Hmdb loader
You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:52 UTC
Update Date2020-02-26 21:42:02 UTC
HMDB IDHMDB0015680
Secondary Accession Numbers
  • HMDB15680
Metabolite Identification
Common NameNonoxynol-9
DescriptionNonoxynol-9 (N-9) is a typical surfactant used as a vaginal spermicide. Spermicides are locally acting non-hormonal contraceptives. When present in the vagina during intercourse, they immobilize/inactivate/damage and/or kill sperms without eliciting systemic effects. N-9 has been in use for more than 30 years as an over-the-counter (OTC) drug in creams, gels, foams and condom lubricants. It is the most commonly used spermicidal contraceptive in the UK and the USA. In several European countries, spermicides are no longer on the market.
Structure
Data?1582753322
Synonyms
ValueSource
26-(Nonylphenoxy)-3,6,9,12,15,18,21,24-octaoxahexacosan-1-olChEBI
Nonaethylene glycol mono(nonylphenyl) etherChEBI
Nonaethylene glycol nonylphenyl etherChEBI
Nonoxynol 9ChEBI
Nonylphenol octa(oxyethylene) ethanolChEBI
p-Nonylphenyl polyethylene glycol etherChEBI
PEG-9 nonyl phenyl etherChEBI
Polyoxyethylene (9) nonyl phenyl etherChEBI
Tergitol NP9ChEBI
N-9HMDB
Advantage-SHMDB
Nonoxinol mertz brandHMDB
NonylphenoxypolyethoxyethanolHMDB
NonylphenoxypolyethoxyethanolsHMDB
Oval, patentexHMDB
Advantage SHMDB
Emulgen 911HMDB
Mertz brand OF nonoxinolHMDB
NonoxinolsHMDB
Delfen creamHMDB
Emulgin 913HMDB
NonoxinolHMDB
NonoxynolHMDB
Nonoxynol, 1(4)-sulfate, sodium saltHMDB
Nonoxynol, 4-sulfate, ammonium saltHMDB
NonoxynolsHMDB
Patentex ovalHMDB
Delfen creamsHMDB
Nonoxynol-9MeSH
Chemical FormulaC33H60O10
Average Molecular Weight616.8235
Monoisotopic Molecular Weight616.41864814
IUPAC Name26-(4-nonylphenoxy)-3,6,9,12,15,18,21,24-octaoxahexacosan-1-ol
Traditional Name26-(4-nonylphenoxy)-3,6,9,12,15,18,21,24-octaoxahexacosan-1-ol
CAS Registry Number26571-11-9
SMILES
CCCCCCCCCC1=CC=C(OCCOCCOCCOCCOCCOCCOCCOCCOCCO)C=C1
InChI Identifier
InChI=1S/C33H60O10/c1-2-3-4-5-6-7-8-9-32-10-12-33(13-11-32)43-31-30-42-29-28-41-27-26-40-25-24-39-23-22-38-21-20-37-19-18-36-17-16-35-15-14-34/h10-13,34H,2-9,14-31H2,1H3
InChI KeyFBWNMEQMRUMQSO-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as polyethylene glycols. These are oligomers or polymers of ethylene oxide, with the general formula (C2H4O)n (with n>=3).
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassEthers
Direct ParentPolyethylene glycols
Alternative Parents
Substituents
  • Polyethylene glycol
  • Phenoxy compound
  • Phenol ether
  • Alkyl aryl ether
  • Benzenoid
  • Monocyclic benzene moiety
  • Hydrocarbon derivative
  • Primary alcohol
  • Alcohol
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Disposition

Biological location

Source

Route of exposure

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Spectral Properties

Experimental Collision Cross Sections

PredictorAdduct TypeData SourceCCS Value (Å2)Reference
AllCCS[M+H]+Not Available245.782http://allccs.zhulab.cn/database/detail?ID=AllCCS00001335
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.00021 g/LALOGPS
logP10(3.49) g/LALOGPS
logP10(4.82) g/LChemAxon
logS10(-6.5) g/LALOGPS
pKa (Strongest Acidic)15.12ChemAxon
pKa (Strongest Basic)-2.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count10ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area103.3 ŲChemAxon
Rotatable Bond Count35ChemAxon
Refractivity169.01 m³·mol⁻¹ChemAxon
Polarizability77.07 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Spectral Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+245.06631661259
DarkChem[M-H]-235.09531661259

Predicted Kovats Retention Indices

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Nonoxynol-9,1TMS,#1CCCCCCCCCC1=CC=C(OCCOCCOCCOCCOCCOCCOCCOCCOCCO[Si](C)(C)C)C=C14453.2Semi standard non polarLange, M. and Fedorova, M. (2020) Evaluation of lipid quantification accuracy using HILIC and RPLC MS on the example of NIST SRM 1950 metabolites in human plasma. Anal. Bioanal. Chem. 412(15), 3573-3584.
Nonoxynol-9,1TBDMS,#1CCCCCCCCCC1=CC=C(OCCOCCOCCOCCOCCOCCOCCOCCOCCO[Si](C)(C)C(C)(C)C)C=C14698.6Semi standard non polarLange, M. and Fedorova, M. (2020) Evaluation of lipid quantification accuracy using HILIC and RPLC MS on the example of NIST SRM 1950 metabolites in human plasma. Anal. Bioanal. Chem. 412(15), 3573-3584.
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Nonoxynol-9 GC-MS (Non-derivatized) - 70eV, Positivesplash10-004l-2297650000-f45e05e61aae9a285a242017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Nonoxynol-9 GC-MS (1 TMS) - 70eV, Positivesplash10-0fkc-2489841000-5b7e2364df078f9670542017-10-06Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Nonoxynol-9 10V, Positive-QTOFsplash10-014i-1175229000-2ab5c9bbb0e11c4ebde92016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Nonoxynol-9 20V, Positive-QTOFsplash10-0fdk-3298361000-5c78baa66fa61b58b1bb2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Nonoxynol-9 40V, Positive-QTOFsplash10-00di-5292130000-9efad90b08486f00b1562016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Nonoxynol-9 10V, Negative-QTOFsplash10-014i-2396237000-a78293555df13a376ba62016-08-04Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Nonoxynol-9 20V, Negative-QTOFsplash10-014i-1191000000-75f15700fe3ea4c825812016-08-04Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Nonoxynol-9 40V, Negative-QTOFsplash10-014i-2390000000-0e28041c7320a24d55942016-08-04Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Nonoxynol-9 10V, Positive-QTOFsplash10-014j-9212025000-b23db3ab5c67685d30772021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Nonoxynol-9 20V, Positive-QTOFsplash10-0292-9100112000-2986b11d5943bb4b30a52021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Nonoxynol-9 40V, Positive-QTOFsplash10-0002-9200000000-eb029ba675072da815352021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Nonoxynol-9 10V, Negative-QTOFsplash10-0cdi-9731021000-2f53a95d63aedc4ae3902021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Nonoxynol-9 20V, Negative-QTOFsplash10-0bt9-9322231000-004f747cb905ac9a2fdb2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Nonoxynol-9 40V, Negative-QTOFsplash10-07be-7940000000-ef6989aa23af8f4fe29b2021-10-11Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB06804 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB06804 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB06804
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID65319
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNonoxynol-9
METLIN IDNot Available
PubChem Compound72385
PDB IDNot Available
ChEBI ID53775
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Iyer V, Poddar SS: Update on nonoxynol-9 as vaginal spermicide. Eur J Contracept Reprod Health Care. 2008 Dec;13(4):339-50. doi: 10.1080/13625180802263515. [PubMed:19117251 ]

Enzymes

General function:
Involved in peroxidase activity
Specific function:
Mediates the formation of prostaglandins from arachidonate. May have a role as a major mediator of inflammation and/or a role for prostanoid signaling in activity-dependent plasticity.
Gene Name:
PTGS2
Uniprot ID:
P35354
Molecular weight:
68995.625
References
  1. Zalenskaya IA, Cerocchi OG, Joseph T, Donaghay MA, Schriver SD, Doncel GF: Increased COX-2 expression in human vaginal epithelial cells exposed to nonoxynol-9, a vaginal contraceptive microbicide that failed to protect women from HIV-1 infection. Am J Reprod Immunol. 2011 Jun;65(6):569-77. doi: 10.1111/j.1600-0897.2010.00964.x. Epub 2011 Jan 18. [PubMed:21241401 ]