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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-12 00:19:45 UTC

Update Date

2022-03-07 02:56:01 UTC

HMDB ID

HMDB0038982

Secondary Accession Numbers

HMDB38982

Metabolite Identification

Common Name

4-Nonylphenol

Description

Environmental pollutant arising from the degradation of nonionic surfactants in sewage Nonoxynol-9, one of the APEs, is used as a surfactant in cleaning and cosmetic products, and as a spermicide in contraceptives. Nonylphenol is an organic compound of the wider family of alkylphenols. It is a product of industrial synthesis formed during the alkylation process of phenols, particularly in the synthesis of polyethoxylate detergents. Because of their man-made origins, nonylphenols are classified as xenobiotics. In nonylphenols, a hydrocarbon chain of nine carbon atoms is attached to the phenol ring in either the ortho (2), meta (3), or para (4) position, with the most common ring isomers being ortho or para (e.g. figure 1 para-nonylphenol). Moreover, the alkyl chains can exist as either linear n-alkyl chains, or complex branched chains. Nonylphenol is commonly obtained as a mixture of isomers, and is thus usually found as a pale yellow liquid at room temperature with a freezing point of -10Â°C and a boiling point of 295-320Â°C. However, pure isomers of nonylphenol crystallize readily at room temperatures and for example, para-n-nonylphenol, forms white crystals at room temperature. Nonylphenol, and a related compound tert-octylphenol, were first detected as an air pollutant in New York City and New Jersey, probably due to its evaporation from the Hudson river and other smaller rivers in the region that routinely receive municipal wastewaters. It is possible that the atmosphere is a destructive sink for nonylphenol as it is probably reactive with atmospheric radicals and/or is photoactive.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

HMDB0038982
     RDKit          3D
4-Nonylphenol
 40 40  0  0  0  0  0  0  0  0999 V2000
   -5.1860    1.6774   -1.6513 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2571    0.5385   -1.2507 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0591    0.6286    0.2315 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1587   -0.4350    0.7894 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8035   -0.3263    0.1504 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8415   -1.3739    0.6697 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4819   -1.1613   -0.0465 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5013   -2.2001    0.4422 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7831   -1.9702   -0.2722 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4080   -0.6793   -0.1007 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0890    0.3398   -0.9773 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6459    1.6052   -0.8785 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5531    1.8868    0.1191 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1427    3.1458    0.2616 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8833    0.8869    1.0006 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3243   -0.3602    0.8907 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0819    2.5456   -0.9925 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2407    1.3466   -1.6597 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9467    2.0042   -2.6765 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3527    0.6412   -1.8448 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7528   -0.4057   -1.5464 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7696    1.6420    0.5070 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0735    0.4579    0.6980 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6177   -1.4334    0.6453 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0358   -0.2332    1.8698 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3762    0.6612    0.4534 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8432   -0.4033   -0.9557 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6983   -1.3211    1.7504 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2328   -2.3582    0.3424 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3008   -1.3066   -1.1255 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8440   -0.1423    0.1264 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0533   -3.1787    0.1705 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5337   -2.1391    1.5214 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5096   -2.7590    0.0854 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6431   -2.1898   -1.3513 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3764    0.1704   -1.7853 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3992    2.4105   -1.5644 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6772    3.8288    0.8461 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6051    1.1157    1.7921 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5726   -1.1565    1.5744 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 13 15  1  0
 15 16  2  0
 16 10  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  2 20  1  0
  2 21  1  0
  3 22  1  0
  3 23  1  0
  4 24  1  0
  4 25  1  0
  5 26  1  0
  5 27  1  0
  6 28  1  0
  6 29  1  0
  7 30  1  0
  7 31  1  0
  8 32  1  0
  8 33  1  0
  9 34  1  0
  9 35  1  0
 11 36  1  0
 12 37  1  0
 14 38  1  0
 15 39  1  0
 16 40  1  0
M  END

  Mrv0541 05061310462D          

 16 16  0  0  0  0            999 V2000
   -4.2868    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724    5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    6.6000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  3  2  1  0  0  0  0
  4  3  1  0  0  0  0
  5  4  1  0  0  0  0
  6  5  1  0  0  0  0
  7  6  1  0  0  0  0
  8  7  1  0  0  0  0
  9  8  1  0  0  0  0
 12 10  1  0  0  0  0
 13 11  2  0  0  0  0
 14  9  1  0  0  0  0
 14 10  2  0  0  0  0
 14 11  1  0  0  0  0
 15 12  2  0  0  0  0
 15 13  1  0  0  0  0
 16 15  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0038982

> <DATABASE_NAME>
hmdb

> <SMILES>
CCCCCCCCCC1=CC=C(O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C15H24O/c1-2-3-4-5-6-7-8-9-14-10-12-15(16)13-11-14/h10-13,16H,2-9H2,1H3

> <INCHI_KEY>
IGFHQQFPSIBGKE-UHFFFAOYSA-N

> <FORMULA>
C15H24O

> <MOLECULAR_WEIGHT>
220.3505

> <EXACT_MASS>
220.18271539

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
28.57544076539594

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
4-nonylphenol

> <ALOGPS_LOGP>
6.09

> <JCHEM_LOGP>
5.739651203666668

> <ALOGPS_LOGS>
-5.30

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.306872691903164

> <JCHEM_PKA_STRONGEST_BASIC>
-5.440784100452288

> <JCHEM_POLAR_SURFACE_AREA>
20.23

> <JCHEM_REFRACTIVITY>
69.88810000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.11e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-nonylphenol

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0038982
     RDKit          3D
4-Nonylphenol
 40 40  0  0  0  0  0  0  0  0999 V2000
   -5.1860    1.6774   -1.6513 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2571    0.5385   -1.2507 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0591    0.6286    0.2315 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1587   -0.4350    0.7894 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8035   -0.3263    0.1504 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8415   -1.3739    0.6697 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4819   -1.1613   -0.0465 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5013   -2.2001    0.4422 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7831   -1.9702   -0.2722 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4080   -0.6793   -0.1007 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0890    0.3398   -0.9773 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6459    1.6052   -0.8785 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5531    1.8868    0.1191 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1427    3.1458    0.2616 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8833    0.8869    1.0006 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3243   -0.3602    0.8907 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0819    2.5456   -0.9925 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2407    1.3466   -1.6597 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9467    2.0042   -2.6765 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3527    0.6412   -1.8448 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7528   -0.4057   -1.5464 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7696    1.6420    0.5070 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0735    0.4579    0.6980 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6177   -1.4334    0.6453 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0358   -0.2332    1.8698 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3762    0.6612    0.4534 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8432   -0.4033   -0.9557 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6983   -1.3211    1.7504 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2328   -2.3582    0.3424 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3008   -1.3066   -1.1255 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8440   -0.1423    0.1264 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0533   -3.1787    0.1705 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5337   -2.1391    1.5214 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5096   -2.7590    0.0854 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6431   -2.1898   -1.3513 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3764    0.1704   -1.7853 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3992    2.4105   -1.5644 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6772    3.8288    0.8461 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6051    1.1157    1.7921 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5726   -1.1565    1.5744 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 13 15  1  0
 15 16  2  0
 16 10  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  2 20  1  0
  2 21  1  0
  3 22  1  0
  3 23  1  0
  4 24  1  0
  4 25  1  0
  5 26  1  0
  5 27  1  0
  6 28  1  0
  6 29  1  0
  7 30  1  0
  7 31  1  0
  8 32  1  0
  8 33  1  0
  9 34  1  0
  9 35  1  0
 11 36  1  0
 12 37  1  0
 14 38  1  0
 15 39  1  0
 16 40  1  0
M  END

