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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2021-09-14 15:47:11 UTC
HMDB IDHMDB0001427
Secondary Accession Numbers
  • HMDB01427
Metabolite Identification
Common Name5'-Hydroxycotinine
Description5'-Hydroxycotinine belongs to the class of organic compounds known as pyrrolidinylpyridines. Pyrrolidinylpyridines are compounds containing a pyrrolidinylpyridine ring system, which consists of a pyrrolidine ring linked to a pyridine ring. In humans, 5'-hydroxycotinine is involved in the nicotine metabolism pathway. 5'-Hydroxycotinine has been detected, but not quantified in, several different foods, such as mustard spinaches (Brassica perviridis), pepper (capsicum), oats (Avena sativa), black raspberries (Rubus occidentalis), and hazelnuts (Corylus). This could make 5'-hydroxycotinine a potential biomarker for the consumption of these foods. 5'-Hydroxycotinine 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 very few articles have been published on 5'-Hydroxycotinine.
Structure
Data?1582752200
Synonyms
ValueSource
5-HydroxycotinineHMDB
AllohydroxycotinineHMDB
Chemical FormulaC10H12N2O2
Average Molecular Weight192.2145
Monoisotopic Molecular Weight192.089877638
IUPAC Name(5R)-5-hydroxy-1-methyl-5-(pyridin-3-yl)pyrrolidin-2-one
Traditional Name5-hydroxycotinine
CAS Registry Number61192-50-5
SMILES
CN1C(=O)CC[C@@]1(O)C1=CN=CC=C1
InChI Identifier
InChI=1S/C10H12N2O2/c1-12-9(13)4-5-10(12,14)8-3-2-6-11-7-8/h2-3,6-7,14H,4-5H2,1H3/t10-/m1/s1
InChI KeyBBNHNZGTKSWIHD-SNVBAGLBSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as pyrrolidinylpyridines. Pyrrolidinylpyridines are compounds containing a pyrrolidinylpyridine ring system, which consists of a pyrrolidine ring linked to a pyridine ring.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassPyridines and derivatives
Sub ClassPyrrolidinylpyridines
Direct ParentPyrrolidinylpyridines
Alternative Parents
Substituents
  • Pyrrolidinylpyridine
  • Alkaloid or derivatives
  • Pyrrolidone
  • 2-pyrrolidone
  • N-alkylpyrrolidine
  • Pyrrolidine
  • Tertiary carboxylic acid amide
  • Heteroaromatic compound
  • Lactam
  • Carboxamide group
  • Alkanolamine
  • Carboxylic acid derivative
  • Azacycle
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Hydrocarbon derivative
  • Carbonyl group
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Biological location

Source

Route of exposure

Process

Naturally occurring process

Physical Properties
StateSolid
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 Solubility90.2 g/LALOGPS
logP10(-0.31) g/LALOGPS
logP10(-0.21) g/LChemAxon
logS10(-0.33) g/LALOGPS
pKa (Strongest Acidic)12.21ChemAxon
pKa (Strongest Basic)4.56ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area53.43 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity50.86 m³·mol⁻¹ChemAxon
Polarizability19.29 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]+144.7231661259
DarkChem[M-H]-142.44331661259
AllCCS[M+H]+142.56432859911
AllCCS[M-H]-143.77332859911
DeepCCS[M+H]+142.83130932474
DeepCCS[M-H]-140.43530932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
5'-HydroxycotinineCN1C(=O)CC[C@@]1(O)C1=CN=CC=C12741.5Standard polar33892256
5'-HydroxycotinineCN1C(=O)CC[C@@]1(O)C1=CN=CC=C11695.8Standard non polar33892256
5'-HydroxycotinineCN1C(=O)CC[C@@]1(O)C1=CN=CC=C11786.9Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
5'-Hydroxycotinine,1TMS,isomer #1CN1C(=O)CC[C@@]1(O[Si](C)(C)C)C1=CC=CN=C11782.6Semi standard non polar33892256
5'-Hydroxycotinine,1TBDMS,isomer #1CN1C(=O)CC[C@@]1(O[Si](C)(C)C(C)(C)C)C1=CC=CN=C12034.9Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 5'-Hydroxycotinine GC-MS (Non-derivatized) - 70eV, Positivesplash10-0ab9-4900000000-8fdc38303fa2e9d326fb2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 5'-Hydroxycotinine GC-MS (1 TMS) - 70eV, Positivesplash10-0096-8910000000-5a6063a4febbd48d8de42017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 5'-Hydroxycotinine 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 - 5'-Hydroxycotinine 10V, Positive-QTOFsplash10-0006-0900000000-a2649b94dc708d963d162017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5'-Hydroxycotinine 20V, Positive-QTOFsplash10-0006-1900000000-d93e8b5830f8c7b522062017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5'-Hydroxycotinine 40V, Positive-QTOFsplash10-0ini-9300000000-09c593e669cadd74a0212017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5'-Hydroxycotinine 10V, Negative-QTOFsplash10-0006-0900000000-350e405fd056b470d8092017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5'-Hydroxycotinine 20V, Negative-QTOFsplash10-0006-0900000000-e329ecf023780fbb4b782017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5'-Hydroxycotinine 40V, Negative-QTOFsplash10-0a6r-9400000000-be7f33457d59944bfacb2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5'-Hydroxycotinine 10V, Positive-QTOFsplash10-0006-0900000000-326a8bf022204233521d2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5'-Hydroxycotinine 20V, Positive-QTOFsplash10-001u-1900000000-bb5c51deec943ef815472021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5'-Hydroxycotinine 40V, Positive-QTOFsplash10-0059-9300000000-c7ab8eb53e732eb149b42021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5'-Hydroxycotinine 10V, Negative-QTOFsplash10-0006-2900000000-dc09a61c7f2c3099543f2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5'-Hydroxycotinine 20V, Negative-QTOFsplash10-002f-4900000000-725ea1c3192b3356573d2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5'-Hydroxycotinine 40V, Negative-QTOFsplash10-056u-9600000000-5f4aedc4e9f9fde04d4c2021-09-22Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biospecimen LocationsNot Available
Tissue Locations
  • Kidney
  • Liver
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 IDFDB022616
KNApSAcK IDNot Available
Chemspider ID7991265
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID6239
PubChem Compound9815515
PDB IDNot Available
ChEBI ID173530
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