Record Information |
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Version | 1.0 |
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Created at | 2020-11-23 19:42:06 UTC |
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Updated at | 2021-08-12 19:52:20 UTC |
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NP-MRD ID | NP0002855 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | 5-Methoxy-3-indoleacetic acid |
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Provided By | BMRB |
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Description | 5-Methoxyindoleacetate belongs to the class of organic compounds known as indole-3-acetic acid derivatives. Indole-3-acetic acid derivatives are compounds containing an acetic acid (or a derivative) linked to the C3 carbon atom of an indole. 5-Methoxyindoleacetate exists in all living organisms, ranging from bacteria to humans. In humans, 5-methoxyindoleacetate is involved in the tryptophan metabolism pathway. 5-Methoxyindoleacetate is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. 5-Methoxy-3-indoleacetic acid is found in Daphnia pulex. It was first documented in 1985 (PMID: 2580458). Based on a literature review a significant number of articles have been published on 5-Methoxyindoleacetate (PMID: 17984079) (PMID: 26686724) (PMID: 12908946) (PMID: 2446428). |
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Structure | COC1=CC2=C(NC=C2CC(O)=O)C=C1 InChI=1S/C11H11NO3/c1-15-8-2-3-10-9(5-8)7(6-12-10)4-11(13)14/h2-3,5-6,12H,4H2,1H3,(H,13,14) |
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Synonyms | Value | Source |
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2-(5-Methoxy-1H-indol-3-yl)ethanoic acid | ChEBI | 2-(5-Methoxyindole-3-yl)acetic acid | ChEBI | 5-Methoxyindol-3-ylacetic acid | ChEBI | 5-Methoxyindoleacetic acid | ChEBI | 2-(5-Methoxy-1H-indol-3-yl)ethanoate | Generator | 2-(5-Methoxyindole-3-yl)acetate | Generator | 5-Methoxyindol-3-ylacetate | Generator | 5-Methoxyindole-3-acetate | HMDB | 5-Methoxyindole-3-acetic acid | HMDB, MeSH | Methoxyindoleacetate | HMDB | Methoxyindoleacetic acid | HMDB | 5-Methoxy-1H-indole-3-acetic acid | HMDB | (5-Methoxy-1H-indol-3-yl)acetic acid | HMDB | 2-(5-Methoxy-1H-indol-3-yl)acetic acid | HMDB | 2-(5-Methoxy-3-indolyl)acetic acid | HMDB | 5-Methoxy-3-indoleacetic acid | HMDB | 5-Methoxy-3-indolylacetic acid | HMDB | 5-Methoxy-IAA | HMDB | 5-Methyloxyindole-3-acetic acid | HMDB | 5-MIAA | HMDB |
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Chemical Formula | C11H11NO3 |
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Average Mass | 205.2099 Da |
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Monoisotopic Mass | 205.07389 Da |
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IUPAC Name | 2-(5-methoxy-1H-indol-3-yl)acetic acid |
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Traditional Name | 5-methoxyindole-3-acetic acid |
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CAS Registry Number | Not Available |
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SMILES | COC1=CC2=C(NC=C2CC(O)=O)C=C1 |
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InChI Identifier | InChI=1S/C11H11NO3/c1-15-8-2-3-10-9(5-8)7(6-12-10)4-11(13)14/h2-3,5-6,12H,4H2,1H3,(H,13,14) |
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InChI Key | COCNDHOPIHDTHK-UHFFFAOYSA-N |
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Experimental Spectra |
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| Spectrum Type | Description | Depositor Email | Depositor Organization | Depositor | Deposition Date | View |
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1D NMR | 1H NMR Spectrum (1D, 500 MHz, ethanol, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 500 MHz, ethanol, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 500 MHz, ethanol, experimental) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum |
| Predicted Spectra |
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| Not Available | Chemical Shift Submissions |
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| Not Available | Species |
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Species of Origin | |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as indole-3-acetic acid derivatives. Indole-3-acetic acid derivatives are compounds containing an acetic acid (or a derivative) linked to the C3 carbon atom of an indole. |
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Kingdom | Organic compounds |
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Super Class | Organoheterocyclic compounds |
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Class | Indoles and derivatives |
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Sub Class | Indolyl carboxylic acids and derivatives |
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Direct Parent | Indole-3-acetic acid derivatives |
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Alternative Parents | Not Available |
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Substituents | Not Available |
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Molecular Framework | Aromatic heteropolycyclic compounds |
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External Descriptors | Not Available |
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Physical Properties |
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State | Not Available |
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Experimental 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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Predicted Properties | |
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General References | - Ulrich EL, Akutsu H, Doreleijers JF, Harano Y, Ioannidis YE, Lin J, Livny M, Mading S, Maziuk D, Miller Z, Nakatani E, Schulte CF, Tolmie DE, Kent Wenger R, Yao H, Markley JL: BioMagResBank. Nucleic Acids Res. 2008 Jan;36(Database issue):D402-8. doi: 10.1093/nar/gkm957. Epub 2007 Nov 4. [PubMed:17984079 ]
- Hagi T, Kobayashi M, Nomura M: Metabolome analysis of milk fermented by gamma-aminobutyric acid-producing Lactococcus lactis. J Dairy Sci. 2016 Feb;99(2):994-1001. doi: 10.3168/jds.2015-9945. Epub 2015 Dec 10. [PubMed:26686724 ]
- Higa S, Markey SP: Identification and quantification of 5-methoxyindole-3-acetic acid in human urine. Anal Biochem. 1985 Jan;144(1):86-93. doi: 10.1016/0003-2697(85)90087-9. [PubMed:2580458 ]
- Meatherall R, Sharma P: Foxy, a designer tryptamine hallucinogen. J Anal Toxicol. 2003 Jul-Aug;27(5):313-7. doi: 10.1093/jat/27.5.313. [PubMed:12908946 ]
- Sergeeva TI, Raushenbakh TI, Shevchenko MO, Rybal'chenko VG: [Excretion of 5-hydroxyindole-3-acetic and 5-methoxyindole-3-acetic acids in cancer patients]. Vopr Onkol. 1987;33(10):20-5. [PubMed:2446428 ]
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