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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2012-09-11 18:19:49 UTC

Update Date

2023-02-21 17:23:27 UTC

HMDB ID

HMDB0033585

Secondary Accession Numbers

HMDB33585

Metabolite Identification

Common Name

Acesulfame

Description

Acesulfame is a non-nutritive sweetener Acesulfame potassium is a calorie-free artificial sweetener, also known as Acesulfame K or Ace K (K being the symbol for potassium), and marketed under the trade names Sunett and Sweet One. In the European Union, it is known under the E number (additive code) E950. It was discovered accidentally in 1967 by German chemist Karl Clauss at Hoechst AG (now Nutrinova). In chemical structure, acesulfame potassium is the potassium salt of 6-methyl-1,2,3- oxathiazine-4(3H)-one 2,2-dioxide. It is a white crystalline powder with molecular formula C4H4KNO4S and a molecular weight of 201.24.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
Acesulfamo	ChEBI
Acesulfamum	ChEBI
Acesulphamo	Generator
Acesulphamum	Generator
Acesulphame	Generator
1,2,3-Oxathiazin-4(3H)-one, 6-methyl-, 2,2-dioxide	HMDB
3,4-dihydro-6-Methyl-1,2,3-oxathiazin-4-one 2,2-dioxide	HMDB
3,4-dihydro-6-Methyl-1,2,3-oxathiazin-4-one-2,2-dioxide	HMDB
6-Methyl-1,2,3-oxathiazin-4(3H)-ON 2,2-dioxid	HMDB
6-Methyl-1,2,3-oxathiazin-4(3H)-one 2,2-dioxide	HMDB
6-Methyl-1,2,3-oxathiazin-4(3H)-one 2,2-dioxide, 9ci	HMDB
6-Methyl-3,4-dihydro-1,2,3-oxathiazin-4-one 2,2-dioxide	HMDB
Acetosulfam	HMDB, MeSH
Acesulfame potassium	MeSH, HMDB
Acetosulfame calcium	MeSH, HMDB
Acesulfam-K	MeSH, HMDB
Acesulfame K	MeSH, HMDB
Acesulfame sodium	MeSH, HMDB
Acetosulfam, potassium salt	MeSH, HMDB
Acetosulfam, sodium salt	MeSH, HMDB
Acesulfame calcium	MeSH, HMDB
Acetosulfam potassium	MeSH, HMDB
Acetosulfame	MeSH, HMDB

Chemical Formula

C₄H₅NO₄S

Average Molecular Weight

163.152

Monoisotopic Molecular Weight

162.993928343

IUPAC Name

6-methyl-3,4-dihydro-1,2λ⁶,3-oxathiazine-2,2,4-trione

Traditional Name

acesulfame

CAS Registry Number

33665-90-6

SMILES

CC1=CC(=O)NS(=O)(=O)O1

InChI Identifier

InChI=1S/C4H5NO4S/c1-3-2-4(6)5-10(7,8)9-3/h2H,1H3,(H,5,6)

InChI Key

YGCFIWIQZPHFLU-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as organic sulfuric acids and derivatives. These are organic compounds containing the sulfuric acid or a derivative thereof.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Organic sulfuric acids and derivatives

Sub Class

Not Available

Direct Parent

Organic sulfuric acids and derivatives

Alternative Parents

Substituents

Organic sulfuric acid or derivatives
Oxacycle
Azacycle
Organoheterocyclic compound
Carboxylic acid derivative
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Carbonyl group
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

oxacycle (CHEBI:83501 )
organonitrogen heterocyclic compound (CHEBI:83501 )
sulfamate ester (CHEBI:83501 )
organic heteromonocyclic compound (CHEBI:83501 )

Ontology

Physiological effect

Organoleptic effect

Taste

Bitter

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0033585)
Cytoplasm (HMDB: HMDB0033585)

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 32966057)

Organ

Placenta (HMDB: HMDB0033585)

Excreta

Biofluid or Excreta

Feces (PMID: 27543620)
Urine (PMID: 32966057)

Source

Exogenous

Food

Food (HMDB: HMDB0033585)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0033585)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	123 - 123.5 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	910200 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	11.4 g/L	ALOGPS
logP	-0.1	ALOGPS
logP	-0.55	ChemAxon
logS	-1.2	ALOGPS
pKa (Strongest Acidic)	3.02	ChemAxon
pKa (Strongest Basic)	-6	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	72.47 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	33.54 m³·mol⁻¹	ChemAxon
Polarizability	13.34 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	136.177	31661259
DarkChem	[M-H]-	130.265	31661259
DeepCCS	[M+H]+	127.456	30932474
DeepCCS	[M-H]-	124.083	30932474
DeepCCS	[M-2H]-	161.473	30932474
DeepCCS	[M+Na]+	136.402	30932474
AllCCS	[M+H]+	133.9	32859911
AllCCS	[M+H-H2O]+	129.3	32859911
AllCCS	[M+NH4]+	138.2	32859911
AllCCS	[M+Na]+	139.4	32859911
AllCCS	[M-H]-	124.5	32859911
AllCCS	[M+Na-2H]-	126.3	32859911
AllCCS	[M+HCOO]-	128.2	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Acesulfame	CC1=CC(=O)NS(=O)(=O)O1	2641.2	Standard polar	33892256
Acesulfame	CC1=CC(=O)NS(=O)(=O)O1	1517.9	Standard non polar	33892256
Acesulfame	CC1=CC(=O)NS(=O)(=O)O1	1465.0	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Acesulfame,1TMS,isomer #1	CC1=CC(=O)N([Si](C)(C)C)S(=O)(=O)O1	1682.2	Semi standard non polar	33892256
Acesulfame,1TMS,isomer #1	CC1=CC(=O)N([Si](C)(C)C)S(=O)(=O)O1	1524.8	Standard non polar	33892256
Acesulfame,1TBDMS,isomer #1	CC1=CC(=O)N([Si](C)(C)C(C)(C)C)S(=O)(=O)O1	1910.0	Semi standard non polar	33892256
Acesulfame,1TBDMS,isomer #1	CC1=CC(=O)N([Si](C)(C)C(C)(C)C)S(=O)(=O)O1	1824.9	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Acesulfame GC-MS (Non-derivatized) - 70eV, Positive	splash10-01ox-9500000000-1a69f98b5529aabbd255	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Acesulfame GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Acesulfame LC-ESI-ITFT , negative-QTOF	splash10-001i-9100000000-8c9a34894aa5b01ef632	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Acesulfame LC-ESI-ITFT , negative-QTOF	splash10-03di-1900000000-a117c423450aacd418fd	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Acesulfame LC-ESI-ITFT , negative-QTOF	splash10-03e9-6900000000-6032f8c7d16740c7f02c	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Acesulfame LC-ESI-ITFT , negative-QTOF	splash10-001i-9200000000-7bbf958f08a839c3500c	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Acesulfame LC-ESI-ITFT , negative-QTOF	splash10-001i-9000000000-3942c9bf77437a358fa3	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Acesulfame LC-ESI-ITFT , negative-QTOF	splash10-001i-9000000000-12c18fc5ccf31fcc3358	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Acesulfame LC-ESI-ITFT , negative-QTOF	splash10-003r-9000000000-302aa8112af2669ef24d	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Acesulfame LC-ESI-ITFT , negative-QTOF	splash10-03di-0900000000-507fa48f166fc3437668	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Acesulfame LC-ESI-ITFT , negative-QTOF	splash10-03e9-6900000000-1074ea14f77b7f3d6ca7	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Acesulfame LC-ESI-ITFT , negative-QTOF	splash10-001i-9100000000-e1c3b82243db7de28960	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Acesulfame LC-ESI-ITFT , negative-QTOF	splash10-001i-9000000000-b1747449b341b8994e84	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Acesulfame LC-ESI-ITFT , negative-QTOF	splash10-001i-9000000000-c50316f35fb17b270868	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Acesulfame LC-ESI-ITFT , negative-QTOF	splash10-003r-9000000000-f9137bddd7e58f357da5	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Acesulfame LC-ESI-ITFT , negative-QTOF	splash10-001i-9000000000-a1683592e58f45fea025	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Acesulfame 60V, Negative-QTOF	splash10-001i-9000000000-3942c9bf77437a358fa3	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Acesulfame 75V, Negative-QTOF	splash10-001i-9000000000-12c18fc5ccf31fcc3358	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Acesulfame 45V, Negative-QTOF	splash10-001i-9200000000-ffa5f42ff132988b26b4	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Acesulfame 30V, Negative-QTOF	splash10-03e9-6900000000-cc770eef8e5c74f0b274	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Acesulfame 75V, Negative-QTOF	splash10-001i-9000000000-9ea1c7ee419cd7e9339c	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Acesulfame 10V, Positive-QTOF	splash10-03di-0900000000-666d816acbe519cfe2b4	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Acesulfame 20V, Positive-QTOF	splash10-0171-9200000000-e8a6d73912d910029be1	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Acesulfame 40V, Positive-QTOF	splash10-0006-9300000000-97a648067b13226566d0	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Acesulfame 10V, Negative-QTOF	splash10-03di-0900000000-35fada1e8a866778fb51	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Acesulfame 20V, Negative-QTOF	splash10-03di-3900000000-2d9367a7d615f005a70b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Acesulfame 40V, Negative-QTOF	splash10-0006-9000000000-fd144afc5c05c6c4f5be	2016-08-03	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)	2023-02-04	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-04	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-04	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

Biospecimen Locations

Blood
Feces
Urine

Tissue Locations

Placenta

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	27543620	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	29808030	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB011661

KNApSAcK ID

Not Available

Chemspider ID

33607

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Acesulfame potassium

METLIN ID

Not Available

PubChem Compound

36573

PDB ID

Not Available

ChEBI ID

83501

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1836901

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]
(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for Acesulfame (HMDB0033585)

MOL for HMDB0033585 (Acesulfame)

3D MOL for HMDB0033585 (Acesulfame)

3D SDF for HMDB0033585 (Acesulfame)

3D-SDF for HMDB0033585 (Acesulfame)

PDB for HMDB0033585 (Acesulfame)

3D PDB for HMDB0033585 (Acesulfame)

SMILES for HMDB0033585 (Acesulfame)

INCHI for HMDB0033585 (Acesulfame)

Structure for HMDB0033585 (Acesulfame)

3D Structure for HMDB0033585 (Acesulfame)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra