Human Metabolome Database Version 3.5

Showing metabocard for p-Octopamine (HMDB04825)

Record Information
Version 3.5
Creation Date 2006-08-24 08:25:57 -0600
Update Date 2013-05-29 13:41:08 -0600
HMDB ID HMDB04825
Secondary Accession Numbers None
Metabolite Identification
Common Name p-Octopamine
Description p-Octopamine is an amine in traces quantities in plasma and cerebrospinal fluid in humans with septic encephalopathy (PMID 15932098 Link_out).
Structure Thumb
Download: MOL | SDF | PDB | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. (RS)-Octopamine
  2. 1-(p-Hydroxyphenyl)-2-aminoethanol
  3. 2-Amino-1-(4-hydroxyphenyl)ethanol
  4. 4-Hydroxyphenethanolamine
  5. 4-[2-Amino-1-hydroxyethyl]phenol
  6. Analet
  7. DL-Octopamine
  8. ND 50
  9. Norden
  10. Norphen
  11. Norsympathol
  12. Norsympatol
  13. Norsynephrine
  14. Norton
  15. Octopamine
  16. p-Hydroxyphenylethanolamine
  17. Racemic octopamine
Chemical Formula C8H11NO2
Average Molecular Weight 153.1784
Monoisotopic Molecular Weight 153.078978601
IUPAC Name 4-[(1R)-2-amino-1-hydroxyethyl]phenol
Traditional IUPAC Name (R)-octopamine
CAS Registry Number 104-14-3
SMILES NC[C@H](O)C1=CC=C(O)C=C1
InChI Identifier InChI=1S/C8H11NO2/c9-5-8(11)6-1-3-7(10)4-2-6/h1-4,8,10-11H,5,9H2/t8-/m0/s1
InChI Key QHGUCRYDKWKLMG-QMMMGPOBSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Aromatic Homomonocyclic Compounds
Class Phenethylamines
Sub Class N/A
Other Descriptors
  • Organic Compounds
  • phenylethanolamines(ChEBI)
  • tyramines(ChEBI)
Substituents
  • 1,2 Aminoalcohol
  • Benzyl Alcohol Derivative
  • Phenol
  • Phenol Derivative
  • Primary Aliphatic Amine (Alkylamine)
  • Secondary Alcohol
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 -0.90 SANGSTER (1994)
Predicted Properties
Property Value Source
Water Solubility 17.2 g/L ALOGPS
LogP -0.94 ALOGPS
LogP -0.32 ChemAxon
LogS -0.95 ALOGPS
pKa (strongest acidic) 9.64 ChemAxon
pKa (strongest basic) 8.98 ChemAxon
Hydrogen Acceptor Count 3 ChemAxon
Hydrogen Donor Count 3 ChemAxon
Polar Surface Area 66.48 A2 ChemAxon
Rotatable Bond Count 2 ChemAxon
Refractivity 42.47 ChemAxon
Polarizability 16.13 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge 1 ChemAxon
Spectra
Not Available
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
0.0026 +/- 0.0014 uM Adult (>18 years old) Both Normal
  • Geigy Scient...
Blood Detected and Quantified
0.00075 +/- 0.0005 uM Adult (>18 years old) Both Normal
Urine Detected and Quantified
0.024 +/- 0.0030 umol/mmol creatinine Adult (>18 years old) Both Normal
  • Geigy Scient...
  • West Cadwell...
  • Basel, Switz...
Urine Detected and Quantified
0.00820 (0.00-0.0168) umol/mmol creatinine Adult (>18 years old) Both Normal
Abnormal Concentrations
Biofluid Status Value Age Sex Condition Reference
Blood Detected and Quantified 0.00036 +/- 0.000065 uM Adult (>18 years old) Both Hypertension
Blood Detected and Quantified 0.0026 +/- 0.0024 uM Adult (>18 years old) Both Cirrhosis
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
      Cirrhosis
      • Yonekura T, Kamata S, Wasa M, Okada A, Yamatodani A, Watanabe T, Wada H: Simultaneous determination of plasma phenethylamine, phenylethanolamine, tyramine and octopamine by high-performance liquid chromatography using derivatization with fluorescamine. J Chromatogr. 1988 Jun 3;427(2):320-5. Pubmed: 3137238 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 FDB010583
          KNApSAcK ID C00001425 Link_out
          Chemspider ID 389242 Link_out
          KEGG Compound ID C04227 Link_out
          BioCyc ID Not Available
          BiGG ID Not Available
          Wikipedia Link Norden Link_out
          NuGOwiki Link HMDB04825 Link_out
          Metagene Link HMDB04825 Link_out
          METLIN ID 7087 Link_out
          PubChem Compound 440266 Link_out
          PDB ID OTR Link_out
          ChEBI ID 44715 Link_out
          References
          Synthesis Reference Hinsberg, O. Nucleus-substituted hydroxyl derivatives of b-amino-a-hydroxy-a-arylethanes and b-amino-a-bisarylethanes. (1923), DE 373286 CAN 18:14396 AN 1924:14396
          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. Balbi T, Fusco M, Vasapollo D, Boschetto R, Cocco P, Leon A, Farruggio A: The presence of trace amines in postmortem cerebrospinal fluid in humans. J Forensic Sci. 2005 May;50(3):630-2. Pubmed: 15932098 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