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0      -8.002   9.240   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -6.668  10.010   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -5.335   9.240   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -4.001  10.010   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.667   9.240   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.334  10.010   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000   9.240   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.334  10.010   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.667   9.240   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.335   9.240   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.001  11.550   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.668  10.010   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.335  12.320   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.001  10.010   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.668  11.550   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       8.002  12.320   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   14                                                       
CONECT   10   12   14                                                       
CONECT   11   13   14                                                       
CONECT   12   10   15                                                       
CONECT   13   11   15                                                       
CONECT   14    9   10   11                                                  
CONECT   15   12   13   16                                                  
CONECT   16   15                                                            
MASTER        0    0    0    0    0    0    0    0   16    0   32    0
END

COMPND    HMDB0038982
HETATM    1  C1  UNL     1      -5.186   1.677  -1.651  1.00  0.00           C  
HETATM    2  C2  UNL     1      -4.257   0.539  -1.251  1.00  0.00           C  
HETATM    3  C3  UNL     1      -4.059   0.629   0.231  1.00  0.00           C  
HETATM    4  C4  UNL     1      -3.159  -0.435   0.789  1.00  0.00           C  
HETATM    5  C5  UNL     1      -1.803  -0.326   0.150  1.00  0.00           C  
HETATM    6  C6  UNL     1      -0.842  -1.374   0.670  1.00  0.00           C  
HETATM    7  C7  UNL     1       0.482  -1.161  -0.046  1.00  0.00           C  
HETATM    8  C8  UNL     1       1.501  -2.200   0.442  1.00  0.00           C  
HETATM    9  C9  UNL     1       2.783  -1.970  -0.272  1.00  0.00           C  
HETATM   10  C10 UNL     1       3.408  -0.679  -0.101  1.00  0.00           C  
HETATM   11  C11 UNL     1       3.089   0.340  -0.977  1.00  0.00           C  
HETATM   12  C12 UNL     1       3.646   1.605  -0.879  1.00  0.00           C  
HETATM   13  C13 UNL     1       4.553   1.887   0.119  1.00  0.00           C  
HETATM   14  O1  UNL     1       5.143   3.146   0.262  1.00  0.00           O  
HETATM   15  C14 UNL     1       4.883   0.887   1.001  1.00  0.00           C  
HETATM   16  C15 UNL     1       4.324  -0.360   0.891  1.00  0.00           C  
HETATM   17  H1  UNL     1      -5.082   2.546  -0.992  1.00  0.00           H  
HETATM   18  H2  UNL     1      -6.241   1.347  -1.660  1.00  0.00           H  
HETATM   19  H3  UNL     1      -4.947   2.004  -2.676  1.00  0.00           H  
HETATM   20  H4  UNL     1      -3.353   0.641  -1.845  1.00  0.00           H  
HETATM   21  H5  UNL     1      -4.753  -0.406  -1.546  1.00  0.00           H  
HETATM   22  H6  UNL     1      -3.770   1.642   0.507  1.00  0.00           H  
HETATM   23  H7  UNL     1      -5.074   0.458   0.698  1.00  0.00           H  
HETATM   24  H8  UNL     1      -3.618  -1.433   0.645  1.00  0.00           H  
HETATM   25  H9  UNL     1      -3.036  -0.233   1.870  1.00  0.00           H  
HETATM   26  H10 UNL     1      -1.376   0.661   0.453  1.00  0.00           H  
HETATM   27  H11 UNL     1      -1.843  -0.403  -0.956  1.00  0.00           H  
HETATM   28  H12 UNL     1      -0.698  -1.321   1.750  1.00  0.00           H  
HETATM   29  H13 UNL     1      -1.233  -2.358   0.342  1.00  0.00           H  
HETATM   30  H14 UNL     1       0.301  -1.307  -1.125  1.00  0.00           H  
HETATM   31  H15 UNL     1       0.844  -0.142   0.126  1.00  0.00           H  
HETATM   32  H16 UNL     1       1.053  -3.179   0.170  1.00  0.00           H  
HETATM   33  H17 UNL     1       1.534  -2.139   1.521  1.00  0.00           H  
HETATM   34  H18 UNL     1       3.510  -2.759   0.085  1.00  0.00           H  
HETATM   35  H19 UNL     1       2.643  -2.190  -1.351  1.00  0.00           H  
HETATM   36  H20 UNL     1       2.376   0.170  -1.785  1.00  0.00           H  
HETATM   37  H21 UNL     1       3.399   2.410  -1.564  1.00  0.00           H  
HETATM   38  H22 UNL     1       4.677   3.829   0.846  1.00  0.00           H  
HETATM   39  H23 UNL     1       5.605   1.116   1.792  1.00  0.00           H  
HETATM   40  H24 UNL     1       4.573  -1.157   1.574  1.00  0.00           H  
CONECT    1    2   17   18   19
CONECT    2    3   20   21
CONECT    3    4   22   23
CONECT    4    5   24   25
CONECT    5    6   26   27
CONECT    6    7   28   29
CONECT    7    8   30   31
CONECT    8    9   32   33
CONECT    9   10   34   35
CONECT   10   11   11   16
CONECT   11   12   36
CONECT   12   13   13   37
CONECT   13   14   15
CONECT   14   38
CONECT   15   16   16   39
CONECT   16   40
END

