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Showing NP-Card for 4-Nonylphenol (NP0337834)

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Record Information
Version2.0
Created at2024-09-11 12:40:05 UTC
Updated at2024-09-11 12:40:05 UTC
NP-MRD IDNP0337834
Secondary Accession NumbersNone
Natural Product Identification
Common Name4-Nonylphenol
Description4-Nonylphenol, also known as para nonyl phenol or PPT, belongs to the class of organic compounds known as 1-hydroxy-2-unsubstituted benzenoids. These are phenols that are unsubstituted at the 2-position. 4-Nonylphenol is an extremely weak basic (essentially neutral) compound (based on its pKa). 4-Nonylphenol is a potentially toxic compound. Nonylphenol is an organic compound of the wider family of alkylphenols. 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). 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 -10°C and a boiling point of 295-320°C. It is possible that the atmosphere is a destructive sink for nonylphenol as it is probably reactive with atmospheric radicals and/or is photoactive. It was first documented in 2007 (PMID: 17900002). Moreover, the alkyl chains can exist as either linear n-alkyl chains, or complex branched chains (PMID: 18506497) (PMID: 21823570) (PMID: 22133150) (PMID: 24805085) (PMID: 22739433) (PMID: 19004476).
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0337834 (4-Nonylphenol)


  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
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3D MOL for NP0337834 (4-Nonylphenol)

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3D SDF for NP0337834 (4-Nonylphenol)

  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>
NP0337834

> <DATABASE_NAME>
NP-MRD

> <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

$$$$

Download
3D-SDF for NP0337834 (4-Nonylphenol)
Download
PDB for NP0337834 (4-Nonylphenol)
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

Download
3D PDB for NP0337834 (4-Nonylphenol)
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SMILES for NP0337834 (4-Nonylphenol)
CCCCCCCCCC1=CC=C(O)C=C1
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INCHI for NP0337834 (4-Nonylphenol)
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
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View in JSmol
Synonyms
ValueSource
4-N-NonylphenolChEBI
p-N-NonylphenolChEBI
p-NonylphenolChEBI
Para nonyl phenolChEBI
4-N-Nonyl phenolHMDB
4-Nonyl-phenolHMDB
4-Tert-nonylphenolHMDB
Nonyl-phenolHMDB
NonylphenolHMDB
Nonylphenol (mixed)HMDB
p -N -NonylphenolHMDB
p-Nonyl-phenolHMDB
p-Nonylphenol (endocrine disrupter)HMDB
Para-nonylphenolHMDB
Phenol, nonyl derivs.HMDB
PPTHMDB
4-NonylphenolKEGG
Chemical FormulaC15H24O
Average Mass220.3505 Da
Monoisotopic Mass220.18272 Da
IUPAC Name4-nonylphenol
Traditional Name4-nonylphenol
CAS Registry NumberNot Available
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 KeyIGFHQQFPSIBGKE-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of OriginNot Available
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
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP6.09ALOGPS
logP5.74ChemAxon
logS-5.3ALOGPS
pKa (Strongest Acidic)10.31ChemAxon
pKa (Strongest Basic)-5.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity69.89 m³·mol⁻¹ChemAxon
Polarizability28.58 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0038982  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB018468  
KNApSAcK IDNot Available
Chemspider ID1688  
KEGG Compound IDC14550  
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNonylphenol  
METLIN IDNot Available
PubChem Compound1752  
PDB IDNot Available
ChEBI ID34440  
Good Scents IDNot Available
References
General References
  1. Hohne C, Puttmann W: Occurrence and temporal variations of the xenoestrogens bisphenol A, 4-tert-octylphenol, and tech. 4-nonylphenol in two German wastewater treatment plants. Environ Sci Pollut Res Int. 2008 Jul;15(5):405-16. doi:  10.1007/s11356-008-0007-2. Epub 2008 May 28. [PubMed:18506497  ] 
  2. Shan J, Jiang B, Yu B, Li C, Sun Y, Guo H, Wu J, Klumpp E, Schaffer A, Ji R: Isomer-specific degradation of branched and linear 4-nonylphenol isomers in an oxic soil. Environ Sci Technol. 2011 Oct 1;45(19):8283-9. doi: 10.1021/es200224c. Epub 2011  Sep 1. [PubMed:21823570  ] 
  3. Iwaki H, Takada K, Hasegawa Y: Maricurvus nonylphenolicus gen. nov., sp. nov., a nonylphenol-degrading bacterium isolated from seawater. FEMS Microbiol Lett. 2012 Feb;327(2):142-7. doi:  10.1111/j.1574-6968.2011.02471.x. Epub 2011 Dec 19. [PubMed:22133150  ] 
  4. El-Sayed Ali T, Abdel-Aziz SH, El-Sayed AF, Zeid S: Structural and functional effects of early exposure to 4-nonylphenol on gonadal development of Nile tilapia (Oreochromis niloticus): b-histological alterations in testes. Fish Physiol Biochem. 2014 Oct;40(5):1495-507. doi: 10.1007/s10695-014-9944-5.  Epub 2014 May 8. [PubMed:24805085  ] 
  5. 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  ] 
  6. 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  ] 
  7. 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. doi: 10.7888/juoeh.29.221. [PubMed:17900002  ]