Human Metabolome Database Version 3.5

Showing metabocard for p-Synephrine (HMDB04826)

Record Information
Version 3.5
Creation Date 2006-08-24 08:32:31 -0600
Update Date 2013-05-29 13:41:09 -0600
HMDB ID HMDB04826
Secondary Accession Numbers None
Metabolite Identification
Common Name p-Synephrine
Description p-Synephrine is an endogenous amine in plasma, in variable levels with a tendency to be higher in hypertensive patients (PMID 8255371 Link_out).
Structure Thumb
Download: MOL | SDF | PDB | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. (+)-p-Synephrine
  2. (+)-Synephrine
  3. (+)-[(methylamino)methyl]-Benzenemethano
  4. Analeptin
  5. Oxedrine
  6. Parasympatol
  7. Simpalon
  8. Simpatol
  9. Sympaethamin
  10. Sympaethamine
  11. Sympatol
  12. Synephrine
Chemical Formula C9H13NO2
Average Molecular Weight 167.205
Monoisotopic Molecular Weight 167.094628665
IUPAC Name 4-[1-hydroxy-2-(methylamino)ethyl]phenol
Traditional IUPAC Name synephrine
CAS Registry Number 94-07-5
SMILES CNCC(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
InChI Key YRCWQPVGYLYSOX-UHFFFAOYSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Aromatic Homomonocyclic Compounds
Class Phenethylamines
Sub Class N/A
Other Descriptors
  • Organic Compounds
  • ethanolamines(ChEBI)
Substituents
  • 1,2 Aminoalcohol
  • Benzyl Alcohol Derivative
  • Phenol
  • Phenol Derivative
  • Secondary Alcohol
  • Secondary Aliphatic Amine (Dialkylamine)
Direct Parent Phenethylamines
Ontology
Status Detected and Quantified
Origin
  • Endogenous
Biofunction Not Available
Application Not Available
Cellular locations Not Available
Physical Properties
State Solid
Experimental Properties
Property Value Reference
Melting Point Not Available Not Available
Boiling Point Not Available Not Available
Water Solubility Not Available Not Available
LogP -0.45 HANSCH,C ET AL. (1995)
Predicted Properties
Property Value Source
Water Solubility 18.6 g/L ALOGPS
LogP -0.62 ALOGPS
LogP -0.071 ChemAxon
LogS -0.95 ALOGPS
pKa (strongest acidic) 9.76 ChemAxon
pKa (strongest basic) 9.15 ChemAxon
Hydrogen Acceptor Count 3 ChemAxon
Hydrogen Donor Count 3 ChemAxon
Polar Surface Area 52.49 A2 ChemAxon
Rotatable Bond Count 3 ChemAxon
Refractivity 47.25 ChemAxon
Polarizability 18.23 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge 1 ChemAxon
Spectra
MS/MS Spectrum GC-MS
Biological Properties
Cellular Locations Not Available
Biofluid Locations
  • Blood
  • Urine
Tissue Location Not Available
Pathways Not Available
Normal Concentrations
Biofluid Status Value Age Sex Condition Reference
Blood Detected and Quantified
0.00034 +/- 0.0001 uM Adult (>18 years old) Both Normal
Urine Detected and Quantified
0.017 umol/mmol creatinine Adult (>18 years old) Both Normal
Urine Detected and Quantified
0.0107 (0.00440-0.017) umol/mmol creatinine Adult (>18 years old) Both Normal
Abnormal Concentrations
Biofluid Status Value Age Sex Condition Reference
Blood Detected and Quantified 0.0009 +/- 0.0004 uM Adult (>18 years old) Both Hypertension
Associated Disorders and Diseases
Disease References
Hypertension
  • Andrew R, Best SA, Watson DG, Midgley JM, Reid JL, Squire IB: Analysis of biogenic amines in plasma of hypertensive patients and a control group. Neurochem Res. 1993 Nov;18(11):1179-82. Pubmed: 8255371 Link_out
      Associated OMIM IDs
      DrugBank ID Not Available
      DrugBank Metabolite ID Not Available
      Phenol Explorer Compound ID Not Available
      Phenol Explorer Metabolite ID Not Available
      FoodDB ID FDB000709
      KNApSAcK ID Not Available
      Chemspider ID 6904 Link_out
      KEGG Compound ID C04548 Link_out
      BioCyc ID Not Available
      BiGG ID Not Available
      Wikipedia Link Not Available
      NuGOwiki Link HMDB04826 Link_out
      Metagene Link HMDB04826 Link_out
      METLIN ID 7088 Link_out
      PubChem Compound 7172 Link_out
      PDB ID Not Available
      ChEBI ID 29081 Link_out
      References
      Synthesis Reference Not Available
      Material Safety Data Sheet (MSDS) Download (PDF)
      General References
      1. Andrew R, Watson DG, Best SA, Midgley JM, Wenlong H, Petty RK: The determination of hydroxydopamines and other trace amines in the urine of parkinsonian patients and normal controls. Neurochem Res. 1993 Nov;18(11):1175-7. Pubmed: 8255370 Link_out
      2. Andrew R, Best SA, Watson DG, Midgley JM, Reid JL, Squire IB: Analysis of biogenic amines in plasma of hypertensive patients and a control group. Neurochem Res. 1993 Nov;18(11):1179-82. Pubmed: 8255371 Link_out

      Enzymes
      Name: Alpha-2A adrenergic receptor
      Reactions: Not Available
      Gene Name: ADRA2A
      Uniprot ID: P08913 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: Alpha-2B adrenergic receptor
      Reactions: Not Available
      Gene Name: ADRA2B
      Uniprot ID: P18089 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA