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Showing NP-Card for Phenylpropiolic acid (NP0000270)

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Record Information
Version2.0
Created at2006-05-22 14:17:50 UTC
Updated at2024-09-17 15:41:29 UTC
NP-MRD IDNP0000270
Secondary Accession NumbersNone
Natural Product Identification
Common NamePhenylpropiolic acid
DescriptionPhenylpropiolic acid is an acetylenic compound that is propynoic acid in which the acetylenic hydrogen is replaced by a phenyl group. It is an alpha,beta-unsaturated monocarboxylic acid, an acetylenic compound and a member of benzenes. It derives from a propynoic acid. Phenylpropiolic acid is one of a number of phenylpropanoid, natural products occurring in plants pathways involved in plant resistance providing building units of physical barriers against pathogen invasion, synthesizing an array of antibiotic compounds, and producing signals implicated in the mounting of plant resistance. (PMID 15199968 ). Phenylpropiolic acid is a cis-pyrrolidinone that has been tested as an inhibitors of type II 17beta-hydroxysteroid dehydrogenase for the treatment of osteoporosis. (PMID 16806919 ). Phenylpropiolic acid (C6H5CCCO2H) is formed by the action of alcoholic potash on cinnamic acid dibromide (C6H5CHBrCHBrCO2H), crystallizes in long needles or prisms which melt at 136–137 °C. When heated with water to 120 °C, it yields phenylacetylene (C6H5CCH). Chromic acid oxidizes it to benzoic acid; zinc and acetic acid reduce it to cinnamic acid, C6H5CH=CHCO2H, whilst sodium amalgam reduces it to hydrocinnamic acid, C6H5CH2CH2CO2H. Ortho-nitrophenylpropiolic acid, NO2C6H4CCCO2H, prepared by the action of alcoholic potash on ortho-nitrocinnamic acid dibromide, crystallizes in needles which decompose when heated to 155–156 °C. It is readily converted into indigo.
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0000270 (Phenylpropiolic acid)


  Mrv1652305271900262D          

 11 11  0  0  0  0            999 V2000
   15.9806  -12.5103    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6974  -12.9188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2675  -12.9188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6974  -13.7432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2675  -13.7432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9806  -14.1592    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9797  -11.6854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9788  -10.8604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9780  -10.0354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2630   -9.6237    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.6920   -9.6222    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  3  1  2  0  0  0  0
  4  2  2  0  0  0  0
  5  3  1  0  0  0  0
  6  4  1  0  0  0  0
  6  5  2  0  0  0  0
  8  7  3  0  0  0  0
  1  7  1  0  0  0  0
 10  9  2  0  0  0  0
 11  9  1  0  0  0  0
  8  9  1  0  0  0  0
M  END
Download

3D MOL for NP0000270 (Phenylpropiolic acid)

HMDB0002359
     RDKit          3D
Phenylpropiolic acid
 17 17  0  0  0  0  0  0  0  0999 V2000
    4.3653   -0.6670   -1.3347 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8229   -0.3741   -0.2381 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6203   -0.1827    0.8754 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3919   -0.2578   -0.2213 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1875   -0.1506   -0.1882 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2460   -0.0175   -0.1277 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8787    1.1771   -0.3934 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2525    1.3230   -0.3401 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0487    0.2493   -0.0111 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4122   -0.9594    0.2580 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0419   -1.0953    0.2024 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2936    0.2502    1.7287 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2830    2.0340   -0.6533 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7566    2.2570   -0.5472 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1368    0.3144    0.0440 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0105   -1.8367    0.5233 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6145   -2.0640    0.4234 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
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11  6  1  0
  3 12  1  0
  7 13  1  0
  8 14  1  0
  9 15  1  0
 10 16  1  0
 11 17  1  0
M  END
Download

3D SDF for NP0000270 (Phenylpropiolic acid)


  Mrv1652305271900262D          

 11 11  0  0  0  0            999 V2000
   15.9806  -12.5103    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6974  -12.9188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2675  -12.9188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6974  -13.7432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2675  -13.7432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9806  -14.1592    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9797  -11.6854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9788  -10.8604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9780  -10.0354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2630   -9.6237    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.6920   -9.6222    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  3  1  2  0  0  0  0
  4  2  2  0  0  0  0
  5  3  1  0  0  0  0
  6  4  1  0  0  0  0
  6  5  2  0  0  0  0
  8  7  3  0  0  0  0
  1  7  1  0  0  0  0
 10  9  2  0  0  0  0
 11  9  1  0  0  0  0
  8  9  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0000270

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC(=O)C#CC1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C9H6O2/c10-9(11)7-6-8-4-2-1-3-5-8/h1-5H,(H,10,11)

> <INCHI_KEY>
XNERWVPQCYSMLC-UHFFFAOYSA-N

> <FORMULA>
C9H6O2

> <MOLECULAR_WEIGHT>
146.1427

> <EXACT_MASS>
146.036779436

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
17

> <JCHEM_AVERAGE_POLARIZABILITY>
14.955031662274806

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-phenylprop-2-ynoic acid

> <ALOGPS_LOGP>
1.70

> <JCHEM_LOGP>
2.1522037989999996

> <ALOGPS_LOGS>
-2.87

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.7746714851315857

> <JCHEM_POLAR_SURFACE_AREA>
37.3

> <JCHEM_REFRACTIVITY>
38.4483

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.97e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
phenylpropiolic acid

