Record Information |
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Version | 5.0 |
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Status | Expected but not Quantified |
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Creation Date | 2012-09-12 03:02:57 UTC |
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Update Date | 2022-03-07 02:56:59 UTC |
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HMDB ID | HMDB0041370 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | Na-p-Hydroxycoumaroyltryptophan |
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Description | Na-p-Hydroxycoumaroyltryptophan belongs to the class of organic compounds known as n-acyl-alpha amino acids. N-acyl-alpha amino acids are compounds containing an alpha amino acid which bears an acyl group at its terminal nitrogen atom. Na-p-Hydroxycoumaroyltryptophan has been detected, but not quantified in, a few different foods, such as arabica coffees (Coffea arabica), coffee and coffee products, and robusta coffees (Coffea canephora). This could make na-p-hydroxycoumaroyltryptophan a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Na-p-Hydroxycoumaroyltryptophan. |
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Structure | OC(=O)C(CC1=CNC2=C1C=CC=C2)NC(=O)\C=C\C1=CC=C(O)C=C1 InChI=1S/C20H18N2O4/c23-15-8-5-13(6-9-15)7-10-19(24)22-18(20(25)26)11-14-12-21-17-4-2-1-3-16(14)17/h1-10,12,18,21,23H,11H2,(H,22,24)(H,25,26)/b10-7+ |
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Synonyms | Value | Source |
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2-{[(2E)-1-hydroxy-3-(4-hydroxyphenyl)prop-2-en-1-ylidene]amino}-3-(1H-indol-3-yl)propanoate | HMDB |
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Chemical Formula | C20H18N2O4 |
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Average Molecular Weight | 350.3679 |
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Monoisotopic Molecular Weight | 350.126657074 |
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IUPAC Name | 2-[(2E)-3-(4-hydroxyphenyl)prop-2-enamido]-3-(1H-indol-3-yl)propanoic acid |
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Traditional Name | 2-[(2E)-3-(4-hydroxyphenyl)prop-2-enamido]-3-(1H-indol-3-yl)propanoic acid |
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CAS Registry Number | Not Available |
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SMILES | OC(=O)C(CC1=CNC2=C1C=CC=C2)NC(=O)\C=C\C1=CC=C(O)C=C1 |
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InChI Identifier | InChI=1S/C20H18N2O4/c23-15-8-5-13(6-9-15)7-10-19(24)22-18(20(25)26)11-14-12-21-17-4-2-1-3-16(14)17/h1-10,12,18,21,23H,11H2,(H,22,24)(H,25,26)/b10-7+ |
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InChI Key | IDUPBPKKEQWWCP-JXMROGBWSA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as n-acyl-alpha amino acids. N-acyl-alpha amino acids are compounds containing an alpha amino acid which bears an acyl group at its terminal nitrogen atom. |
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Kingdom | Organic compounds |
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Super Class | Organic acids and derivatives |
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Class | Carboxylic acids and derivatives |
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Sub Class | Amino acids, peptides, and analogues |
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Direct Parent | N-acyl-alpha amino acids |
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Alternative Parents | |
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Substituents | - N-acyl-alpha-amino acid
- Cinnamic acid amide
- Cinnamic acid or derivatives
- Coumaric acid or derivatives
- Hydroxycinnamic acid or derivatives
- Indolyl carboxylic acid derivative
- 3-alkylindole
- Indole
- Indole or derivatives
- Styrene
- 1-hydroxy-2-unsubstituted benzenoid
- Phenol
- Monocyclic benzene moiety
- Benzenoid
- Substituted pyrrole
- Pyrrole
- Heteroaromatic compound
- Secondary carboxylic acid amide
- Carboxamide group
- Organoheterocyclic compound
- Azacycle
- Monocarboxylic acid or derivatives
- Carboxylic acid
- Organooxygen compound
- Organopnictogen compound
- Organic oxygen compound
- Organic nitrogen compound
- Organic oxide
- Hydrocarbon derivative
- Carbonyl group
- Organonitrogen compound
- Aromatic heteropolycyclic compound
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Molecular Framework | Aromatic heteropolycyclic 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 | |
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Physical Properties |
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State | Solid |
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Experimental Molecular Properties | Property | Value | Reference |
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Melting Point | 208 °C | 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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Na-p-Hydroxycoumaroyltryptophan,1TMS,isomer #1 | C[Si](C)(C)OC(=O)C(CC1=C[NH]C2=CC=CC=C12)NC(=O)/C=C/C1=CC=C(O)C=C1 | 3767.7 | Semi standard non polar | 33892256 | Na-p-Hydroxycoumaroyltryptophan,1TMS,isomer #2 | C[Si](C)(C)OC1=CC=C(/C=C/C(=O)NC(CC2=C[NH]C3=CC=CC=C23)C(=O)O)C=C1 | 3750.1 | Semi standard non polar | 33892256 | Na-p-Hydroxycoumaroyltryptophan,1TMS,isomer #3 | C[Si](C)(C)N1C=C(CC(NC(=O)/C=C/C2=CC=C(O)C=C2)C(=O)O)C2=CC=CC=C21 | 3837.1 | Semi standard non polar | 33892256 | Na-p-Hydroxycoumaroyltryptophan,1TMS,isomer #4 | C[Si](C)(C)N(C(=O)/C=C/C1=CC=C(O)C=C1)C(CC1=C[NH]C2=CC=CC=C12)C(=O)O | 3755.7 | Semi standard non polar | 33892256 | Na-p-Hydroxycoumaroyltryptophan,2TMS,isomer #1 | C[Si](C)(C)OC(=O)C(CC1=C[NH]C2=CC=CC=C12)NC(=O)/C=C/C1=CC=C(O[Si](C)(C)C)C=C1 | 3663.5 | Semi standard non polar | 33892256 | Na-p-Hydroxycoumaroyltryptophan,2TMS,isomer #2 | C[Si](C)(C)OC(=O)C(CC1=CN([Si](C)(C)C)C2=CC=CC=C12)NC(=O)/C=C/C1=CC=C(O)C=C1 | 3796.9 | Semi standard non polar | 33892256 | Na-p-Hydroxycoumaroyltryptophan,2TMS,isomer #3 | C[Si](C)(C)OC(=O)C(CC1=C[NH]C2=CC=CC=C12)N(C(=O)/C=C/C1=CC=C(O)C=C1)[Si](C)(C)C | 3698.4 | Semi standard non polar | 33892256 | Na-p-Hydroxycoumaroyltryptophan,2TMS,isomer #4 | C[Si](C)(C)OC1=CC=C(/C=C/C(=O)N(C(CC2=C[NH]C3=CC=CC=C23)C(=O)O)[Si](C)(C)C)C=C1 | 3701.2 | Semi standard non polar | 33892256 | Na-p-Hydroxycoumaroyltryptophan,2TMS,isomer #5 | C[Si](C)(C)OC1=CC=C(/C=C/C(=O)NC(CC2=CN([Si](C)(C)C)C3=CC=CC=C23)C(=O)O)C=C1 | 3816.1 | Semi standard non polar | 33892256 | Na-p-Hydroxycoumaroyltryptophan,2TMS,isomer #6 | C[Si](C)(C)N(C(=O)/C=C/C1=CC=C(O)C=C1)C(CC1=CN([Si](C)(C)C)C2=CC=CC=C12)C(=O)O | 3809.7 | Semi standard non polar | 33892256 | Na-p-Hydroxycoumaroyltryptophan,3TMS,isomer #1 | C[Si](C)(C)OC(=O)C(CC1=CN([Si](C)(C)C)C2=CC=CC=C12)NC(=O)/C=C/C1=CC=C(O[Si](C)(C)C)C=C1 | 3715.8 | Semi standard non polar | 33892256 | Na-p-Hydroxycoumaroyltryptophan,3TMS,isomer #1 | C[Si](C)(C)OC(=O)C(CC1=CN([Si](C)(C)C)C2=CC=CC=C12)NC(=O)/C=C/C1=CC=C(O[Si](C)(C)C)C=C1 | 3438.6 | Standard non polar | 33892256 | Na-p-Hydroxycoumaroyltryptophan,3TMS,isomer #2 | C[Si](C)(C)OC(=O)C(CC1=C[NH]C2=CC=CC=C12)N(C(=O)/C=C/C1=CC=C(O[Si](C)(C)C)C=C1)[Si](C)(C)C | 3642.3 | Semi standard non polar | 33892256 | Na-p-Hydroxycoumaroyltryptophan,3TMS,isomer #2 | C[Si](C)(C)OC(=O)C(CC1=C[NH]C2=CC=CC=C12)N(C(=O)/C=C/C1=CC=C(O[Si](C)(C)C)C=C1)[Si](C)(C)C | 3435.7 | Standard non polar | 33892256 | Na-p-Hydroxycoumaroyltryptophan,3TMS,isomer #3 | C[Si](C)(C)OC(=O)C(CC1=CN([Si](C)(C)C)C2=CC=CC=C12)N(C(=O)/C=C/C1=CC=C(O)C=C1)[Si](C)(C)C | 3703.7 | Semi standard non polar | 33892256 | Na-p-Hydroxycoumaroyltryptophan,3TMS,isomer #3 | C[Si](C)(C)OC(=O)C(CC1=CN([Si](C)(C)C)C2=CC=CC=C12)N(C(=O)/C=C/C1=CC=C(O)C=C1)[Si](C)(C)C | 3458.4 | Standard non polar | 33892256 | Na-p-Hydroxycoumaroyltryptophan,3TMS,isomer #4 | C[Si](C)(C)OC1=CC=C(/C=C/C(=O)N(C(CC2=CN([Si](C)(C)C)C3=CC=CC=C23)C(=O)O)[Si](C)(C)C)C=C1 | 3734.3 | Semi standard non polar | 33892256 | Na-p-Hydroxycoumaroyltryptophan,3TMS,isomer #4 | C[Si](C)(C)OC1=CC=C(/C=C/C(=O)N(C(CC2=CN([Si](C)(C)C)C3=CC=CC=C23)C(=O)O)[Si](C)(C)C)C=C1 | 3492.8 | Standard non polar | 33892256 | Na-p-Hydroxycoumaroyltryptophan,4TMS,isomer #1 | C[Si](C)(C)OC(=O)C(CC1=CN([Si](C)(C)C)C2=CC=CC=C12)N(C(=O)/C=C/C1=CC=C(O[Si](C)(C)C)C=C1)[Si](C)(C)C | 3674.0 | Semi standard non polar | 33892256 | Na-p-Hydroxycoumaroyltryptophan,4TMS,isomer #1 | C[Si](C)(C)OC(=O)C(CC1=CN([Si](C)(C)C)C2=CC=CC=C12)N(C(=O)/C=C/C1=CC=C(O[Si](C)(C)C)C=C1)[Si](C)(C)C | 3387.9 | Standard non polar | 33892256 | Na-p-Hydroxycoumaroyltryptophan,1TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)OC(=O)C(CC1=C[NH]C2=CC=CC=C12)NC(=O)/C=C/C1=CC=C(O)C=C1 | 4047.2 | Semi standard non polar | 33892256 | Na-p-Hydroxycoumaroyltryptophan,1TBDMS,isomer #2 | CC(C)(C)[Si](C)(C)OC1=CC=C(/C=C/C(=O)NC(CC2=C[NH]C3=CC=CC=C23)C(=O)O)C=C1 | 4052.6 | Semi standard non polar | 33892256 | Na-p-Hydroxycoumaroyltryptophan,1TBDMS,isomer #3 | CC(C)(C)[Si](C)(C)N1C=C(CC(NC(=O)/C=C/C2=CC=C(O)C=C2)C(=O)O)C2=CC=CC=C21 | 4078.5 | Semi standard non polar | 33892256 | Na-p-Hydroxycoumaroyltryptophan,1TBDMS,isomer #4 | CC(C)(C)[Si](C)(C)N(C(=O)/C=C/C1=CC=C(O)C=C1)C(CC1=C[NH]C2=CC=CC=C12)C(=O)O | 4021.8 | Semi standard non polar | 33892256 | Na-p-Hydroxycoumaroyltryptophan,2TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)OC(=O)C(CC1=C[NH]C2=CC=CC=C12)NC(=O)/C=C/C1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1 | 4247.4 | Semi standard non polar | 33892256 | Na-p-Hydroxycoumaroyltryptophan,2TBDMS,isomer #2 | CC(C)(C)[Si](C)(C)OC(=O)C(CC1=CN([Si](C)(C)C(C)(C)C)C2=CC=CC=C12)NC(=O)/C=C/C1=CC=C(O)C=C1 | 4287.6 | Semi standard non polar | 33892256 | Na-p-Hydroxycoumaroyltryptophan,2TBDMS,isomer #3 | CC(C)(C)[Si](C)(C)OC(=O)C(CC1=C[NH]C2=CC=CC=C12)N(C(=O)/C=C/C1=CC=C(O)C=C1)[Si](C)(C)C(C)(C)C | 4223.2 | Semi standard non polar | 33892256 | Na-p-Hydroxycoumaroyltryptophan,2TBDMS,isomer #4 | CC(C)(C)[Si](C)(C)OC1=CC=C(/C=C/C(=O)N(C(CC2=C[NH]C3=CC=CC=C23)C(=O)O)[Si](C)(C)C(C)(C)C)C=C1 | 4246.5 | Semi standard non polar | 33892256 | Na-p-Hydroxycoumaroyltryptophan,2TBDMS,isomer #5 | CC(C)(C)[Si](C)(C)OC1=CC=C(/C=C/C(=O)NC(CC2=CN([Si](C)(C)C(C)(C)C)C3=CC=CC=C23)C(=O)O)C=C1 | 4318.1 | Semi standard non polar | 33892256 | Na-p-Hydroxycoumaroyltryptophan,2TBDMS,isomer #6 | CC(C)(C)[Si](C)(C)N(C(=O)/C=C/C1=CC=C(O)C=C1)C(CC1=CN([Si](C)(C)C(C)(C)C)C2=CC=CC=C12)C(=O)O | 4287.3 | Semi standard non polar | 33892256 | Na-p-Hydroxycoumaroyltryptophan,3TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)OC(=O)C(CC1=CN([Si](C)(C)C(C)(C)C)C2=CC=CC=C12)NC(=O)/C=C/C1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1 | 4424.0 | Semi standard non polar | 33892256 | Na-p-Hydroxycoumaroyltryptophan,3TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)OC(=O)C(CC1=CN([Si](C)(C)C(C)(C)C)C2=CC=CC=C12)NC(=O)/C=C/C1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1 | 4048.7 | Standard non polar | 33892256 | Na-p-Hydroxycoumaroyltryptophan,3TBDMS,isomer #2 | CC(C)(C)[Si](C)(C)OC(=O)C(CC1=C[NH]C2=CC=CC=C12)N(C(=O)/C=C/C1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1)[Si](C)(C)C(C)(C)C | 4391.2 | Semi standard non polar | 33892256 | Na-p-Hydroxycoumaroyltryptophan,3TBDMS,isomer #2 | CC(C)(C)[Si](C)(C)OC(=O)C(CC1=C[NH]C2=CC=CC=C12)N(C(=O)/C=C/C1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1)[Si](C)(C)C(C)(C)C | 4063.2 | Standard non polar | 33892256 | Na-p-Hydroxycoumaroyltryptophan,3TBDMS,isomer #3 | CC(C)(C)[Si](C)(C)OC(=O)C(CC1=CN([Si](C)(C)C(C)(C)C)C2=CC=CC=C12)N(C(=O)/C=C/C1=CC=C(O)C=C1)[Si](C)(C)C(C)(C)C | 4398.2 | Semi standard non polar | 33892256 | Na-p-Hydroxycoumaroyltryptophan,3TBDMS,isomer #3 | CC(C)(C)[Si](C)(C)OC(=O)C(CC1=CN([Si](C)(C)C(C)(C)C)C2=CC=CC=C12)N(C(=O)/C=C/C1=CC=C(O)C=C1)[Si](C)(C)C(C)(C)C | 4045.7 | Standard non polar | 33892256 | Na-p-Hydroxycoumaroyltryptophan,3TBDMS,isomer #4 | CC(C)(C)[Si](C)(C)OC1=CC=C(/C=C/C(=O)N(C(CC2=CN([Si](C)(C)C(C)(C)C)C3=CC=CC=C23)C(=O)O)[Si](C)(C)C(C)(C)C)C=C1 | 4461.0 | Semi standard non polar | 33892256 | Na-p-Hydroxycoumaroyltryptophan,3TBDMS,isomer #4 | CC(C)(C)[Si](C)(C)OC1=CC=C(/C=C/C(=O)N(C(CC2=CN([Si](C)(C)C(C)(C)C)C3=CC=CC=C23)C(=O)O)[Si](C)(C)C(C)(C)C)C=C1 | 4044.7 | Standard non polar | 33892256 | Na-p-Hydroxycoumaroyltryptophan,4TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)OC(=O)C(CC1=CN([Si](C)(C)C(C)(C)C)C2=CC=CC=C12)N(C(=O)/C=C/C1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1)[Si](C)(C)C(C)(C)C | 4515.9 | Semi standard non polar | 33892256 | Na-p-Hydroxycoumaroyltryptophan,4TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)OC(=O)C(CC1=CN([Si](C)(C)C(C)(C)C)C2=CC=CC=C12)N(C(=O)/C=C/C1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1)[Si](C)(C)C(C)(C)C | 4124.4 | 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 - Na-p-Hydroxycoumaroyltryptophan GC-MS (Non-derivatized) - 70eV, Positive | splash10-0002-0901000000-116ee215d9b125e0cd3b | 2017-09-01 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Na-p-Hydroxycoumaroyltryptophan GC-MS (2 TMS) - 70eV, Positive | splash10-004i-4239300000-c714ac237efe8a7b740a | 2017-10-06 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Na-p-Hydroxycoumaroyltryptophan 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 - Na-p-Hydroxycoumaroyltryptophan 10V, Positive-QTOF | splash10-0zgi-0519000000-3439835289393c5b6577 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Na-p-Hydroxycoumaroyltryptophan 20V, Positive-QTOF | splash10-0a4i-0912000000-8ef7af860f5fcaf5c322 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Na-p-Hydroxycoumaroyltryptophan 40V, Positive-QTOF | splash10-001i-1900000000-b8dac02b71c4d4ede956 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Na-p-Hydroxycoumaroyltryptophan 10V, Negative-QTOF | splash10-0002-0019000000-b1975c14aba879ff1fd2 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Na-p-Hydroxycoumaroyltryptophan 20V, Negative-QTOF | splash10-0532-1968000000-6b162ebd20a9bb528087 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Na-p-Hydroxycoumaroyltryptophan 40V, Negative-QTOF | splash10-05mo-4900000000-a4e56b1a0c8116424c00 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Na-p-Hydroxycoumaroyltryptophan 10V, Positive-QTOF | splash10-0ue9-0109000000-8eed14550732e9ec0344 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Na-p-Hydroxycoumaroyltryptophan 20V, Positive-QTOF | splash10-052f-0903000000-51ebd253538b164c964e | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Na-p-Hydroxycoumaroyltryptophan 40V, Positive-QTOF | splash10-014i-1900000000-a6d4b313701a5aa7643b | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Na-p-Hydroxycoumaroyltryptophan 10V, Negative-QTOF | splash10-0a4j-0229000000-27c47d8f38d780f2cc05 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Na-p-Hydroxycoumaroyltryptophan 20V, Negative-QTOF | splash10-066r-0915000000-835634e73002855d2941 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Na-p-Hydroxycoumaroyltryptophan 40V, Negative-QTOF | splash10-014i-0900000000-2d428f9c164506ef1e25 | 2021-09-22 | Wishart Lab | View Spectrum |
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