Survey with prize
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
Version4.0
StatusDetected and Quantified
Creation Date2014-10-08 15:55:56 UTC
Update Date2019-07-23 07:17:19 UTC
HMDB IDHMDB0061854
Secondary Accession Numbers
  • HMDB61854
Metabolite Identification
Common Name8-Anilino-1-naphthalene sulfonate
Description8-Anilino-1-naphthalene sulfonate, also known as 8-anilinonaphthalene-1-sulphonic acid or ANS, belongs to the class of organic compounds known as 1-naphthalene sulfonates. These are organic aromatic compounds that contain a naphthalene moiety that carries a sulfonic acid group at the 1-position. Naphthalene is a bicyclic compound that is made up of two fused benzene ring. 8-Anilino-1-naphthalene sulfonate is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
Data?1563866239
Synonyms
ValueSource
1-(Phenylamino)-8-naphthalenesulfonic acidChEBI
1-ANILINO-8-naphthalene sulfonATEChEBI
1-Anilino-8-naphthalenesulfonateChEBI
1-Anilino-8-naphthalenesulfonic acidChEBI
8-Anilino-1-naphthalene sulfonic acidChEBI
8-Anilinonaphthalene-1-sulphonic acidChEBI
ANSChEBI
1-(Phenylamino)-8-naphthalenesulfonateGenerator
1-(Phenylamino)-8-naphthalenesulphonateGenerator
1-(Phenylamino)-8-naphthalenesulphonic acidGenerator
1-ANILINO-8-naphthalene sulfonic acidGenerator
1-ANILINO-8-naphthalene sulphonateGenerator
1-ANILINO-8-naphthalene sulphonic acidGenerator
1-Anilino-8-naphthalenesulphonateGenerator
1-Anilino-8-naphthalenesulphonic acidGenerator
8-Anilino-1-naphthalene sulphonateGenerator
8-Anilino-1-naphthalene sulphonic acidGenerator
8-Anilinonaphthalene-1-sulfonateGenerator
8-Anilinonaphthalene-1-sulfonic acidGenerator
8-Anilinonaphthalene-1-sulphonateGenerator
1-Anilino-8-naphthalenesulfonate, monoammonium salt, hemihydrateHMDB
1-Anilino-8-naphthalenesulfonate, monosodium saltHMDB
1-Anilinonaphthalene-8-sulfonic acidHMDB
1-Anilino-8-naphthalenesulfonate, magnesium (2:1)HMDB
1,8-ANSHMDB
1-Anilino-8-naphthalenesulfonate, 3H-labeledHMDB
1-Anilino-8-naphthalenesulfonate, ion(1-)HMDB
1-Anilino-8-naphthalenesulfonate, monoammonium saltHMDB
Chemical FormulaC16H13NO3S
Average Molecular Weight299.344
Monoisotopic Molecular Weight299.061613977
IUPAC Name8-(phenylamino)naphthalene-1-sulfonic acid
Traditional Namephenyl-peri acid
CAS Registry Number82-76-8
SMILES
OS(=O)(=O)C1=C2C(NC3=CC=CC=C3)=CC=CC2=CC=C1
InChI Identifier
InChI=1S/C16H13NO3S/c18-21(19,20)15-11-5-7-12-6-4-10-14(16(12)15)17-13-8-2-1-3-9-13/h1-11,17H,(H,18,19,20)
InChI KeyFWEOQOXTVHGIFQ-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as 1-naphthalene sulfonates. These are organic aromatic compounds that contain a naphthalene moiety that carries a sulfonic acid group at the 1-position. Naphthalene is a bicyclic compound that is made up of two fused benzene ring.
KingdomOrganic compounds
Super ClassBenzenoids
ClassNaphthalenes
Sub ClassNaphthalene sulfonic acids and derivatives
Direct Parent1-naphthalene sulfonates
Alternative Parents
Substituents
  • 1-naphthalene sulfonate
  • 1-naphthalene sulfonic acid or derivatives
  • Arylsulfonic acid or derivatives
  • 1-sulfo,2-unsubstituted aromatic compound
  • Aniline or substituted anilines
  • Monocyclic benzene moiety
  • Organic sulfonic acid or derivatives
  • Organosulfonic acid or derivatives
  • Sulfonyl
  • Organosulfonic acid
  • Secondary amine
  • Amine
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organosulfur compound
  • Organonitrogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Aromatic homopolycyclic compound
Molecular FrameworkAromatic homopolycyclic compounds
External Descriptors
Ontology
Disposition

Biological location:

Role

Industrial application:

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
Water Solubility0.015 g/LALOGPS
logP1.54ALOGPS
logP2.11ChemAxon
logS-4.3ALOGPS
pKa (Strongest Acidic)-2ChemAxon
pKa (Strongest Basic)-0.083ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area66.4 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity81.62 m³·mol⁻¹ChemAxon
Polarizability30.34 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-000y-3390000000-88bf291ae990c371c011Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0002-0090000000-d8b40286eee5cab4c11eSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0002-0090000000-951fefb571a3261b6f30Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0002-1090000000-219da52d66dd8e9128c8Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-001j-5090000000-afe8d593924605ca15cbSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-004i-9220000000-0a72c42bfb56dc661288Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0039000000-cbf68748c3713dfbef7cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0gb9-0095000000-876cf3d641e4dd0e2fbaSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014i-1490000000-3e3595c9f27e0d200309Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-1090000000-485889805cfc11ca0b2cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00l2-2090000000-a491439ef8aaa662eba6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001i-9020000000-69e86931935af599af0bSpectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Saliva
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
SalivaDetected and Quantified0.330 +/- 0.182 uMAdult (>18 years old)Male
Normal
    • Sugimoto et al. (...
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB04474
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDC11326
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia Link8-Anilinonaphthalene-1-sulfonic_acid
METLIN IDNot Available
PubChem Compound1369
PDB IDNot Available
ChEBI ID39708
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Lewin M, Saccomani G, Schackmann R, Sachs G: Use of 1-anilino-8-naphthalene-sulfonate as a probe of gastric vesicle transport. J Membr Biol. 1977 Apr 22;32(3-4):301-18. [PubMed:17006 ]
  2. Stiborova M, Lapka R, Leblova S: The bonding of 8-anilino-1-naphthalene sulfonate to rape (Brassica napus) alcohol dehydrogenase. FEBS Lett. 1979 Aug 15;104(2):309-12. [PubMed:477994 ]
  3. Mantsala P, Lang M: 1 Anilino-8-naphthalene sulfonate and n-phenyl-1-naphthylamine as the indicators of bacterial thermosensitivity. FEBS Lett. 1973 Nov 1;36(3):265-7. [PubMed:4202820 ]
  4. Vanderkooi J, Martonosi A: Sarcoplasmic reticulum. 8. Use of 8-anilino-1-naphthalene sulfonate as conformational probe on biological membranes. Arch Biochem Biophys. 1969 Aug;133(1):153-63. [PubMed:4309361 ]
  5. Vanderkooi JM, Martonosi A: Sarcoplasmic reticulum. XII. The interaction of 8-anilino-1-naphthalene sulfonate with skeletal muscle microsomes. Arch Biochem Biophys. 1971 May;144(1):87-98. [PubMed:4330132 ]
  6. Nakatani H, Haga M, Hiromi K: Kinetic studies on binding of bovine serum albumin with 1-anilino-8-naphthalene sulfonate. FEBS Lett. 1974 Aug 1;43(3):293-6. [PubMed:4472167 ]
  7. Nagradova NK, Asryants RA, Ivanov MV: Interaction of 1-anilino-8-naphthalene sulfonate with yeast glyceraldehyde-3-phosphate dehydrogenase. Experientia. 1971 Oct 15;27(10):1169-70. [PubMed:5127865 ]
  8. Nerli B, Pico G: Influence of the medium conditions on the 1-anilino-8-naphthalene sulfonate-bovine serum albumin binding. Arch Int Physiol Biochim Biophys. 1994 Jan-Feb;102(1):5-8. [PubMed:7516732 ]
  9. Gabellieri E, Strambini GB: Perturbation of protein tertiary structure in frozen solutions revealed by 1-anilino-8-naphthalene sulfonate fluorescence. Biophys J. 2003 Nov;85(5):3214-20. [PubMed:14581221 ]