> <JCHEM_VEBER_RULE>
1

$$$$
Download

3D-SDF for NP0000270 (Phenylpropiolic acid)

HMDB0002359
     RDKit          3D
Phenylpropiolic acid
 17 17  0  0  0  0  0  0  0  0999 V2000
    4.3653   -0.6670   -1.3347 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8229   -0.3741   -0.2381 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6203   -0.1827    0.8754 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3919   -0.2578   -0.2213 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1875   -0.1506   -0.1882 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2460   -0.0175   -0.1277 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8787    1.1771   -0.3934 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2525    1.3230   -0.3401 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0487    0.2493   -0.0111 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4122   -0.9594    0.2580 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0419   -1.0953    0.2024 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2936    0.2502    1.7287 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2830    2.0340   -0.6533 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7566    2.2570   -0.5472 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1368    0.3144    0.0440 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0105   -1.8367    0.5233 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6145   -2.0640    0.4234 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
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11  6  1  0
  3 12  1  0
  7 13  1  0
  8 14  1  0
  9 15  1  0
 10 16  1  0
 11 17  1  0
M  END
Download

PDB for NP0000270 (Phenylpropiolic acid)

HEADER    PROTEIN                                 27-MAY-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-19         0                                  
HETATM    1  C   UNK     0      29.830 -23.353   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      31.168 -24.115   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      28.499 -24.115   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      31.168 -25.654   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      28.499 -25.654   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      29.830 -26.431   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      29.829 -21.813   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      29.827 -20.273   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      29.826 -18.733   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      28.491 -17.964   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0      31.158 -17.961   0.000  0.00  0.00           O+0
CONECT    1    2    3    7                                                  
CONECT    2    1    4                                                       
CONECT    3    1    5                                                       
CONECT    4    2    6                                                       
CONECT    5    3    6                                                       
CONECT    6    4    5                                                       
CONECT    7    8    1                                                       
CONECT    8    7    9                                                       
CONECT    9   10   11    8                                                  
CONECT   10    9                                                            
CONECT   11    9                                                            
MASTER        0    0    0    0    0    0    0    0   11    0   22    0
END
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3D PDB for NP0000270 (Phenylpropiolic acid)

COMPND    HMDB0002359
HETATM    1  O1  UNL     1       4.365  -0.667  -1.335  1.00  0.00           O  
HETATM    2  C1  UNL     1       3.823  -0.374  -0.238  1.00  0.00           C  
HETATM    3  O2  UNL     1       4.620  -0.183   0.875  1.00  0.00           O  
HETATM    4  C2  UNL     1       2.392  -0.258  -0.221  1.00  0.00           C  
HETATM    5  C3  UNL     1       1.188  -0.151  -0.188  1.00  0.00           C  
HETATM    6  C4  UNL     1      -0.246  -0.018  -0.128  1.00  0.00           C  
HETATM    7  C5  UNL     1      -0.879   1.177  -0.393  1.00  0.00           C  
HETATM    8  C6  UNL     1      -2.252   1.323  -0.340  1.00  0.00           C  
HETATM    9  C7  UNL     1      -3.049   0.249  -0.011  1.00  0.00           C  
HETATM   10  C8  UNL     1      -2.412  -0.959   0.258  1.00  0.00           C  
HETATM   11  C9  UNL     1      -1.042  -1.095   0.202  1.00  0.00           C  
HETATM   12  H1  UNL     1       4.294   0.250   1.729  1.00  0.00           H  
HETATM   13  H2  UNL     1      -0.283   2.034  -0.653  1.00  0.00           H  
HETATM   14  H3  UNL     1      -2.757   2.257  -0.547  1.00  0.00           H  
HETATM   15  H4  UNL     1      -4.137   0.314   0.044  1.00  0.00           H  
HETATM   16  H5  UNL     1      -3.010  -1.837   0.523  1.00  0.00           H  
HETATM   17  H6  UNL     1      -0.614  -2.064   0.423  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    4
CONECT    3   12
CONECT    4    5    5    5
CONECT    5    6
CONECT    6    7    7   11
CONECT    7    8   13
CONECT    8    9    9   14
CONECT    9   10   15
CONECT   10   11   11   16
CONECT   11   17
END
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SMILES for NP0000270 (Phenylpropiolic acid)

OC(=O)C#CC1=CC=CC=C1
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INCHI for NP0000270 (Phenylpropiolic acid)

