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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2017-03-23 06:28:26 UTC
Update Date2022-03-07 03:18:00 UTC
HMDB IDHMDB0062811
Secondary Accession Numbers
  • HMDB62811
Metabolite Identification
Common NameD-synephrine
DescriptionD-synephrine, also known as (-)-Oxedrine or (-)-Sympatol, is classified as a member of the 1-hydroxy-2-unsubstituted benzenoids. 1-hydroxy-2-unsubstituted benzenoids are phenols that a unsubstituted at the 2-position. D-synephrine is considered to be soluble (in water) and acidic
Structure
Data?1563866364
Synonyms
ValueSource
(-)-4-Hydroxy-alpha-[(methylamino)methyl]benzenemethanolChEBI
(-)-OxedrineChEBI
(-)-p-Hydroxy-alpha-[(methylamino)methyl]benzyl alcoholChEBI
(-)-SynephrineChEBI
(-)-SympatolChEBI
D(-)-SynephrineChEBI
(R)-SynephrineKegg
(-)-4-Hydroxy-a-[(methylamino)methyl]benzenemethanolGenerator
(-)-4-Hydroxy-α-[(methylamino)methyl]benzenemethanolGenerator
(-)-p-Hydroxy-a-[(methylamino)methyl]benzyl alcoholGenerator
(-)-p-Hydroxy-α-[(methylamino)methyl]benzyl alcoholGenerator
Chemical FormulaC9H13NO2
Average Molecular Weight167.208
Monoisotopic Molecular Weight167.094628663
IUPAC Name4-[(1R)-1-hydroxy-2-(methylamino)ethyl]phenol
Traditional Name( )-synephrine
CAS Registry Number614-35-7
SMILES
CNC[C@H](O)C1=CC=C(O)C=C1
InChI Identifier
InChI=1S/C9H13NO2/c1-10-6-9(12)7-2-4-8(11)5-3-7/h2-5,9-12H,6H2,1H3/t9-/m0/s1
InChI KeyYRCWQPVGYLYSOX-VIFPVBQESA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as 1-hydroxy-2-unsubstituted benzenoids. These are phenols that are unsubstituted at the 2-position.
KingdomOrganic compounds
Super ClassBenzenoids
ClassPhenols
Sub Class1-hydroxy-2-unsubstituted benzenoids
Direct Parent1-hydroxy-2-unsubstituted benzenoids
Alternative Parents
Substituents
  • 1-hydroxy-2-unsubstituted benzenoid
  • Aralkylamine
  • Monocyclic benzene moiety
  • 1,2-aminoalcohol
  • Secondary alcohol
  • Secondary amine
  • Secondary aliphatic amine
  • Organic oxygen compound
  • Aromatic alcohol
  • Alcohol
  • Organooxygen compound
  • Organonitrogen compound
  • Organic nitrogen compound
  • Amine
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Not AvailableNot Available
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility18.6 g/lALOGPS
LogP-0.62ALOGPS
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
logP-0.62ALOGPS
logP-0.071ChemAxon
logS-0.95ALOGPS
pKa (Strongest Acidic)9.76ChemAxon
pKa (Strongest Basic)9.15ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area52.49 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity47.25 m³·mol⁻¹ChemAxon
Polarizability18.25 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]+140.61731661259
DarkChem[M-H]-134.95331661259
DeepCCS[M+H]+137.65930932474
DeepCCS[M-H]-134.84630932474
DeepCCS[M-2H]-170.98730932474
DeepCCS[M+Na]+146.52530932474
AllCCS[M+H]+137.832859911
AllCCS[M+H-H2O]+133.532859911
AllCCS[M+NH4]+141.932859911
AllCCS[M+Na]+143.032859911
AllCCS[M-H]-138.132859911
AllCCS[M+Na-2H]-139.332859911
AllCCS[M+HCOO]-140.732859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
D-synephrineCNC[C@H](O)C1=CC=C(O)C=C12689.3Standard polar33892256
D-synephrineCNC[C@H](O)C1=CC=C(O)C=C11642.2Standard non polar33892256
D-synephrineCNC[C@H](O)C1=CC=C(O)C=C11672.7Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
D-synephrine,1TMS,isomer #1CNC[C@H](O[Si](C)(C)C)C1=CC=C(O)C=C11745.2Semi standard non polar33892256
D-synephrine,1TMS,isomer #2CNC[C@H](O)C1=CC=C(O[Si](C)(C)C)C=C11677.5Semi standard non polar33892256
D-synephrine,1TMS,isomer #3CN(C[C@H](O)C1=CC=C(O)C=C1)[Si](C)(C)C1811.7Semi standard non polar33892256
D-synephrine,2TMS,isomer #1CNC[C@H](O[Si](C)(C)C)C1=CC=C(O[Si](C)(C)C)C=C11663.1Semi standard non polar33892256
D-synephrine,2TMS,isomer #2CN(C[C@H](O[Si](C)(C)C)C1=CC=C(O)C=C1)[Si](C)(C)C1861.0Semi standard non polar33892256
D-synephrine,2TMS,isomer #3CN(C[C@H](O)C1=CC=C(O[Si](C)(C)C)C=C1)[Si](C)(C)C1839.1Semi standard non polar33892256
D-synephrine,3TMS,isomer #1CN(C[C@H](O[Si](C)(C)C)C1=CC=C(O[Si](C)(C)C)C=C1)[Si](C)(C)C1834.5Semi standard non polar33892256
D-synephrine,3TMS,isomer #1CN(C[C@H](O[Si](C)(C)C)C1=CC=C(O[Si](C)(C)C)C=C1)[Si](C)(C)C1818.5Standard non polar33892256
D-synephrine,3TMS,isomer #1CN(C[C@H](O[Si](C)(C)C)C1=CC=C(O[Si](C)(C)C)C=C1)[Si](C)(C)C1846.1Standard polar33892256
D-synephrine,1TBDMS,isomer #1CNC[C@H](O[Si](C)(C)C(C)(C)C)C1=CC=C(O)C=C11970.7Semi standard non polar33892256
D-synephrine,1TBDMS,isomer #2CNC[C@H](O)C1=CC=C(O[Si](C)(C)C(C)(C)C)C=C11927.9Semi standard non polar33892256
D-synephrine,1TBDMS,isomer #3CN(C[C@H](O)C1=CC=C(O)C=C1)[Si](C)(C)C(C)(C)C2034.5Semi standard non polar33892256
D-synephrine,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=C12137.2Semi standard non polar33892256
D-synephrine,2TBDMS,isomer #2CN(C[C@H](O[Si](C)(C)C(C)(C)C)C1=CC=C(O)C=C1)[Si](C)(C)C(C)(C)C2334.5Semi standard non polar33892256
D-synephrine,2TBDMS,isomer #3CN(C[C@H](O)C1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1)[Si](C)(C)C(C)(C)C2346.2Semi standard non polar33892256
D-synephrine,3TBDMS,isomer #1CN(C[C@H](O[Si](C)(C)C(C)(C)C)C1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1)[Si](C)(C)C(C)(C)C2560.1Semi standard non polar33892256
D-synephrine,3TBDMS,isomer #1CN(C[C@H](O[Si](C)(C)C(C)(C)C)C1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1)[Si](C)(C)C(C)(C)C2470.3Standard non polar33892256
D-synephrine,3TBDMS,isomer #1CN(C[C@H](O[Si](C)(C)C(C)(C)C)C1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1)[Si](C)(C)C(C)(C)C2239.5Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - D-synephrine GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9200000000-0b89ec1502bbf0bb18792017-09-20Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - D-synephrine GC-MS (2 TMS) - 70eV, Positivesplash10-006x-9150000000-b5f2dbddba7baed4d7742017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - D-synephrine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - D-synephrine 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 - D-synephrine 10V, Positive-QTOFsplash10-0uxr-0900000000-63ab15460551b5c908672017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - D-synephrine 20V, Positive-QTOFsplash10-0uxr-0900000000-5a26ad0ce3c3f5a256082017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - D-synephrine 40V, Positive-QTOFsplash10-0aor-6900000000-9a0f0e1fecffa43dcfdb2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - D-synephrine 10V, Negative-QTOFsplash10-014i-0900000000-8561535681faf138ceea2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - D-synephrine 20V, Negative-QTOFsplash10-014j-2900000000-59329a14b178ca50c0b12017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - D-synephrine 40V, Negative-QTOFsplash10-0006-9300000000-040c43b57212bf81ad8a2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - D-synephrine 10V, Negative-QTOFsplash10-014i-1900000000-832cda2fe5651203ce372021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - D-synephrine 20V, Negative-QTOFsplash10-0avl-2900000000-6a789e30e9999b4391e72021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - D-synephrine 40V, Negative-QTOFsplash10-014l-6900000000-2944a38d623d1305021c2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - D-synephrine 10V, Positive-QTOFsplash10-0udi-0900000000-59284684d3d1f5845efb2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - D-synephrine 20V, Positive-QTOFsplash10-0q29-1900000000-eccd6882ea86aed6f8242021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - D-synephrine 40V, Positive-QTOFsplash10-0a4i-7900000000-2f829c6bfc720e5264532021-09-24Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 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, 1000 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, 200 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, 300 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, 400 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, 500 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, 600 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, 700 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, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C 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 IDC01869
BioCyc ID1-4-HYDROXYPHENYL-2-METHYLAMINOETHAN
BiGG IDNot Available
Wikipedia LinkSynephrine
METLIN IDNot Available
PubChem Compound854067
PDB IDNot Available
ChEBI ID119
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