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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2014-04-21 13:10:20 UTC
Update Date2021-09-14 15:47:07 UTC
HMDB IDHMDB0061718
Secondary Accession Numbers
  • HMDB61718
Metabolite Identification
Common Name3-Methylthiofentanyl
Description3-Methylthiofentanyl belongs to the class of organic compounds known as anilides. These are organic heterocyclic compounds derived from oxoacids RkE(=O)l(OH)m (l not 0) by replacing an OH group by the NHPh group or derivative formed by ring substitution. 3-Methylthiofentanyl is a very strong basic compound (based on its pKa). In humans, 3-methylthiofentanyl is involved in 3-methylthiofentanyl action pathway. A piperidine compound having a (2-thienyl)ethyl substituent at the 1-position, a methyl group at the 3-position and an N-phenylpropanamido group at the 4-position.
Structure
Data?1563866223
Synonyms
ValueSource
3-Methyl-thiofentanylChEBI
N-(3-Methyl-1-(2-thienyl)ethyl-4-piperidinyl)-N-phenylpropanamideChEBI
Chemical FormulaC21H28N2OS
Average Molecular Weight356.525
Monoisotopic Molecular Weight356.192234218
IUPAC NameN-{3-methyl-1-[2-(thiophen-2-yl)ethyl]piperidin-4-yl}-N-phenylpropanamide
Traditional Name3-methylthiofentanyl
CAS Registry NumberNot Available
SMILES
CCC(=O)N(C1CCN(CCC2=CC=CS2)CC1C)C1=CC=CC=C1
InChI Identifier
InChI=1S/C21H28N2OS/c1-3-21(24)23(18-8-5-4-6-9-18)20-12-14-22(16-17(20)2)13-11-19-10-7-15-25-19/h4-10,15,17,20H,3,11-14,16H2,1-2H3
InChI KeySRARDYUHGVMEQI-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as anilides. These are organic heterocyclic compounds derived from oxoacids RkE(=O)l(OH)m (l not 0) by replacing an OH group by the NHPh group or derivative formed by ring substitution.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassAnilides
Direct ParentAnilides
Alternative Parents
Substituents
  • Anilide
  • Aralkylamine
  • Piperidine
  • Tertiary carboxylic acid amide
  • Heteroaromatic compound
  • Thiophene
  • Amino acid or derivatives
  • Carboxamide group
  • Tertiary amine
  • Tertiary aliphatic amine
  • Carboxylic acid derivative
  • Azacycle
  • Organoheterocyclic compound
  • Organic oxide
  • Organopnictogen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Amine
  • Organic oxygen compound
  • Carbonyl group
  • Hydrocarbon derivative
  • Organic nitrogen 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 Solubility0.018 g/LALOGPS
logP4.32ALOGPS
logP4.21ChemAxon
logS-4.3ALOGPS
pKa (Strongest Basic)9.07ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area23.55 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity104.9 m³·mol⁻¹ChemAxon
Polarizability39.97 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+182.49331661259
DarkChem[M-H]-179.06631661259
DeepCCS[M+H]+180.44430932474
DeepCCS[M-H]-178.08630932474
DeepCCS[M-2H]-211.73630932474
DeepCCS[M+Na]+186.96330932474
AllCCS[M+H]+188.632859911
AllCCS[M+H-H2O]+185.832859911
AllCCS[M+NH4]+191.132859911
AllCCS[M+Na]+191.932859911
AllCCS[M-H]-186.032859911
AllCCS[M+Na-2H]-186.332859911
AllCCS[M+HCOO]-186.832859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
3-MethylthiofentanylCCC(=O)N(C1CCN(CCC2=CC=CS2)CC1C)C1=CC=CC=C13919.9Standard polar33892256
3-MethylthiofentanylCCC(=O)N(C1CCN(CCC2=CC=CS2)CC1C)C1=CC=CC=C12890.2Standard non polar33892256
3-MethylthiofentanylCCC(=O)N(C1CCN(CCC2=CC=CS2)CC1C)C1=CC=CC=C12842.9Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 3-Methylthiofentanyl GC-MS (Non-derivatized) - 70eV, Positivesplash10-0zfr-4491000000-03d6184b38c36d4525f32017-09-20Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-Methylthiofentanyl 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 - 3-Methylthiofentanyl 10V, Positive-QTOFsplash10-0a4i-0119000000-54f9c1eb043c9933fcaf2017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Methylthiofentanyl 20V, Positive-QTOFsplash10-0bt9-6977000000-8f4697c94488f660e8f02017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Methylthiofentanyl 40V, Positive-QTOFsplash10-08g0-5940000000-829c4b6545a49cfadff42017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Methylthiofentanyl 10V, Negative-QTOFsplash10-0a4i-1019000000-744235df09c4260d57732017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Methylthiofentanyl 20V, Negative-QTOFsplash10-052b-3379000000-3e421b298cdc8fae46412017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Methylthiofentanyl 40V, Negative-QTOFsplash10-0a4r-9750000000-26f677e71ec303d732ae2017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Methylthiofentanyl 10V, Negative-QTOFsplash10-0a4i-0009000000-91527def881cb6b045732021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Methylthiofentanyl 20V, Negative-QTOFsplash10-052b-5094000000-bdf6c050dbe99cba1d302021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Methylthiofentanyl 40V, Negative-QTOFsplash10-0006-8390000000-7771bf260f878cac442b2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Methylthiofentanyl 10V, Positive-QTOFsplash10-0a4i-0009000000-64262cbdc554d9fb1dd52021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Methylthiofentanyl 20V, Positive-QTOFsplash10-0pb9-0159000000-8664defa8fb87d2e89b42021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Methylthiofentanyl 40V, Positive-QTOFsplash10-03di-2920000000-e03d1cb110fd3818cf392021-09-24Wishart 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 IDDB01439
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia Link3-Methylthiofentanyl
METLIN IDNot Available
PubChem Compound62296
PDB IDNot Available
ChEBI ID53763
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