HMDB0038982
     RDKit          3D
4-Nonylphenol
 40 40  0  0  0  0  0  0  0  0999 V2000
   -5.1860    1.6774   -1.6513 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2571    0.5385   -1.2507 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0591    0.6286    0.2315 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1587   -0.4350    0.7894 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8035   -0.3263    0.1504 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8415   -1.3739    0.6697 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4819   -1.1613   -0.0465 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5013   -2.2001    0.4422 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7831   -1.9702   -0.2722 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4080   -0.6793   -0.1007 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0890    0.3398   -0.9773 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6459    1.6052   -0.8785 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5531    1.8868    0.1191 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1427    3.1458    0.2616 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8833    0.8869    1.0006 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3243   -0.3602    0.8907 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0819    2.5456   -0.9925 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2407    1.3466   -1.6597 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9467    2.0042   -2.6765 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3527    0.6412   -1.8448 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7528   -0.4057   -1.5464 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7696    1.6420    0.5070 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0735    0.4579    0.6980 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6177   -1.4334    0.6453 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0358   -0.2332    1.8698 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3762    0.6612    0.4534 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8432   -0.4033   -0.9557 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6983   -1.3211    1.7504 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2328   -2.3582    0.3424 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3008   -1.3066   -1.1255 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8440   -0.1423    0.1264 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0533   -3.1787    0.1705 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5337   -2.1391    1.5214 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5096   -2.7590    0.0854 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6431   -2.1898   -1.3513 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3764    0.1704   -1.7853 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3992    2.4105   -1.5644 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6772    3.8288    0.8461 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6051    1.1157    1.7921 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5726   -1.1565    1.5744 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 13 15  1  0
 15 16  2  0
 16 10  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  2 20  1  0
  2 21  1  0
  3 22  1  0
  3 23  1  0
  4 24  1  0
  4 25  1  0
  5 26  1  0
  5 27  1  0
  6 28  1  0
  6 29  1  0
  7 30  1  0
  7 31  1  0
  8 32  1  0
  8 33  1  0
  9 34  1  0
  9 35  1  0
 11 36  1  0
 12 37  1  0
 14 38  1  0
 15 39  1  0
 16 40  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
4-N-Nonylphenol	ChEBI
p-N-Nonylphenol	ChEBI
p-Nonylphenol	ChEBI
Para nonyl phenol	ChEBI
4-N-Nonyl phenol	HMDB
4-Nonyl-phenol	HMDB
4-Tert-nonylphenol	HMDB, MeSH
Nonyl-phenol	HMDB
Nonylphenol	HMDB
Nonylphenol (mixed)	HMDB
P -N -Nonylphenol	HMDB
P-Nonyl-phenol	HMDB
P-Nonylphenol (endocrine disrupter)	HMDB
Para-nonylphenol	HMDB, MeSH
Phenol, nonyl derivs.	HMDB
PPT	HMDB
4-Nonylphenol	KEGG

