Np mrd loader

Showing NP-Card for 4-Ethylphenol (NP0000801)

Jump To Section:
IdentificationSpectraBioTaxonomyChemoTaxonomyPhysical propertiesLinksReferencesXML
Record Information
Version1.0
Created at2012-09-11 17:29:34 UTC
Updated at2021-08-19 23:58:29 UTC
NP-MRD IDNP0000801
Secondary Accession NumbersNone
Natural Product Identification
Common Name4-Ethylphenol
Description4-Ethylphenol belongs to the class of organic compounds known as 1-hydroxy-4-alkyl benzenoids. These are phenols that are substituted by an alkyl group at the para-position. 4-Ethylphenol exists in all living species, ranging from bacteria to humans. 4-Ethylphenol is an alcohol tasting compound. 4-Ethylphenol has been detected, but not quantified, in several different foods, such as arabica coffee, beers, corns, milk (cow), and red raspberries. 4-Ethylphenol is a potentially toxic compound, capable of producing respiratory distress, cardiovascular collapse, shock, ventricular tachycardia, and coma in an adult. Liver, lung, central nervous system and renal injury may also occur. In case of exposure to eyes, irrigate exposed eyes with copious amounts of room temperature water for at least 15 minutes. Monitor for respiratory distress in case of inhalation exposure. Systemic manifestations of toxicity may include nausea, vomiting, diarrhea, dyspnea, tachypnea, pallor, and profuse sweating.
Structure
Thumb
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0000801 (4-Ethylphenol)


  Mrv1652304272018562D          

  9  9  0  0  0  0            999 V2000
    1.6500    1.4290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    1.4290    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
   -0.4125    0.7144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4125   -0.7144    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
    0.4125    0.7144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125   -0.7144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8250   -1.4290    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  7  1  0  0  0  0
  3  5  2  0  0  0  0
  3  7  1  0  0  0  0
  4  6  1  0  0  0  0
  4  7  2  0  0  0  0
  5  8  1  0  0  0  0
  6  8  2  0  0  0  0
  8  9  1  0  0  0  0
M  END
Download

3D MOL for NP0000801 (4-Ethylphenol)

HMDB0029306
     RDKit          3D
4-Ethylphenol
 19 19  0  0  0  0  0  0  0  0999 V2000
   -2.6791    0.0678   -0.6189 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8675    0.1180    0.6621 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4201   -0.0300    0.4050 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3374    1.0951    0.1773 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6922    1.0427   -0.0700 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3172   -0.1818   -0.0910 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6920   -0.2651   -0.3395 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5887   -1.3469    0.1345 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2359   -1.2411    0.3773 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0131    1.0760   -0.9469 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0955   -0.3820   -1.4431 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6033   -0.5228   -0.4071 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1923   -0.6816    1.3457 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0467    1.1139    1.1197 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1630    2.0650    0.1948 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2492    1.9769   -0.2458 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1999    0.5740   -0.4989 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0796   -2.3113    0.1183 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3113   -2.1665    0.5506 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  6  8  1  0
  8  9  2  0
  9  3  1  0
  1 10  1  0
  1 11  1  0
  1 12  1  0
  2 13  1  0
  2 14  1  0
  4 15  1  0
  5 16  1  0
  7 17  1  0
  8 18  1  0
  9 19  1  0
M  END
Download

3D SDF for NP0000801 (4-Ethylphenol)


  Mrv1652304272018562D          

  9  9  0  0  0  0            999 V2000
    1.6500    1.4290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    1.4290    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
   -0.4125    0.7144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4125   -0.7144    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
    0.4125    0.7144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125   -0.7144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8250   -1.4290    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  7  1  0  0  0  0
  3  5  2  0  0  0  0
  3  7  1  0  0  0  0
  4  6  1  0  0  0  0
  4  7  2  0  0  0  0
  5  8  1  0  0  0  0
  6  8  2  0  0  0  0
  8  9  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0000801

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCC1=CC=C(O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C8H10O/c1-2-7-3-5-8(9)6-4-7/h3-6,9H,2H2,1H3

> <INCHI_KEY>
HXDOZKJGKXYMEW-UHFFFAOYSA-N

> <FORMULA>
C8H10O

> <MOLECULAR_WEIGHT>
122.1644

> <EXACT_MASS>
122.073164942

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
19

> <JCHEM_AVERAGE_POLARIZABILITY>
13.85867636702929

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
4-ethylphenol

> <ALOGPS_LOGP>
2.54

> <JCHEM_LOGP>
2.627670548666667

> <ALOGPS_LOGS>
-1.30

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.319334469148892

> <JCHEM_PKA_STRONGEST_BASIC>
-5.439522161866621

> <JCHEM_POLAR_SURFACE_AREA>
20.23

> <JCHEM_REFRACTIVITY>
37.6811

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.15e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
ethylphenol