InChI=1S/C9H6O2/c10-9(11)7-6-8-4-2-1-3-5-8/h1-5H,(H,10,11)
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View in JSmolView NMR Assignments
Synonyms
ValueSource
3-Phenylpropiolic acidChEBI
3-Phenylpropynoic acidChEBI
beta-Phenylpropargylic acidChEBI
Phenylacetylene monocarboxylic acidChEBI
Phenylacetylenecarboxylic acidChEBI
Phenylpropynoic acidChEBI
3-PhenylpropiolateGenerator
3-PhenylpropynoateGenerator
b-PhenylpropargylateGenerator
b-Phenylpropargylic acidGenerator
beta-PhenylpropargylateGenerator
Β-phenylpropargylateGenerator
Β-phenylpropargylic acidGenerator
Phenylacetylene monocarboxylateGenerator
PhenylacetylenecarboxylateGenerator
PhenylpropynoateGenerator
PhenylpropiolateGenerator
3-Phenyl-2-propynoateHMDB
3-Phenyl-2-propynoic acidHMDB
3-Phenyl-propiolateHMDB
3-Phenyl-propiolic acidHMDB
Phenyl-(8ci)propiolateHMDB
Phenyl-(8ci)propiolic acidHMDB
Phenyl-propiolateHMDB
Phenyl-propiolic acidHMDB
PhenylpropioplateHMDB
Phenylpropioplic acidHMDB
Chemical FormulaC9H6O2
Average Mass146.1427 Da
Monoisotopic Mass146.03678 Da
IUPAC Name3-phenylprop-2-ynoic acid
Traditional Namephenylpropiolic acid
CAS Registry Number637-44-5
SMILES
OC(=O)C#CC1=CC=CC=C1
InChI Identifier
InChI=1S/C9H6O2/c10-9(11)7-6-8-4-2-1-3-5-8/h1-5H,(H,10,11)
InChI KeyXNERWVPQCYSMLC-UHFFFAOYSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
  • Plantae
    • Chemical Taxonomy
    Description Belongs to the class of organic compounds known as benzene and substituted derivatives. These are aromatic compounds containing one monocyclic ring system consisting of benzene.
    KingdomOrganic compounds
    Super ClassBenzenoids
    ClassBenzene and substituted derivatives
    Sub ClassNot Available
    Direct ParentBenzene and substituted derivatives
    Alternative Parents
    Substituents
    • Monocyclic benzene moiety
    • Monocarboxylic acid or derivatives
    • Carboxylic acid
    • Carboxylic acid derivative
    • Organic oxygen compound
    • Organic oxide
    • Hydrocarbon derivative
    • Organooxygen compound
    • Carbonyl group
    • Aromatic homomonocyclic compound
    Molecular FrameworkAromatic homomonocyclic compounds
    External DescriptorsNot Available
    Physical Properties
    StateSolid
    Experimental Properties
    PropertyValueReference
    Melting Point136 - 139 °CNot Available
    Boiling PointNot AvailableNot Available
    Water SolubilityNot AvailableNot Available
    LogPNot AvailableNot Available
    Predicted Properties
    PropertyValueSource
    Water Solubility0.2 g/LALOGPS
    logP1.7ALOGPS
    logP2.15ChemAxon
    logS-2.9ALOGPS
    pKa (Strongest Acidic)2.77ChemAxon
    Physiological Charge-1ChemAxon
    Hydrogen Acceptor Count2ChemAxon
    Hydrogen Donor Count1ChemAxon
    Polar Surface Area37.3 ŲChemAxon
    Rotatable Bond Count2ChemAxon
    Refractivity38.45 m³·mol⁻¹ChemAxon
    Polarizability14.96 ųChemAxon
    Number of Rings1ChemAxon
    BioavailabilityYesChemAxon
    Rule of FiveYesChemAxon
    Ghose FilterNoChemAxon
    Veber's RuleYesChemAxon
    MDDR-like RuleNoChemAxon
    HMDB IDHMDB0002359
    DrugBank IDNot Available
    Phenol Explorer Compound IDNot Available
    FoodDB IDFDB022977
    KNApSAcK IDNot Available
    Chemspider ID62682
    KEGG Compound IDNot Available
    BioCyc IDNot Available
    BiGG IDNot Available
    Wikipedia LinkPhenylpropiolic_acid
    METLIN ID6644
    PubChem Compound69475
    PDB IDNot Available
    ChEBI ID90355
    Good Scents IDNot Available
    References
    General References
    1. Zielinski M, Zielinska A, Papiernik-Zielinska H, Ogrinc N, Kobal I: Carbon isotope fractionation in the decarboxylation of phenylpropiolic acid in hydrogen donating media. Isotopes Environ Health Stud. 2001;37(3):239-52. doi: 10.1080/10256010108033299. [PubMed:11924854 ]
    2. Okuma K, Koda M, Maekawa S, Shioji K, Inoue T, Kurisaki T, Wakita H, Yokomori Y: Reaction of thioketones with propiolic acids. Org Biomol Chem. 2006 Jul 21;4(14):2745-52. doi: 10.1039/b605068a. Epub 2006 Jun 12. [PubMed:16826299 ]
    3. Arderne C, Olivier DK, Ndinteh DT: Charge-assisted hydrogen bonding in salts of 2-amino-1H-benzimidazole with 3-phenylpropynoic acid and oct-2-ynoic acid. Acta Crystallogr C Struct Chem. 2015 Feb;71(Pt 2):146-51. doi: 10.1107/S2053229615001047. Epub 2015 Jan 24. [PubMed:25652283 ]