Chemical Formula

C₁₅H₂₄O

Average Molecular Weight

220.3505

Monoisotopic Molecular Weight

220.18271539

IUPAC Name

4-nonylphenol

Traditional Name

4-nonylphenol

CAS Registry Number

104-40-5

SMILES

CCCCCCCCCC1=CC=C(O)C=C1

InChI Identifier

InChI=1S/C15H24O/c1-2-3-4-5-6-7-8-9-14-10-12-15(16)13-11-14/h10-13,16H,2-9H2,1H3

InChI Key

IGFHQQFPSIBGKE-UHFFFAOYSA-N

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.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Phenols

Sub Class

1-hydroxy-2-unsubstituted benzenoids

Direct Parent

1-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 Framework

Aromatic homomonocyclic compounds

External Descriptors

phenols (CHEBI:34440 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0038982)
Cell membrane (HMDB: HMDB0038982)

Source

Exogenous

Exogenous (HMDB: HMDB0038982)

Food

Food (HMDB: HMDB0038982)

Synthetic

Synthetic (HMDB: HMDB0038982)

Environmental

Wastewater (HMDB: HMDB0038982)

Process

Industrial process

Disinfection

Water Disinfection (HMDB: HMDB0038982)

Role

Environmental role

Water pollutant (HMDB: HMDB0038982)

Biological role

Nutrient (HMDB: HMDB0038982)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	41 - 42.5 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.007 mg/mL at 25 °C	Not Available
LogP	5.76	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.0011 g/L	ALOGPS
logP	6.09	ALOGPS
logP	5.74	ChemAxon
logS	-5.3	ALOGPS
pKa (Strongest Acidic)	10.31	ChemAxon
pKa (Strongest Basic)	-5.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	20.23 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	69.89 m³·mol⁻¹	ChemAxon
Polarizability	28.58 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	156.179	31661259
DarkChem	[M-H]-	155.279	31661259
DeepCCS	[M+H]+	162.028	30932474
DeepCCS	[M-H]-	158.007	30932474
DeepCCS	[M-2H]-	195.784	30932474
DeepCCS	[M+Na]+	171.448	30932474
AllCCS	[M+H]+	156.6	32859911
AllCCS	[M+H-H2O]+	152.8	32859911
AllCCS	[M+NH4]+	160.1	32859911
AllCCS	[M+Na]+	161.1	32859911
AllCCS	[M-H]-	162.7	32859911
AllCCS	[M+Na-2H]-	163.6	32859911
AllCCS	[M+HCOO]-	164.7	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
4-Nonylphenol	CCCCCCCCCC1=CC=C(O)C=C1	2818.9	Standard polar	33892256
4-Nonylphenol	CCCCCCCCCC1=CC=C(O)C=C1	1869.4	Standard non polar	33892256
4-Nonylphenol	CCCCCCCCCC1=CC=C(O)C=C1	1888.0	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
4-Nonylphenol,1TMS,isomer #1	CCCCCCCCCC1=CC=C(O[Si](C)(C)C)C=C1	1908.9	Semi standard non polar	33892256
4-Nonylphenol,1TBDMS,isomer #1	CCCCCCCCCC1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1	2180.4	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - 4-Nonylphenol EI-B (Non-derivatized)	splash10-000i-2900000000-20e92b9b8f11cb8548c0	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 4-Nonylphenol EI-B (Non-derivatized)	splash10-000i-2900000000-7a162fc7755b07f777e5	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 4-Nonylphenol EI-B (Non-derivatized)	splash10-000i-2900000000-20e92b9b8f11cb8548c0	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 4-Nonylphenol EI-B (Non-derivatized)	splash10-000i-2900000000-7a162fc7755b07f777e5	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Nonylphenol GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4l-9700000000-fe61e00c002a2c662478	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Nonylphenol GC-MS (1 TMS) - 70eV, Positive	splash10-05i3-9340000000-6ce055b46c7aed006da8	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Nonylphenol GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Nonylphenol GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0a4i-0910000000-6dc5d11f43433e2b7f59	2014-09-20	Not Available	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - 4-Nonylphenol 60V, Negative-QTOF	splash10-014i-0090000000-12014c03fa338ffb5aa7	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 4-Nonylphenol 45V, Negative-QTOF	splash10-014i-0090000000-f719b8dd054b6c059a5a	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Nonylphenol 10V, Positive-QTOF	splash10-00di-0190000000-1088749f8c1369b2a470	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Nonylphenol 20V, Positive-QTOF	splash10-00di-7940000000-07de75334bf5f62511d9	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Nonylphenol 40V, Positive-QTOF	splash10-052f-9200000000-ce735aee103f15b85e14	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Nonylphenol 10V, Negative-QTOF	splash10-014i-0090000000-39c2fa3f29590455b87a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Nonylphenol 20V, Negative-QTOF	splash10-014i-0090000000-16076e327a7f5affad33	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Nonylphenol 40V, Negative-QTOF	splash10-100c-5930000000-d3a16d7fd9d653998a31	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Nonylphenol 10V, Positive-QTOF	splash10-00di-9280000000-977825d44a9757c52a0e	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Nonylphenol 20V, Positive-QTOF	splash10-0a59-9100000000-3adc01f7ad81dc62e6ed	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Nonylphenol 40V, Positive-QTOF	splash10-0apl-9200000000-3004aa4985fb6258b4e6	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Nonylphenol 10V, Negative-QTOF	splash10-014i-0090000000-4af4c4ee1c4acef7e18b	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Nonylphenol 20V, Negative-QTOF	splash10-014i-0090000000-4af4c4ee1c4acef7e18b	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Nonylphenol 40V, Negative-QTOF	splash10-05mo-7900000000-61a13c97ec4075e97e9b	2021-09-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB018468

