Hmdb loader
Survey
You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2013-07-09 16:12:21 UTC
Update Date2019-07-23 07:15:34 UTC
HMDB IDHMDB0061010
Secondary Accession Numbers
  • HMDB61010
Metabolite Identification
Common NameNoralfentanil
DescriptionNoralfentanil is a metabolite of alfentanil. Alfentanil (R-39209, trade name Alfenta, Rapifen in Australia) is a potent but short-acting synthetic opioid analgesic drug, used for anaesthesia in surgery. It is an analogue of fentanyl with around 1/4 the potency of fentanyl and around 1/3 of the duration of action, but with an onset of effects 4x faster than fentanyl. It is an OP3 mu-agonist. (Wikipedia)
Structure
Data?1563866134
Synonyms
ValueSource
4-MPPPHMDB
N-(4-(Methoxymethyl)-4-piperidinyl)-N-phenylpropanamideHMDB
Noralfentanil, (phenyl-3-t)-labeled CPDHMDB
Chemical FormulaC16H24N2O2
Average Molecular Weight276.374
Monoisotopic Molecular Weight276.183778022
IUPAC NameN-[4-(methoxymethyl)piperidin-4-yl]-N-phenylpropanamide
Traditional NameN-[4-(methoxymethyl)piperidin-4-yl]-N-phenylpropanamide
CAS Registry Number61086-18-8
SMILES
CCC(=O)N(C1=CC=CC=C1)C1(COC)CCNCC1
InChI Identifier
InChI=1S/C16H24N2O2/c1-3-15(19)18(14-7-5-4-6-8-14)16(13-20-2)9-11-17-12-10-16/h4-8,17H,3,9-13H2,1-2H3
InChI KeyULOZGJWEIWAWML-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
  • Piperidine
  • Tertiary carboxylic acid amide
  • Amino acid or derivatives
  • Carboxamide group
  • Carboxylic acid derivative
  • Dialkyl ether
  • Secondary aliphatic amine
  • Ether
  • Secondary amine
  • Organoheterocyclic compound
  • Azacycle
  • Organonitrogen compound
  • Carbonyl group
  • Organooxygen compound
  • Organopnictogen compound
  • Organic oxygen compound
  • Organic oxide
  • Amine
  • Hydrocarbon derivative
  • Organic nitrogen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic 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
Water Solubility1.63 g/LALOGPS
logP1.42ALOGPS
logP1.3ChemAxon
logS-2.2ALOGPS
pKa (Strongest Basic)10ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area41.57 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity79.75 m³·mol⁻¹ChemAxon
Polarizability30.84 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
DarkChem[M+H]+162.71231661259
DarkChem[M-H]-164.3331661259
DeepCCS[M+H]+164.63430932474
DeepCCS[M-H]-162.27730932474
DeepCCS[M-2H]-195.16230932474
DeepCCS[M+Na]+170.72830932474
AllCCS[M+H]+165.532859911
AllCCS[M+H-H2O]+162.032859911
AllCCS[M+NH4]+168.732859911
AllCCS[M+Na]+169.632859911
AllCCS[M-H]-168.332859911
AllCCS[M+Na-2H]-168.632859911
AllCCS[M+HCOO]-169.032859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
NoralfentanilCCC(=O)N(C1=CC=CC=C1)C1(COC)CCNCC13201.9Standard polar33892256
NoralfentanilCCC(=O)N(C1=CC=CC=C1)C1(COC)CCNCC12111.7Standard non polar33892256
NoralfentanilCCC(=O)N(C1=CC=CC=C1)C1(COC)CCNCC12091.2Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Noralfentanil,1TMS,isomer #1CCC(=O)N(C1=CC=CC=C1)C1(COC)CCN([Si](C)(C)C)CC12154.2Semi standard non polar33892256
Noralfentanil,1TMS,isomer #1CCC(=O)N(C1=CC=CC=C1)C1(COC)CCN([Si](C)(C)C)CC12210.5Standard non polar33892256
Noralfentanil,1TMS,isomer #1CCC(=O)N(C1=CC=CC=C1)C1(COC)CCN([Si](C)(C)C)CC12829.3Standard polar33892256
Noralfentanil,1TBDMS,isomer #1CCC(=O)N(C1=CC=CC=C1)C1(COC)CCN([Si](C)(C)C(C)(C)C)CC12402.3Semi standard non polar33892256
Noralfentanil,1TBDMS,isomer #1CCC(=O)N(C1=CC=CC=C1)C1(COC)CCN([Si](C)(C)C(C)(C)C)CC12404.3Standard non polar33892256
Noralfentanil,1TBDMS,isomer #1CCC(=O)N(C1=CC=CC=C1)C1(COC)CCN([Si](C)(C)C(C)(C)C)CC12954.5Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Noralfentanil GC-MS (Non-derivatized) - 70eV, Positivesplash10-004l-7960000000-e3902ef7785f3e4fcae72017-09-20Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Noralfentanil GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Noralfentanil 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 - Noralfentanil 10V, Positive-QTOFsplash10-004i-0090000000-b50f8d64da344bd3f0d42016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Noralfentanil 20V, Positive-QTOFsplash10-0551-6690000000-bb9bf87f38d973378d292016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Noralfentanil 40V, Positive-QTOFsplash10-0a73-9510000000-0eee630156a75a36bed42016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Noralfentanil 10V, Negative-QTOFsplash10-004i-0090000000-255fc5f958d9915651e12016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Noralfentanil 20V, Negative-QTOFsplash10-00mt-2390000000-fbc2b068bf2b3541abff2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Noralfentanil 40V, Negative-QTOFsplash10-05fu-6930000000-3bf8909d6063abcd58df2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Noralfentanil 10V, Negative-QTOFsplash10-004i-0090000000-1213655852961d5e7fbf2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Noralfentanil 20V, Negative-QTOFsplash10-052g-9800000000-64ce4e6b4b9c955d7b352021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Noralfentanil 40V, Negative-QTOFsplash10-0006-9710000000-7b6db57377a8449e2a002021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Noralfentanil 10V, Positive-QTOFsplash10-004i-0090000000-fb5857ed89f2e0e25f592021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Noralfentanil 20V, Positive-QTOFsplash10-002b-9670000000-d9df0f9e679f27e0a4462021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Noralfentanil 40V, Positive-QTOFsplash10-002v-6900000000-a50554a475db51dc35c32021-09-24Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen Locations
  • Blood
  • Urine
Tissue Locations
  • Kidney
  • Liver
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableNormal
      Not Available
details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableNormal
      Not Available
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 IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound162172
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