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Showing metabocard for Acetylenedicarboxylic acid (HMDB0247933)

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IdentificationTaxonomyOntologyPhysical propertiesSpectraBiological propertiesConcentrationsLinksReferencesXML
Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2021-09-11 01:05:09 UTC
Update Date2021-09-26 22:57:53 UTC
HMDB IDHMDB0247933
Secondary Accession NumbersNone
Metabolite Identification
Common NameAcetylenedicarboxylic acid
Descriptionbutynedioic acid, also known as 2-butynedioate, belongs to the class of organic compounds known as dicarboxylic acids and derivatives. These are organic compounds containing exactly two carboxylic acid groups. butynedioic acid is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. Based on a literature review a small amount of articles have been published on butynedioic acid. This compound has been identified in human blood as reported by (PMID: 31557052 ). Acetylenedicarboxylic acid is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Acetylenedicarboxylic acid 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 HMDB0247933 (Acetylenedicarboxylic acid)


  Mrv1652311232020392D          

  8  7  0  0  0  0            999 V2000
    0.8250    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8250    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625    0.7145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625   -0.7145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2375   -0.7145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2375    0.7145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  3  0  0  0  0
  3  1  1  0  0  0  0
  4  2  1  0  0  0  0
  5  3  2  0  0  0  0
  6  3  1  0  0  0  0
  7  4  2  0  0  0  0
  8  4  1  0  0  0  0
M  END
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3D MOL for HMDB0247933 (Acetylenedicarboxylic acid)

HMDB0247933
     RDKit          3D
Acetylenedicarboxylic acid
 10  9  0  0  0  0  0  0  0  0999 V2000
   -2.4963    1.6522    0.7327 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0904    0.6456    0.1127 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9983   -0.0729   -0.6385 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7134    0.2822    0.2063 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4559   -0.0284    0.2663 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8387   -0.4183    0.3294 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2583   -1.2446    1.1976 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7781    0.0918   -0.5573 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7805   -1.0587   -0.8525 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7479    0.1511   -0.3196 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  3  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  3  9  1  0
  8 10  1  0
M  END
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3D SDF for HMDB0247933 (Acetylenedicarboxylic acid)


  Mrv1652311232020392D          

  8  7  0  0  0  0            999 V2000
    0.8250    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8250    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625    0.7145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625   -0.7145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2375   -0.7145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2375    0.7145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  3  0  0  0  0
  3  1  1  0  0  0  0
  4  2  1  0  0  0  0
  5  3  2  0  0  0  0
  6  3  1  0  0  0  0
  7  4  2  0  0  0  0
  8  4  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0247933

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C4H2O4/c5-3(6)1-2-4(7)8/h(H,5,6)(H,7,8)

> <INCHI_KEY>
YTIVTFGABIZHHX-UHFFFAOYSA-N

> <FORMULA>
C4H2O4

> <MOLECULAR_WEIGHT>
114.056

> <EXACT_MASS>
113.995308544

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
10

> <JCHEM_AVERAGE_POLARIZABILITY>
8.964350274077521

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
but-2-ynedioic acid

> <ALOGPS_LOGP>
-0.31

> <JCHEM_LOGP>
0.21009242533333328

> <ALOGPS_LOGS>
-1.76

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
2.3859500244461347

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.1306460197286032

> <JCHEM_POLAR_SURFACE_AREA>
74.6

> <JCHEM_REFRACTIVITY>
23.002

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.00e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
acetylenedicarboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for HMDB0247933 (Acetylenedicarboxylic acid)

HMDB0247933
     RDKit          3D
Acetylenedicarboxylic acid
 10  9  0  0  0  0  0  0  0  0999 V2000
   -2.4963    1.6522    0.7327 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0904    0.6456    0.1127 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9983   -0.0729   -0.6385 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7134    0.2822    0.2063 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4559   -0.0284    0.2663 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8387   -0.4183    0.3294 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2583   -1.2446    1.1976 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7781    0.0918   -0.5573 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7805   -1.0587   -0.8525 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7479    0.1511   -0.3196 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  3  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  3  9  1  0
  8 10  1  0
M  END
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PDB for HMDB0247933 (Acetylenedicarboxylic acid)

HEADER    PROTEIN                                 23-NOV-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-NOV-20         0                                  
HETATM    1  C   UNK     0       1.540   0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.080   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.540   0.000   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       3.850   1.334   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0       3.850  -1.334   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0      -2.310  -1.334   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0      -2.310   1.334   0.000  0.00  0.00           O+0
CONECT    1    2    3                                                       
CONECT    2    1    4                                                       
CONECT    3    1    5    6                                                  
CONECT    4    2    7    8                                                  
CONECT    5    3                                                            
CONECT    6    3                                                            
CONECT    7    4                                                            
CONECT    8    4                                                            
MASTER        0    0    0    0    0    0    0    0    8    0   14    0
END
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3D PDB for HMDB0247933 (Acetylenedicarboxylic acid)

COMPND    HMDB0247933
HETATM    1  O1  UNL     1      -2.496   1.652   0.733  1.00  0.00           O  
HETATM    2  C1  UNL     1      -2.090   0.646   0.113  1.00  0.00           C  
HETATM    3  O2  UNL     1      -2.998  -0.073  -0.639  1.00  0.00           O  
HETATM    4  C2  UNL     1      -0.713   0.282   0.206  1.00  0.00           C  
HETATM    5  C3  UNL     1       0.456  -0.028   0.266  1.00  0.00           C  
HETATM    6  C4  UNL     1       1.839  -0.418   0.329  1.00  0.00           C  
HETATM    7  O3  UNL     1       2.258  -1.245   1.198  1.00  0.00           O  
HETATM    8  O4  UNL     1       2.778   0.092  -0.557  1.00  0.00           O  
HETATM    9  H1  UNL     1      -2.781  -1.059  -0.853  1.00  0.00           H  
HETATM   10  H2  UNL     1       3.748   0.151  -0.320  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    4
CONECT    3    9
CONECT    4    5    5    5
CONECT    5    6
CONECT    6    7    7    8
CONECT    8   10
END
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SMILES for HMDB0247933 (Acetylenedicarboxylic acid)

OC(=O)C#CC(O)=O
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INCHI for HMDB0247933 (Acetylenedicarboxylic acid)

InChI=1S/C4H2O4/c5-3(6)1-2-4(7)8/h(H,5,6)(H,7,8)
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View in JSmolView Stereo Labels
Synonyms
ValueSource
2-Butynedioic acidChEBI
Acetylenedicarboxylic acidChEBI
2-ButynedioateGenerator
AcetylenedicarboxylateGenerator
ButynedioateGenerator
2-Butynedioic acid, potassium saltMeSH
Chemical FormulaC4H2O4
Average Molecular Weight114.056
Monoisotopic Molecular Weight113.995308544
IUPAC Namebut-2-ynedioic acid
Traditional Nameacetylenedicarboxylic acid
CAS Registry NumberNot Available
SMILES
OC(=O)C#CC(O)=O
InChI Identifier
InChI=1S/C4H2O4/c5-3(6)1-2-4(7)8/h(H,5,6)(H,7,8)
InChI KeyYTIVTFGABIZHHX-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as dicarboxylic acids and derivatives. These are organic compounds containing exactly two carboxylic acid groups.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassDicarboxylic acids and derivatives
Direct ParentDicarboxylic acids and derivatives
Alternative Parents
Substituents
  • Fatty acyl
  • Fatty acid
  • Unsaturated fatty acid
  • Dicarboxylic 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
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-0.31ALOGPS
logP0.21ChemAxon
logS-1.8ALOGPS
pKa (Strongest Acidic)1.13ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area74.6 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity23 m³·mol⁻¹ChemAxon
Polarizability8.96 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+119.56730932474
DeepCCS[M-H]-116.76730932474
DeepCCS[M-2H]-153.15730932474
DeepCCS[M+Na]+127.77730932474
AllCCS[M+H]+125.932859911
AllCCS[M+H-H2O]+121.632859911
AllCCS[M+NH4]+129.932859911
AllCCS[M+Na]+131.132859911
AllCCS[M-H]-119.532859911
AllCCS[M+Na-2H]-122.532859911
AllCCS[M+HCOO]-125.932859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Acetylenedicarboxylic acidOC(=O)C#CC(O)=O1948.4Standard polar33892256
Acetylenedicarboxylic acidOC(=O)C#CC(O)=O967.9Standard non polar33892256
Acetylenedicarboxylic acidOC(=O)C#CC(O)=O1077.5Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Acetylenedicarboxylic acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-02t9-9300000000-633c354098d5b3134da42021-09-23Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Acetylenedicarboxylic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Acetylenedicarboxylic acid GC-MS (TMS_1_1) - 70eV, PositiveNot Available2021-11-03Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Acetylenedicarboxylic acid GC-MS (TMS_2_1) - 70eV, PositiveNot Available2021-11-03Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Acetylenedicarboxylic acid GC-MS (TBDMS_1_1) - 70eV, PositiveNot Available2021-11-03Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Acetylenedicarboxylic acid GC-MS (TBDMS_2_1) - 70eV, PositiveNot Available2021-11-03Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Acetylenedicarboxylic acid 10V, Positive-QTOFsplash10-0002-9000000000-b7295c0b58eb2db879bd2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Acetylenedicarboxylic acid 20V, Positive-QTOFsplash10-0gba-9000000000-12d56b36f307d7fc5a8d2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Acetylenedicarboxylic acid 40V, Positive-QTOFsplash10-0udi-9000000000-3e0ba403a6a5a32e80562021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Acetylenedicarboxylic acid 10V, Negative-QTOFsplash10-014i-9300000000-8dfc296297b789866a1f2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Acetylenedicarboxylic acid 20V, Negative-QTOFsplash10-014i-9000000000-7ead964aa3fde51fb5d02021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Acetylenedicarboxylic acid 40V, Negative-QTOFsplash10-014i-9000000000-7ead964aa3fde51fb5d02021-10-12Wishart 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 IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID362
KEGG Compound IDC03248
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkAcetylenedicarboxylic_acid
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI ID30781
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 ]