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Record Information
Version4.0
StatusDetected but not Quantified
Creation Date2012-09-11 17:42:24 UTC
Update Date2020-11-09 23:29:38 UTC
HMDB IDHMDB0031340
Secondary Accession Numbers
  • HMDB31340
Metabolite Identification
Common NameCyclamic acid
DescriptionCyclamic acid, also known as cyclamate or hexamic acid, belongs to the class of organic compounds known as cyclamates. Cyclamates are compounds containing a cyclohexylsulfamic acid moiety. Cyclamic acid is an extremely weak basic (essentially neutral) compound (based on its pKa). Cyclamic acid is a permitted in EU at levels of 250-1600 ppm in food products. Use suspended in some countries, including USA, because of possible weak carcinogenic activity (disputed). Cyclamic acid is a compound with formula C6H11NHSO2OH.
Structure
Data?1563862111
Synonyms
ValueSource
Cyclohexylamide sulfateChEBI
Cyclohexylaminesulphonic acidChEBI
CyclohexylsulfamateChEBI
Cylamic acidChEBI
Cyclohexylsulfamic acidKegg
Hexamic acidKegg
Cyclohexylamide sulfuric acidGenerator
Cyclohexylamide sulphateGenerator
Cyclohexylamide sulphuric acidGenerator
CyclohexylaminesulfonateGenerator
Cyclohexylaminesulfonic acidGenerator
CyclohexylaminesulphonateGenerator
CyclohexylsulphamateGenerator
Cyclohexylsulphamic acidGenerator
CylamateGenerator
HexamateGenerator
CyclamateGenerator
AsugrynHMDB
Cyclamic acid, ban, usanHMDB
Cyclohexanesulfamic acidHMDB
Cyclohexanesulphamic acidHMDB
Cyclohexyl-sulfamic acidHMDB
Cyclohexylamidosulfuric acidHMDB
Cyclohexylamidosulphuric acidHMDB
Cyclohexylamine sulfamic acidHMDB
Cyclohexylamine-N-sulfonic acidHMDB
e952HMDB
N-Cyclohexyl-sulfamic acidHMDB
N-Cyclohexyl-sulfuric acid monoamideHMDB
N-Cyclohexylsulfamic acidHMDB
N-Cyclohexylsulphamic acidHMDB
Polycat 200HMDB
Sucaryl acidHMDB
Sucaryl acidxineHMDB
Cyclamate calcium (2:1) saltHMDB
Cyclamate, calcium (2:1) salt, dihydrateHMDB
Cyclamate, sodium saltHMDB
CyclamatesHMDB
Calcium cyclamateHMDB
Cyclamate, calciumHMDB
Cyclamate, sodiumHMDB
Sodium cyclamateHMDB
Cyclamate, potassiumHMDB
Potassium cyclamateHMDB
Cyclamic acidMeSH
Chemical FormulaC6H13NO3S
Average Molecular Weight179.237
Monoisotopic Molecular Weight179.061613977
IUPAC NameN-cyclohexylsulfamic acid
Traditional Namecyclamate
CAS Registry Number100-88-9
SMILES
OS(=O)(=O)NC1CCCCC1
InChI Identifier
InChI=1S/C6H13NO3S/c8-11(9,10)7-6-4-2-1-3-5-6/h6-7H,1-5H2,(H,8,9,10)
InChI KeyHCAJEUSONLESMK-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as cyclamates. Cyclamates are compounds containing a cyclohexylsulfamic acid moiety.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassSulfamic acid derivatives
Sub ClassCyclamates
Direct ParentCyclamates
Alternative Parents
Substituents
  • Cyclamic_acid_derivative
  • Sulfuric acid monoamide
  • Organic sulfuric acid or derivatives
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External Descriptors
Ontology
Disposition

Source:

Biological location:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point169 - 170 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility7.68 g/LALOGPS
logP-1.2ALOGPS
logP0.61ChemAxon
logS-1.4ALOGPS
pKa (Strongest Acidic)-0.83ChemAxon
pKa (Strongest Basic)-9.7ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area66.4 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity41.22 m³·mol⁻¹ChemAxon
Polarizability17.7 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-000t-1920000000-71d8c55a8248f07d31faSpectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0r00-2950000000-b241576cc12775852e45Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-000t-1920000000-71d8c55a8248f07d31faSpectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0r00-2950000000-b241576cc12775852e45Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-000b-9500000000-b134852630cc9649f1a4Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-004i-3900000000-d31d7db47401444be240Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-004i-0900000000-7225999f2a2be4bc507eSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-004i-0900000000-7225999f2a2be4bc507eSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-004i-0900000000-02a4d672dec437bd9861Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-004i-3900000000-3d9623c04b547439d527Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-004i-9400000000-3f6a5df7711a1058255aSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-004i-9000000000-d8a9eb17286248cd242aSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-004i-0900000000-da254663d1e4556eda5cSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-004i-0900000000-7f4eedb2425bf2986ad5Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-004i-0900000000-4d648a0d9afdabcb7f9cSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-004i-3900000000-999e8807d53dec365f76Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-004i-9300000000-854636ff5385c1ff4479Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-004i-9000000000-f5d2a227947fb7840c73Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-004i-3900000000-94d290f9556780ba0009Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-004i-0900000000-940aa6412d3f3115fc23Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-001i-9000000000-5b83047a37a9d6474e40Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-001i-9100000000-e8eb1e4fc04fa6226b1eSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-001i-9000000000-68a4fe340a4126e7a04cSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-001i-9000000000-07ec17a1ab8598984302Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-6900000000-499ad855bd2dc992dc1bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-9300000000-c84eb6aaec80ac771f40Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-053u-9000000000-758f0931c377bfda783dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-5900000000-b721555f97d374340634Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-005a-9400000000-e61f5f9b0d6082249d0dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001i-9000000000-3df5c83909d4ebda51e2Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB003404
KNApSAcK IDNot Available
Chemspider ID7252
KEGG Compound IDC02824
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkCyclamic_acid
METLIN IDNot Available
PubChem Compound7533
PDB IDNot Available
ChEBI ID15964
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB ID
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Unterhalt B, Boschemeyer L: [Cycloalkylsulfamic acids and their salts. i.v. (author's transl)]. Z Lebensm Unters Forsch. 1975 May 30;158(1):35-6. [PubMed:178120 ]
  2. Wort DJ, Patel KM: Structure of some cyclohexyl compounds as related to their ability to stimulate plant growth. Plant Physiol. 1974 Oct;54(4):656-8. [PubMed:16658947 ]
  3. Unterhalt B, Boschemeyer L: [Cycloalkylsulfamic acids and their salts. V. (author's transl)]. Z Lebensm Unters Forsch. 1976;161(3):275-6. [PubMed:973466 ]
  4. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .