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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2014-06-23 11:34:47 UTC
Update Date2019-07-23 07:17:04 UTC
HMDB IDHMDB0061722
Secondary Accession Numbers
  • HMDB61722
Metabolite Identification
Common NameMetiamide
DescriptionMetiamide, also known as SK and F92058 or sk&f 92058, belongs to the class of organic compounds known as imidazoles. Imidazoles are compounds containing an imidazole ring, which is an aromatic five-member ring with two nitrogen atoms at positions 1 and 3, and three carbon atoms. Metiamide is a very strong basic compound (based on its pKa). Metiamide is a histamine H2-receptor antagonist. In humans, metiamide is involved in the metabolic disorder called the metiamide action pathway. This competitive inhibition results in reduced gastric acid secretion and a reduction in gastric volume and acidity. Other actions of Metiamide include an increase in gastric bacterial flora such as nitrate-reducing organisms. It was an intermediate product on the path to developing cimetidine. Metiamide is an H-2 receptor antagonist derived from burimamide. Metiamide inhibits many of the isoenzymes of the hepatic CYP450 enzyme system. Metiamide binds to an H2-receptor located on the basolateral membrane of the gastric parietal cell, blocking histamine effects. It reduces basal and nocturnal gastric acid secretion and a reduction in gastric volume, acidity, and amount of gastric acid released in response to stimuli including food, caffeine, insulin, betazole, or pentagastrin.
Structure
Data?1563866224
Synonyms
ValueSource
SK&F 92058HMDB
Metiamide monohydrochlorideHMDB
SK And F92058HMDB
Monohydrochloride, metiamideHMDB
SK And F 92058HMDB
SK And F-92058HMDB
Chemical FormulaC9H16N4S2
Average Molecular Weight244.38
Monoisotopic Molecular Weight244.081637912
IUPAC Name3-methyl-1-(2-{[(5-methyl-1H-imidazol-4-yl)methyl]sulfanyl}ethyl)thiourea
Traditional Namemethiamide
CAS Registry NumberNot Available
SMILES
CNC(=S)NCCSCC1=C(C)NC=N1
InChI Identifier
InChI=1S/C9H16N4S2/c1-7-8(13-6-12-7)5-15-4-3-11-9(14)10-2/h6H,3-5H2,1-2H3,(H,12,13)(H2,10,11,14)
InChI KeyFPBPLBWLMYGIQR-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as imidazoles. Imidazoles are compounds containing an imidazole ring, which is an aromatic five-member ring with two nitrogen atoms at positions 1 and 3, and three carbon atoms.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassAzoles
Sub ClassImidazoles
Direct ParentImidazoles
Alternative Parents
Substituents
  • Heteroaromatic compound
  • Imidazole
  • Thiourea
  • Azacycle
  • Dialkylthioether
  • Sulfenyl compound
  • Thioether
  • Organic nitrogen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Organosulfur compound
  • Organonitrogen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
DispositionNot Available
Process
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
Water Solubility0.029 g/LALOGPS
logP0.5ALOGPS
logP0.34ChemAxon
logS-3.9ALOGPS
pKa (Strongest Acidic)12.48ChemAxon
pKa (Strongest Basic)6.91ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area52.74 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity70.4 m³·mol⁻¹ChemAxon
Polarizability27.19 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+154.66131661259
DarkChem[M-H]-150.89631661259
DeepCCS[M+H]+150.5530932474
DeepCCS[M-H]-147.25330932474
DeepCCS[M-2H]-184.2430932474
DeepCCS[M+Na]+159.90330932474
AllCCS[M+H]+152.332859911
AllCCS[M+H-H2O]+148.932859911
AllCCS[M+NH4]+155.532859911
AllCCS[M+Na]+156.432859911
AllCCS[M-H]-155.532859911
AllCCS[M+Na-2H]-156.532859911
AllCCS[M+HCOO]-157.632859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
MetiamideCNC(=S)NCCSCC1=C(C)NC=N13595.9Standard polar33892256
MetiamideCNC(=S)NCCSCC1=C(C)NC=N12234.9Standard non polar33892256
MetiamideCNC(=S)NCCSCC1=C(C)NC=N12760.4Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Metiamide,1TMS,isomer #1CC1=C(CSCCNC(=S)N(C)[Si](C)(C)C)N=C[NH]12508.8Semi standard non polar33892256
Metiamide,1TMS,isomer #1CC1=C(CSCCNC(=S)N(C)[Si](C)(C)C)N=C[NH]12165.7Standard non polar33892256
Metiamide,1TMS,isomer #1CC1=C(CSCCNC(=S)N(C)[Si](C)(C)C)N=C[NH]13460.1Standard polar33892256
Metiamide,1TMS,isomer #2CNC(=S)N(CCSCC1=C(C)[NH]C=N1)[Si](C)(C)C2465.3Semi standard non polar33892256
Metiamide,1TMS,isomer #2CNC(=S)N(CCSCC1=C(C)[NH]C=N1)[Si](C)(C)C2209.1Standard non polar33892256
Metiamide,1TMS,isomer #2CNC(=S)N(CCSCC1=C(C)[NH]C=N1)[Si](C)(C)C3495.5Standard polar33892256
Metiamide,1TMS,isomer #3CNC(=S)NCCSCC1=C(C)N([Si](C)(C)C)C=N12590.0Semi standard non polar33892256
Metiamide,1TMS,isomer #3CNC(=S)NCCSCC1=C(C)N([Si](C)(C)C)C=N12177.6Standard non polar33892256
Metiamide,1TMS,isomer #3CNC(=S)NCCSCC1=C(C)N([Si](C)(C)C)C=N13897.2Standard polar33892256
Metiamide,2TMS,isomer #1CC1=C(CSCCNC(=S)N(C)[Si](C)(C)C)N=CN1[Si](C)(C)C2583.6Semi standard non polar33892256
Metiamide,2TMS,isomer #1CC1=C(CSCCNC(=S)N(C)[Si](C)(C)C)N=CN1[Si](C)(C)C2307.7Standard non polar33892256
Metiamide,2TMS,isomer #1CC1=C(CSCCNC(=S)N(C)[Si](C)(C)C)N=CN1[Si](C)(C)C3340.8Standard polar33892256
Metiamide,2TMS,isomer #2CC1=C(CSCCN(C(=S)N(C)[Si](C)(C)C)[Si](C)(C)C)N=C[NH]12467.6Semi standard non polar33892256
Metiamide,2TMS,isomer #2CC1=C(CSCCN(C(=S)N(C)[Si](C)(C)C)[Si](C)(C)C)N=C[NH]12288.6Standard non polar33892256
Metiamide,2TMS,isomer #2CC1=C(CSCCN(C(=S)N(C)[Si](C)(C)C)[Si](C)(C)C)N=C[NH]13118.8Standard polar33892256
Metiamide,2TMS,isomer #3CNC(=S)N(CCSCC1=C(C)N([Si](C)(C)C)C=N1)[Si](C)(C)C2535.4Semi standard non polar33892256
Metiamide,2TMS,isomer #3CNC(=S)N(CCSCC1=C(C)N([Si](C)(C)C)C=N1)[Si](C)(C)C2349.4Standard non polar33892256
Metiamide,2TMS,isomer #3CNC(=S)N(CCSCC1=C(C)N([Si](C)(C)C)C=N1)[Si](C)(C)C3364.9Standard polar33892256
Metiamide,3TMS,isomer #1CC1=C(CSCCN(C(=S)N(C)[Si](C)(C)C)[Si](C)(C)C)N=CN1[Si](C)(C)C2502.2Semi standard non polar33892256
Metiamide,3TMS,isomer #1CC1=C(CSCCN(C(=S)N(C)[Si](C)(C)C)[Si](C)(C)C)N=CN1[Si](C)(C)C2417.4Standard non polar33892256
Metiamide,3TMS,isomer #1CC1=C(CSCCN(C(=S)N(C)[Si](C)(C)C)[Si](C)(C)C)N=CN1[Si](C)(C)C2948.2Standard polar33892256
Metiamide,1TBDMS,isomer #1CC1=C(CSCCNC(=S)N(C)[Si](C)(C)C(C)(C)C)N=C[NH]12748.1Semi standard non polar33892256
Metiamide,1TBDMS,isomer #1CC1=C(CSCCNC(=S)N(C)[Si](C)(C)C(C)(C)C)N=C[NH]12411.5Standard non polar33892256
Metiamide,1TBDMS,isomer #1CC1=C(CSCCNC(=S)N(C)[Si](C)(C)C(C)(C)C)N=C[NH]13536.1Standard polar33892256
Metiamide,1TBDMS,isomer #2CNC(=S)N(CCSCC1=C(C)[NH]C=N1)[Si](C)(C)C(C)(C)C2701.3Semi standard non polar33892256
Metiamide,1TBDMS,isomer #2CNC(=S)N(CCSCC1=C(C)[NH]C=N1)[Si](C)(C)C(C)(C)C2433.5Standard non polar33892256
Metiamide,1TBDMS,isomer #2CNC(=S)N(CCSCC1=C(C)[NH]C=N1)[Si](C)(C)C(C)(C)C3538.7Standard polar33892256
Metiamide,1TBDMS,isomer #3CNC(=S)NCCSCC1=C(C)N([Si](C)(C)C(C)(C)C)C=N12804.7Semi standard non polar33892256
Metiamide,1TBDMS,isomer #3CNC(=S)NCCSCC1=C(C)N([Si](C)(C)C(C)(C)C)C=N12391.1Standard non polar33892256
Metiamide,1TBDMS,isomer #3CNC(=S)NCCSCC1=C(C)N([Si](C)(C)C(C)(C)C)C=N13900.5Standard polar33892256
Metiamide,2TBDMS,isomer #1CC1=C(CSCCNC(=S)N(C)[Si](C)(C)C(C)(C)C)N=CN1[Si](C)(C)C(C)(C)C3016.9Semi standard non polar33892256
