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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2017-03-23 02:12:17 UTC
Update Date2021-09-14 15:45:14 UTC
HMDB IDHMDB0062493
Secondary Accession Numbers
  • HMDB62493
Metabolite Identification
Common NameL-Metanephrine
Description4-[(1R)-1-hydroxy-2-(methylamino)ethyl]-2-methoxyphenol belongs to the class of organic compounds known as methoxyphenols. Methoxyphenols are compounds containing a methoxy group attached to the benzene ring of a phenol moiety. 4-[(1R)-1-hydroxy-2-(methylamino)ethyl]-2-methoxyphenol is a very strong basic compound (based on its pKa). 4-[(1R)-1-hydroxy-2-(methylamino)ethyl]-2-methoxyphenol exists in all living organisms, ranging from bacteria to humans.
Structure
Data?1563866319
SynonymsNot Available
Chemical FormulaC10H15NO3
Average Molecular Weight197.234
Monoisotopic Molecular Weight197.105193347
IUPAC Name4-[(1R)-1-hydroxy-2-(methylamino)ethyl]-2-methoxyphenol
Traditional NameL-metanephrine
CAS Registry NumberNot Available
SMILES
CNC[C@H](O)C1=CC(OC)=C(O)C=C1
InChI Identifier
InChI=1S/C10H15NO3/c1-11-6-9(13)7-3-4-8(12)10(5-7)14-2/h3-5,9,11-13H,6H2,1-2H3/t9-/m0/s1
InChI KeyJWJCTZKFYGDABJ-VIFPVBQESA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as methoxyphenols. Methoxyphenols are compounds containing a methoxy group attached to the benzene ring of a phenol moiety.
KingdomOrganic compounds
Super ClassBenzenoids
ClassPhenols
Sub ClassMethoxyphenols
Direct ParentMethoxyphenols
Alternative Parents
Substituents
  • Methoxyphenol
  • Phenoxy compound
  • Anisole
  • Phenol ether
  • Methoxybenzene
  • Alkyl aryl ether
  • 1-hydroxy-2-unsubstituted benzenoid
  • Aralkylamine
  • Monocyclic benzene moiety
  • Secondary alcohol
  • 1,2-aminoalcohol
  • Secondary amine
  • Ether
  • Secondary aliphatic amine
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Organopnictogen compound
  • Organic oxygen compound
  • Amine
  • Organic nitrogen compound
  • Alcohol
  • Aromatic alcohol
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Disposition

Source

Route of exposure

Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility13 g/lALOGPS
LogP-0.27ALOGPS
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
logP10(-0.27) g/LALOGPS
logP10(-0.00068) g/LChemAxon
logS10(-1.2) g/LALOGPS
pKa (Strongest Acidic)10.05ChemAxon
pKa (Strongest Basic)9.25ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area61.72 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity53.71 m³·mol⁻¹ChemAxon
Polarizability21.22 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]+149.86631661259
DarkChem[M-H]-146.18431661259
DeepCCS[M+H]+148.09330932474
DeepCCS[M-H]-145.73530932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
L-MetanephrineCNC[C@H](O)C1=CC(OC)=C(O)C=C12884.0Standard polar33892256
L-MetanephrineCNC[C@H](O)C1=CC(OC)=C(O)C=C11762.1Standard non polar33892256
L-MetanephrineCNC[C@H](O)C1=CC(OC)=C(O)C=C11732.6Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
L-Metanephrine,1TMS,isomer #1CNC[C@H](O[Si](C)(C)C)C1=CC=C(O)C(OC)=C11768.0Semi standard non polar33892256
L-Metanephrine,1TMS,isomer #2CNC[C@H](O)C1=CC=C(O[Si](C)(C)C)C(OC)=C11817.1Semi standard non polar33892256
L-Metanephrine,1TMS,isomer #3COC1=CC([C@@H](O)CN(C)[Si](C)(C)C)=CC=C1O1905.1Semi standard non polar33892256
L-Metanephrine,2TMS,isomer #1CNC[C@H](O[Si](C)(C)C)C1=CC=C(O[Si](C)(C)C)C(OC)=C11808.9Semi standard non polar33892256
L-Metanephrine,2TMS,isomer #2COC1=CC([C@H](CN(C)[Si](C)(C)C)O[Si](C)(C)C)=CC=C1O1898.1Semi standard non polar33892256
L-Metanephrine,2TMS,isomer #3COC1=CC([C@@H](O)CN(C)[Si](C)(C)C)=CC=C1O[Si](C)(C)C1957.2Semi standard non polar33892256
L-Metanephrine,3TMS,isomer #1COC1=CC([C@H](CN(C)[Si](C)(C)C)O[Si](C)(C)C)=CC=C1O[Si](C)(C)C1968.2Semi standard non polar33892256
L-Metanephrine,3TMS,isomer #1COC1=CC([C@H](CN(C)[Si](C)(C)C)O[Si](C)(C)C)=CC=C1O[Si](C)(C)C1966.0Standard non polar33892256
L-Metanephrine,3TMS,isomer #1COC1=CC([C@H](CN(C)[Si](C)(C)C)O[Si](C)(C)C)=CC=C1O[Si](C)(C)C2050.5Standard polar33892256
L-Metanephrine,1TBDMS,isomer #1CNC[C@H](O[Si](C)(C)C(C)(C)C)C1=CC=C(O)C(OC)=C12002.9Semi standard non polar33892256
L-Metanephrine,1TBDMS,isomer #2CNC[C@H](O)C1=CC=C(O[Si](C)(C)C(C)(C)C)C(OC)=C12072.0Semi standard non polar33892256
L-Metanephrine,1TBDMS,isomer #3COC1=CC([C@@H](O)CN(C)[Si](C)(C)C(C)(C)C)=CC=C1O2163.0Semi standard non polar33892256
L-Metanephrine,2TBDMS,isomer #1CNC[C@H](O[Si](C)(C)C(C)(C)C)C1=CC=C(O[Si](C)(C)C(C)(C)C)C(OC)=C12275.2Semi standard non polar33892256
L-Metanephrine,2TBDMS,isomer #2COC1=CC([C@H](CN(C)[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)=CC=C1O2410.3Semi standard non polar33892256
L-Metanephrine,2TBDMS,isomer #3COC1=CC([C@@H](O)CN(C)[Si](C)(C)C(C)(C)C)=CC=C1O[Si](C)(C)C(C)(C)C2446.4Semi standard non polar33892256
L-Metanephrine,3TBDMS,isomer #1COC1=CC([C@H](CN(C)[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)=CC=C1O[Si](C)(C)C(C)(C)C2666.9Semi standard non polar33892256
L-Metanephrine,3TBDMS,isomer #1COC1=CC([C@H](CN(C)[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)=CC=C1O[Si](C)(C)C(C)(C)C2612.1Standard non polar33892256
L-Metanephrine,3TBDMS,isomer #1COC1=CC([C@H](CN(C)[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)=CC=C1O[Si](C)(C)C(C)(C)C2439.6Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - L-Metanephrine GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9300000000-99e319cf43defe7cc6112017-09-20Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - L-Metanephrine GC-MS (2 TMS) - 70eV, Positivesplash10-0096-9143000000-9228a106476f67d8ffdc2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - L-Metanephrine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - L-Metanephrine 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 - L-Metanephrine 10V, Positive-QTOFsplash10-001j-0900000000-2f8735bdcad17a503e022017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - L-Metanephrine 20V, Positive-QTOFsplash10-001j-0900000000-21b5acc76caecb4954772017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - L-Metanephrine 40V, Positive-QTOFsplash10-00rm-5900000000-2276d571b783598f12b82017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - L-Metanephrine 10V, Negative-QTOFsplash10-0002-0900000000-76cfe6d6b32b3089d8522017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - L-Metanephrine 20V, Negative-QTOFsplash10-0032-1900000000-fae6f4013e7d68a009d82017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - L-Metanephrine 40V, Negative-QTOFsplash10-0abc-4900000000-9aba74f7d671328ab0bf2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - L-Metanephrine 10V, Negative-QTOFsplash10-0002-0900000000-33b506e73b8f2abe6bdb2021-09-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - L-Metanephrine 20V, Negative-QTOFsplash10-000b-0900000000-361e5b74103dd493ac472021-09-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - L-Metanephrine 40V, Negative-QTOFsplash10-0a4m-6900000000-49bdcf483f24e0b4ffd42021-09-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - L-Metanephrine 10V, Positive-QTOFsplash10-001j-0900000000-545ae65ccf6b1aaf8f432021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - L-Metanephrine 20V, Positive-QTOFsplash10-001a-1900000000-ad33b1d4593df03f60e12021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - L-Metanephrine 40V, Positive-QTOFsplash10-000i-5900000000-61cd5865cf7abd2bba672021-09-25Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart 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 IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDC05588
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound688084
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