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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 19:46:42 UTC
Update Date2022-03-07 02:54:15 UTC
HMDB IDHMDB0034850
Secondary Accession Numbers
  • HMDB34850
Metabolite Identification
Common NameMetosulam
DescriptionMetosulam belongs to the class of organic compounds known as 1,2,4-triazolopyrimidine-2-sulfonanilides. These are polycyclic aromatic compounds containing a 1,2,4-triazolo[1,5-a]pyrimidine ring system, which is substituted with a sulfonanilide at the 2-position. Based on a literature review a significant number of articles have been published on Metosulam.
Structure
Data?1563862624
Synonyms
ValueSource
DE 511HMDB
N-(2,6-dichloro-3-Methylphenyl)-5,7-dimethoxy[1,2,4]triazolo[1,5-a]pyrimidine-2-sulfonamide, 9ciHMDB
XDE 511HMDB
XRD 511HMDB
N-(2,6-Dichloro-3-methylphenyl)-5,7-dimethoxy-1,2,4-triazolo-(1,5a)-pyrimidine-2-sulfonamideMeSH
Chemical FormulaC14H13Cl2N5O4S
Average Molecular Weight418.255
Monoisotopic Molecular Weight417.006530033
IUPAC NameN-(2,6-dichloro-3-methylphenyl)-5,7-dimethoxy-[1,2,4]triazolo[1,5-a]pyrimidine-2-sulfonamide
Traditional Namemetosulam
CAS Registry Number139528-85-1
SMILES
COC1=NC2=NC(=NN2C(OC)=C1)S(=O)(=O)NC1=C(Cl)C=CC(C)=C1Cl
InChI Identifier
InChI=1S/C14H13Cl2N5O4S/c1-7-4-5-8(15)12(11(7)16)20-26(22,23)14-18-13-17-9(24-2)6-10(25-3)21(13)19-14/h4-6,20H,1-3H3
InChI KeyVGHPMIFEKOFHHQ-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as 1,2,4-triazolopyrimidine-2-sulfonanilides. These are polycyclic aromatic compounds containing a 1,2,4-triazolo[1,5-a]pyrimidine ring system, which is substituted with a sulfonanilide at the 2-position.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassTriazolopyrimidines
Sub Class1,2,4-triazolopyrimidine-2-sulfonamides
Direct Parent1,2,4-triazolopyrimidine-2-sulfonanilides
Alternative Parents
Substituents
  • 1,2,4-triazolopyrimidine-2-sulfonanilide
  • Sulfanilide
  • 1,3-dichlorobenzene
  • Alkyl aryl ether
  • Chlorobenzene
  • Halobenzene
  • Toluene
  • Aryl chloride
  • Aryl halide
  • Monocyclic benzene moiety
  • Benzenoid
  • Pyrimidine
  • Organosulfonic acid amide
  • Azole
  • Heteroaromatic compound
  • Aminosulfonyl compound
  • 1,2,4-triazole
  • Organic sulfonic acid or derivatives
  • Organosulfonic acid or derivatives
  • Triazole
  • Sulfonyl
  • Azacycle
  • Ether
  • Organonitrogen compound
  • Organochloride
  • Organohalogen compound
  • Organooxygen compound
  • Organosulfur compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Organic nitrogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Source

Route of exposure

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point224 - 226 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.2 mg/mL at 20 °CNot Available
LogP3.08Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.02 g/LALOGPS
logP3.76ALOGPS
logP3.47ChemAxon
logS-4.3ALOGPS
pKa (Strongest Acidic)8.79ChemAxon
pKa (Strongest Basic)-3.5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area107.71 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity107.53 m³·mol⁻¹ChemAxon
Polarizability39.17 ųChemAxon
Number of Rings3ChemAxon
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]+181.85630932474
DeepCCS[M-H]-179.49830932474
DeepCCS[M-2H]-213.55930932474
DeepCCS[M+Na]+188.70930932474
AllCCS[M+H]+187.232859911
AllCCS[M+H-H2O]+184.532859911
AllCCS[M+NH4]+189.632859911
AllCCS[M+Na]+190.332859911
AllCCS[M-H]-183.432859911
AllCCS[M+Na-2H]-183.032859911
AllCCS[M+HCOO]-182.832859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
MetosulamCOC1=NC2=NC(=NN2C(OC)=C1)S(=O)(=O)NC1=C(Cl)C=CC(C)=C1Cl4486.5Standard polar33892256
MetosulamCOC1=NC2=NC(=NN2C(OC)=C1)S(=O)(=O)NC1=C(Cl)C=CC(C)=C1Cl3191.8Standard non polar33892256
MetosulamCOC1=NC2=NC(=NN2C(OC)=C1)S(=O)(=O)NC1=C(Cl)C=CC(C)=C1Cl3285.9Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Metosulam,1TMS,isomer #1COC1=NC2=NC(S(=O)(=O)N(C3=C(Cl)C=CC(C)=C3Cl)[Si](C)(C)C)=NN2C(OC)=C13205.4Semi standard non polar33892256
Metosulam,1TMS,isomer #1COC1=NC2=NC(S(=O)(=O)N(C3=C(Cl)C=CC(C)=C3Cl)[Si](C)(C)C)=NN2C(OC)=C13306.4Standard non polar33892256
