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Record Information
Version4.0
StatusDetected but not Quantified
Creation Date2012-09-11 17:32:15 UTC
Update Date2018-05-20 09:59:05 UTC
HMDB IDHMDB0029723
Secondary Accession Numbers
  • HMDB29723
Metabolite Identification
Common NameSaccharin
DescriptionSaccharin, ammonium salt is used as a food additive [EAFUS] (EAFUS: Everything Added to Food in the United States). Saccharin belongs to the family of aromatic homomonocyclic compounds. These are aromatic compounds containing only one ring, which is homocyclic.
Structure
Thumb
Synonyms
ValueSource
1,1-dioxo-1,2-Benzisothiazol-3(2H)-oneChEBI
1,1-dioxo-1,2-dihydro-benzo[D]Isothiazol-3-oneChEBI
1,2-Benzisothiazol-3(2H)-one 1,1-dioxideChEBI
1,2-Benzisothiazolin-3-one 1,1-dioxideChEBI
1,2-dihydro-2-KetobenzisosulfonazoleChEBI
1,2-dihydro-2-KetobenzisosulphonazoleChEBI
2,3-dihydro-3-OxobenzisosulfonazoleChEBI
2,3-dihydro-3-OxobenzisosulphonazoleChEBI
3-Hydroxybenzisothiazole-S,S-dioxideChEBI
anhydro-O-Sulfaminebenzoic acidChEBI
benzo-2-SulphimideChEBI
Benzoic acid sulfimideChEBI
Benzoic sulfimideChEBI
Benzoic sulphimideChEBI
BenzosulfimideChEBI
BenzosulphimideChEBI
Benzoylsulfonic imideChEBI
O-Benzoic sulfimideChEBI
O-BenzosulfimideChEBI
O-SulfobenzimideChEBI
O-Sulfobenzoic acid imideChEBI
SaccharimideChEBI
SaccharineChEBI
anhydro-O-SulfaminebenzoateGenerator
anhydro-O-SulphaminebenzoateGenerator
anhydro-O-Sulphaminebenzoic acidGenerator
benzo-2-SulfimideGenerator
Benzoate sulfimideGenerator
Benzoate sulphimideGenerator
Benzoic acid sulphimideGenerator
Benzoylsulphonic imideGenerator
O-Benzoic sulphimideGenerator
O-BenzosulphimideGenerator
O-SulphobenzimideGenerator
O-Sulfobenzoate imideGenerator
O-Sulphobenzoate imideGenerator
O-Sulphobenzoic acid imideGenerator
1, 2-Benzisothiazol-3(2H)-one, 1,1-dioxideHMDB
1, 2-Benzisothiazolin-3-one 1,1-dioxideHMDB
1, 2-dihydro-2-KetobenzisosulfonazoleHMDB
1,1-Diox-1,2-benzisothiazol-3-oneHMDB
1,1-Dioxide-1,2-benzisothiazol-3(2H)-oneHMDB
1,1-Dioxide-1,2-benzisothiazolin-3-oneHMDB
1,1-dioxo-1,2-dihydro-1Lambda*6*-benzo[D]isothiazol-3-oneHMDB
1,2-Benzisothiazol-3(2H)-one 1,1-dioxide, 9ciHMDB
1,2-Benzisothiazol-3(2H)-one, 1,1-dioxideHMDB
1,2-Benzisothiazolin-3-one, 1,1-dioxideHMDB
1,2-Benzisothiazoline-3-one 1,1-dioxideHMDB
1,2-Benzothiazol-3(2H)-one 1,1-dioxideHMDB
2, 3-dihydro-3-OxobenzisosulfonazoleHMDB
2,3-dihydro-1,2-Benzoisothiazol-3-one-1,1-dioxideHMDB
2,3-dihydro-3-oxo-BenzisosulfonazoleHMDB
2,3-Dihydroxy-1,2-benzisothiazol-3-one-1,1-dioxideHMDB
2-Sulfobenzoic acid imideHMDB
2-SulfobenzoicimideHMDB
2-Sulphobenzoic imideHMDB
3-Benzisothiazolinone 1, 1-dioxideHMDB
3-Benzisothiazolinone 1,1-dioxideHMDB
3-Hydroxybenzisothiazole S,S-dioxideHMDB
benzo-2-SulfiideHMDB
benzo-SulphinideHMDB
BenzosulfinideHMDB
e954HMDB
GarantoseHMDB
GlucidHMDB
GlusideHMDB
GlycophenolHMDB
HermesetasHMDB
Insoluble saccharinHMDB
KandisetHMDB
LSAHMDB
NeosaccharinHMDB
O-Benzoic acid sulfimideHMDB
O-Benzoyl sulfimideHMDB
O-Benzoyl sulphimideHMDB
O-BenzoylsulfimideHMDB
O-Sulfobenzoic imideHMDB
SacarinaHMDB
Saccharin (JP15/nf)HMDB
Saccharin acidHMDB
Saccharin insolubleHMDB
Saccharin, insolubleHMDB
SaccharinolHMDB
SaccharinoseHMDB
SaccharolHMDB
SacharinHMDB
StilalginHMDB
Sucre edulcorHMDB
SucretteHMDB
SweetaHMDB
SyncalHMDB
ZaharinaHMDB
Saccharin sodiumMeSH
Saccharin calciumMeSH
Calcium, saccharinMeSH
Chemical FormulaC7H5NO3S
Average Molecular Weight183.185
Monoisotopic Molecular Weight182.999013721
IUPAC Name2,3-dihydro-1lambda6,2-benzothiazole-1,1,3-trione
Traditional Name2H-1lambda6,2-benzothiazole-1,1,3-trione
CAS Registry Number81-07-2
SMILES
O=C1NS(=O)(=O)C2=C1C=CC=C2
InChI Identifier
InChI=1S/C7H5NO3S/c9-7-5-3-1-2-4-6(5)12(10,11)8-7/h1-4H,(H,8,9)
InChI KeyCVHZOJJKTDOEJC-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as benzothiazoles. These are organic compounds containing a benzene fused to a thiazole ring (a five-membered ring with four carbon atoms, one nitrogen atom and one sulfur atom).
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassBenzothiazoles
Sub ClassNot Available
Direct ParentBenzothiazoles
Alternative Parents
Substituents
  • 1,2-benzothiazole
  • Benzenoid
  • Organosulfonic acid or derivatives
  • Organic sulfonic acid or derivatives
  • Azacycle
  • Carboxylic acid derivative
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Source:

Biological location:

Role

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point224 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility4 mg/mL at 25 °CNot Available
LogP0.91Not Available
Predicted Properties
PropertyValueSource
Water Solubility6.51 g/LALOGPS
logP0.09ALOGPS
logP0.45ChemAxon
logS-1.4ALOGPS
pKa (Strongest Acidic)1.94ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area63.24 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity42.39 m³·mol⁻¹ChemAxon
Polarizability16.02 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MS (1 TMS)splash10-006x-5940000000-c3d4fc7537245087aa01View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0fiv-9200000000-3cbd853d90d67ac630abView in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-006x-5940000000-c3d4fc7537245087aa01View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0006-2940000000-42addba0b789ed51670dView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0f89-2900000000-becdd7f75934373f608eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-001i-0900000000-4b6ed2bc790c007ba1d2View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-001i-0900000000-1548a4ac4e5c19442679View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-001i-0900000000-34f1a9ce4b083851e69fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-001i-0900000000-20951911ba1a4f08d891View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-001i-0900000000-668e33ca497d39237e85View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-001i-0900000000-fdb874ff651646e63cabView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-001i-0900000000-65c93c049826341bedddView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-001i-0900000000-1548a4ac4e5c19442679View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-001i-0900000000-1548a4ac4e5c19442679View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-001i-0900000000-54eafaf51ea31a4d23c6View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-001i-0900000000-d248f91c063ab27c21d0View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-001i-0900000000-c92646389218a59f37b9View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-001i-1900000000-b50ceac4dba57f7be6c7View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-001i-0900000000-73352f91026a3f00a604View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT , negativesplash10-001i-0900000000-c9c9334260025c49503cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-001i-0900000000-1548a4ac4e5c19442679View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0900000000-a62962f93c65565c0ef0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001l-0900000000-9388e78a777b8d51a622View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001i-2900000000-8b225ba6c3775d43faa3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0900000000-d247850c8363d99c278aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-1900000000-6caddc90acdcf108de82View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9300000000-db3e2a46b225fde95a28View in MoNA
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen Locations
  • Feces
  • Saliva
Tissue LocationNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not Quantified Adult (>18 years old)Both
Normal
details
FecesDetected but not Quantified Adult (>18 years old)Both
Normal
details
SalivaDetected but not Quantified Adult (>18 years old)Male
Normal
details
SalivaDetected but not Quantified Adult (>18 years old)Male
Normal
details
SalivaDetected but not Quantified Adult (>18 years old)Male
Normal
details
SalivaDetected but not Quantified Adult (>18 years old)Male
Normal
details
SalivaDetected but not Quantified Adult (>18 years old)Male
Normal
details
SalivaDetected but not Quantified Adult (>18 years old)Male
Normal
details
SalivaDetected but not Quantified Adult (>18 years old)Male
Normal
details
SalivaDetected but not Quantified Adult (>18 years old)Male
Normal
details
SalivaDetected but not Quantified Adult (>18 years old)Male
Normal
details
SalivaDetected but not Quantified Adult (>18 years old)Male
Normal
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not Quantified Adult (>18 years old)Both
Colorectal cancer
details
FecesDetected but not Quantified Adult (>18 years old)BothColorectal Cancer details
Associated Disorders and Diseases
Disease References
Colorectal cancer
  1. Brown DG, Rao S, Weir TL, O'Malia J, Bazan M, Brown RJ, Ryan EP: Metabolomics and metabolic pathway networks from human colorectal cancers, adjacent mucosa, and stool. Cancer Metab. 2016 Jun 6;4:11. doi: 10.1186/s40170-016-0151-y. eCollection 2016. [PubMed:27275383 ]
  2. Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB000918
KNApSAcK IDNot Available
Chemspider ID4959
KEGG Compound IDC12283
BioCyc IDCPD-5581
BiGG IDNot Available
Wikipedia LinkSaccharin
METLIN IDNot Available
PubChem Compound5143
PDB IDLSA
ChEBI ID32111
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. (). EAFUS: Everything Added to Food in the United States.. .