> <JCHEM_VEBER_RULE>
1

$$$$
Download

3D-SDF for NP0000801 (4-Ethylphenol)

HMDB0029306
     RDKit          3D
4-Ethylphenol
 19 19  0  0  0  0  0  0  0  0999 V2000
   -2.6791    0.0678   -0.6189 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8675    0.1180    0.6621 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4201   -0.0300    0.4050 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3374    1.0951    0.1773 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6922    1.0427   -0.0700 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3172   -0.1818   -0.0910 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6920   -0.2651   -0.3395 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5887   -1.3469    0.1345 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2359   -1.2411    0.3773 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0131    1.0760   -0.9469 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0955   -0.3820   -1.4431 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6033   -0.5228   -0.4071 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1923   -0.6816    1.3457 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0467    1.1139    1.1197 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1630    2.0650    0.1948 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2492    1.9769   -0.2458 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1999    0.5740   -0.4989 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0796   -2.3113    0.1183 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3113   -2.1665    0.5506 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  6  8  1  0
  8  9  2  0
  9  3  1  0
  1 10  1  0
  1 11  1  0
  1 12  1  0
  2 13  1  0
  2 14  1  0
  4 15  1  0
  5 16  1  0
  7 17  1  0
  8 18  1  0
  9 19  1  0
M  END
Download

PDB for NP0000801 (4-Ethylphenol)

HEADER    PROTEIN                                 27-APR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-APR-20         0                                  
HETATM    1  C   UNK     0       3.080   2.667   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.540   2.667   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.540   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.770   1.334   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.770  -1.334   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.540   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.770   1.334   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.770  -1.334   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -1.540  -2.667   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    7                                                       
CONECT    3    5    7                                                       
CONECT    4    6    7                                                       
CONECT    5    3    8                                                       
CONECT    6    4    8                                                       
CONECT    7    2    3    4                                                  
CONECT    8    5    6    9                                                  
CONECT    9    8                                                            
MASTER        0    0    0    0    0    0    0    0    9    0   18    0
END
Download

3D PDB for NP0000801 (4-Ethylphenol)

COMPND    HMDB0029306
HETATM    1  C1  UNL     1      -2.679   0.068  -0.619  1.00  0.00           C  
HETATM    2  C2  UNL     1      -1.867   0.118   0.662  1.00  0.00           C  
HETATM    3  C3  UNL     1      -0.420  -0.030   0.405  1.00  0.00           C  
HETATM    4  C4  UNL     1       0.337   1.095   0.177  1.00  0.00           C  
HETATM    5  C5  UNL     1       1.692   1.043  -0.070  1.00  0.00           C  
HETATM    6  C6  UNL     1       2.317  -0.182  -0.091  1.00  0.00           C  
HETATM    7  O1  UNL     1       3.692  -0.265  -0.340  1.00  0.00           O  
HETATM    8  C7  UNL     1       1.589  -1.347   0.135  1.00  0.00           C  
HETATM    9  C8  UNL     1       0.236  -1.241   0.377  1.00  0.00           C  
HETATM   10  H1  UNL     1      -3.013   1.076  -0.947  1.00  0.00           H  
HETATM   11  H2  UNL     1      -2.096  -0.382  -1.443  1.00  0.00           H  
HETATM   12  H3  UNL     1      -3.603  -0.523  -0.407  1.00  0.00           H  
HETATM   13  H4  UNL     1      -2.192  -0.682   1.346  1.00  0.00           H  
HETATM   14  H5  UNL     1      -2.047   1.114   1.120  1.00  0.00           H  
HETATM   15  H6  UNL     1      -0.163   2.065   0.195  1.00  0.00           H  
HETATM   16  H7  UNL     1       2.249   1.977  -0.246  1.00  0.00           H  
HETATM   17  H8  UNL     1       4.200   0.574  -0.499  1.00  0.00           H  
HETATM   18  H9  UNL     1       2.080  -2.311   0.118  1.00  0.00           H  
HETATM   19  H10 UNL     1      -0.311  -2.167   0.551  1.00  0.00           H  
CONECT    1    2   10   11   12
CONECT    2    3   13   14
CONECT    3    4    4    9
CONECT    4    5   15
CONECT    5    6    6   16
CONECT    6    7    8
CONECT    7   17
CONECT    8    9    9   18
CONECT    9   19
END
Download

SMILES for NP0000801 (4-Ethylphenol)

CCC1=CC=C(O)C=C1
Download

INCHI for NP0000801 (4-Ethylphenol)

