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Showing NP-Card for Acesulfame (NP0336638)

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Record Information
Version2.0
Created at2024-09-11 07:11:44 UTC
Updated at2024-09-11 07:11:44 UTC
NP-MRD IDNP0336638
Secondary Accession NumbersNone
Natural Product Identification
Common NameAcesulfame
DescriptionAcesulfame, also known as acesulphamo or acesulfame sodium, 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. Acesulfame is an extremely weak basic (essentially neutral) compound (based on its pKa). Acesulfame is a bitter tasting compound. Outside of the human body,. Acesulfame was first documented in 2014 (PMID: 25046375). A sulfamate ester that is 1,2,3-oxathiazin-4(3H)-one 2,2-dioxide substituted by a methyl group at position 6 (PMID: 25085815).
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0336638 (Acesulfame)


  Mrv0541 02241214402D          

 10 10  0  0  0  0            999 V2000
    0.7609   -0.2000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0397   -0.6006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0397   -1.4019    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6006   -0.2000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6807    0.6006    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4821    0.4404    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9211    1.4019    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0397    1.0013    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7609    0.6006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4821    1.0013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  9  2  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  2  0  0  0  0
  5  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
M  END
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3D MOL for NP0336638 (Acesulfame)

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3D SDF for NP0336638 (Acesulfame)

  Mrv0541 02241214402D          

 10 10  0  0  0  0            999 V2000
    0.7609   -0.2000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0397   -0.6006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0397   -1.4019    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6006   -0.2000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6807    0.6006    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4821    0.4404    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9211    1.4019    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0397    1.0013    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7609    0.6006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4821    1.0013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  9  2  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  2  0  0  0  0
  5  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0336638

> <DATABASE_NAME>
NP-MRD

> <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

> <FORMULA>
C4H5NO4S

> <MOLECULAR_WEIGHT>
163.152

> <EXACT_MASS>
162.993928343

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
13.337512932945941

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
-0.10

> <JCHEM_LOGP>
-0.5515277416666667

> <ALOGPS_LOGS>
-1.15

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.0168871797817904

> <JCHEM_PKA_STRONGEST_BASIC>
-6.039302247560139

> <JCHEM_POLAR_SURFACE_AREA>
72.47

> <JCHEM_REFRACTIVITY>
33.537600000000005

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.14e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
acesulfame

> <JCHEM_VEBER_RULE>
0

$$$$

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3D-SDF for NP0336638 (Acesulfame)
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PDB for NP0336638 (Acesulfame)
HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0       1.420  -0.373   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.074  -1.121   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       0.074  -2.617   0.000  0.00  0.00           O+0
HETATM    4  N   UNK     0      -1.121  -0.373   0.000  0.00  0.00           N+0
HETATM    5  S   UNK     0      -1.271   1.121   0.000  0.00  0.00           S+0
HETATM    6  O   UNK     0      -2.767   0.822   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0      -1.719   2.617   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0       0.074   1.869   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       1.420   1.121   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.767   1.869   0.000  0.00  0.00           C+0
CONECT    1    2    9                                                       
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6    7    8                                             
CONECT    6    5                                                            
CONECT    7    5                                                            
CONECT    8    5    9                                                       
CONECT    9    1    8   10                                                  
CONECT   10    9                                                            
MASTER        0    0    0    0    0    0    0    0   10    0   20    0
END

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3D PDB for NP0336638 (Acesulfame)
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SMILES for NP0336638 (Acesulfame)
CC1=CC(=O)NS(=O)(=O)O1
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INCHI for NP0336638 (Acesulfame)
InChI=1S/C4H5NO4S/c1-3-2-4(6)5-10(7,8)9-3/h2H,1H3,(H,5,6)
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View in JSmol
Synonyms
ValueSource
AcesulfamoChEBI
AcesulfamumChEBI
AcesulphamoGenerator
AcesulphamumGenerator
AcesulphameGenerator
1,2,3-Oxathiazin-4(3H)-one, 6-methyl-, 2,2-dioxideHMDB
3,4-Dihydro-6-methyl-1,2,3-oxathiazin-4-one 2,2-dioxideHMDB
3,4-Dihydro-6-methyl-1,2,3-oxathiazin-4-one-2,2-dioxideHMDB
6-Methyl-1,2,3-oxathiazin-4(3H)-ON 2,2-dioxidHMDB
6-Methyl-1,2,3-oxathiazin-4(3H)-one 2,2-dioxideHMDB
6-Methyl-1,2,3-oxathiazin-4(3H)-one 2,2-dioxide, 9ciHMDB
6-Methyl-3,4-dihydro-1,2,3-oxathiazin-4-one 2,2-dioxideHMDB
AcetosulfamHMDB
Acesulfame potassiumHMDB
Acetosulfame calciumHMDB
Acesulfam-KHMDB
Acesulfame KHMDB
Acesulfame sodiumHMDB
Acetosulfam, potassium saltHMDB
Acetosulfam, sodium saltHMDB
Acesulfame calciumHMDB
Acetosulfam potassiumHMDB
AcetosulfameHMDB
Chemical FormulaC4H5NO4S
Average Mass163.1520 Da
Monoisotopic Mass162.99393 Da
IUPAC Name6-methyl-3,4-dihydro-1,2λ⁶,3-oxathiazine-2,2,4-trione
Traditional Nameacesulfame
CAS Registry NumberNot Available
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 KeyYGCFIWIQZPHFLU-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of OriginNot Available
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.
KingdomOrganic compounds  
Super ClassOrganic acids and derivatives  
ClassOrganic sulfuric acids and derivatives  
Sub ClassNot Available
Direct ParentOrganic 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 FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP-0.1ALOGPS
logP-0.55ChemAxon
logS-1.2ALOGPS
pKa (Strongest Acidic)3.02ChemAxon
pKa (Strongest Basic)-6ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area72.47 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity33.54 m³·mol⁻¹ChemAxon
Polarizability13.34 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0033585  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB011661  
KNApSAcK IDNot Available
Chemspider ID33607  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkAcesulfame potassium  
METLIN IDNot Available
PubChem Compound36573  
PDB IDNot Available
ChEBI ID83501  
Good Scents IDNot Available
References
General References
  1. Gan Z, Sun H, Wang R, Hu H, Zhang P, Ren X: Transformation of acesulfame in water under natural sunlight: joint effect of photolysis and biodegradation. Water Res. 2014 Nov 1;64:113-122. doi: 10.1016/j.watres.2014.07.002. Epub 2014  Jul 10. [PubMed:25046375  ] 
  2. Wu M, Qian Y, Boyd JM, Hrudey SE, Le XC, Li XF: Direct large volume injection ultra-high performance liquid chromatography-tandem mass spectrometry determination of artificial sweeteners sucralose and acesulfame in well water. J Chromatogr A. 2014 Sep 12;1359:156-61. doi: 10.1016/j.chroma.2014.07.035. Epub  2014 Jul 19. [PubMed:25085815  ]