Metiamide,2TBDMS,isomer #1CC1=C(CSCCNC(=S)N(C)[Si](C)(C)C(C)(C)C)N=CN1[Si](C)(C)C(C)(C)C2736.7Standard non polar33892256
Metiamide,2TBDMS,isomer #1CC1=C(CSCCNC(=S)N(C)[Si](C)(C)C(C)(C)C)N=CN1[Si](C)(C)C(C)(C)C3397.8Standard polar33892256
Metiamide,2TBDMS,isomer #2CC1=C(CSCCN(C(=S)N(C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N=C[NH]12934.2Semi standard non polar33892256
Metiamide,2TBDMS,isomer #2CC1=C(CSCCN(C(=S)N(C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N=C[NH]12730.5Standard non polar33892256
Metiamide,2TBDMS,isomer #2CC1=C(CSCCN(C(=S)N(C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N=C[NH]13219.1Standard polar33892256
Metiamide,2TBDMS,isomer #3CNC(=S)N(CCSCC1=C(C)N([Si](C)(C)C(C)(C)C)C=N1)[Si](C)(C)C(C)(C)C2963.5Semi standard non polar33892256
Metiamide,2TBDMS,isomer #3CNC(=S)N(CCSCC1=C(C)N([Si](C)(C)C(C)(C)C)C=N1)[Si](C)(C)C(C)(C)C2756.2Standard non polar33892256
Metiamide,2TBDMS,isomer #3CNC(=S)N(CCSCC1=C(C)N([Si](C)(C)C(C)(C)C)C=N1)[Si](C)(C)C(C)(C)C3391.7Standard polar33892256
Metiamide,3TBDMS,isomer #1CC1=C(CSCCN(C(=S)N(C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N=CN1[Si](C)(C)C(C)(C)C3219.7Semi standard non polar33892256
Metiamide,3TBDMS,isomer #1CC1=C(CSCCN(C(=S)N(C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N=CN1[Si](C)(C)C(C)(C)C3016.1Standard non polar33892256
Metiamide,3TBDMS,isomer #1CC1=C(CSCCN(C(=S)N(C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N=CN1[Si](C)(C)C(C)(C)C3149.2Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Metiamide GC-MS (Non-derivatized) - 70eV, Positivesplash10-0005-9300000000-907f73f8f938674a54582017-08-28Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Metiamide 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 - Metiamide 10V, Positive-QTOFsplash10-0002-7970000000-6270ca74d4ef8b47ab522017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Metiamide 20V, Positive-QTOFsplash10-0092-9810000000-1cf11ce57b088bbc79442017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Metiamide 40V, Positive-QTOFsplash10-00dm-9100000000-d640ef6b5070ab66edd52017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Metiamide 10V, Negative-QTOFsplash10-002f-6960000000-9c8740cd4df5596727842017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Metiamide 20V, Negative-QTOFsplash10-00vi-8920000000-f302b9dcfb00f3db74772017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Metiamide 40V, Negative-QTOFsplash10-006x-9100000000-716c4b942353dd80ae742017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Metiamide 10V, Negative-QTOFsplash10-0006-1190000000-421f42ae40c1562bba182021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Metiamide 20V, Negative-QTOFsplash10-014i-5900000000-d6b80ce1f1381c2803c02021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Metiamide 40V, Negative-QTOFsplash10-00xr-9200000000-e805a0b1a704bafe97512021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Metiamide 10V, Positive-QTOFsplash10-0002-1190000000-497de74916d0c5d978052021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Metiamide 20V, Positive-QTOFsplash10-002b-9300000000-f932af11961ea77f716f2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Metiamide 40V, Positive-QTOFsplash10-000t-9100000000-87be1cad0bd6e916dea52021-09-25Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
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 IDDB08805
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDC07449
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkMetiamide
METLIN IDNot Available
PubChem Compound1548992
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 ReferencesNot Available