Metosulam,1TBDMS,isomer #1COC1=NC2=NC(S(=O)(=O)N(C3=C(Cl)C=CC(C)=C3Cl)[Si](C)(C)C(C)(C)C)=NN2C(OC)=C13430.4Semi standard non polar33892256
Metosulam,1TBDMS,isomer #1COC1=NC2=NC(S(=O)(=O)N(C3=C(Cl)C=CC(C)=C3Cl)[Si](C)(C)C(C)(C)C)=NN2C(OC)=C13559.5Standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Metosulam GC-MS (Non-derivatized) - 70eV, Positivesplash10-00fr-1901000000-23b7edb5285cc3e532da2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Metosulam GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Metosulam GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Metosulam LC-ESI-QFT , negative-QTOFsplash10-004i-0900300000-4ae433576b73cf5557292017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Metosulam LC-ESI-QFT , negative-QTOFsplash10-004i-0900000000-c108efba7da6eb13d77f2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Metosulam LC-ESI-QFT , negative-QTOFsplash10-03fr-1900000000-412dcd27ef7a795ea3352017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Metosulam LC-ESI-QFT , negative-QTOFsplash10-02t9-6900000000-184829c3a2880c58a8b12017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Metosulam LC-ESI-QFT , negative-QTOFsplash10-014i-9300000000-45ef62498931fcfb2f082017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Metosulam LC-ESI-QFT , negative-QTOFsplash10-014i-9100000000-564193de3dcd6f5d02022017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Metosulam LC-ESI-QFT , positive-QTOFsplash10-014i-0000900000-cb75f9032f7a4f7516242017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Metosulam LC-ESI-QFT , positive-QTOFsplash10-00di-0900000000-cc66636c952080c945022017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Metosulam LC-ESI-QFT , positive-QTOFsplash10-00di-0900000000-a14bd0a79cef05c2e4e42017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Metosulam LC-ESI-QFT , positive-QTOFsplash10-00di-0900000000-03e7aa4f802c423e33de2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Metosulam LC-ESI-QFT , positive-QTOFsplash10-006x-0900000000-aca363f3934ced2b496e2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Metosulam LC-ESI-QFT , positive-QTOFsplash10-0006-1900000000-74a784fe1dfc0100c4572017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Metosulam 60V, Negative-QTOFsplash10-02t9-6900000000-a25e133c81dd6c32b0912021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Metosulam 45V, Negative-QTOFsplash10-03fr-1900000000-ffbdef9e333c34c8f4892021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Metosulam 30V, Negative-QTOFsplash10-004i-0900000000-0d461f8c2e51fc9d9bc52021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Metosulam 45V, Positive-QTOFsplash10-00di-0900000000-2b150fcbafac9bad65482021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Metosulam 30V, Positive-QTOFsplash10-00di-0900000000-7cfb81f8c686cd14a2fd2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Metosulam 60V, Positive-QTOFsplash10-00di-0900000000-efcba083eec32dad7f5a2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Metosulam 15V, Negative-QTOFsplash10-004i-0900300000-74ab6d596cb982582bd72021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Metosulam 10V, Positive-QTOFsplash10-014i-0000900000-fc23f4f7f8ff18d11d702016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Metosulam 20V, Positive-QTOFsplash10-00kr-0090700000-abc96b7f1b11ad29eda92016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Metosulam 40V, Positive-QTOFsplash10-00s9-8429700000-031cb292892bf69bd6ac2016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Metosulam 10V, Negative-QTOFsplash10-014i-0200900000-ea49eea92f929edb90272016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Metosulam 20V, Negative-QTOFsplash10-014r-1137900000-b092bda2b4f2c23aa6e32016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Metosulam 40V, Negative-QTOFsplash10-000i-5192000000-be42220f00f8121602812016-08-03Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Membrane
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB013416
KNApSAcK IDNot Available
Chemspider ID77938
KEGG Compound IDC18867
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound86422
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1071731
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .