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Showing NP-Card for Acetylenedicarboxylic acid (NP0002731)

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Record Information
Version2.0
Created at2020-11-23 19:39:02 UTC
Updated at2021-08-12 19:51:59 UTC
NP-MRD IDNP0002731
Secondary Accession NumbersNone
Natural Product Identification
Common NameAcetylenedicarboxylic acid
Provided ByBMRBBMRB logo
DescriptionAcetylenedicarboxylic acid, also known as 2-butynedioic acid, belongs to the class of organic compounds known as dicarboxylic acids and derivatives. These are organic compounds containing exactly two carboxylic acid groups. Acetylenedicarboxylic 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. Acetylenedicarboxylic acid was first documented in 2000 (PMID: 10843633). Based on a literature review a small amount of articles have been published on Acetylenedicarboxylic acid (PMID: 33403487) (PMID: 20795634).
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0002731 (Acetylenedicarboxylic acid)


     RDKit          2D

 10  9  0  0  0  0  0  0  0  0999 V2000
   -2.7786    1.7225    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2260    0.3280    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1573   -0.8479    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7420    0.1093    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7420   -0.1093    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2260   -0.3280    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7786   -1.7225    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1573    0.8479    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6413   -0.6292    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6413    0.6292    0.0000 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 MOL for NP0002731 (Acetylenedicarboxylic acid)

NP0002731
     RDKit          3D

 10  9  0  0  0  0  0  0  0  0999 V2000
   -2.4256   -1.8554    0.1898 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0244   -0.6603    0.2577 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9366    0.3464    0.3532 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6080   -0.4182    0.2305 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5934   -0.2343    0.2074 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0228   -0.0297    0.1600 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8406   -0.9535    0.4476 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5582    1.1951   -0.2049 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8242    1.2476    0.7523 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8038    1.3623   -1.1716 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 NP0002731 (Acetylenedicarboxylic acid)


     RDKit          2D

 10  9  0  0  0  0  0  0  0  0999 V2000
   -2.7786    1.7225    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2260    0.3280    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1573   -0.8479    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7420    0.1093    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7420   -0.1093    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2260   -0.3280    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7786   -1.7225    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1573    0.8479    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6413   -0.6292    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6413    0.6292    0.0000 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
> <DATABASE_ID>
NP0002731

> <DATABASE_NAME>
NP-MRD

> <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

> <JCHEM_LOGP>
0.21009242533333328

> <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

> <JCHEM_TRADITIONAL_IUPAC>
acetylenedicarboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for NP0002731 (Acetylenedicarboxylic acid)

NP0002731
     RDKit          3D

 10  9  0  0  0  0  0  0  0  0999 V2000
   -2.4256   -1.8554    0.1898 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0244   -0.6603    0.2577 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9366    0.3464    0.3532 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6080   -0.4182    0.2305 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5934   -0.2343    0.2074 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0228   -0.0297    0.1600 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8406   -0.9535    0.4476 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5582    1.1951   -0.2049 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8242    1.2476    0.7523 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8038    1.3623   -1.1716 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 NP0002731 (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 NP0002731 (Acetylenedicarboxylic acid)

COMPND    NP0002731
HETATM    1  O1  UNL     1      -2.426  -1.855   0.190  1.00  0.00           O  
HETATM    2  C1  UNL     1      -2.024  -0.660   0.258  1.00  0.00           C  
HETATM    3  O2  UNL     1      -2.937   0.346   0.353  1.00  0.00           O  
HETATM    4  C2  UNL     1      -0.608  -0.418   0.230  1.00  0.00           C  
HETATM    5  C3  UNL     1       0.593  -0.234   0.207  1.00  0.00           C  
HETATM    6  C4  UNL     1       2.023  -0.030   0.160  1.00  0.00           C  
HETATM    7  O3  UNL     1       2.841  -0.954   0.448  1.00  0.00           O  
HETATM    8  O4  UNL     1       2.558   1.195  -0.205  1.00  0.00           O  
HETATM    9  H1  UNL     1      -2.824   1.248   0.752  1.00  0.00           H  
HETATM   10  H2  UNL     1       2.804   1.362  -1.172  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 NP0002731 (Acetylenedicarboxylic acid)

OC(=O)C#CC(O)=O
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INCHI for NP0002731 (Acetylenedicarboxylic acid)

InChI=1S/C4H2O4/c5-3(6)1-2-4(7)8/h(H,5,6)(H,7,8)
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Synonyms
ValueSource
2-Butynedioic acidChEBI
2-ButynedioateGenerator
AcetylenedicarboxylateGenerator
ButynedioateHMDB
2-Butynedioic acid, potassium saltHMDB
Acetylenedicarboxylic acidChEBI
Chemical FormulaC4H2O4
Average Mass114.0560 Da
Monoisotopic Mass113.99531 Da
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
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of OriginNot Available
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
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP0.21ChemAxon
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
HMDB IDHMDB0247933
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID362
KEGG Compound IDC03248
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkAcetylenedicarboxylic_acid
METLIN IDNot Available
PubChem Compound371
PDB IDNot Available
ChEBI ID30781
Good Scents IDNot Available
References
General References
  1. Domingo LR, Picher MT, Andres J: Toward an understanding of the selectivity in domino reactions. A DFT study of the reaction between acetylenedicarboxylic acid and 1, 3-Bis(2-furyl)propane J Org Chem. 2000 Jun 2;65(11):3473-7. doi: 10.1021/jo000030k. [PubMed:10843633 ]
  2. Pahlavan Yali M, Hajmalek M: Interactions Between Brassicae napus and Pseudomonas putida (Strain ATCC12633) and Characterization of Volatile Organic Compounds Produced by the Bacterium. Curr Microbiol. 2021 Feb;78(2):679-687. doi: 10.1007/s00284-020-02335-2. Epub 2021 Jan 5. [PubMed:33403487 ]
  3. Park K, Bae G, Moon J, Choe J, Song KH, Lee S: Synthesis of symmetrical and unsymmetrical diarylalkynes from propiolic acid using palladium-catalyzed decarboxylative coupling. J Org Chem. 2010 Sep 17;75(18):6244-51. doi: 10.1021/jo101398a. [PubMed:20795634 ]