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Record Information |
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Version | 5.0 |
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Status | Expected but not Quantified |
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Creation Date | 2009-02-03 11:51:29 UTC |
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Update Date | 2023-02-21 17:17:33 UTC |
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HMDB ID | HMDB0011664 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | 3-Methylene-indolenine |
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Description | 3-Methylene-indolenine is an electrophilic molecule produced by the action of cytochrome P450 2F1 on 3-methylindole (3MI). 3-Methylindole (3MI) is a naturally occurring pulmonary toxin that requires metabolic activation. In particular, 3MI-induced pneumotoxicity arises from cytochrome P-450-catalyzed dehydrogenation of 3MI to an electrophilic methylene imine (3-methyleneindolenine), which covalently binds to cellular macromolecules. Members of the CYP2F gene subfamily are selectively expressed in lung tissues and have been implicated as important catalysts in the formation of reactive intermediates from several pneumotoxic chemicals. (PMID: 10383923 ). |
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Structure | InChI=1S/C9H7N/c1-7-6-10-9-5-3-2-4-8(7)9/h2-6H,1H2 |
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Synonyms | Value | Source |
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3-Methylene-3H-indole | HMDB | 3-Methyleneindolenine | HMDB | 3-Methyleneindolenine, conjugate acid | MeSH, HMDB | 3-Methylene-indolenine | MeSH |
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Chemical Formula | C9H7N |
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Average Molecular Weight | 129.1586 |
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Monoisotopic Molecular Weight | 129.057849229 |
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IUPAC Name | 3-methylidene-3H-indole |
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Traditional Name | 3-methyleneindolenine |
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CAS Registry Number | 40642-83-9 |
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SMILES | C=C1C=NC2=CC=CC=C12 |
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InChI Identifier | InChI=1S/C9H7N/c1-7-6-10-9-5-3-2-4-8(7)9/h2-6H,1H2 |
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InChI Key | BCNUXXXHEIUHJB-UHFFFAOYSA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as indoles and derivatives. These are organic compounds containing an indole, which is a bicyclic ring system made up of a six-membered benzene ring fused to a five-membered nitrogen-containing pyrrole ring. |
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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 | Not Available |
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Direct Parent | Indoles and derivatives |
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Alternative Parents | |
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Substituents | - Indole or derivatives
- Benzenoid
- Azacycle
- Organic 1,3-dipolar compound
- Propargyl-type 1,3-dipolar organic compound
- Organic nitrogen compound
- Organopnictogen compound
- Hydrocarbon derivative
- Organonitrogen compound
- Imine
- Aromatic heteropolycyclic compound
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Molecular Framework | Aromatic heteropolycyclic compounds |
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External Descriptors | |
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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 | Solid |
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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 IndicesUnderivatized |
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Spectra |
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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 - 3-Methylene-indolenine GC-MS (Non-derivatized) - 70eV, Positive | splash10-0fb9-0900000000-3d84acfd95cbc3a7b679 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 3-Methylene-indolenine 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 - 3-Methylene-indolenine 10V, Positive-QTOF | splash10-001i-0900000000-dfa6172462414820c044 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 3-Methylene-indolenine 20V, Positive-QTOF | splash10-001i-0900000000-6e9ca0aeeaa7b26ee4c4 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 3-Methylene-indolenine 40V, Positive-QTOF | splash10-0udi-3900000000-f2394a06312955f7f201 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 3-Methylene-indolenine 10V, Negative-QTOF | splash10-004i-0900000000-bb1e304ced3d5e0fad57 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 3-Methylene-indolenine 20V, Negative-QTOF | splash10-004i-0900000000-bb1e304ced3d5e0fad57 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 3-Methylene-indolenine 40V, Negative-QTOF | splash10-004i-2900000000-3ea963fdae7c03597512 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 3-Methylene-indolenine 10V, Positive-QTOF | splash10-001i-0900000000-0040a9215518cbf57898 | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 3-Methylene-indolenine 20V, Positive-QTOF | splash10-001i-0900000000-39afe1a13df2499e1f7f | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 3-Methylene-indolenine 40V, Positive-QTOF | splash10-0fb9-5900000000-361d14169ac7b58a59bf | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 3-Methylene-indolenine 10V, Negative-QTOF | splash10-004i-0900000000-ab7ccc734ae03b00fe88 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 3-Methylene-indolenine 20V, Negative-QTOF | splash10-004i-0900000000-ab7ccc734ae03b00fe88 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 3-Methylene-indolenine 40V, Negative-QTOF | splash10-004i-0900000000-ab7ccc734ae03b00fe88 | 2021-09-24 | Wishart Lab | View Spectrum |
IR SpectraSpectrum Type | Description | Deposition Date | Source | View |
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Predicted IR Spectrum | IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+) | 2023-02-03 | FELIX lab | View Spectrum | Predicted IR Spectrum | IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+) | 2023-02-03 | FELIX lab | View Spectrum |
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Biological Properties |
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Cellular Locations | - Membrane (predicted from logP)
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Biospecimen Locations | Not Available |
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Tissue Locations | Not Available |
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Pathways | |
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Normal Concentrations |
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| Not Available |
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Abnormal Concentrations |
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| Not Available |
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Associated Disorders and Diseases |
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Disease References | None |
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Associated OMIM IDs | None |
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External Links |
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DrugBank ID | Not Available |
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Phenol Explorer Compound ID | Not Available |
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FooDB ID | FDB028355 |
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KNApSAcK ID | Not Available |
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Chemspider ID | 148991 |
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KEGG Compound ID | Not Available |
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BioCyc ID | Not Available |
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BiGG ID | Not Available |
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Wikipedia Link | Not Available |
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METLIN ID | Not Available |
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PubChem Compound | 170404 |
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PDB ID | Not Available |
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ChEBI ID | 63905 |
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Food Biomarker Ontology | Not Available |
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VMH ID | Not Available |
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MarkerDB ID | Not Available |
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Good Scents ID | Not Available |
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References |
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Synthesis Reference | Not Available |
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Material Safety Data Sheet (MSDS) | Not Available |
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General References | - Lanza DL, Code E, Crespi CL, Gonzalez FJ, Yost GS: Specific dehydrogenation of 3-methylindole and epoxidation of naphthalene by recombinant human CYP2F1 expressed in lymphoblastoid cells. Drug Metab Dispos. 1999 Jul;27(7):798-803. [PubMed:10383923 ]
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