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Showing metabocard for Phenylpropiolic acid (HMDB0002359)

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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2006-05-22 14:17:50 UTC
Update Date2023-02-21 17:16:22 UTC
HMDB IDHMDB0002359
Secondary Accession Numbers
  • HMDB02359
Metabolite 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
Data?1676999782
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0002359 (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 HMDB0002359 (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
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3D SDF for HMDB0002359 (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>
HMDB0002359

> <DATABASE_NAME>
hmdb

> <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

$$$$
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3D-SDF for HMDB0002359 (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
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PDB for HMDB0002359 (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 HMDB0002359 (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 HMDB0002359 (Phenylpropiolic acid)

OC(=O)C#CC1=CC=CC=C1
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INCHI for HMDB0002359 (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 Stereo Labels
Synonyms
Chemical FormulaC9H6O2
Average Molecular Weight146.1427
Monoisotopic Molecular Weight146.036779436
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
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
Ontology
Physiological effectNot Available
Disposition
Biological locationSource
ProcessNot Available
Role
Industrial application
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point136 - 139 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
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 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
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. La Camera S, Gouzerh G, Dhondt S, Hoffmann L, Fritig B, Legrand M, Heitz T: Metabolic reprogramming in plant innate immunity: the contributions of phenylpropanoid and oxylipin pathways. Immunol Rev. 2004 Apr;198:267-84. [PubMed:15199968 ]
  2. Wood J, Bagi CM, Akuche C, Bacchiocchi A, Baryza J, Blue ML, Brennan C, Campbell AM, Choi S, Cook JH, Conrad P, Dixon BR, Ehrlich PP, Gane T, Gunn D, Joe T, Johnson JS, Jordan J, Kramss R, Liu P, Levy J, Lowe DB, McAlexander I, Natero R, Redman AM, Scott WJ, Town C, Wang M, Wang Y, Zhang Z: 4,5-Disubstituted cis-pyrrolidinones as inhibitors of type II 17beta-hydroxysteroid dehydrogenase. Part 3. Identification of lead candidate. Bioorg Med Chem Lett. 2006 Sep 15;16(18):4965-8. Epub 2006 Jun 27. [PubMed:16806919 ]