Record Information |
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Version | 5.0 |
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Status | Detected but not Quantified |
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Creation Date | 2012-09-13 11:49:13 UTC |
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Update Date | 2022-09-22 18:35:11 UTC |
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HMDB ID | HMDB0041943 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | N-Acetyldopamine |
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Description | N-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 ). |
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Structure | CC(O)=NCCC1=CC(O)=C(O)C=C1 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) |
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Synonyms | Value | Source |
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N-Acetyl-dopamine | ChEBI | NADA | ChEBI | NSC 314644 | ChEBI | N-(2-(3,4-Dihydroxyphenyl)ethyl)acetamide (acd/name 4.0) | HMDB | N-(3,4-Dihydroxyphenethyl)-acetamide | HMDB | {N-[2-(3,} 4-dihydroxyphenyl)ethyl]-acetamide | HMDB | N-Acetyldopamine hydrobromide | HMDB |
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Chemical Formula | C10H13NO3 |
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Average Molecular Weight | 195.2151 |
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Monoisotopic Molecular Weight | 195.089543287 |
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IUPAC Name | N-[2-(3,4-dihydroxyphenyl)ethyl]ethanimidic acid |
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Traditional Name | N-[2-(3,4-dihydroxyphenyl)ethyl]ethanimidic acid |
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CAS Registry Number | 2494-12-4 |
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SMILES | CC(O)=NCCC1=CC(O)=C(O)C=C1 |
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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) |
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InChI Key | OFSAJYZMIPNPHE-UHFFFAOYSA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as catechols. Catechols are compounds containing a 1,2-benzenediol moiety. |
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Kingdom | Organic compounds |
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Super Class | Benzenoids |
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Class | Phenols |
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Sub Class | Benzenediols |
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Direct Parent | Catechols |
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Alternative Parents | |
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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
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Molecular Framework | Aromatic homomonocyclic compounds |
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External Descriptors | Not Available |
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Ontology |
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Physiological effect | Not Available |
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Disposition | |
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Process | Not Available |
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Role | Not Available |
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Physical Properties |
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State | Not Available |
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Experimental Molecular Properties | Property | Value | Reference |
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Melting Point | Not Available | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | Not Available | Not Available | LogP | Not Available | Not Available |
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Experimental Chromatographic Properties | Not Available |
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Predicted Molecular Properties | |
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Predicted Chromatographic Properties | Predicted Collision Cross SectionsPredicted Kovats Retention IndicesUnderivatizedDerivatizedDerivative Name / Structure | SMILES | Kovats RI Value | Column Type | Reference |
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N-Acetyldopamine,1TMS,isomer #1 | CC(=NCCC1=CC=C(O)C(O)=C1)O[Si](C)(C)C | 2026.2 | Semi standard non polar | 33892256 | N-Acetyldopamine,1TMS,isomer #2 | CC(O)=NCCC1=CC=C(O)C(O[Si](C)(C)C)=C1 | 1999.7 | Semi standard non polar | 33892256 | N-Acetyldopamine,1TMS,isomer #3 | CC(O)=NCCC1=CC=C(O[Si](C)(C)C)C(O)=C1 | 2004.2 | Semi standard non polar | 33892256 | N-Acetyldopamine,2TMS,isomer #1 | CC(=NCCC1=CC=C(O[Si](C)(C)C)C(O)=C1)O[Si](C)(C)C | 1961.7 | Semi standard non polar | 33892256 | N-Acetyldopamine,2TMS,isomer #2 | CC(=NCCC1=CC=C(O)C(O[Si](C)(C)C)=C1)O[Si](C)(C)C | 1945.8 | Semi standard non polar | 33892256 | N-Acetyldopamine,2TMS,isomer #3 | CC(O)=NCCC1=CC=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C1 | 1990.2 | Semi standard non polar | 33892256 | N-Acetyldopamine,3TMS,isomer #1 | CC(=NCCC1=CC=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C1)O[Si](C)(C)C | 2001.8 | Semi standard non polar | 33892256 | N-Acetyldopamine,1TBDMS,isomer #1 | CC(=NCCC1=CC=C(O)C(O)=C1)O[Si](C)(C)C(C)(C)C | 2249.9 | Semi standard non polar | 33892256 | N-Acetyldopamine,1TBDMS,isomer #2 | CC(O)=NCCC1=CC=C(O)C(O[Si](C)(C)C(C)(C)C)=C1 | 2228.3 | Semi standard non polar | 33892256 | N-Acetyldopamine,1TBDMS,isomer #3 | CC(O)=NCCC1=CC=C(O[Si](C)(C)C(C)(C)C)C(O)=C1 | 2233.3 | Semi standard non polar | 33892256 | N-Acetyldopamine,2TBDMS,isomer #1 | CC(=NCCC1=CC=C(O[Si](C)(C)C(C)(C)C)C(O)=C1)O[Si](C)(C)C(C)(C)C | 2406.4 | Semi standard non polar | 33892256 | N-Acetyldopamine,2TBDMS,isomer #2 | CC(=NCCC1=CC=C(O)C(O[Si](C)(C)C(C)(C)C)=C1)O[Si](C)(C)C(C)(C)C | 2396.0 | Semi standard non polar | 33892256 | N-Acetyldopamine,2TBDMS,isomer #3 | CC(O)=NCCC1=CC=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C1 | 2425.9 | Semi standard non polar | 33892256 | N-Acetyldopamine,3TBDMS,isomer #1 | CC(=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)C | 2607.4 | Semi standard non polar | 33892256 |
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| GC-MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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Predicted GC-MS | Predicted GC-MS Spectrum - N-Acetyldopamine GC-MS (Non-derivatized) - 70eV, Positive | splash10-00di-5900000000-322baeb37e562f230d6e | 2017-09-01 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - N-Acetyldopamine GC-MS (3 TMS) - 70eV, Positive | splash10-0002-2329000000-67034caa51f29fc1db94 | 2017-10-06 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - N-Acetyldopamine GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum |
MS/MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - N-Acetyldopamine 10V, Positive-QTOF | splash10-0udj-0900000000-9d6d5d62affd310fe9da | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - N-Acetyldopamine 20V, Positive-QTOF | splash10-0udr-0900000000-6789a4a05a27ffc8c72e | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - N-Acetyldopamine 40V, Positive-QTOF | splash10-0a73-7900000000-39cce604b533a5ea53da | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - N-Acetyldopamine 10V, Negative-QTOF | splash10-0006-0900000000-33688bbd5f6fa611ffac | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - N-Acetyldopamine 20V, Negative-QTOF | splash10-0udi-2900000000-0abff677c304f51b62c5 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - N-Acetyldopamine 40V, Negative-QTOF | splash10-052f-9200000000-7dbb91adef85d3970a15 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - N-Acetyldopamine 10V, Negative-QTOF | splash10-0006-0900000000-aa47bc65a9bc174ac576 | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - N-Acetyldopamine 20V, Negative-QTOF | splash10-0ff0-2900000000-b990a78ff0427d33066b | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - N-Acetyldopamine 40V, Negative-QTOF | splash10-006x-9500000000-8b0884fc3dcbb60f7b8a | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - N-Acetyldopamine 10V, Positive-QTOF | splash10-000i-0900000000-a264295a056435b1570b | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - N-Acetyldopamine 20V, Positive-QTOF | splash10-0ktr-0900000000-7cbcd712f341a1542c87 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - N-Acetyldopamine 40V, Positive-QTOF | splash10-014i-7900000000-87e5ec45e15e5843ebe9 | 2021-09-24 | Wishart Lab | View Spectrum |
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