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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2021-09-11 07:19:02 UTC
Update Date2021-09-26 23:01:42 UTC
HMDB IDHMDB0250313
Secondary Accession NumbersNone
Metabolite Identification
Common NameClamikalant
Description5-chloro-2-methoxy-N-{2-[4-methoxy-3-({[methylthio(carbonoimidyl)]amino}sulfonyl)phenyl]ethyl}benzene-1-carboximidic acid belongs to the class of organic compounds known as benzenesulfonamides. These are organic compounds containing a sulfonamide group that is S-linked to a benzene ring. Based on a literature review very few articles have been published on 5-chloro-2-methoxy-N-{2-[4-methoxy-3-({[methylthio(carbonoimidyl)]amino}sulfonyl)phenyl]ethyl}benzene-1-carboximidic acid. This compound has been identified in human blood as reported by (PMID: 31557052 ). Clamikalant is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Clamikalant is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.
Structure
Thumb
Synonyms
ValueSource
5-Chloro-2-methoxy-N-{2-[4-methoxy-3-({[methylthio(carbonoimidyl)]amino}sulfonyl)phenyl]ethyl}benzene-1-carboximidateGenerator
5-Chloro-2-methoxy-N-{2-[4-methoxy-3-({[methylthio(carbonoimidyl)]amino}sulphonyl)phenyl]ethyl}benzene-1-carboximidateGenerator
5-Chloro-2-methoxy-N-{2-[4-methoxy-3-({[methylthio(carbonoimidyl)]amino}sulphonyl)phenyl]ethyl}benzene-1-carboximidic acidGenerator
Chemical FormulaC19H22ClN3O5S2
Average Molecular Weight471.97
Monoisotopic Molecular Weight471.0689409
IUPAC Name5-chloro-2-methoxy-N-[2-(4-methoxy-3-{[(methylcarbamothioyl)amino]sulfonyl}phenyl)ethyl]benzamide
Traditional Name5-chloro-2-methoxy-N-(2-{4-methoxy-3-[(methylcarbamothioyl)aminosulfonyl]phenyl}ethyl)benzamide
CAS Registry NumberNot Available
SMILES
CNC(=S)NS(=O)(=O)C1=C(OC)C=CC(CCNC(=O)C2=C(OC)C=CC(Cl)=C2)=C1
InChI Identifier
InChI=1S/C19H22ClN3O5S2/c1-21-19(29)23-30(25,26)17-10-12(4-6-16(17)28-3)8-9-22-18(24)14-11-13(20)5-7-15(14)27-2/h4-7,10-11H,8-9H2,1-3H3,(H,22,24)(H2,21,23,29)
InChI KeyVXTKXGKPBOLHRY-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as benzenesulfonamides. These are organic compounds containing a sulfonamide group that is S-linked to a benzene ring.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassBenzenesulfonamides
Direct ParentBenzenesulfonamides
Alternative Parents
Substituents
  • Benzenesulfonamide
  • 3-halobenzoic acid or derivatives
  • Halobenzoic acid or derivatives
  • Benzamide
  • Benzoic acid or derivatives
  • Benzenesulfonyl group
  • Anisole
  • Phenoxy compound
  • Benzoyl
  • Phenol ether
  • Methoxybenzene
  • Alkyl aryl ether
  • Halobenzene
  • Chlorobenzene
  • Aryl chloride
  • Aryl halide
  • Organosulfonic acid or derivatives
  • Organic sulfonic acid or derivatives
  • Aminosulfonyl compound
  • Sulfonyl
  • Secondary carboxylic acid amide
  • Carboxamide group
  • Ether
  • Carboxylic acid derivative
  • Organosulfur compound
  • Organohalogen compound
  • Organic oxygen compound
  • Organochloride
  • Organic nitrogen compound
  • Organonitrogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
logP2.54ALOGPS
logP2.72ChemAxon
logS-5.3ALOGPS
pKa (Strongest Acidic)5.99ChemAxon
pKa (Strongest Basic)-1.4ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area105.76 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity120.42 m³·mol⁻¹ChemAxon
Polarizability46.71 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+210.47330932474
DeepCCS[M-H]-208.11530932474
DeepCCS[M-2H]-241.57830932474
DeepCCS[M+Na]+216.80630932474
AllCCS[M+H]+204.332859911
AllCCS[M+H-H2O]+202.232859911
AllCCS[M+NH4]+206.332859911
AllCCS[M+Na]+206.832859911
AllCCS[M-H]-201.032859911
AllCCS[M+Na-2H]-201.532859911
AllCCS[M+HCOO]-202.332859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
ClamikalantCNC(=S)NS(=O)(=O)C1=C(OC)C=CC(CCNC(=O)C2=C(OC)C=CC(Cl)=C2)=C16327.2Standard polar33892256
ClamikalantCNC(=S)NS(=O)(=O)C1=C(OC)C=CC(CCNC(=O)C2=C(OC)C=CC(Cl)=C2)=C13021.0Standard non polar33892256
ClamikalantCNC(=S)NS(=O)(=O)C1=C(OC)C=CC(CCNC(=O)C2=C(OC)C=CC(Cl)=C2)=C14180.5Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Clamikalant,1TMS,isomer #1COC1=CC=C(Cl)C=C1C(=O)NCCC1=CC=C(OC)C(S(=O)(=O)NC(=S)N(C)[Si](C)(C)C)=C14016.6Semi standard non polar33892256
Clamikalant,1TMS,isomer #1COC1=CC=C(Cl)C=C1C(=O)NCCC1=CC=C(OC)C(S(=O)(=O)NC(=S)N(C)[Si](C)(C)C)=C13893.1Standard non polar33892256
Clamikalant,1TMS,isomer #1COC1=CC=C(Cl)C=C1C(=O)NCCC1=CC=C(OC)C(S(=O)(=O)NC(=S)N(C)[Si](C)(C)C)=C15536.8Standard polar33892256
Clamikalant,1TMS,isomer #2CNC(=S)N([Si](C)(C)C)S(=O)(=O)C1=CC(CCNC(=O)C2=CC(Cl)=CC=C2OC)=CC=C1OC3871.5Semi standard non polar33892256
Clamikalant,1TMS,isomer #2CNC(=S)N([Si](C)(C)C)S(=O)(=O)C1=CC(CCNC(=O)C2=CC(Cl)=CC=C2OC)=CC=C1OC3756.7Standard non polar33892256
Clamikalant,1TMS,isomer #2CNC(=S)N([Si](C)(C)C)S(=O)(=O)C1=CC(CCNC(=O)C2=CC(Cl)=CC=C2OC)=CC=C1OC5634.1Standard polar33892256
Clamikalant,1TMS,isomer #3CNC(=S)NS(=O)(=O)C1=CC(CCN(C(=O)C2=CC(Cl)=CC=C2OC)[Si](C)(C)C)=CC=C1OC3980.5Semi standard non polar33892256
Clamikalant,1TMS,isomer #3CNC(=S)NS(=O)(=O)C1=CC(CCN(C(=O)C2=CC(Cl)=CC=C2OC)[Si](C)(C)C)=CC=C1OC3868.7Standard non polar33892256
Clamikalant,1TMS,isomer #3CNC(=S)NS(=O)(=O)C1=CC(CCN(C(=O)C2=CC(Cl)=CC=C2OC)[Si](C)(C)C)=CC=C1OC5763.8Standard polar33892256
Clamikalant,2TMS,isomer #1COC1=CC=C(Cl)C=C1C(=O)N(CCC1=CC=C(OC)C(S(=O)(=O)NC(=S)N(C)[Si](C)(C)C)=C1)[Si](C)(C)C3843.0Semi standard non polar33892256
Clamikalant,2TMS,isomer #1COC1=CC=C(Cl)C=C1C(=O)N(CCC1=CC=C(OC)C(S(=O)(=O)NC(=S)N(C)[Si](C)(C)C)=C1)[Si](C)(C)C4000.1Standard non polar33892256
Clamikalant,2TMS,isomer #1COC1=CC=C(Cl)C=C1C(=O)N(CCC1=CC=C(OC)C(S(=O)(=O)NC(=S)N(C)[Si](C)(C)C)=C1)[Si](C)(C)C5227.2Standard polar33892256
Clamikalant,2TMS,isomer #2COC1=CC=C(Cl)C=C1C(=O)NCCC1=CC=C(OC)C(S(=O)(=O)N(C(=S)N(C)[Si](C)(C)C)[Si](C)(C)C)=C13822.4Semi standard non polar33892256
Clamikalant,2TMS,isomer #2COC1=CC=C(Cl)C=C1C(=O)NCCC1=CC=C(OC)C(S(=O)(=O)N(C(=S)N(C)[Si](C)(C)C)[Si](C)(C)C)=C13919.7Standard non polar33892256
Clamikalant,2TMS,isomer #2COC1=CC=C(Cl)C=C1C(=O)NCCC1=CC=C(OC)C(S(=O)(=O)N(C(=S)N(C)[Si](C)(C)C)[Si](C)(C)C)=C15144.8Standard polar33892256
Clamikalant,2TMS,isomer #3CNC(=S)N([Si](C)(C)C)S(=O)(=O)C1=CC(CCN(C(=O)C2=CC(Cl)=CC=C2OC)[Si](C)(C)C)=CC=C1OC3716.0Semi standard non polar33892256
Clamikalant,2TMS,isomer #3CNC(=S)N([Si](C)(C)C)S(=O)(=O)C1=CC(CCN(C(=O)C2=CC(Cl)=CC=C2OC)[Si](C)(C)C)=CC=C1OC3887.5Standard non polar33892256
Clamikalant,2TMS,isomer #3CNC(=S)N([Si](C)(C)C)S(=O)(=O)C1=CC(CCN(C(=O)C2=CC(Cl)=CC=C2OC)[Si](C)(C)C)=CC=C1OC5356.1Standard polar33892256
Clamikalant,3TMS,isomer #1COC1=CC=C(Cl)C=C1C(=O)N(CCC1=CC=C(OC)C(S(=O)(=O)N(C(=S)N(C)[Si](C)(C)C)[Si](C)(C)C)=C1)[Si](C)(C)C3702.0Semi standard non polar33892256
Clamikalant,3TMS,isomer #1COC1=CC=C(Cl)C=C1C(=O)N(CCC1=CC=C(OC)C(S(=O)(=O)N(C(=S)N(C)[Si](C)(C)C)[Si](C)(C)C)=C1)[Si](C)(C)C4049.2Standard non polar33892256
Clamikalant,3TMS,isomer #1COC1=CC=C(Cl)C=C1C(=O)N(CCC1=CC=C(OC)C(S(=O)(=O)N(C(=S)N(C)[Si](C)(C)C)[Si](C)(C)C)=C1)[Si](C)(C)C4862.6Standard polar33892256
Clamikalant,1TBDMS,isomer #1COC1=CC=C(Cl)C=C1C(=O)NCCC1=CC=C(OC)C(S(=O)(=O)NC(=S)N(C)[Si](C)(C)C(C)(C)C)=C14250.8Semi standard non polar33892256
Clamikalant,1TBDMS,isomer #1COC1=CC=C(Cl)C=C1C(=O)NCCC1=CC=C(OC)C(S(=O)(=O)NC(=S)N(C)[Si](C)(C)C(C)(C)C)=C14108.7Standard non polar33892256
Clamikalant,1TBDMS,isomer #1COC1=CC=C(Cl)C=C1C(=O)NCCC1=CC=C(OC)C(S(=O)(=O)NC(=S)N(C)[Si](C)(C)C(C)(C)C)=C15490.4Standard polar33892256
Clamikalant,1TBDMS,isomer #2CNC(=S)N([Si](C)(C)C(C)(C)C)S(=O)(=O)C1=CC(CCNC(=O)C2=CC(Cl)=CC=C2OC)=CC=C1OC4124.0Semi standard non polar33892256
Clamikalant,1TBDMS,isomer #2CNC(=S)N([Si](C)(C)C(C)(C)C)S(=O)(=O)C1=CC(CCNC(=O)C2=CC(Cl)=CC=C2OC)=CC=C1OC3965.1Standard non polar33892256
Clamikalant,1TBDMS,isomer #2CNC(=S)N([Si](C)(C)C(C)(C)C)S(=O)(=O)C1=CC(CCNC(=O)C2=CC(Cl)=CC=C2OC)=CC=C1OC5538.1Standard polar33892256
Clamikalant,1TBDMS,isomer #3CNC(=S)NS(=O)(=O)C1=CC(CCN(C(=O)C2=CC(Cl)=CC=C2OC)[Si](C)(C)C(C)(C)C)=CC=C1OC4237.8Semi standard non polar33892256
Clamikalant,1TBDMS,isomer #3CNC(=S)NS(=O)(=O)C1=CC(CCN(C(=O)C2=CC(Cl)=CC=C2OC)[Si](C)(C)C(C)(C)C)=CC=C1OC4070.8Standard non polar33892256
Clamikalant,1TBDMS,isomer #3CNC(=S)NS(=O)(=O)C1=CC(CCN(C(=O)C2=CC(Cl)=CC=C2OC)[Si](C)(C)C(C)(C)C)=CC=C1OC5693.2Standard polar33892256
Clamikalant,2TBDMS,isomer #1COC1=CC=C(Cl)C=C1C(=O)N(CCC1=CC=C(OC)C(S(=O)(=O)NC(=S)N(C)[Si](C)(C)C(C)(C)C)=C1)[Si](C)(C)C(C)(C)C4293.4Semi standard non polar33892256
Clamikalant,2TBDMS,isomer #1COC1=CC=C(Cl)C=C1C(=O)N(CCC1=CC=C(OC)C(S(=O)(=O)NC(=S)N(C)[Si](C)(C)C(C)(C)C)=C1)[Si](C)(C)C(C)(C)C4395.4Standard non polar33892256
Clamikalant,2TBDMS,isomer #1COC1=CC=C(Cl)C=C1C(=O)N(CCC1=CC=C(OC)C(S(=O)(=O)NC(=S)N(C)[Si](C)(C)C(C)(C)C)=C1)[Si](C)(C)C(C)(C)C5165.5Standard polar33892256
Clamikalant,2TBDMS,isomer #2COC1=CC=C(Cl)C=C1C(=O)NCCC1=CC=C(OC)C(S(=O)(=O)N(C(=S)N(C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C14306.8Semi standard non polar33892256
Clamikalant,2TBDMS,isomer #2COC1=CC=C(Cl)C=C1C(=O)NCCC1=CC=C(OC)C(S(=O)(=O)N(C(=S)N(C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C14330.7Standard non polar33892256
Clamikalant,2TBDMS,isomer #2COC1=CC=C(Cl)C=C1C(=O)NCCC1=CC=C(OC)C(S(=O)(=O)N(C(=S)N(C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C15071.7Standard polar33892256
Clamikalant,2TBDMS,isomer #3CNC(=S)N([Si](C)(C)C(C)(C)C)S(=O)(=O)C1=CC(CCN(C(=O)C2=CC(Cl)=CC=C2OC)[Si](C)(C)C(C)(C)C)=CC=C1OC4168.6Semi standard non polar33892256
Clamikalant,2TBDMS,isomer #3CNC(=S)N([Si](C)(C)C(C)(C)C)S(=O)(=O)C1=CC(CCN(C(=O)C2=CC(Cl)=CC=C2OC)[Si](C)(C)C(C)(C)C)=CC=C1OC4283.8Standard non polar33892256
Clamikalant,2TBDMS,isomer #3CNC(=S)N([Si](C)(C)C(C)(C)C)S(=O)(=O)C1=CC(CCN(C(=O)C2=CC(Cl)=CC=C2OC)[Si](C)(C)C(C)(C)C)=CC=C1OC5251.8Standard polar33892256
Clamikalant,3TBDMS,isomer #1COC1=CC=C(Cl)C=C1C(=O)N(CCC1=CC=C(OC)C(S(=O)(=O)N(C(=S)N(C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C1)[Si](C)(C)C(C)(C)C4381.6Semi standard non polar33892256
Clamikalant,3TBDMS,isomer #1COC1=CC=C(Cl)C=C1C(=O)N(CCC1=CC=C(OC)C(S(=O)(=O)N(C(=S)N(C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C1)[Si](C)(C)C(C)(C)C4638.6Standard non polar33892256
Clamikalant,3TBDMS,isomer #1COC1=CC=C(Cl)C=C1C(=O)N(CCC1=CC=C(OC)C(S(=O)(=O)N(C(=S)N(C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C1)[Si](C)(C)C(C)(C)C4886.5Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Clamikalant GC-MS (Non-derivatized) - 70eV, Positivesplash10-01b9-3932300000-03ea7837e7d779fce7652021-09-23Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Clamikalant GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Clamikalant 10V, Positive-QTOFsplash10-006t-0109500000-3ae17c95c8f5b482e3282021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Clamikalant 20V, Positive-QTOFsplash10-014i-0619300000-5228347ebd457e7ea24f2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Clamikalant 40V, Positive-QTOFsplash10-0v70-2922200000-fa5ca1ddb10bc364a23e2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Clamikalant 10V, Negative-QTOFsplash10-00di-1100900000-59f4a37f0b0f968563fc2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Clamikalant 20V, Negative-QTOFsplash10-0gc9-4029000000-91878324345b6fbac42d2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Clamikalant 40V, Negative-QTOFsplash10-001i-9313200000-2e10667956cc34862dc32021-10-12Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID2301423
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]