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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:52 UTC
Update Date2022-03-07 02:52:03 UTC
HMDB IDHMDB0015627
Secondary Accession Numbers
  • HMDB15627
Metabolite Identification
Common NameDroxidopa
DescriptionDroxidopa is a precursor of noradrenaline that is used in the treatment of Parkinsonism. It is approved for use in Japan and is currently in trials in the U.S. The racaemic form (dl-threo-3,4-dihydroxyphenylserine) has also been used, and has been investigated in the treatment of orthostatic hypotension. There is a deficit of noradrenaline as well as of dopamine in Parkinson's disease and it has been proposed that this underlies the sudden transient freezing seen usually in advanced disease.
Structure
Data?1582753317
Synonyms
ValueSource
DopsKegg
NortheraKegg
DroxydopaHMDB
L-DihydroxyphenylserineHMDB
L-DOPSHMDB
L-Threo-3,4-dihydroxyphenylserineHMDB
3,4 DihydroxyphenylserineHMDB
3,4 Threo dopsHMDB
3,4-DihydroxyphenylserineHMDB
3,4-Threo-dopsHMDB
DL Threo 3,4 dihydroxyphenylserineHMDB
DL-Threo-3,4-dihydroxyphenylserineHMDB
Droxidopa, (DL-tyr)-isomerHMDB
Erythro 3,4 dihydroxyphenylserineHMDB
Erythro-3,4-dihydroxyphenylserineHMDB
Threo dopsHMDB
Threo-dopsHMDB
(2R,3S)-2-Amino-3-(3,4-dihydroxyphenyl)-3-hydroxypropanoateGenerator
Chemical FormulaC9H11NO5
Average Molecular Weight213.1873
Monoisotopic Molecular Weight213.063722467
IUPAC Name(2R,3S)-2-amino-3-(3,4-dihydroxyphenyl)-3-hydroxypropanoic acid
Traditional Namedroxidopa
CAS Registry Number23651-95-8
SMILES
N[C@H]([C@@H](O)C1=CC(O)=C(O)C=C1)C(O)=O
InChI Identifier
InChI=1S/C9H11NO5/c10-7(9(14)15)8(13)4-1-2-5(11)6(12)3-4/h1-3,7-8,11-13H,10H2,(H,14,15)/t7-,8+/m1/s1
InChI KeyQXWYKJLNLSIPIN-SFYZADRCSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as tyrosine and derivatives. Tyrosine and derivatives are compounds containing tyrosine or a derivative thereof resulting from reaction of tyrosine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentTyrosine and derivatives
Alternative Parents
Substituents
  • Tyrosine or derivatives
  • Phenylalanine or derivatives
  • 3-phenylpropanoic-acid
  • Alpha-amino acid
  • D-alpha-amino acid
  • Catechol
  • Beta-hydroxy acid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Aralkylamine
  • 1-hydroxy-4-unsubstituted benzenoid
  • Phenol
  • Monocyclic benzene moiety
  • Benzenoid
  • Hydroxy acid
  • Amino acid
  • Secondary alcohol
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Organic oxide
  • Organooxygen compound
  • Organonitrogen compound
  • Primary amine
  • Primary aliphatic amine
  • Aromatic alcohol
  • Alcohol
  • Hydrocarbon derivative
  • Carbonyl group
  • Organic oxygen compound
  • Organopnictogen compound
  • Amine
  • Organic nitrogen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility15.3 g/LNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility15.3 g/LALOGPS
logP-2.4ALOGPS
logP-2.7ChemAxon
logS-1.1ALOGPS
pKa (Strongest Acidic)1.46ChemAxon
pKa (Strongest Basic)8.72ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area124.01 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity50.29 m³·mol⁻¹ChemAxon
Polarizability19.63 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+150.32331661259
DarkChem[M-H]-146.60531661259
DeepCCS[M+H]+152.73930932474
DeepCCS[M-H]-150.34430932474
DeepCCS[M-2H]-183.44330932474
DeepCCS[M+Na]+158.65230932474
AllCCS[M+H]+148.032859911
AllCCS[M+H-H2O]+144.032859911
AllCCS[M+NH4]+151.732859911
AllCCS[M+Na]+152.732859911
AllCCS[M-H]-143.432859911
AllCCS[M+Na-2H]-143.932859911
AllCCS[M+HCOO]-144.532859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
DroxidopaN[C@H]([C@@H](O)C1=CC(O)=C(O)C=C1)C(O)=O3529.4Standard polar33892256
DroxidopaN[C@H]([C@@H](O)C1=CC(O)=C(O)C=C1)C(O)=O2359.6Standard non polar33892256
DroxidopaN[C@H]([C@@H](O)C1=CC(O)=C(O)C=C1)C(O)=O2191.1Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Droxidopa,1TMS,isomer #1C[Si](C)(C)O[C@@H](C1=CC=C(O)C(O)=C1)[C@@H](N)C(=O)O2182.5Semi standard non polar33892256
Droxidopa,1TMS,isomer #2C[Si](C)(C)OC1=CC([C@H](O)[C@@H](N)C(=O)O)=CC=C1O2180.8Semi standard non polar33892256
Droxidopa,1TMS,isomer #3C[Si](C)(C)OC1=CC=C([C@H](O)[C@@H](N)C(=O)O)C=C1O2198.2Semi standard non polar33892256
Droxidopa,1TMS,isomer #4C[Si](C)(C)OC(=O)[C@H](N)[C@@H](O)C1=CC=C(O)C(O)=C12218.2Semi standard non polar33892256
Droxidopa,1TMS,isomer #5C[Si](C)(C)N[C@@H](C(=O)O)[C@@H](O)C1=CC=C(O)C(O)=C12260.5Semi standard non polar33892256
Droxidopa,2TMS,isomer #1C[Si](C)(C)OC1=CC=C([C@H](O[Si](C)(C)C)[C@@H](N)C(=O)O)C=C1O2120.7Semi standard non polar33892256
Droxidopa,2TMS,isomer #10C[Si](C)(C)N[C@@H](C(=O)O[Si](C)(C)C)[C@@H](O)C1=CC=C(O)C(O)=C12203.2Semi standard non polar33892256
Droxidopa,2TMS,isomer #11C[Si](C)(C)N([C@@H](C(=O)O)[C@@H](O)C1=CC=C(O)C(O)=C1)[Si](C)(C)C2378.5Semi standard non polar33892256
Droxidopa,2TMS,isomer #2C[Si](C)(C)OC1=CC([C@H](O[Si](C)(C)C)[C@@H](N)C(=O)O)=CC=C1O2134.1Semi standard non polar33892256
Droxidopa,2TMS,isomer #3C[Si](C)(C)OC(=O)[C@H](N)[C@@H](O[Si](C)(C)C)C1=CC=C(O)C(O)=C12180.8Semi standard non polar33892256
Droxidopa,2TMS,isomer #4C[Si](C)(C)N[C@@H](C(=O)O)[C@@H](O[Si](C)(C)C)C1=CC=C(O)C(O)=C12226.1Semi standard non polar33892256
Droxidopa,2TMS,isomer #5C[Si](C)(C)OC(=O)[C@H](N)[C@@H](O)C1=CC=C(O)C(O[Si](C)(C)C)=C12132.2Semi standard non polar33892256
Droxidopa,2TMS,isomer #6C[Si](C)(C)OC1=CC=C([C@H](O)[C@@H](N)C(=O)O)C=C1O[Si](C)(C)C2187.1Semi standard non polar33892256
Droxidopa,2TMS,isomer #7C[Si](C)(C)N[C@@H](C(=O)O)[C@@H](O)C1=CC=C(O)C(O[Si](C)(C)C)=C12175.1Semi standard non polar33892256
Droxidopa,2TMS,isomer #8C[Si](C)(C)OC(=O)[C@H](N)[C@@H](O)C1=CC=C(O[Si](C)(C)C)C(O)=C12149.0Semi standard non polar33892256
Droxidopa,2TMS,isomer #9C[Si](C)(C)N[C@@H](C(=O)O)[C@@H](O)C1=CC=C(O[Si](C)(C)C)C(O)=C12205.1Semi standard non polar33892256
Droxidopa,3TMS,isomer #1C[Si](C)(C)OC(=O)[C@H](N)[C@@H](O[Si](C)(C)C)C1=CC=C(O[Si](C)(C)C)C(O)=C12144.0Semi standard non polar33892256
Droxidopa,3TMS,isomer #10C[Si](C)(C)N[C@@H](C(=O)O)[C@@H](O)C1=CC=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C12186.0Semi standard non polar33892256
Droxidopa,3TMS,isomer #11C[Si](C)(C)OC1=CC([C@H](O)[C@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)=CC=C1O2311.5Semi standard non polar33892256
Droxidopa,3TMS,isomer #12C[Si](C)(C)N[C@@H](C(=O)O[Si](C)(C)C)[C@@H](O)C1=CC=C(O[Si](C)(C)C)C(O)=C12164.3Semi standard non polar33892256
Droxidopa,3TMS,isomer #13C[Si](C)(C)OC1=CC=C([C@H](O)[C@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)C=C1O2337.8Semi standard non polar33892256
Droxidopa,3TMS,isomer #14C[Si](C)(C)OC(=O)[C@@H]([C@@H](O)C1=CC=C(O)C(O)=C1)N([Si](C)(C)C)[Si](C)(C)C2351.9Semi standard non polar33892256
Droxidopa,3TMS,isomer #2C[Si](C)(C)OC1=CC=C([C@H](O[Si](C)(C)C)[C@@H](N)C(=O)O)C=C1O[Si](C)(C)C2154.1Semi standard non polar33892256
Droxidopa,3TMS,isomer #3C[Si](C)(C)N[C@@H](C(=O)O)[C@@H](O[Si](C)(C)C)C1=CC=C(O[Si](C)(C)C)C(O)=C12160.1Semi standard non polar33892256
Droxidopa,3TMS,isomer #4C[Si](C)(C)OC(=O)[C@H](N)[C@@H](O[Si](C)(C)C)C1=CC=C(O)C(O[Si](C)(C)C)=C12135.3Semi standard non polar33892256
Droxidopa,3TMS,isomer #5C[Si](C)(C)N[C@@H](C(=O)O)[C@@H](O[Si](C)(C)C)C1=CC=C(O)C(O[Si](C)(C)C)=C12171.3Semi standard non polar33892256
Droxidopa,3TMS,isomer #6C[Si](C)(C)N[C@@H](C(=O)O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)C1=CC=C(O)C(O)=C12178.7Semi standard non polar33892256
Droxidopa,3TMS,isomer #7C[Si](C)(C)O[C@@H](C1=CC=C(O)C(O)=C1)[C@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C2342.5Semi standard non polar33892256
Droxidopa,3TMS,isomer #8C[Si](C)(C)OC(=O)[C@H](N)[C@@H](O)C1=CC=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C12172.2Semi standard non polar33892256
Droxidopa,3TMS,isomer #9C[Si](C)(C)N[C@@H](C(=O)O[Si](C)(C)C)[C@@H](O)C1=CC=C(O)C(O[Si](C)(C)C)=C12150.1Semi standard non polar33892256
Droxidopa,4TMS,isomer #1C[Si](C)(C)OC(=O)[C@H](N)[C@@H](O[Si](C)(C)C)C1=CC=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C12190.0Semi standard non polar33892256
Droxidopa,4TMS,isomer #10C[Si](C)(C)OC1=CC=C([C@H](O)[C@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)C=C1O[Si](C)(C)C2333.3Semi standard non polar33892256
Droxidopa,4TMS,isomer #11C[Si](C)(C)OC(=O)[C@@H]([C@@H](O)C1=CC=C(O[Si](C)(C)C)C(O)=C1)N([Si](C)(C)C)[Si](C)(C)C2319.5Semi standard non polar33892256
Droxidopa,4TMS,isomer #2C[Si](C)(C)N[C@@H](C(=O)O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)C1=CC=C(O[Si](C)(C)C)C(O)=C12186.8Semi standard non polar33892256
Droxidopa,4TMS,isomer #3C[Si](C)(C)N[C@@H](C(=O)O)[C@@H](O[Si](C)(C)C)C1=CC=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C12218.9Semi standard non polar33892256
Droxidopa,4TMS,isomer #4C[Si](C)(C)OC1=CC=C([C@H](O[Si](C)(C)C)[C@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)C=C1O2305.8Semi standard non polar33892256
Droxidopa,4TMS,isomer #5C[Si](C)(C)N[C@@H](C(=O)O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)C1=CC=C(O)C(O[Si](C)(C)C)=C12187.7Semi standard non polar33892256
Droxidopa,4TMS,isomer #6C[Si](C)(C)OC1=CC([C@H](O[Si](C)(C)C)[C@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)=CC=C1O2297.7Semi standard non polar33892256
Droxidopa,4TMS,isomer #7C[Si](C)(C)OC(=O)[C@@H]([C@@H](O[Si](C)(C)C)C1=CC=C(O)C(O)=C1)N([Si](C)(C)C)[Si](C)(C)C2314.8Semi standard non polar33892256
Droxidopa,4TMS,isomer #8C[Si](C)(C)N[C@@H](C(=O)O[Si](C)(C)C)[C@@H](O)C1=CC=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C12185.8Semi standard non polar33892256
Droxidopa,4TMS,isomer #9C[Si](C)(C)OC(=O)[C@@H]([C@@H](O)C1=CC=C(O)C(O[Si](C)(C)C)=C1)N([Si](C)(C)C)[Si](C)(C)C2302.6Semi standard non polar33892256
Droxidopa,5TMS,isomer #1C[Si](C)(C)N[C@@H](C(=O)O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)C1=CC=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C12252.7Semi standard non polar33892256
Droxidopa,5TMS,isomer #1C[Si](C)(C)N[C@@H](C(=O)O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)C1=CC=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C12205.0Standard non polar33892256
Droxidopa,5TMS,isomer #1C[Si](C)(C)N[C@@H](C(=O)O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)C1=CC=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C12289.6Standard polar33892256
Droxidopa,5TMS,isomer #2C[Si](C)(C)OC(=O)[C@@H]([C@@H](O[Si](C)(C)C)C1=CC=C(O[Si](C)(C)C)C(O)=C1)N([Si](C)(C)C)[Si](C)(C)C2364.5Semi standard non polar33892256
Droxidopa,5TMS,isomer #2C[Si](C)(C)OC(=O)[C@@H]([C@@H](O[Si](C)(C)C)C1=CC=C(O[Si](C)(C)C)C(O)=C1)N([Si](C)(C)C)[Si](C)(C)C2342.4Standard non polar33892256
Droxidopa,5TMS,isomer #2C[Si](C)(C)OC(=O)[C@@H]([C@@H](O[Si](C)(C)C)C1=CC=C(O[Si](C)(C)C)C(O)=C1)N([Si](C)(C)C)[Si](C)(C)C2361.6Standard polar33892256
Droxidopa,5TMS,isomer #3C[Si](C)(C)OC1=CC=C([C@H](O[Si](C)(C)C)[C@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)C=C1O[Si](C)(C)C2367.1Semi standard non polar33892256
Droxidopa,5TMS,isomer #3C[Si](C)(C)OC1=CC=C([C@H](O[Si](C)(C)C)[C@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)C=C1O[Si](C)(C)C2294.5Standard non polar33892256
Droxidopa,5TMS,isomer #3C[Si](C)(C)OC1=CC=C([C@H](O[Si](C)(C)C)[C@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)C=C1O[Si](C)(C)C2381.1Standard polar33892256
Droxidopa,5TMS,isomer #4C[Si](C)(C)OC(=O)[C@@H]([C@@H](O[Si](C)(C)C)C1=CC=C(O)C(O[Si](C)(C)C)=C1)N([Si](C)(C)C)[Si](C)(C)C2361.4Semi standard non polar33892256
Droxidopa,5TMS,isomer #4C[Si](C)(C)OC(=O)[C@@H]([C@@H](O[Si](C)(C)C)C1=CC=C(O)C(O[Si](C)(C)C)=C1)N([Si](C)(C)C)[Si](C)(C)C2367.5Standard non polar33892256
Droxidopa,5TMS,isomer #4C[Si](C)(C)OC(=O)[C@@H]([C@@H](O[Si](C)(C)C)C1=CC=C(O)C(O[Si](C)(C)C)=C1)N([Si](C)(C)C)[Si](C)(C)C2392.4Standard polar33892256
Droxidopa,5TMS,isomer #5C[Si](C)(C)OC(=O)[C@@H]([C@@H](O)C1=CC=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C1)N([Si](C)(C)C)[Si](C)(C)C2371.2Semi standard non polar33892256
Droxidopa,5TMS,isomer #5C[Si](C)(C)OC(=O)[C@@H]([C@@H](O)C1=CC=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C1)N([Si](C)(C)C)[Si](C)(C)C2324.5Standard non polar33892256
Droxidopa,5TMS,isomer #5C[Si](C)(C)OC(=O)[C@@H]([C@@H](O)C1=CC=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C1)N([Si](C)(C)C)[Si](C)(C)C2453.3Standard polar33892256
Droxidopa,6TMS,isomer #1C[Si](C)(C)OC(=O)[C@@H]([C@@H](O[Si](C)(C)C)C1=CC=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C1)N([Si](C)(C)C)[Si](C)(C)C2450.8Semi standard non polar33892256
Droxidopa,6TMS,isomer #1C[Si](C)(C)OC(=O)[C@@H]([C@@H](O[Si](C)(C)C)C1=CC=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C1)N([Si](C)(C)C)[Si](C)(C)C2340.2Standard non polar33892256
Droxidopa,6TMS,isomer #1C[Si](C)(C)OC(=O)[C@@H]([C@@H](O[Si](C)(C)C)C1=CC=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C1)N([Si](C)(C)C)[Si](C)(C)C2294.3Standard polar33892256
Droxidopa,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)O[C@@H](C1=CC=C(O)C(O)=C1)[C@@H](N)C(=O)O2459.4Semi standard non polar33892256
Droxidopa,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC1=CC([C@H](O)[C@@H](N)C(=O)O)=CC=C1O2455.7Semi standard non polar33892256
Droxidopa,1TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC1=CC=C([C@H](O)[C@@H](N)C(=O)O)C=C1O2485.9Semi standard non polar33892256
Droxidopa,1TBDMS,isomer #4CC(C)(C)[Si](C)(C)OC(=O)[C@H](N)[C@@H](O)C1=CC=C(O)C(O)=C12470.3Semi standard non polar33892256
Droxidopa,1TBDMS,isomer #5CC(C)(C)[Si](C)(C)N[C@@H](C(=O)O)[C@@H](O)C1=CC=C(O)C(O)=C12528.9Semi standard non polar33892256
Droxidopa,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC=C([C@H](O[Si](C)(C)C(C)(C)C)[C@@H](N)C(=O)O)C=C1O2672.7Semi standard non polar33892256
Droxidopa,2TBDMS,isomer #10CC(C)(C)[Si](C)(C)N[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)[C@@H](O)C1=CC=C(O)C(O)=C12685.0Semi standard non polar33892256
Droxidopa,2TBDMS,isomer #11CC(C)(C)[Si](C)(C)N([C@@H](C(=O)O)[C@@H](O)C1=CC=C(O)C(O)=C1)[Si](C)(C)C(C)(C)C2826.8Semi standard non polar33892256
Droxidopa,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC1=CC([C@H](O[Si](C)(C)C(C)(C)C)[C@@H](N)C(=O)O)=CC=C1O2671.9Semi standard non polar33892256
Droxidopa,2TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC(=O)[C@H](N)[C@@H](O[Si](C)(C)C(C)(C)C)C1=CC=C(O)C(O)=C12649.8Semi standard non polar33892256
Droxidopa,2TBDMS,isomer #4CC(C)(C)[Si](C)(C)N[C@@H](C(=O)O)[C@@H](O[Si](C)(C)C(C)(C)C)C1=CC=C(O)C(O)=C12697.4Semi standard non polar33892256
Droxidopa,2TBDMS,isomer #5CC(C)(C)[Si](C)(C)OC(=O)[C@H](N)[C@@H](O)C1=CC=C(O)C(O[Si](C)(C)C(C)(C)C)=C12629.0Semi standard non polar33892256
Droxidopa,2TBDMS,isomer #6CC(C)(C)[Si](C)(C)OC1=CC=C([C@H](O)[C@@H](N)C(=O)O)C=C1O[Si](C)(C)C(C)(C)C2690.9Semi standard non polar33892256
Droxidopa,2TBDMS,isomer #7CC(C)(C)[Si](C)(C)N[C@@H](C(=O)O)[C@@H](O)C1=CC=C(O)C(O[Si](C)(C)C(C)(C)C)=C12710.8Semi standard non polar33892256
Droxidopa,2TBDMS,isomer #8CC(C)(C)[Si](C)(C)OC(=O)[C@H](N)[C@@H](O)C1=CC=C(O[Si](C)(C)C(C)(C)C)C(O)=C12676.1Semi standard non polar33892256
Droxidopa,2TBDMS,isomer #9CC(C)(C)[Si](C)(C)N[C@@H](C(=O)O)[C@@H](O)C1=CC=C(O[Si](C)(C)C(C)(C)C)C(O)=C12744.0Semi standard non polar33892256
Droxidopa,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)[C@H](N)[C@@H](O[Si](C)(C)C(C)(C)C)C1=CC=C(O[Si](C)(C)C(C)(C)C)C(O)=C12857.5Semi standard non polar33892256
Droxidopa,3TBDMS,isomer #10CC(C)(C)[Si](C)(C)N[C@@H](C(=O)O)[C@@H](O)C1=CC=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C12929.9Semi standard non polar33892256
Droxidopa,3TBDMS,isomer #11CC(C)(C)[Si](C)(C)OC1=CC([C@H](O)[C@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=CC=C1O3066.1Semi standard non polar33892256
Droxidopa,3TBDMS,isomer #12CC(C)(C)[Si](C)(C)N[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)[C@@H](O)C1=CC=C(O[Si](C)(C)C(C)(C)C)C(O)=C12910.0Semi standard non polar33892256
Droxidopa,3TBDMS,isomer #13CC(C)(C)[Si](C)(C)OC1=CC=C([C@H](O)[C@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C1O3091.7Semi standard non polar33892256
Droxidopa,3TBDMS,isomer #14CC(C)(C)[Si](C)(C)OC(=O)[C@@H]([C@@H](O)C1=CC=C(O)C(O)=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2992.6Semi standard non polar33892256
Droxidopa,3TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC1=CC=C([C@H](O[Si](C)(C)C(C)(C)C)[C@@H](N)C(=O)O)C=C1O[Si](C)(C)C(C)(C)C2875.6Semi standard non polar33892256
Droxidopa,3TBDMS,isomer #3CC(C)(C)[Si](C)(C)N[C@@H](C(=O)O)[C@@H](O[Si](C)(C)C(C)(C)C)C1=CC=C(O[Si](C)(C)C(C)(C)C)C(O)=C12902.9Semi standard non polar33892256
Droxidopa,3TBDMS,isomer #4CC(C)(C)[Si](C)(C)OC(=O)[C@H](N)[C@@H](O[Si](C)(C)C(C)(C)C)C1=CC=C(O)C(O[Si](C)(C)C(C)(C)C)=C12852.7Semi standard non polar33892256
Droxidopa,3TBDMS,isomer #5CC(C)(C)[Si](C)(C)N[C@@H](C(=O)O)[C@@H](O[Si](C)(C)C(C)(C)C)C1=CC=C(O)C(O[Si](C)(C)C(C)(C)C)=C12903.4Semi standard non polar33892256
Droxidopa,3TBDMS,isomer #6CC(C)(C)[Si](C)(C)N[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)C1=CC=C(O)C(O)=C12858.3Semi standard non polar33892256
Droxidopa,3TBDMS,isomer #7CC(C)(C)[Si](C)(C)O[C@@H](C1=CC=C(O)C(O)=C1)[C@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3023.1Semi standard non polar33892256
Droxidopa,3TBDMS,isomer #8CC(C)(C)[Si](C)(C)OC(=O)[C@H](N)[C@@H](O)C1=CC=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C12870.9Semi standard non polar33892256
Droxidopa,3TBDMS,isomer #9CC(C)(C)[Si](C)(C)N[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)[C@@H](O)C1=CC=C(O)C(O[Si](C)(C)C(C)(C)C)=C12878.1Semi standard non polar33892256
Droxidopa,4TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)[C@H](N)[C@@H](O[Si](C)(C)C(C)(C)C)C1=CC=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C13073.7Semi standard non polar33892256
Droxidopa,4TBDMS,isomer #10CC(C)(C)[Si](C)(C)OC1=CC=C([C@H](O)[C@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C1O[Si](C)(C)C(C)(C)C3305.1Semi standard non polar33892256
Droxidopa,4TBDMS,isomer #11CC(C)(C)[Si](C)(C)OC(=O)[C@@H]([C@@H](O)C1=CC=C(O[Si](C)(C)C(C)(C)C)C(O)=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3255.3Semi standard non polar33892256
Droxidopa,4TBDMS,isomer #2CC(C)(C)[Si](C)(C)N[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)C1=CC=C(O[Si](C)(C)C(C)(C)C)C(O)=C13088.1Semi standard non polar33892256
Droxidopa,4TBDMS,isomer #3CC(C)(C)[Si](C)(C)N[C@@H](C(=O)O)[C@@H](O[Si](C)(C)C(C)(C)C)C1=CC=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C13103.2Semi standard non polar33892256
Droxidopa,4TBDMS,isomer #4CC(C)(C)[Si](C)(C)OC1=CC=C([C@H](O[Si](C)(C)C(C)(C)C)[C@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C1O3286.7Semi standard non polar33892256
Droxidopa,4TBDMS,isomer #5CC(C)(C)[Si](C)(C)N[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)C1=CC=C(O)C(O[Si](C)(C)C(C)(C)C)=C13081.2Semi standard non polar33892256
Droxidopa,4TBDMS,isomer #6CC(C)(C)[Si](C)(C)OC1=CC([C@H](O[Si](C)(C)C(C)(C)C)[C@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=CC=C1O3266.5Semi standard non polar33892256
Droxidopa,4TBDMS,isomer #7CC(C)(C)[Si](C)(C)OC(=O)[C@@H]([C@@H](O[Si](C)(C)C(C)(C)C)C1=CC=C(O)C(O)=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3174.0Semi standard non polar33892256
Droxidopa,4TBDMS,isomer #8CC(C)(C)[Si](C)(C)N[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)[C@@H](O)C1=CC=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C13119.4Semi standard non polar33892256
Droxidopa,4TBDMS,isomer #9CC(C)(C)[Si](C)(C)OC(=O)[C@@H]([C@@H](O)C1=CC=C(O)C(O[Si](C)(C)C(C)(C)C)=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3220.3Semi standard non polar33892256
Droxidopa,5TBDMS,isomer #1CC(C)(C)[Si](C)(C)N[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)C1=CC=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C13281.8Semi standard non polar33892256
Droxidopa,5TBDMS,isomer #1CC(C)(C)[Si](C)(C)N[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)C1=CC=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C13111.8Standard non polar33892256
Droxidopa,5TBDMS,isomer #1CC(C)(C)[Si](C)(C)N[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)C1=CC=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C12842.1Standard polar33892256
Droxidopa,5TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC(=O)[C@@H]([C@@H](O[Si](C)(C)C(C)(C)C)C1=CC=C(O[Si](C)(C)C(C)(C)C)C(O)=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3454.4Semi standard non polar33892256
Droxidopa,5TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC(=O)[C@@H]([C@@H](O[Si](C)(C)C(C)(C)C)C1=CC=C(O[Si](C)(C)C(C)(C)C)C(O)=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3235.3Standard non polar33892256
Droxidopa,5TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC(=O)[C@@H]([C@@H](O[Si](C)(C)C(C)(C)C)C1=CC=C(O[Si](C)(C)C(C)(C)C)C(O)=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2859.7Standard polar33892256
Droxidopa,5TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC1=CC=C([C@H](O[Si](C)(C)C(C)(C)C)[C@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C1O[Si](C)(C)C(C)(C)C3494.0Semi standard non polar33892256
Droxidopa,5TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC1=CC=C([C@H](O[Si](C)(C)C(C)(C)C)[C@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C1O[Si](C)(C)C(C)(C)C3178.1Standard non polar33892256
Droxidopa,5TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC1=CC=C([C@H](O[Si](C)(C)C(C)(C)C)[C@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C1O[Si](C)(C)C(C)(C)C2857.9Standard polar33892256
Droxidopa,5TBDMS,isomer #4CC(C)(C)[Si](C)(C)OC(=O)[C@@H]([C@@H](O[Si](C)(C)C(C)(C)C)C1=CC=C(O)C(O[Si](C)(C)C(C)(C)C)=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3450.1Semi standard non polar33892256
Droxidopa,5TBDMS,isomer #4CC(C)(C)[Si](C)(C)OC(=O)[C@@H]([C@@H](O[Si](C)(C)C(C)(C)C)C1=CC=C(O)C(O[Si](C)(C)C(C)(C)C)=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3253.0Standard non polar33892256
Droxidopa,5TBDMS,isomer #4CC(C)(C)[Si](C)(C)OC(=O)[C@@H]([C@@H](O[Si](C)(C)C(C)(C)C)C1=CC=C(O)C(O[Si](C)(C)C(C)(C)C)=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2888.2Standard polar33892256
Droxidopa,5TBDMS,isomer #5CC(C)(C)[Si](C)(C)OC(=O)[C@@H]([C@@H](O)C1=CC=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3464.6Semi standard non polar33892256
Droxidopa,5TBDMS,isomer #5CC(C)(C)[Si](C)(C)OC(=O)[C@@H]([C@@H](O)C1=CC=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3220.0Standard non polar33892256
Droxidopa,5TBDMS,isomer #5CC(C)(C)[Si](C)(C)OC(=O)[C@@H]([C@@H](O)C1=CC=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2929.3Standard polar33892256
Droxidopa,6TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)[C@@H]([C@@H](O[Si](C)(C)C(C)(C)C)C1=CC=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3693.2Semi standard non polar33892256
Droxidopa,6TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)[C@@H]([C@@H](O[Si](C)(C)C(C)(C)C)C1=CC=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3385.7Standard non polar33892256
Droxidopa,6TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)[C@@H]([C@@H](O[Si](C)(C)C(C)(C)C)C1=CC=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2910.2Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Droxidopa GC-MS (Non-derivatized) - 70eV, Positivesplash10-000l-5900000000-26d8c8b25b21dcbfb87d2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Droxidopa GC-MS (4 TMS) - 70eV, Positivesplash10-0006-7271900000-8468af78d196fe459e972017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Droxidopa GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Droxidopa 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 - Droxidopa 10V, Positive-QTOFsplash10-01ot-0940000000-d059d190e9925a91bb492017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Droxidopa 20V, Positive-QTOFsplash10-0gbi-0900000000-21fe9bcddd0a26397d422017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Droxidopa 40V, Positive-QTOFsplash10-0pl0-8900000000-0f85172898c2ab4638a52017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Droxidopa 10V, Negative-QTOFsplash10-03di-0790000000-f5095ebf8a9b065f90092017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Droxidopa 20V, Negative-QTOFsplash10-05tr-2910000000-a5edeec2ecf0079c55b02017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Droxidopa 40V, Negative-QTOFsplash10-05fr-9100000000-f65a73dc75323d770d982017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Droxidopa 10V, Positive-QTOFsplash10-0ika-0930000000-63950caad6161af279212021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Droxidopa 20V, Positive-QTOFsplash10-0uk9-4900000000-0ed20264ffa0b87fc0792021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Droxidopa 40V, Positive-QTOFsplash10-11ca-9400000000-d0691ef57b270c8be7922021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Droxidopa 10V, Negative-QTOFsplash10-03di-0790000000-8d929b56c43e76b57bdb2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Droxidopa 20V, Negative-QTOFsplash10-0kmr-2900000000-07c5874e7034667489862021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Droxidopa 40V, Negative-QTOFsplash10-0a4i-9600000000-3d254647f1b3fd33b5e02021-10-12Wishart 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 Locations
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB06262 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB06262 details
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 ID391994
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkDroxidopa
METLIN IDNot Available
PubChem Compound443940
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 References
  1. Goldstein DS: L-Dihydroxyphenylserine (L-DOPS): a norepinephrine prodrug. Cardiovasc Drug Rev. 2006 Fall-Winter;24(3-4):189-203. [PubMed:17214596 ]
  2. Goldstein DS, Holmes C, Kaufmann H, Freeman R: Clinical pharmacokinetics of the norepinephrine precursor L-threo-DOPS in primary chronic autonomic failure. Clin Auton Res. 2004 Dec;14(6):363-8. [PubMed:15666063 ]
  3. Balk SH, Yoshioka H, Yukawa H, Harayama S: Synthesis of L-threo-3,4-dihydroxyphenylserine (L-threo-DOPS) with thermostabilized low-specific L-threonine aldolase from Streptomyces coelicolor A3(2). J Microbiol Biotechnol. 2007 May;17(5):721-7. [PubMed:18051291 ]
  4. Kaufmann H: L-dihydroxyphenylserine (Droxidopa): a new therapy for neurogenic orthostatic hypotension: the US experience. Clin Auton Res. 2008 Mar;18 Suppl 1:19-24. doi: 10.1007/s10286-007-1002-2. Epub 2008 Mar 27. [PubMed:18368303 ]
  5. Mathias CJ: L-dihydroxyphenylserine (Droxidopa) in the treatment of orthostatic hypotension: the European experience. Clin Auton Res. 2008 Mar;18 Suppl 1:25-9. doi: 10.1007/s10286-007-1005-z. Epub 2008 Mar 27. [PubMed:18368304 ]

Only showing the first 10 proteins. There are 13 proteins in total.

Enzymes

General function:
Involved in carboxy-lyase activity
Specific function:
Catalyzes the decarboxylation of L-3,4-dihydroxyphenylalanine (DOPA) to dopamine, L-5-hydroxytryptophan to serotonin and L-tryptophan to tryptamine.
Gene Name:
DDC
Uniprot ID:
P20711
Molecular weight:
53893.755
References
  1. Goldstein DS: L-Dihydroxyphenylserine (L-DOPS): a norepinephrine prodrug. Cardiovasc Drug Rev. 2006 Fall-Winter;24(3-4):189-203. [PubMed:17214596 ]
  2. Maruyama W, Naoi M, Narabayashi H: [The effect of droxidopa on the monoamine metabolsim in the human brain]. Rinsho Shinkeigaku. 1994 Oct;34(10):985-90. [PubMed:7834959 ]
General function:
Involved in amino acid binding
Specific function:
Not Available
Gene Name:
PAH
Uniprot ID:
P00439
Molecular weight:
51861.565
References
  1. Martinez A, Andersson KK, Haavik J, Flatmark T: EPR and 1H-NMR spectroscopic studies on the paramagnetic iron at the active site of phenylalanine hydroxylase and its interaction with substrates and inhibitors. Eur J Biochem. 1991 Jun 15;198(3):675-82. [PubMed:1646718 ]
  2. Martinez A, Haavik J, Flatmark T: Cooperative homotropic interaction of L-noradrenaline with the catalytic site of phenylalanine 4-monooxygenase. Eur J Biochem. 1990 Oct 5;193(1):211-9. [PubMed:2226440 ]
  3. Molinoff PB: The regulation of the noradrenergic neuron. J Psychiatr Res. 1974;11:339-45. [PubMed:4156788 ]
General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
Alpha-2 adrenergic receptors mediate the catecholamine- induced inhibition of adenylate cyclase through the action of G proteins. The rank order of potency for agonists of this receptor is oxymetazoline > clonidine > epinephrine > norepinephrine > phenylephrine > dopamine > p-synephrine > p-tyramine > serotonin = p-octopamine. For antagonists, the rank order is yohimbine > phentolamine = mianserine > chlorpromazine = spiperone = prazosin > propanolol > alprenolol = pindolol
Gene Name:
ADRA2A
Uniprot ID:
P08913
Molecular weight:
48956.3
References
  1. Davis MP: Recent advances in the treatment of pain. F1000 Med Rep. 2010 Aug 19;2:63. doi: 10.3410/M2-63. [PubMed:21173850 ]
  2. Giovannoni MP, Ghelardini C, Vergelli C, Dal Piaz V: Alpha2-agonists as analgesic agents. Med Res Rev. 2009 Mar;29(2):339-68. doi: 10.1002/med.20134. [PubMed:18680204 ]
  3. Nyronen T, Pihlavisto M, Peltonen JM, Hoffren AM, Varis M, Salminen T, Wurster S, Marjamaki A, Kanerva L, Katainen E, Laaksonen L, Savola JM, Scheinin M, Johnson MS: Molecular mechanism for agonist-promoted alpha(2A)-adrenoceptor activation by norepinephrine and epinephrine. Mol Pharmacol. 2001 May;59(5):1343-54. [PubMed:11306720 ]
General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
Alpha-2 adrenergic receptors mediate the catecholamine- induced inhibition of adenylate cyclase through the action of G proteins. The rank order of potency for agonists of this receptor is clonidine > norepinephrine > epinephrine = oxymetazoline > dopamine > p-tyramine = phenylephrine > serotonin > p-synephrine / p-octopamine. For antagonists, the rank order is yohimbine > chlorpromazine > phentolamine > mianserine > spiperone > prazosin > alprenolol > propanolol > pindolol
Gene Name:
ADRA2B
Uniprot ID:
P18089
Molecular weight:
49953.1
References
  1. Davis MP: Recent advances in the treatment of pain. F1000 Med Rep. 2010 Aug 19;2:63. doi: 10.3410/M2-63. [PubMed:21173850 ]
  2. Giovannoni MP, Ghelardini C, Vergelli C, Dal Piaz V: Alpha2-agonists as analgesic agents. Med Res Rev. 2009 Mar;29(2):339-68. doi: 10.1002/med.20134. [PubMed:18680204 ]
  3. Gilsbach R, Hein L: Presynaptic metabotropic receptors for acetylcholine and adrenaline/noradrenaline. Handb Exp Pharmacol. 2008;(184):261-88. [PubMed:18064417 ]
General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
Beta-adrenergic receptors mediate the catecholamine- induced activation of adenylate cyclase through the action of G proteins. This receptor binds epinephrine and norepinephrine with approximately equal affinity
Gene Name:
ADRB1
Uniprot ID:
P08588
Molecular weight:
51322.1
References
  1. Mersmann HJ: Overview of the effects of beta-adrenergic receptor agonists on animal growth including mechanisms of action. J Anim Sci. 1998 Jan;76(1):160-72. [PubMed:9464897 ]
  2. El-Armouche A, Eschenhagen T: Beta-adrenergic stimulation and myocardial function in the failing heart. Heart Fail Rev. 2009 Dec;14(4):225-41. doi: 10.1007/s10741-008-9132-8. [PubMed:19110970 ]
  3. Gilsbach R, Hein L: Presynaptic metabotropic receptors for acetylcholine and adrenaline/noradrenaline. Handb Exp Pharmacol. 2008;(184):261-88. [PubMed:18064417 ]
General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
Beta-adrenergic receptors mediate the catecholamine- induced activation of adenylate cyclase through the action of G proteins. The beta-2-adrenergic receptor binds epinephrine with an approximately 30-fold greater affinity than it does norepinephrine
Gene Name:
ADRB2
Uniprot ID:
P07550
Molecular weight:
46458.3
References
  1. Mersmann HJ: Overview of the effects of beta-adrenergic receptor agonists on animal growth including mechanisms of action. J Anim Sci. 1998 Jan;76(1):160-72. [PubMed:9464897 ]
  2. Sanders VM: The role of norepinephrine and beta-2-adrenergic receptor stimulation in the modulation of Th1, Th2, and B lymphocyte function. Adv Exp Med Biol. 1998;437:269-78. [PubMed:9666280 ]
  3. Tarizzo VI, Coppes RP, Dahlof C, Zaagsma J: Pre- and postganglionic stimulation-induced noradrenaline overflow is markedly facilitated by a prejunctional beta 2-adrenoceptor-mediated control mechanism in the pithed rat. Naunyn Schmiedebergs Arch Pharmacol. 1994 Jun;349(6):570-7. [PubMed:7969507 ]
  4. El-Armouche A, Eschenhagen T: Beta-adrenergic stimulation and myocardial function in the failing heart. Heart Fail Rev. 2009 Dec;14(4):225-41. doi: 10.1007/s10741-008-9132-8. [PubMed:19110970 ]
  5. Gilsbach R, Hein L: Presynaptic metabotropic receptors for acetylcholine and adrenaline/noradrenaline. Handb Exp Pharmacol. 2008;(184):261-88. [PubMed:18064417 ]
General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
This alpha-adrenergic receptor mediates its action by association with G proteins that activate a phosphatidylinositol- calcium second messenger system. Its effect is mediated by G(q) and G(11) proteins
Gene Name:
ADRA1A
Uniprot ID:
P35348
Molecular weight:
51486.0
References
  1. Senard JM, Brefel-Courbon C, Rascol O, Montastruc JL: Orthostatic hypotension in patients with Parkinson's disease: pathophysiology and management. Drugs Aging. 2001;18(7):495-505. [PubMed:11482743 ]
  2. Bishop MJ: Recent advances in the discovery of alpha1-adrenoceptor agonists. Curr Top Med Chem. 2007;7(2):135-45. [PubMed:17266602 ]
  3. Du L, Li M: Modeling the interactions between alpha(1)-adrenergic receptors and their antagonists. Curr Comput Aided Drug Des. 2010 Sep;6(3):165-78. [PubMed:20412040 ]
  4. Lachnit WG, Tran AM, Clarke DE, Ford AP: Pharmacological characterization of an alpha 1A-adrenoceptor mediating contractile responses to noradrenaline in isolated caudal artery of rat. Br J Pharmacol. 1997 Mar;120(5):819-26. [PubMed:9138687 ]
  5. Burt RP, Chapple CR, Marshall I: The role of diacylglycerol and activation of protein kinase C in alpha 1A-adrenoceptor-mediated contraction to noradrenaline of rat isolated epididymal vas deferens. Br J Pharmacol. 1996 Jan;117(1):224-30. [PubMed:8825367 ]
General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
This alpha-adrenergic receptor mediates its action by association with G proteins that activate a phosphatidylinositol- calcium second messenger system
Gene Name:
ADRA1B
Uniprot ID:
P35368
Molecular weight:
56835.4
References
  1. Bishop MJ: Recent advances in the discovery of alpha1-adrenoceptor agonists. Curr Top Med Chem. 2007;7(2):135-45. [PubMed:17266602 ]
  2. Du L, Li M: Modeling the interactions between alpha(1)-adrenergic receptors and their antagonists. Curr Comput Aided Drug Des. 2010 Sep;6(3):165-78. [PubMed:20412040 ]
  3. Testa R, Guarneri L, Poggesi E, Simonazzi I, Taddei C, Leonardi A: Mediation of noradrenaline-induced contractions of rat aorta by the alpha 1B-adrenoceptor subtype. Br J Pharmacol. 1995 Feb;114(4):745-50. [PubMed:7773533 ]
  4. Izzo NJ Jr, Colucci WS: Regulation of alpha 1B-adrenergic receptor half-life: protein synthesis dependence and effect of norepinephrine. Am J Physiol. 1994 Mar;266(3 Pt 1):C771-5. [PubMed:8166240 ]
General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
This alpha-adrenergic receptor mediates its effect through the influx of extracellular calcium
Gene Name:
ADRA1D
Uniprot ID:
P25100
Molecular weight:
60462.2
References
  1. Bishop MJ: Recent advances in the discovery of alpha1-adrenoceptor agonists. Curr Top Med Chem. 2007;7(2):135-45. [PubMed:17266602 ]
  2. Du L, Li M: Modeling the interactions between alpha(1)-adrenergic receptors and their antagonists. Curr Comput Aided Drug Des. 2010 Sep;6(3):165-78. [PubMed:20412040 ]
  3. Kenny BA, Chalmers DH, Philpott PC, Naylor AM: Characterization of an alpha 1D-adrenoceptor mediating the contractile response of rat aorta to noradrenaline. Br J Pharmacol. 1995 Jul;115(6):981-6. [PubMed:7582530 ]
  4. Testa R, Destefani C, Guarneri L, Poggesi E, Simonazzi I, Taddei C, Leonardi A: The alpha 1d-adrenoceptor subtype is involved in the noradrenaline-induced contractions of rat aorta. Life Sci. 1995;57(13):PL159-63. [PubMed:7674815 ]
General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
Beta-adrenergic receptors mediate the catecholamine- induced activation of adenylate cyclase through the action of G proteins. Beta-3 is involved in the regulation of lipolysis and thermogenesis
Gene Name:
ADRB3
Uniprot ID:
P13945
Molecular weight:
43518.6
References
  1. Coman OA, Paunescu H, Ghita I, Coman L, Badararu A, Fulga I: Beta 3 adrenergic receptors: molecular, histological, functional and pharmacological approaches. Rom J Morphol Embryol. 2009;50(2):169-79. [PubMed:19434307 ]
  2. Mersmann HJ: Overview of the effects of beta-adrenergic receptor agonists on animal growth including mechanisms of action. J Anim Sci. 1998 Jan;76(1):160-72. [PubMed:9464897 ]
  3. El-Armouche A, Eschenhagen T: Beta-adrenergic stimulation and myocardial function in the failing heart. Heart Fail Rev. 2009 Dec;14(4):225-41. doi: 10.1007/s10741-008-9132-8. [PubMed:19110970 ]
  4. Gilsbach R, Hein L: Presynaptic metabotropic receptors for acetylcholine and adrenaline/noradrenaline. Handb Exp Pharmacol. 2008;(184):261-88. [PubMed:18064417 ]

Transporters

General function:
Involved in neurotransmitter:sodium symporter activity
Specific function:
Amine transporter. Terminates the action of noradrenaline by its high affinity sodium-dependent reuptake into presynaptic terminals.
Gene Name:
SLC6A2
Uniprot ID:
P23975
Molecular weight:
69331.42
References
  1. Habecker BA, Willison BD, Shi X, Woodward WR: Chronic depolarization stimulates norepinephrine transporter expression via catecholamines. J Neurochem. 2006 May;97(4):1044-51. Epub 2006 Mar 29. [PubMed:16573647 ]
  2. Bonisch H, Bruss M: The norepinephrine transporter in physiology and disease. Handb Exp Pharmacol. 2006;(175):485-524. [PubMed:16722247 ]
  3. Mandela P, Ordway GA: KCl stimulation increases norepinephrine transporter function in PC12 cells. J Neurochem. 2006 Sep;98(5):1521-30. Epub 2006 Jul 31. [PubMed:16879714 ]
  4. Gutman DA, Owens MJ: Serotonin and norepinephrine transporter binding profile of SSRIs. Essent Psychopharmacol. 2006;7(1):35-41. [PubMed:16989291 ]
  5. Ksiazek P, Buraczynska K, Buraczynska M: Norepinephrine transporter gene (NET) polymorphism in patients with type 2 diabetes. Kidney Blood Press Res. 2006;29(6):338-43. Epub 2006 Nov 23. [PubMed:17124432 ]
General function:
Involved in transmembrane transport
Specific function:
Sodium-independent transporter that mediates the update of aromatic acid. Can function as a net efflux pathway for aromatic amino acids in the basosolateral epithelial cells
Gene Name:
SLC16A10
Uniprot ID:
Q8TF71
Molecular weight:
55492.1
References
  1. Kim DK, Kanai Y, Chairoungdua A, Matsuo H, Cha SH, Endou H: Expression cloning of a Na+-independent aromatic amino acid transporter with structural similarity to H+/monocarboxylate transporters. J Biol Chem. 2001 May 18;276(20):17221-8. Epub 2001 Feb 20. [PubMed:11278508 ]

Only showing the first 10 proteins. There are 13 proteins in total.