KNApSAcK ID

Not Available

Chemspider ID

1688

KEGG Compound ID

C14550

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Nonylphenol

METLIN ID

Not Available

PubChem Compound

1752

PDB ID

Not Available

ChEBI ID

34440

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1331081

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Hao CJ, Cheng XJ, Xia HF, Ma X: The endocrine disruptor 4-nonylphenol promotes adipocyte differentiation and induces obesity in mice. Cell Physiol Biochem. 2012;30(2):382-94. doi: 10.1159/000339032. Epub 2012 Jul 3. [PubMed:22739433 ]
Palumbo AJ, Koivunen M, Tjeerdema RS: Optimization and validation of a California halibut environmental estrogen bioassay using a heterologous ELISA. Sci Total Environ. 2009 Jan 1;407(2):953-61. doi: 10.1016/j.scitotenv.2008.09.046. Epub 2008 Nov 11. [PubMed:19004476 ]
Okai Y, Sato EF, Higashi-Okai K, Inoue M: Potentiating effect of an endocrine disruptor, paranonylphenol, on the generation of reactive oxygen species (ROS) in human venous blood -- association with the activation of signal transduction pathway. J UOEH. 2007 Sep 1;29(3):221-33. [PubMed:17900002 ]
(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for 4-Nonylphenol (HMDB0038982)

MOL for HMDB0038982 (4-Nonylphenol)

3D MOL for HMDB0038982 (4-Nonylphenol)

3D SDF for HMDB0038982 (4-Nonylphenol)

3D-SDF for HMDB0038982 (4-Nonylphenol)

PDB for HMDB0038982 (4-Nonylphenol)

3D PDB for HMDB0038982 (4-Nonylphenol)

SMILES for HMDB0038982 (4-Nonylphenol)

INCHI for HMDB0038982 (4-Nonylphenol)

Structure for HMDB0038982 (4-Nonylphenol)

3D Structure for HMDB0038982 (4-Nonylphenol)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra