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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-12 00:19:45 UTC
Update Date2022-03-07 02:56:01 UTC
HMDB IDHMDB0038982
Secondary Accession Numbers
  • HMDB38982
Metabolite Identification
Common Name4-Nonylphenol
DescriptionEnvironmental 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 -10°C and a boiling point of 295-320°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
Data?1563863291
Synonyms
ValueSource
4-N-NonylphenolChEBI
p-N-NonylphenolChEBI
p-NonylphenolChEBI
Para nonyl phenolChEBI
4-N-Nonyl phenolHMDB
4-Nonyl-phenolHMDB
4-Tert-nonylphenolHMDB, MeSH
Nonyl-phenolHMDB
NonylphenolHMDB
Nonylphenol (mixed)HMDB
P -N -NonylphenolHMDB
P-Nonyl-phenolHMDB
P-Nonylphenol (endocrine disrupter)HMDB
Para-nonylphenolHMDB, MeSH
Phenol, nonyl derivs.HMDB
PPTHMDB
4-NonylphenolKEGG
Chemical FormulaC15H24O
Average Molecular Weight220.3505
Monoisotopic Molecular Weight220.18271539
IUPAC Name4-nonylphenol
Traditional Name4-nonylphenol
CAS Registry Number104-40-5
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 KeyIGFHQQFPSIBGKE-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.
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
Ontology
Disposition

Source

Route of exposure

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point41 - 42.5 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.007 mg/mL at 25 °CNot Available
LogP5.76Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.0011 g/LALOGPS
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
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+156.17931661259
DarkChem[M-H]-155.27931661259
DeepCCS[M+H]+162.02830932474
DeepCCS[M-H]-158.00730932474
DeepCCS[M-2H]-195.78430932474
DeepCCS[M+Na]+171.44830932474
AllCCS[M+H]+156.632859911
AllCCS[M+H-H2O]+152.832859911
AllCCS[M+NH4]+160.132859911
AllCCS[M+Na]+161.132859911
AllCCS[M-H]-162.732859911
AllCCS[M+Na-2H]-163.632859911
AllCCS[M+HCOO]-164.732859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
4-NonylphenolCCCCCCCCCC1=CC=C(O)C=C12818.9Standard polar33892256
4-NonylphenolCCCCCCCCCC1=CC=C(O)C=C11869.4Standard non polar33892256
4-NonylphenolCCCCCCCCCC1=CC=C(O)C=C11888.0Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
4-Nonylphenol,1TMS,isomer #1CCCCCCCCCC1=CC=C(O[Si](C)(C)C)C=C11908.9Semi standard non polar33892256
4-Nonylphenol,1TBDMS,isomer #1CCCCCCCCCC1=CC=C(O[Si](C)(C)C(C)(C)C)C=C12180.4Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - 4-Nonylphenol EI-B (Non-derivatized)splash10-000i-2900000000-20e92b9b8f11cb8548c02017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 4-Nonylphenol EI-B (Non-derivatized)splash10-000i-2900000000-7a162fc7755b07f777e52017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 4-Nonylphenol EI-B (Non-derivatized)splash10-000i-2900000000-20e92b9b8f11cb8548c02018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 4-Nonylphenol EI-B (Non-derivatized)splash10-000i-2900000000-7a162fc7755b07f777e52018-05-18HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4-Nonylphenol GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4l-9700000000-fe61e00c002a2c6624782017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4-Nonylphenol GC-MS (1 TMS) - 70eV, Positivesplash10-05i3-9340000000-6ce055b46c7aed006da82017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4-Nonylphenol GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4-Nonylphenol GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-0a4i-0910000000-6dc5d11f43433e2b7f592014-09-20Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - 4-Nonylphenol 60V, Negative-QTOFsplash10-014i-0090000000-12014c03fa338ffb5aa72021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 4-Nonylphenol 45V, Negative-QTOFsplash10-014i-0090000000-f719b8dd054b6c059a5a2021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Nonylphenol 10V, Positive-QTOFsplash10-00di-0190000000-1088749f8c1369b2a4702016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Nonylphenol 20V, Positive-QTOFsplash10-00di-7940000000-07de75334bf5f62511d92016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Nonylphenol 40V, Positive-QTOFsplash10-052f-9200000000-ce735aee103f15b85e142016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Nonylphenol 10V, Negative-QTOFsplash10-014i-0090000000-39c2fa3f29590455b87a2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Nonylphenol 20V, Negative-QTOFsplash10-014i-0090000000-16076e327a7f5affad332016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Nonylphenol 40V, Negative-QTOFsplash10-100c-5930000000-d3a16d7fd9d653998a312016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Nonylphenol 10V, Positive-QTOFsplash10-00di-9280000000-977825d44a9757c52a0e2021-09-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Nonylphenol 20V, Positive-QTOFsplash10-0a59-9100000000-3adc01f7ad81dc62e6ed2021-09-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Nonylphenol 40V, Positive-QTOFsplash10-0apl-9200000000-3004aa4985fb6258b4e62021-09-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Nonylphenol 10V, Negative-QTOFsplash10-014i-0090000000-4af4c4ee1c4acef7e18b2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Nonylphenol 20V, Negative-QTOFsplash10-014i-0090000000-4af4c4ee1c4acef7e18b2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Nonylphenol 40V, Negative-QTOFsplash10-05mo-7900000000-61a13c97ec4075e97e9b2021-09-25Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Membrane
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 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
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1331081
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. 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 ]
  2. 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 ]
  3. 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 ]
  4. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .