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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2012-09-11 17:32:15 UTC
Update Date2020-11-09 23:19:57 UTC
HMDB IDHMDB0029723
Secondary Accession Numbers
  • HMDB29723
Metabolite Identification
Common NameSaccharin
DescriptionSaccharin, also known as benzosulfimide or O-sulfobenzimide, 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). Saccharin is a bitter and odorless tasting compound. Saccharin has been detected, but not quantified in, milk (cow). This could make saccharin a potential biomarker for the consumption of these foods. Saccharin is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. Based on a literature review a small amount of articles have been published on Saccharin.
Structure
Data?1582753456
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
SweetaKegg
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
SyncalHMDB
ZaharinaHMDB
Saccharin sodiumMeSH, HMDB
Saccharin calciumMeSH, HMDB
Calcium, saccharinMeSH, HMDB
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
OC1=NS(=O)(=O)C2=CC=CC=C12
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
Description 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

Biological location

Source

Route of exposure

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point224 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility4 mg/mL at 25 °CNot Available
LogP0.91Not Available
Experimental Spectral PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility6.51 g/LALOGPS
logP10(0.02) g/LALOGPS
logP10(0.45) g/LChemAxon
logS10(-2) g/LALOGPS
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Spectral Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+140.4731661259
DarkChem[M-H]-135.10131661259

Predicted Kovats Retention Indices

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Saccharin,1TMS,#1C[Si](C)(C)OC1=NS(=O)(=O)C2=CC=CC=C121782.2Semi standard non polarhttps://arxiv.org/abs/1905.12712
Saccharin,1TBDMS,#1CC(C)(C)[Si](C)(C)OC1=NS(=O)(=O)C2=CC=CC=C122029.5Semi standard non polarhttps://arxiv.org/abs/1905.12712
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Saccharin GC-MS (1 TMS)splash10-006x-5940000000-c3d4fc7537245087aa012014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Saccharin EI-B (Non-derivatized)splash10-0fiv-9200000000-3cbd853d90d67ac630ab2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Saccharin GC-MS (Non-derivatized)splash10-006x-5940000000-c3d4fc7537245087aa012017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Saccharin GC-EI-TOF (Non-derivatized)splash10-0006-2940000000-42addba0b789ed51670d2017-09-12HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Saccharin GC-MS (Non-derivatized) - 70eV, Positivesplash10-0f89-2900000000-becdd7f75934373f608e2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Saccharin 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 - Saccharin LC-ESI-ITFT , negative-QTOFsplash10-001i-0900000000-4b6ed2bc790c007ba1d22017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Saccharin LC-ESI-ITFT , negative-QTOFsplash10-001i-0900000000-1548a4ac4e5c194426792017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Saccharin LC-ESI-ITFT , negative-QTOFsplash10-001i-0900000000-34f1a9ce4b083851e69f2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Saccharin LC-ESI-ITFT , negative-QTOFsplash10-001i-0900000000-20951911ba1a4f08d8912017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Saccharin LC-ESI-ITFT , negative-QTOFsplash10-001i-0900000000-668e33ca497d39237e852017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Saccharin LC-ESI-ITFT , negative-QTOFsplash10-001i-0900000000-fdb874ff651646e63cab2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Saccharin LC-ESI-ITFT , negative-QTOFsplash10-001i-0900000000-65c93c049826341beddd2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Saccharin LC-ESI-ITFT , negative-QTOFsplash10-001i-0900000000-1548a4ac4e5c194426792017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Saccharin LC-ESI-ITFT , negative-QTOFsplash10-001i-0900000000-1548a4ac4e5c194426792017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Saccharin LC-ESI-ITFT , negative-QTOFsplash10-001i-0900000000-54eafaf51ea31a4d23c62017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Saccharin LC-ESI-ITFT , negative-QTOFsplash10-001i-0900000000-d248f91c063ab27c21d02017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Saccharin LC-ESI-ITFT , negative-QTOFsplash10-001i-0900000000-c92646389218a59f37b92017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Saccharin LC-ESI-ITFT , negative-QTOFsplash10-001i-1900000000-b50ceac4dba57f7be6c72017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Saccharin LC-ESI-ITFT , negative-QTOFsplash10-001i-0900000000-73352f91026a3f00a6042017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Saccharin LC-ESI-IT , negative-QTOFsplash10-001i-0900000000-c9c9334260025c49503c2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Saccharin LC-ESI-QFT , negative-QTOFsplash10-001i-0900000000-1548a4ac4e5c194426792017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Saccharin 10V, Negative-QTOFsplash10-001i-0900000000-8541df3050a01079f8cb2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Saccharin 20V, Negative-QTOFsplash10-001l-7900000000-b92b2b5563f0682cf4c52021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Saccharin 35V, Negative-QTOFsplash10-001i-0900000000-d11c013b29981671dfd32021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Saccharin 10V, Positive-QTOFsplash10-001i-0900000000-a62962f93c65565c0ef02016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Saccharin 20V, Positive-QTOFsplash10-001l-0900000000-9388e78a777b8d51a6222016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Saccharin 40V, Positive-QTOFsplash10-001i-2900000000-8b225ba6c3775d43faa32016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Saccharin 10V, Negative-QTOFsplash10-001i-0900000000-d247850c8363d99c278a2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Saccharin 20V, Negative-QTOFsplash10-001i-1900000000-6caddc90acdcf108de822016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Saccharin 40V, Negative-QTOFsplash10-0006-9300000000-db3e2a46b225fde95a282016-08-03Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen Locations
  • Blood
  • Feces
  • Saliva
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal
details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>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 IDDB12418
Phenol Explorer Compound IDNot Available
FooDB IDFDB000918
KNApSAcK IDC00002728
Chemspider ID4959
KEGG Compound IDC12283
BioCyc IDCPD-5581
BiGG IDNot Available
Wikipedia LinkSaccharin
METLIN IDNot Available
PubChem Compound5143
PDB IDLSA
ChEBI ID32111
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1281441
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. (). EAFUS: Everything Added to Food in the United States.. .