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Showing NP-Card for phenylacetylene (NP0197004)

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Record Information
Version2.0
Created at2022-09-04 15:11:22 UTC
Updated at2022-09-04 15:11:22 UTC
NP-MRD IDNP0197004
Secondary Accession NumbersNone
Natural Product Identification
Common Namephenylacetylene
DescriptionEthynylbenzene, also known as phenylacetylene, 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. In the laboratory, phenylacetylene can be prepared by elimination of hydrogen bromide from styrene dibromide using sodium amide in ammonia:It can also be prepared by the elimination of hydrogen bromide from bromostyrene using molten potassium hydroxide. Ethynylbenzene is possibly neutral. In research, it is sometimes used as an analog for acetylene; being a liquid, it is easier to handle than acetylene gas. Phenylacetylene is an alkyne hydrocarbon containing a phenyl group. Phenylacetylene can be reduced (hydrogenated) by hydrogen over Lindlar catalyst to give styrene. phenylacetylene is found in Tuber borchii. It exists as a colorless, viscous liquid (III) or mercury.
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0197004 (phenylacetylene)


  Mrv1533004181502022D          

  8  8  0  0  0  0            999 V2000
    0.7145    2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    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
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  3  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  3  8  1  0  0  0  0
M  END
Download

3D MOL for NP0197004 (phenylacetylene)

     RDKit          3D

 14 14  0  0  0  0  0  0  0  0999 V2000
    3.3752   -0.0738   -0.2806 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1628   -0.0428   -0.1897 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7272   -0.0074   -0.0645 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0226   -1.1358   -0.3049 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4039   -1.1067   -0.1858 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0807    0.0404    0.1745 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3361    1.1779    0.4177 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0383    1.1343    0.2953 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4295   -0.0930   -0.3457 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4903   -2.0608   -0.5927 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9874   -1.9971   -0.3761 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1650    0.0671    0.2690 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8689    2.0760    0.7000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6414    2.0217    0.4832 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
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  3  1  0
  1  9  1  0
  4 10  1  0
  5 11  1  0
  6 12  1  0
  7 13  1  0
  8 14  1  0
M  END
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3D SDF for NP0197004 (phenylacetylene)


  Mrv1533004181502022D          

  8  8  0  0  0  0            999 V2000
    0.7145    2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    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
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  3  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  3  8  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0197004

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C#CC1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C8H6/c1-2-8-6-4-3-5-7-8/h1,3-7H

> <INCHI_KEY>
UEXCJVNBTNXOEH-UHFFFAOYSA-N

> <FORMULA>
C8H6

> <MOLECULAR_WEIGHT>
102.136

> <EXACT_MASS>
102.046950193

> <JCHEM_ACCEPTOR_COUNT>
0

> <JCHEM_ATOM_COUNT>
14

> <JCHEM_AVERAGE_POLARIZABILITY>
11.593088867680159

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
ethynylbenzene

> <ALOGPS_LOGP>
2.50

> <JCHEM_LOGP>
2.1240811066666665

> <ALOGPS_LOGS>
-2.98

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_POLAR_SURFACE_AREA>
0.0

> <JCHEM_REFRACTIVITY>
31.2303

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.08e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
phenylacetylene

> <JCHEM_VEBER_RULE>
1

$$$$
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3D-SDF for NP0197004 (phenylacetylene)

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PDB for NP0197004 (phenylacetylene)
HEADER    PROTEIN                                 18-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   18-APR-15         0                                  
HETATM    1  C   UNK     0       1.334   5.390   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    8                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    3                                                       
MASTER        0    0    0    0    0    0    0    0    8    0   16    0
END

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3D PDB for NP0197004 (phenylacetylene)
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SMILES for NP0197004 (phenylacetylene)
C#CC1=CC=CC=C1
Download
INCHI for NP0197004 (phenylacetylene)
InChI=1S/C8H6/c1-2-8-6-4-3-5-7-8/h1,3-7H
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View in JSmol
Synonyms
ValueSource
PhenylacetyleneMeSH
Phenyl-acetyleneMeSH
PhenylethyneMeSH
1-EthynylbenzeneChEMBL
Chemical FormulaC8H6
Average Mass102.1360 Da
Monoisotopic Mass102.04695 Da
IUPAC Nameethynylbenzene
Traditional Namephenylacetylene
CAS Registry NumberNot Available
SMILES
C#CC1=CC=CC=C1
InChI Identifier
InChI=1S/C8H6/c1-2-8-6-4-3-5-7-8/h1,3-7H
InChI KeyUEXCJVNBTNXOEH-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Tuber borchiiLOTUS Database
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
    • 

  • Aromatic hydrocarbon
    • 

  • Acetylide
    • 

  • Unsaturated hydrocarbon
    • 

  • Acetylene
    • 

  • Hydrocarbon
    • 

  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
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
logP2.5ALOGPS
logP2.12ChemAxon
logS-3ALOGPS
Physiological Charge0ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area0 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity31.23 m³·mol⁻¹ChemAxon
Polarizability11.59 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkPhenylacetylene  
METLIN IDNot Available
PubChem Compound10821  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. LOTUS database [Link]