InChI=1S/C8H10O/c1-2-7-3-5-8(9)6-4-7/h3-6,9H,2H2,1H3
Download
View in JSmolView NMR Assignments
Synonyms
ValueSource
1-Ethyl-4-hydroxybenzeneChEBI
1-Hydroxy-4-ethylbenzeneChEBI
p-EthylphenolChEBI
Para-ethylphenolChEBI
ParaethylphenolChEBI
4-HydroxyphenylethaneHMDB
4-Ethylphenol, sodium saltHMDB
Chemical FormulaC8H10O
Average Mass122.1644 Da
Monoisotopic Mass122.07316 Da
IUPAC Name4-ethylphenol
Traditional Nameethylphenol
CAS Registry Number123-07-9
SMILES
CCC1=CC=C(O)C=C1
InChI Identifier
InChI=1S/C8H10O/c1-2-7-3-5-8(9)6-4-7/h3-6,9H,2H2,1H3
InChI KeyHXDOZKJGKXYMEW-UHFFFAOYSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 25 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 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 NMR1H NMR Spectrum (1D, 200 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 NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 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 NMR1H NMR Spectrum (1D, 500 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 NMR1H NMR Spectrum (1D, 600 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 NMR1H NMR Spectrum (1D, 700 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 NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 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
Species NameSourceReference
Aloe africanaLOTUS Database
Artemisia capillarisLOTUS Database
Aspalathus linearisLOTUS Database
Brettanomuces sp.-
Brettanomyces anomalusLOTUS Database
Coffea arabica L.FooDB
Gossypium hirsutumLOTUS Database
Leptolejeunea ellipticaLOTUS Database
Podocarpus fasciculusKNApSAcK Database
Pueraria montanaLOTUS Database
Rubus idaeusFooDB
Zea mays L.FooDB
Species Where Detected
Species NameSourceReference
Homo sapiens (Urine)KNApSAcK Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as 1-hydroxy-2-unsubstituted benzenoids. These are phenols that are unsubstituted at the 2-position.
KingdomOrganic compounds
Super ClassBenzenoids
ClassPhenols
Sub Class1-hydroxy-2-unsubstituted benzenoids
Direct Parent1-hydroxy-2-unsubstituted benzenoids
Alternative Parents
Substituents
  • 1-hydroxy-2-unsubstituted benzenoid
  • Monocyclic benzene moiety
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point44.00 to 46.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Boiling Point218.00 to 219.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility2346 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP2.580The Good Scents Company Information System
Predicted Properties
PropertyValueSource
Water Solubility6.15 g/LALOGPS
logP2.54ALOGPS
logP2.63ChemAxon
logS-1.3ALOGPS
pKa (Strongest Acidic)10.32ChemAxon
pKa (Strongest Basic)-5.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity37.68 m³·mol⁻¹ChemAxon
Polarizability13.86 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0029306
DrugBank IDNot Available
Phenol Explorer Compound ID707
FoodDB IDFDB000358
KNApSAcK IDC00029528
Chemspider ID28982
KEGG Compound IDC13637
BioCyc IDCPD-10596
BiGG IDNot Available
Wikipedia Link4-Ethylphenol
METLIN IDNot Available
PubChem Compound31242
PDB IDETY
ChEBI ID49584
Good Scents IDrw1035341
References
General References
  1. Mung D, Li L: Development of Chemical Isotope Labeling LC-MS for Milk Metabolomics: Comprehensive and Quantitative Profiling of the Amine/Phenol Submetabolome. Anal Chem. 2017 Apr 18;89(8):4435-4443. doi: 10.1021/acs.analchem.6b03737. Epub 2017 Mar 28. [PubMed:28306241 ]
  2. Yasuda T, Ueda J, Ohsawa K: Urinary metabolites of genistein administered orally to rats. Chem Pharm Bull (Tokyo). 2001 Nov;49(11):1495-7. doi: 10.1248/cpb.49.1495. [PubMed:11724248 ]
  3. Tofalo R, Schirone M, Corsetti A, Suzzi G: Detection of Brettanomyces spp. in red wines using real-time PCR. J Food Sci. 2012 Sep;77(9):M545-9. doi: 10.1111/j.1750-3841.2012.02871.x. Epub 2012 Aug 21. [PubMed:22908955 ]
  4. Sangorrin MP, Garcia V, Lopes CA, Saez JS, Martinez C, Ganga MA: Molecular and physiological comparison of spoilage wine yeasts. J Appl Microbiol. 2013 Apr;114(4):1066-74. doi: 10.1111/jam.12134. Epub 2013 Feb 4. [PubMed:23311591 ]
  5. Nieto-Rojo R, Ancin-Azpilicueta C, Garrido JJ: Sorption of 4-ethylguaiacol and 4-ethylphenol on yeast cell walls, using a synthetic wine. Food Chem. 2014;152:399-406. doi: 10.1016/j.foodchem.2013.11.157. Epub 2013 Dec 5. [PubMed:24444954 ]