOGPS
logP10(0.03) g/LALOGPS
logP10(0.18) g/LChemAxon
logS10(-1.7) g/LALOGPS
pKa (Strongest Acidic)1.99ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity15.78 m³·mol⁻¹ChemAxon
Polarizability5.8 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]+111.68331661259
DarkChem[M-H]-103.38831661259
DeepCCS[M+H]+121.630932474
DeepCCS[M-H]-119.41930932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Propynoic acidOC(=O)C#C1496.2Standard polar33892256
Propynoic acidOC(=O)C#C642.3Standard non polar33892256
Propynoic acidOC(=O)C#C637.2Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Propynoic acid,1TMS,isomer #1C#CC(=O)O[Si](C)(C)C848.3Semi standard non polar33892256
Propynoic acid,1TBDMS,isomer #1C#CC(=O)O[Si](C)(C)C(C)(C)C1053.7Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Propynoic acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-00di-9000000000-4fe50bf7867f36e6b60b2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Propynoic acid GC-MS (1 TMS) - 70eV, Positivesplash10-00fr-9200000000-11dc3ec87a0f5813dfb22017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Propynoic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Propynoic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Propynoic acid LC-ESI-QQ , negative-QTOFsplash10-014i-9000000000-f647da344adbdf7bfb1b2017-09-14HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Propynoic acid 10V, Positive-QTOFsplash10-0udi-9000000000-aba6a2cb7cc1d727c5282017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Propynoic acid 20V, Positive-QTOFsplash10-0udi-9000000000-ac8e6e47367ea0619a462017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Propynoic acid 40V, Positive-QTOFsplash10-0ufr-9000000000-8dd4db44558079fb672f2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Propynoic acid 10V, Negative-QTOFsplash10-014i-9000000000-e10d8d809cd357e5fa452017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Propynoic acid 20V, Negative-QTOFsplash10-014i-9000000000-5272016322c64eb3692a2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Propynoic acid 40V, Negative-QTOFsplash10-014i-9000000000-85636846b0be925cb6da2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Propynoic acid 10V, Negative-QTOFsplash10-014i-9000000000-7ead964aa3fde51fb5d02021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Propynoic acid 20V, Negative-QTOFsplash10-014i-9000000000-7ead964aa3fde51fb5d02021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Propynoic acid 40V, Negative-QTOFsplash10-014i-9000000000-7ead964aa3fde51fb5d02021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Propynoic acid 10V, Positive-QTOFsplash10-0udi-9000000000-4b05fbfee0b3c72773db2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Propynoic acid 20V, Positive-QTOFsplash10-0udi-9000000000-4b05fbfee0b3c72773db2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Propynoic acid 40V, Positive-QTOFsplash10-0udi-9000000000-4b05fbfee0b3c72773db2021-09-23Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 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, 1000 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, 200 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, 300 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, 400 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, 500 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, 600 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, 700 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, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart 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 IDFDB024090
KNApSAcK IDNot Available
Chemspider ID9706
KEGG Compound IDC00804
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkPropiolic acid
METLIN IDNot Available
PubChem Compound10110
PDB IDNot Available
ChEBI ID33199
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

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
Reactions
2-Propyn-1-al + NAD + Water → Propynoic acid + NADH + Hydrogen Iondetails
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
Reactions
2-Propyn-1-al + NAD + Water → Propynoic acid + NADH + Hydrogen Iondetails
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
Reactions
2-Propyn-1-al + NAD + Water → Propynoic acid + NADH + Hydrogen Iondetails
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
Reactions
2-Propyn-1-al + NAD + Water → Propynoic acid + NADH + Hydrogen Iondetails
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
Reactions
2-Propyn-1-al + NAD + Water → Propynoic acid + NADH + Hydrogen Iondetails