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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2014-10-08 15:55:56 UTC
Update Date2022-03-07 03:17:48 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
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+168.24731661259
DarkChem[M-H]-165.62431661259
DeepCCS[M+H]+169.18430932474
DeepCCS[M-H]-166.82630932474
DeepCCS[M-2H]-200.39730932474
DeepCCS[M+Na]+175.62430932474
AllCCS[M+H]+167.832859911
AllCCS[M+H-H2O]+164.332859911
AllCCS[M+NH4]+171.132859911
AllCCS[M+Na]+172.032859911
AllCCS[M-H]-165.032859911
AllCCS[M+Na-2H]-164.132859911
AllCCS[M+HCOO]-163.332859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
8-Anilino-1-naphthalene sulfonateOS(=O)(=O)C1=C2C(NC3=CC=CC=C3)=CC=CC2=CC=C14499.9Standard polar33892256
8-Anilino-1-naphthalene sulfonateOS(=O)(=O)C1=C2C(NC3=CC=CC=C3)=CC=CC2=CC=C12604.9Standard non polar33892256
8-Anilino-1-naphthalene sulfonateOS(=O)(=O)C1=C2C(NC3=CC=CC=C3)=CC=CC2=CC=C12972.2Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
8-Anilino-1-naphthalene sulfonate,1TMS,isomer #1C[Si](C)(C)OS(=O)(=O)C1=CC=CC2=CC=CC(NC3=CC=CC=C3)=C122769.2Semi standard non polar33892256
8-Anilino-1-naphthalene sulfonate,1TMS,isomer #1C[Si](C)(C)OS(=O)(=O)C1=CC=CC2=CC=CC(NC3=CC=CC=C3)=C122654.3Standard non polar33892256
8-Anilino-1-naphthalene sulfonate,1TMS,isomer #1C[Si](C)(C)OS(=O)(=O)C1=CC=CC2=CC=CC(NC3=CC=CC=C3)=C123865.9Standard polar33892256
8-Anilino-1-naphthalene sulfonate,1TMS,isomer #2C[Si](C)(C)N(C1=CC=CC=C1)C1=CC=CC2=CC=CC(S(=O)(=O)O)=C122720.2Semi standard non polar33892256
8-Anilino-1-naphthalene sulfonate,1TMS,isomer #2C[Si](C)(C)N(C1=CC=CC=C1)C1=CC=CC2=CC=CC(S(=O)(=O)O)=C122643.0Standard non polar33892256
8-Anilino-1-naphthalene sulfonate,1TMS,isomer #2C[Si](C)(C)N(C1=CC=CC=C1)C1=CC=CC2=CC=CC(S(=O)(=O)O)=C123744.3Standard polar33892256
8-Anilino-1-naphthalene sulfonate,2TMS,isomer #1C[Si](C)(C)OS(=O)(=O)C1=CC=CC2=CC=CC(N(C3=CC=CC=C3)[Si](C)(C)C)=C122663.6Semi standard non polar33892256
8-Anilino-1-naphthalene sulfonate,2TMS,isomer #1C[Si](C)(C)OS(=O)(=O)C1=CC=CC2=CC=CC(N(C3=CC=CC=C3)[Si](C)(C)C)=C122696.2Standard non polar33892256
8-Anilino-1-naphthalene sulfonate,2TMS,isomer #1C[Si](C)(C)OS(=O)(=O)C1=CC=CC2=CC=CC(N(C3=CC=CC=C3)[Si](C)(C)C)=C123462.4Standard polar33892256
8-Anilino-1-naphthalene sulfonate,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OS(=O)(=O)C1=CC=CC2=CC=CC(NC3=CC=CC=C3)=C123017.1Semi standard non polar33892256
8-Anilino-1-naphthalene sulfonate,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OS(=O)(=O)C1=CC=CC2=CC=CC(NC3=CC=CC=C3)=C122892.2Standard non polar33892256
8-Anilino-1-naphthalene sulfonate,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OS(=O)(=O)C1=CC=CC2=CC=CC(NC3=CC=CC=C3)=C123863.0Standard polar33892256
8-Anilino-1-naphthalene sulfonate,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)N(C1=CC=CC=C1)C1=CC=CC2=CC=CC(S(=O)(=O)O)=C122954.3Semi standard non polar33892256
8-Anilino-1-naphthalene sulfonate,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)N(C1=CC=CC=C1)C1=CC=CC2=CC=CC(S(=O)(=O)O)=C122835.2Standard non polar33892256
8-Anilino-1-naphthalene sulfonate,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)N(C1=CC=CC=C1)C1=CC=CC2=CC=CC(S(=O)(=O)O)=C123747.2Standard polar33892256
8-Anilino-1-naphthalene sulfonate,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OS(=O)(=O)C1=CC=CC2=CC=CC(N(C3=CC=CC=C3)[Si](C)(C)C(C)(C)C)=C123117.5Semi standard non polar33892256
8-Anilino-1-naphthalene sulfonate,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OS(=O)(=O)C1=CC=CC2=CC=CC(N(C3=CC=CC=C3)[Si](C)(C)C(C)(C)C)=C123161.8Standard non polar33892256
8-Anilino-1-naphthalene sulfonate,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OS(=O)(=O)C1=CC=CC2=CC=CC(N(C3=CC=CC=C3)[Si](C)(C)C(C)(C)C)=C123506.3Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 8-Anilino-1-naphthalene sulfonate GC-MS (Non-derivatized) - 70eV, Positivesplash10-000y-3390000000-88bf291ae990c371c0112017-08-28Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 8-Anilino-1-naphthalene sulfonate GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - 8-Anilino-1-naphthalene sulfonate LC-ESI-QQ , negative-QTOFsplash10-0002-0090000000-d8b40286eee5cab4c11e2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 8-Anilino-1-naphthalene sulfonate LC-ESI-QQ , negative-QTOFsplash10-0002-0090000000-951fefb571a3261b6f302017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 8-Anilino-1-naphthalene sulfonate LC-ESI-QQ , negative-QTOFsplash10-0002-1090000000-219da52d66dd8e9128c82017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 8-Anilino-1-naphthalene sulfonate LC-ESI-QQ , negative-QTOFsplash10-001j-5090000000-afe8d593924605ca15cb2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 8-Anilino-1-naphthalene sulfonate LC-ESI-QQ , negative-QTOFsplash10-004i-9220000000-0a72c42bfb56dc6612882017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 8-Anilino-1-naphthalene sulfonate 40V, Negative-QTOFsplash10-004i-9120000000-49ab342d332f7b088a382021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 8-Anilino-1-naphthalene sulfonate 40V, Positive-QTOFsplash10-014i-0090000000-cb53ca7d81dab90dceb72021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 8-Anilino-1-naphthalene sulfonate 20V, Positive-QTOFsplash10-014i-0090000000-35dcc13181af8154cb632021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 8-Anilino-1-naphthalene sulfonate 10V, Negative-QTOFsplash10-0002-0090000000-7010f9c284b96f889a8a2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 8-Anilino-1-naphthalene sulfonate 20V, Negative-QTOFsplash10-0002-1090000000-b60326b535948e4c67b82021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 8-Anilino-1-naphthalene sulfonate 10V, Positive-QTOFsplash10-0gb9-0095000000-bacff9c33bc38bfe19ce2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 8-Anilino-1-naphthalene sulfonate 40V, Positive-QTOFsplash10-014i-0090000000-6b3fa801747394e80da22021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 8-Anilino-1-naphthalene sulfonate 10V, Positive-QTOFsplash10-0gb9-0095000000-d6829efd0dbfe398f3f22021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 8-Anilino-1-naphthalene sulfonate 20V, Positive-QTOFsplash10-014i-0090000000-2243e9165c2c2b560ede2021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 8-Anilino-1-naphthalene sulfonate 10V, Positive-QTOFsplash10-0udi-0039000000-cbf68748c3713dfbef7c2017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 8-Anilino-1-naphthalene sulfonate 20V, Positive-QTOFsplash10-0gb9-0095000000-876cf3d641e4dd0e2fba2017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 8-Anilino-1-naphthalene sulfonate 40V, Positive-QTOFsplash10-014i-1490000000-3e3595c9f27e0d2003092017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 8-Anilino-1-naphthalene sulfonate 10V, Negative-QTOFsplash10-0002-1090000000-485889805cfc11ca0b2c2017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 8-Anilino-1-naphthalene sulfonate 20V, Negative-QTOFsplash10-00l2-2090000000-a491439ef8aaa662eba62017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 8-Anilino-1-naphthalene sulfonate 40V, Negative-QTOFsplash10-001i-9020000000-69e86931935af599af0b2017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 8-Anilino-1-naphthalene sulfonate 10V, Negative-QTOFsplash10-0002-0090000000-11113b918b7abb99642b2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 8-Anilino-1-naphthalene sulfonate 20V, Negative-QTOFsplash10-0002-0090000000-11113b918b7abb99642b2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 8-Anilino-1-naphthalene sulfonate 40V, Negative-QTOFsplash10-014i-0970000000-cef34ff6f9a54d4b75692021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 8-Anilino-1-naphthalene sulfonate 10V, Positive-QTOFsplash10-0udi-0009000000-d2cc5186d759fb153f2e2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 8-Anilino-1-naphthalene sulfonate 20V, Positive-QTOFsplash10-0uxr-0096000000-6d2fcf31ea61bde19a442021-09-22Wishart LabView Spectrum
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
MarkerDB IDNot Available
Good Scents 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 ]