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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2012-09-13 11:49:13 UTC
Update Date2022-09-22 18:35:11 UTC
HMDB IDHMDB0041943
Secondary Accession Numbers
  • HMDB41943
Metabolite Identification
Common NameN-Acetyldopamine
DescriptionN-Acetyldopamine also known as NADA is an acetylated form of dopamine. It is an endogenously produced derivative or metabolite of dopamine. It belongs to the family of compounds known as catecholamines and derivatives. These are compounds containing 4-(2-aminoethyl) pyrocatechol [4-(2-aminoethyl) benzene-1,2-diol] or a derivative thereof. While NADA has been found in the human liver, kidney, and urine, it is unclear what its role is in mammal physiology (PMID: 16179545 ). NADA exists in both free and conjugated (glucuronide) forms. Conjugated NADA accounts for about 90% of the total excretion of NADA. Urinary excretion of total N-acetyldopamine averages 0.485 micromoles/day in healthy humans (PMID: 6513727 ). The concentration of NADA is thirteen times higher in children with neuroblastoma than in normal subjects (PMID: 1321164 ). NADA is known to be a sepiapterin reductase inhibitor (PMID: 16179545 ). N-acetyldopamine has been shown to inhibit lipopolysaccharide-induced lipid peroxidation in rat brains (PMID: 16179545 ).
Structure
Data?1563863717
Synonyms
ValueSource
N-Acetyl-dopamineChEBI
NADAChEBI
NSC 314644ChEBI
N-(2-(3,4-Dihydroxyphenyl)ethyl)acetamide (acd/name 4.0)HMDB
N-(3,4-Dihydroxyphenethyl)-acetamideHMDB
{N-[2-(3,} 4-dihydroxyphenyl)ethyl]-acetamideHMDB
N-Acetyldopamine hydrobromideHMDB
Chemical FormulaC10H13NO3
Average Molecular Weight195.2151
Monoisotopic Molecular Weight195.089543287
IUPAC NameN-[2-(3,4-dihydroxyphenyl)ethyl]ethanimidic acid
Traditional NameN-[2-(3,4-dihydroxyphenyl)ethyl]ethanimidic acid
CAS Registry Number2494-12-4
SMILES
CC(O)=NCCC1=CC(O)=C(O)C=C1
InChI Identifier
InChI=1S/C10H13NO3/c1-7(12)11-5-4-8-2-3-9(13)10(14)6-8/h2-3,6,13-14H,4-5H2,1H3,(H,11,12)
InChI KeyOFSAJYZMIPNPHE-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as catechols. Catechols are compounds containing a 1,2-benzenediol moiety.
KingdomOrganic compounds
Super ClassBenzenoids
ClassPhenols
Sub ClassBenzenediols
Direct ParentCatechols
Alternative Parents
Substituents
  • Catechol
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Monocyclic benzene moiety
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Carboximidic acid derivative
  • Carboximidic acid
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.62 g/LALOGPS
logP1.12ALOGPS
logP0.98ChemAxon
logS-2.5ALOGPS
pKa (Strongest Acidic)4.17ChemAxon
pKa (Strongest Basic)6.16ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area73.05 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity53.21 m³·mol⁻¹ChemAxon
Polarizability20.52 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]+144.03431661259
DarkChem[M-H]-140.68331661259
DeepCCS[M+H]+142.75430932474
DeepCCS[M-H]-140.35930932474
DeepCCS[M-2H]-175.72630932474
DeepCCS[M+Na]+150.40430932474
AllCCS[M+H]+143.132859911
AllCCS[M+H-H2O]+139.032859911
AllCCS[M+NH4]+146.832859911
AllCCS[M+Na]+147.932859911
AllCCS[M-H]-144.332859911
AllCCS[M+Na-2H]-145.032859911
AllCCS[M+HCOO]-145.932859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
N-AcetyldopamineCC(O)=NCCC1=CC(O)=C(O)C=C13176.8Standard polar33892256
N-AcetyldopamineCC(O)=NCCC1=CC(O)=C(O)C=C11992.2Standard non polar33892256
N-AcetyldopamineCC(O)=NCCC1=CC(O)=C(O)C=C11964.1Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
N-Acetyldopamine,1TMS,isomer #1CC(=NCCC1=CC=C(O)C(O)=C1)O[Si](C)(C)C2026.2Semi standard non polar33892256
N-Acetyldopamine,1TMS,isomer #2CC(O)=NCCC1=CC=C(O)C(O[Si](C)(C)C)=C11999.7Semi standard non polar33892256
N-Acetyldopamine,1TMS,isomer #3CC(O)=NCCC1=CC=C(O[Si](C)(C)C)C(O)=C12004.2Semi standard non polar33892256
N-Acetyldopamine,2TMS,isomer #1CC(=NCCC1=CC=C(O[Si](C)(C)C)C(O)=C1)O[Si](C)(C)C1961.7Semi standard non polar33892256
N-Acetyldopamine,2TMS,isomer #2CC(=NCCC1=CC=C(O)C(O[Si](C)(C)C)=C1)O[Si](C)(C)C1945.8Semi standard non polar33892256
N-Acetyldopamine,2TMS,isomer #3CC(O)=NCCC1=CC=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C11990.2Semi standard non polar33892256
N-Acetyldopamine,3TMS,isomer #1CC(=NCCC1=CC=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C1)O[Si](C)(C)C2001.8Semi standard non polar33892256
N-Acetyldopamine,1TBDMS,isomer #1CC(=NCCC1=CC=C(O)C(O)=C1)O[Si](C)(C)C(C)(C)C2249.9Semi standard non polar33892256
N-Acetyldopamine,1TBDMS,isomer #2CC(O)=NCCC1=CC=C(O)C(O[Si](C)(C)C(C)(C)C)=C12228.3Semi standard non polar33892256
N-Acetyldopamine,1TBDMS,isomer #3CC(O)=NCCC1=CC=C(O[Si](C)(C)C(C)(C)C)C(O)=C12233.3Semi standard non polar33892256
N-Acetyldopamine,2TBDMS,isomer #1CC(=NCCC1=CC=C(O[Si](C)(C)C(C)(C)C)C(O)=C1)O[Si](C)(C)C(C)(C)C2406.4Semi standard non polar33892256
N-Acetyldopamine,2TBDMS,isomer #2CC(=NCCC1=CC=C(O)C(O[Si](C)(C)C(C)(C)C)=C1)O[Si](C)(C)C(C)(C)C2396.0Semi standard non polar33892256
N-Acetyldopamine,2TBDMS,isomer #3CC(O)=NCCC1=CC=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C12425.9Semi standard non polar33892256
N-Acetyldopamine,3TBDMS,isomer #1CC(=NCCC1=CC=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C1)O[Si](C)(C)C(C)(C)C2607.4Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - N-Acetyldopamine GC-MS (Non-derivatized) - 70eV, Positivesplash10-00di-5900000000-322baeb37e562f230d6e2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - N-Acetyldopamine GC-MS (3 TMS) - 70eV, Positivesplash10-0002-2329000000-67034caa51f29fc1db942017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - N-Acetyldopamine 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 - N-Acetyldopamine 10V, Positive-QTOFsplash10-0udj-0900000000-9d6d5d62affd310fe9da2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Acetyldopamine 20V, Positive-QTOFsplash10-0udr-0900000000-6789a4a05a27ffc8c72e2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Acetyldopamine 40V, Positive-QTOFsplash10-0a73-7900000000-39cce604b533a5ea53da2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Acetyldopamine 10V, Negative-QTOFsplash10-0006-0900000000-33688bbd5f6fa611ffac2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Acetyldopamine 20V, Negative-QTOFsplash10-0udi-2900000000-0abff677c304f51b62c52017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Acetyldopamine 40V, Negative-QTOFsplash10-052f-9200000000-7dbb91adef85d3970a152017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Acetyldopamine 10V, Negative-QTOFsplash10-0006-0900000000-aa47bc65a9bc174ac5762021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Acetyldopamine 20V, Negative-QTOFsplash10-0ff0-2900000000-b990a78ff0427d33066b2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Acetyldopamine 40V, Negative-QTOFsplash10-006x-9500000000-8b0884fc3dcbb60f7b8a2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Acetyldopamine 10V, Positive-QTOFsplash10-000i-0900000000-a264295a056435b1570b2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Acetyldopamine 20V, Positive-QTOFsplash10-0ktr-0900000000-7cbcd712f341a1542c872021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Acetyldopamine 40V, Positive-QTOFsplash10-014i-7900000000-87e5ec45e15e5843ebe92021-09-24Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedAdult (>18 years old)BothAsthma details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothAsthma details
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB111680
KNApSAcK IDC00033243
Chemspider ID90825
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound100526
PDB IDNot Available
ChEBI ID125678
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. Jouve J, Herault J, Tournade H, Muh JP: Determination by high-performance liquid chromatography with electrochemical detection of free and conjugated N-acetyldopamine excretion in urine of children with neuroblastoma and nephroblastoma. J Chromatogr. 1992 Feb 7;574(1):9-15. [PubMed:1321164 ]
  2. Elchisak MA, Hausner EA: Demonstration of N-acetyldopamine in human kidney and urine. Life Sci. 1984 Dec 17;35(25):2561-9. [PubMed:6513727 ]
  3. Oxenkrug GF, Requintina PJ: N-acetyldopamine inhibits rat brain lipid peroxidation induced by lipopolysaccharide. Ann N Y Acad Sci. 2005 Aug;1053:394-9. doi: 10.1111/j.1749-6632.2005.tb00047.x. [PubMed:16179545 ]