Milk Composition Database: Showing metabocard for Saccharin (BMDB0062045)

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Identification Taxonomy Physical properties Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2018-06-25 21:46:25 UTC

Update Date

2020-04-22 15:51:13 UTC

MCDB ID

BMDB0062045

Secondary Accession Numbers

BMDB62045

Metabolite Identification

Common Name

Saccharin

Description

Saccharin, 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 exists as a solid, possibly soluble (in water), and a moderately acidic compound (based on its pKa) molecule.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
1,1-Dioxo-1,2-benzisothiazol-3(2H)-one	ChEBI
1,1-Dioxo-1,2-dihydro-benzo[D]isothiazol-3-one	ChEBI
1,2-Benzisothiazol-3(2H)-one 1,1-dioxide	ChEBI
1,2-Benzisothiazolin-3-one 1,1-dioxide	ChEBI
1,2-Dihydro-2-ketobenzisosulfonazole	ChEBI
1,2-Dihydro-2-ketobenzisosulphonazole	ChEBI
2,3-Dihydro-3-oxobenzisosulfonazole	ChEBI
2,3-Dihydro-3-oxobenzisosulphonazole	ChEBI
3-Hydroxybenzisothiazole-S,S-dioxide	ChEBI
Anhydro-O-sulfaminebenzoic acid	ChEBI
Benzo-2-sulphimide	ChEBI
Benzoic acid sulfimide	ChEBI
Benzoic sulfimide	ChEBI
Benzoic sulphimide	ChEBI
Benzosulfimide	ChEBI
Benzosulphimide	ChEBI
Benzoylsulfonic imide	ChEBI
O-Benzoic sulfimide	ChEBI
O-Benzosulfimide	ChEBI
O-Sulfobenzimide	ChEBI
O-Sulfobenzoic acid imide	ChEBI
Saccharimide	ChEBI
Saccharine	ChEBI
Sweeta	Kegg
Anhydro-O-sulfaminebenzoate	Generator
Anhydro-O-sulphaminebenzoate	Generator
Anhydro-O-sulphaminebenzoic acid	Generator
Benzo-2-sulfimide	Generator
Benzoate sulfimide	Generator
Benzoate sulphimide	Generator
Benzoic acid sulphimide	Generator
Benzoylsulphonic imide	Generator
O-Benzoic sulphimide	Generator
O-Benzosulphimide	Generator
O-Sulphobenzimide	Generator
O-Sulfobenzoate imide	Generator
O-Sulphobenzoate imide	Generator
O-Sulphobenzoic acid imide	Generator
1, 2-Benzisothiazol-3(2H)-one, 1,1-dioxide	HMDB
1, 2-Benzisothiazolin-3-one 1,1-dioxide	HMDB
1, 2-dihydro-2-Ketobenzisosulfonazole	HMDB
1,1-Diox-1,2-benzisothiazol-3-one	HMDB
1,1-Dioxide-1,2-benzisothiazol-3(2H)-one	HMDB
1,1-Dioxide-1,2-benzisothiazolin-3-one	HMDB
1,1-dioxo-1,2-dihydro-1Lambda6-benzo[D]isothiazol-3-one	HMDB
1,2-Benzisothiazol-3(2H)-one 1,1-dioxide, 9ci	HMDB
1,2-Benzisothiazol-3(2H)-one, 1,1-dioxide	HMDB
1,2-Benzisothiazolin-3-one, 1,1-dioxide	HMDB
1,2-Benzisothiazoline-3-one 1,1-dioxide	HMDB
1,2-Benzothiazol-3(2H)-one 1,1-dioxide	HMDB
2, 3-dihydro-3-Oxobenzisosulfonazole	HMDB
2,3-dihydro-1,2-Benzoisothiazol-3-one-1,1-dioxide	HMDB
2,3-dihydro-3-oxo-Benzisosulfonazole	HMDB
2,3-Dihydroxy-1,2-benzisothiazol-3-one-1,1-dioxide	HMDB
2-Sulfobenzoic acid imide	HMDB
2-Sulfobenzoicimide	HMDB
2-Sulphobenzoic imide	HMDB
3-Benzisothiazolinone 1, 1-dioxide	HMDB
3-Benzisothiazolinone 1,1-dioxide	HMDB
3-Hydroxybenzisothiazole S,S-dioxide	HMDB
benzo-2-Sulfiide	HMDB
benzo-Sulphinide	HMDB
Benzosulfinide	HMDB
e954	HMDB
Garantose	HMDB
Glucid	HMDB
Gluside	HMDB
Glycophenol	HMDB
Hermesetas	HMDB
Insoluble saccharin	HMDB
Kandiset	HMDB
LSA	HMDB
Neosaccharin	HMDB
O-Benzoic acid sulfimide	HMDB
O-Benzoyl sulfimide	HMDB
O-Benzoyl sulphimide	HMDB
O-Benzoylsulfimide	HMDB
O-Sulfobenzoic imide	HMDB
Sacarina	HMDB
Saccharin (JP15/nf)	HMDB
Saccharin acid	HMDB
Saccharin insoluble	HMDB
Saccharin, insoluble	HMDB
Saccharinol	HMDB
Saccharinose	HMDB
Saccharol	HMDB
Sacharin	HMDB
Stilalgin	HMDB
Sucre edulcor	HMDB
Sucrette	HMDB
Syncal	HMDB
Zaharina	HMDB
Saccharin sodium	MeSH, HMDB
Saccharin calcium	MeSH, HMDB
Calcium, saccharin	MeSH, HMDB

Chemical Formula

C₇H₅NO₃S

Average Molecular Weight

183.185

Monoisotopic Molecular Weight

182.999013721

IUPAC Name

2,3-dihydro-1lambda6,2-benzothiazole-1,1,3-trione

Traditional Name

2H-1lambda6,2-benzothiazole-1,1,3-trione

CAS Registry Number

81-07-2

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 Key

CVHZOJJKTDOEJC-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).

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzothiazoles

Sub Class

Not Available

Direct Parent

Benzothiazoles

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 Framework

Aromatic heteropolycyclic compounds

External Descriptors

sulfone (CHEBI:32111 )
lactam (CHEBI:32111 )
1,2-benzisothiazole (CHEBI:32111 )

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	0.02	ALOGPS
logP	0.45	ChemAxon
logS	-2	ALOGPS
pKa (Strongest Acidic)	1.94	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	63.24 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	42.39 m³·mol⁻¹	ChemAxon
Polarizability	16.02 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
GC-MS	GC-MS Spectrum - GC-MS (1 TMS)	splash10-006x-5940000000-c3d4fc7537245087aa01	2014-06-16	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0fiv-9200000000-3cbd853d90d67ac630ab	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-006x-5940000000-c3d4fc7537245087aa01	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0006-2940000000-42addba0b789ed51670d	2017-09-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0f89-2900000000-becdd7f75934373f608e	2017-09-01	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , negative	splash10-001i-0900000000-4b6ed2bc790c007ba1d2	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , negative	splash10-001i-0900000000-1548a4ac4e5c19442679	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , negative	splash10-001i-0900000000-34f1a9ce4b083851e69f	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , negative	splash10-001i-0900000000-20951911ba1a4f08d891	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , negative	splash10-001i-0900000000-668e33ca497d39237e85	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , negative	splash10-001i-0900000000-fdb874ff651646e63cab	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , negative	splash10-001i-0900000000-65c93c049826341beddd	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , negative	splash10-001i-0900000000-1548a4ac4e5c19442679	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , negative	splash10-001i-0900000000-1548a4ac4e5c19442679	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , negative	splash10-001i-0900000000-54eafaf51ea31a4d23c6	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , negative	splash10-001i-0900000000-d248f91c063ab27c21d0	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , negative	splash10-001i-0900000000-c92646389218a59f37b9	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , negative	splash10-001i-1900000000-b50ceac4dba57f7be6c7	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , negative	splash10-001i-0900000000-73352f91026a3f00a604	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-IT , negative	splash10-001i-0900000000-c9c9334260025c49503c	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , negative	splash10-001i-0900000000-1548a4ac4e5c19442679	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-001i-0900000000-8541df3050a01079f8cb	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-001l-7900000000-b92b2b5563f0682cf4c5	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 35V, Negative	splash10-001i-0900000000-d11c013b29981671dfd3	2021-09-20	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-001i-0900000000-a62962f93c65565c0ef0	2016-06-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-001l-0900000000-9388e78a777b8d51a622	2016-06-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-001i-2900000000-8b225ba6c3775d43faa3	2016-06-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-001i-0900000000-d247850c8363d99c278a	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-001i-1900000000-6caddc90acdcf108de82	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9300000000-db3e2a46b225fde95a28	2016-08-03	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Not Available	2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Not Available	2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Not Available	2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Not Available	2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Not Available	2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Not Available	2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Not Available	2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Not Available	2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Not Available	2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Not Available	2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Not Available	2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Not Available	2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Not Available	2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Not Available	2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Not Available	2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Not Available	2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Not Available	2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Not Available	2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Not Available	2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Not Available	2021-09-25	View Spectrum

Concentrations

Status	Value		Reference	Details
Detected but not Quantified	Not Applicable		PMID: 25771043	details
Detected but not Quantified	Not Applicable		PMID: 23438684	details

External Links

HMDB ID

HMDB0029723

DrugBank ID

DB12418

Phenol Explorer Compound ID

Not Available

FoodDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

Saccharin

METLIN ID

Not Available

PubChem Compound

5143

PDB ID

LSA

ChEBI ID

32111

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

Lu J, Boeren S, van Hooijdonk T, Vervoort J, Hettinga K: Effect of the DGAT1 K232A genotype of dairy cows on the milk metabolome and proteome. J Dairy Sci. 2015 May;98(5):3460-9. doi: 10.3168/jds.2014-8872. Epub 2015 Mar 12. [PubMed:25771043 ]

Showing metabocard for Saccharin (BMDB0062045)

Structure for BMDB0062045 (Saccharin)