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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2017-11-16 23:01:43 UTC
Update Date2022-03-07 03:18:13 UTC
HMDB IDHMDB0240216
Secondary Accession NumbersNone
Metabolite Identification
Common NameLafutidine
DescriptionLafutidine, also known as protecadin, belongs to the class of organic compounds known as alkyl aryl ethers. These are organic compounds containing the alkyl aryl ether functional group with the generic formula R-O-R' , where R is an alkyl group and R' is an aryl group. In humans, lafutidine is involved in the lafutidine h2-antihistamine action pathway. Lafutidine is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. Based on a literature review a significant number of articles have been published on Lafutidine.
Structure
Data?1563892730
Synonyms
ValueSource
ProtecadinKegg
(+)-2-[(2-Furanylmethyl)sulfinyl]-N-[(2Z)-4-[[4-(1-piperidinylmethyl)-2-pyridinyl]oxy]-2-butenyl]-acetamideHMDB
(Z)-(+)-2-[(2-Furanylmethyl)sulfinyl]-N-[4-[[4-(1-piperidinylmethyl)-2-pyridinyl]oxy]-2-butenyl]-acetamideHMDB
(+)-2-[(2-Furanylmethyl)sulfinyl]-N-[(2Z)-4-[[4-(1-piperidinylmethyl)-2-pyridinyl]oxy]-2-buten-1-yl]acetamideHMDB
(+)-2-(Furfurylsulfinyl)-N-[(Z)-4-[[4-(piperidinomethyl)-2-pyridyl]oxy]-2-butenyl]acetamideHMDB
(+)-LafutidineHMDB
FRG 8813HMDB
LaflutidineHMDB
LafukemHMDB
StogarHMDB
LafutidineHMDB, MeSH
2-(Furan-2-ylmethylsulphinyl)-N-[(Z)-4-[4-(piperidin-1-ylmethyl)pyridin-2-yl]oxybut-2-enyl]acetamideGenerator, HMDB
N-(4-(4-Piperidinylmethyl)pyridyl-2-oxy)-(Z)-butenyl-2-(furfurylsulfinyl)acetamideMeSH, HMDB
N-(4-(4-Piperidinylmethyl)pyridyl-2-oxy)butenyl-2-(furfurylsulfinyl)acetamideMeSH, HMDB
Chemical FormulaC22H29N3O4S
Average Molecular Weight431.55
Monoisotopic Molecular Weight431.1878776
IUPAC Name2-[(furan-2-yl)methanesulfinyl]-N-[(2Z)-4-({4-[(piperidin-1-yl)methyl]pyridin-2-yl}oxy)but-2-en-1-yl]acetamide
Traditional Namelafutidine
CAS Registry Number118288-08-7
SMILES
O=C(CS(=O)CC1=CC=CO1)NC\C=C/COC1=NC=CC(CN2CCCCC2)=C1
InChI Identifier
InChI=1S/C22H29N3O4S/c26-21(18-30(27)17-20-7-6-14-28-20)23-9-2-5-13-29-22-15-19(8-10-24-22)16-25-11-3-1-4-12-25/h2,5-8,10,14-15H,1,3-4,9,11-13,16-18H2,(H,23,26)/b5-2-
InChI KeyKMZQAVXSMUKBPD-DJWKRKHSSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as alkyl aryl ethers. These are organic compounds containing the alkyl aryl ether functional group with the generic formula R-O-R' , where R is an alkyl group and R' is an aryl group.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassEthers
Direct ParentAlkyl aryl ethers
Alternative Parents
Substituents
  • Alkyl aryl ether
  • Aralkylamine
  • Piperidine
  • Pyridine
  • Furan
  • Heteroaromatic compound
  • Amino acid or derivatives
  • Carboxamide group
  • Secondary carboxylic acid amide
  • Sulfoxide
  • Tertiary aliphatic amine
  • Tertiary amine
  • Carboxylic acid derivative
  • Oxacycle
  • Azacycle
  • Organoheterocyclic compound
  • Sulfinyl compound
  • Organonitrogen compound
  • Hydrocarbon derivative
  • Organic nitrogen compound
  • Organic oxide
  • Organosulfur compound
  • Amine
  • Organopnictogen compound
  • Carbonyl group
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
Process

Naturally occurring process:

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
logP2.59ALOGPS
logP0.86ChemAxon
logS-3.2ALOGPS
pKa (Strongest Acidic)8.87ChemAxon
pKa (Strongest Basic)7.94ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area84.67 ŲChemAxon
Rotatable Bond Count11ChemAxon
Refractivity120.24 m³·mol⁻¹ChemAxon
Polarizability45.27 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
AllCCS[M+H]+200.71931661259
AllCCS[M-H]-190.86731661259
DeepCCS[M+H]+208.2730932474
DeepCCS[M-H]-205.90130932474
DeepCCS[M-2H]-240.20430932474
DeepCCS[M+Na]+215.43130932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
LafutidineO=C(CS(=O)CC1=CC=CO1)NC\C=C/COC1=NC=CC(CN2CCCCC2)=C14001.1Standard polar33892256
LafutidineO=C(CS(=O)CC1=CC=CO1)NC\C=C/COC1=NC=CC(CN2CCCCC2)=C13458.3Standard non polar33892256
LafutidineO=C(CS(=O)CC1=CC=CO1)NC\C=C/COC1=NC=CC(CN2CCCCC2)=C13530.7Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Lafutidine,1TMS,isomer #1C[Si](C)(C)N(C/C=C\COC1=CC(CN2CCCCC2)=CC=N1)C(=O)CS(=O)CC1=CC=CO13540.1Semi standard non polar33892256
Lafutidine,1TMS,isomer #1C[Si](C)(C)N(C/C=C\COC1=CC(CN2CCCCC2)=CC=N1)C(=O)CS(=O)CC1=CC=CO13343.2Standard non polar33892256
Lafutidine,1TMS,isomer #1C[Si](C)(C)N(C/C=C\COC1=CC(CN2CCCCC2)=CC=N1)C(=O)CS(=O)CC1=CC=CO14388.7Standard polar33892256
Lafutidine,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)N(C/C=C\COC1=CC(CN2CCCCC2)=CC=N1)C(=O)CS(=O)CC1=CC=CO13713.6Semi standard non polar33892256
Lafutidine,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)N(C/C=C\COC1=CC(CN2CCCCC2)=CC=N1)C(=O)CS(=O)CC1=CC=CO13454.0Standard non polar33892256
Lafutidine,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)N(C/C=C\COC1=CC(CN2CCCCC2)=CC=N1)C(=O)CS(=O)CC1=CC=CO14425.2Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Lafutidine 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 - Lafutidine LC-ESI-qTof , Positive-QTOFsplash10-00di-0319500000-21e5d3163103c305767b2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Lafutidine , positive-QTOFsplash10-0uec-0629700000-2cad78fc15f4386b36452017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Lafutidine , positive-QTOFsplash10-00di-0319500000-21e5d3163103c305767b2017-09-14HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lafutidine 10V, Positive-QTOFsplash10-01qa-1676900000-3adc00bef17a159fb17e2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lafutidine 20V, Positive-QTOFsplash10-03fu-2971000000-7ee0ab341e67b0ccb95d2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lafutidine 40V, Positive-QTOFsplash10-01t9-4930000000-1265ca526856cae249ff2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lafutidine 10V, Negative-QTOFsplash10-001i-1930700000-aec8e386acbf098257aa2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lafutidine 20V, Negative-QTOFsplash10-0059-2920100000-149ac7afce52861c0b082016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lafutidine 40V, Negative-QTOFsplash10-0016-6900000000-695b1fd2b230388122f42016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lafutidine 10V, Positive-QTOFsplash10-001i-1015900000-d484d58eb169f3ec67432021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lafutidine 20V, Positive-QTOFsplash10-01q9-9453800000-eb9c012110cbed695f732021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lafutidine 40V, Positive-QTOFsplash10-001m-9400000000-c87dcefee5d75f368da02021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lafutidine 10V, Negative-QTOFsplash10-001i-1301900000-6c348a77d8546c865e4c2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lafutidine 20V, Negative-QTOFsplash10-01ox-5902100000-f69667109b92c66678272021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lafutidine 40V, Negative-QTOFsplash10-0h36-9711000000-19ce75902d45bf2db8892021-09-24Wishart 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 IDDB12770
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID4445337
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkLafutidine
METLIN IDNot Available
PubChem Compound5282136
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. Shimatani T, Inoue M, Kuroiwa T, Xu J, Nakamura M, Tazuma S, Ikawa K, Morikawa N: Lafutidine, a newly developed antiulcer drug, elevates postprandial intragastric pH and increases plasma calcitonin gene-related peptide and somatostatin concentrations in humans: comparisons with famotidine. Dig Dis Sci. 2006 Jan;51(1):114-20. [PubMed:16416222 ]