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Record Information |
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Version | 5.0 |
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Status | Detected but not Quantified |
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Creation Date | 2013-07-22 15:42:19 UTC |
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Update Date | 2021-09-14 15:46:16 UTC |
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HMDB ID | HMDB0061115 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | Lenticin |
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Description | Lenticin or hypaphorine is a compound found in lentil extracts. It can also be detected in blood after an individual has consumed lentils and may therefore serve as a food biomarker. Lenticin is an indole alkaloid that is essentially an N-methylated form of tryptophan. It is known to be a sleep-inducing compound (PMID: 18571406 ). In plants it is an agonist of the plant hormone indole acetic acid. |
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Structure | C[N+](C)(C)[C@@H](CC1=CNC2=CC=CC=C12)C([O-])=O InChI=1S/C14H18N2O2/c1-16(2,3)13(14(17)18)8-10-9-15-12-7-5-4-6-11(10)12/h4-7,9,13,15H,8H2,1-3H3/t13-/m0/s1 |
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Synonyms | Value | Source |
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(+)-Hypaphorine | ChEBI | Glyyunnanenine | ChEBI | L-Hypaphorine | ChEBI | L-Tryptophan betaine | ChEBI | N,N,N-Trimethyltryptophan betaine | ChEBI | Tryptophan betaine | ChEBI | Lenticin nitrate | HMDB | Hypaforin | HMDB | Lenticin | ChEBI |
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Chemical Formula | C14H18N2O2 |
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Average Molecular Weight | 246.3049 |
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Monoisotopic Molecular Weight | 246.13682783 |
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IUPAC Name | (2S)-3-(1H-indol-3-yl)-2-(trimethylazaniumyl)propanoate |
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Traditional Name | hypaphorine |
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CAS Registry Number | 487-58-1 |
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SMILES | C[N+](C)(C)[C@@H](CC1=CNC2=CC=CC=C12)C([O-])=O |
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InChI Identifier | InChI=1S/C14H18N2O2/c1-16(2,3)13(14(17)18)8-10-9-15-12-7-5-4-6-11(10)12/h4-7,9,13,15H,8H2,1-3H3/t13-/m0/s1 |
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InChI Key | AOHCBEAZXHZMOR-ZDUSSCGKSA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as l-alpha-amino acids. These are alpha amino acids which have the L-configuration of the alpha-carbon 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 | L-alpha-amino acids |
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Alternative Parents | |
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Substituents | - 3-alkylindole
- L-alpha-amino acid
- Indole
- Indole or derivatives
- Aralkylamine
- Substituted pyrrole
- Benzenoid
- Tetraalkylammonium salt
- Pyrrole
- Heteroaromatic compound
- Quaternary ammonium salt
- Carboxylic acid salt
- Carboxylic acid
- Monocarboxylic acid or derivatives
- Azacycle
- Organoheterocyclic compound
- Organic oxygen compound
- Organooxygen compound
- Organonitrogen compound
- Organic oxide
- Amine
- Organopnictogen compound
- Carbonyl group
- Hydrocarbon derivative
- Organic nitrogen compound
- Organic salt
- 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 | 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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Lenticin,1TMS,isomer #1 | C[N+](C)(C)[C@@H](CC1=CN([Si](C)(C)C)C2=CC=CC=C12)C(=O)[O-] | 2159.5 | Semi standard non polar | 33892256 | Lenticin,1TMS,isomer #1 | C[N+](C)(C)[C@@H](CC1=CN([Si](C)(C)C)C2=CC=CC=C12)C(=O)[O-] | 2120.1 | Standard non polar | 33892256 | Lenticin,1TMS,isomer #1 | C[N+](C)(C)[C@@H](CC1=CN([Si](C)(C)C)C2=CC=CC=C12)C(=O)[O-] | 2583.3 | Standard polar | 33892256 | Lenticin,1TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)N1C=C(C[C@@H](C(=O)[O-])[N+](C)(C)C)C2=CC=CC=C21 | 2358.7 | Semi standard non polar | 33892256 | Lenticin,1TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)N1C=C(C[C@@H](C(=O)[O-])[N+](C)(C)C)C2=CC=CC=C21 | 2336.6 | Standard non polar | 33892256 | Lenticin,1TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)N1C=C(C[C@@H](C(=O)[O-])[N+](C)(C)C)C2=CC=CC=C21 | 2652.8 | Standard polar | 33892256 |
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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 - Lenticin GC-MS (Non-derivatized) - 70eV, Positive | splash10-0udi-5890000000-7a32ae6df95ecbe4b4d5 | 2017-09-20 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Lenticin GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Lenticin 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 - Lenticin 10V, Positive-QTOF | splash10-0002-0290000000-c42f376f71f6e3725267 | 2017-10-06 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Lenticin 20V, Positive-QTOF | splash10-0f7k-0390000000-f1efb195c18ebf5ebaaf | 2017-10-06 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Lenticin 40V, Positive-QTOF | splash10-0f89-0900000000-d8339c908340d1176dc0 | 2017-10-06 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Lenticin 10V, Negative-QTOF | splash10-0002-0290000000-4b553f8b8e9e0606e117 | 2017-10-06 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Lenticin 20V, Negative-QTOF | splash10-000b-0890000000-d5d7c7edd0b4db429160 | 2017-10-06 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Lenticin 40V, Negative-QTOF | splash10-014i-0900000000-8c56dbdaac5dc7a92a2e | 2017-10-06 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Lenticin 10V, Negative-QTOF | splash10-0002-0090000000-fdb1f9281332d5149644 | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Lenticin 20V, Negative-QTOF | splash10-014i-0910000000-a89d64e0d176721c5891 | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Lenticin 40V, Negative-QTOF | splash10-016r-0900000000-b4ddbcb87a2999e94631 | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Lenticin 10V, Positive-QTOF | splash10-0udi-0190000000-ec4a6e5db2f844802dc9 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Lenticin 20V, Positive-QTOF | splash10-001l-0910000000-0b46677e1ee9ee59d663 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Lenticin 40V, Positive-QTOF | splash10-0006-6900000000-c7a3ff32cff4a5522e4d | 2021-09-24 | Wishart Lab | View Spectrum |
NMR SpectraSpectrum Type | Description | Deposition Date | Source | View |
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Predicted 1D NMR | 13C NMR Spectrum (1D, 100 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 100 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 1000 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 200 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 200 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 300 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 300 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 400 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 400 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 500 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 500 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 600 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 600 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 700 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 700 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 800 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 800 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 900 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 900 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum |
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Biological Properties |
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Cellular Locations | Not Available |
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Biospecimen Locations | |
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Tissue Locations | |
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Pathways | |
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Normal Concentrations |
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Blood | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Normal | | details | Urine | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Normal | | details |
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Abnormal Concentrations |
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Feces | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Colorectal Cancer | | details |
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Associated Disorders and Diseases |
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Disease References | Colorectal cancer |
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- Brown DG, Rao S, Weir TL, O'Malia J, Bazan M, Brown RJ, Ryan EP: Metabolomics and metabolic pathway networks from human colorectal cancers, adjacent mucosa, and stool. Cancer Metab. 2016 Jun 6;4:11. doi: 10.1186/s40170-016-0151-y. eCollection 2016. [PubMed:27275383 ]
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Associated OMIM IDs | |
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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 | Not Available |
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KNApSAcK ID | C00001740 |
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Chemspider ID | Not Available |
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KEGG Compound ID | C09213 |
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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 | 442106 |
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PDB ID | Not Available |
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ChEBI ID | 5832 |
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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 | - Ozawa M, Honda K, Nakai I, Kishida A, Ohsaki A: Hypaphorine, an indole alkaloid from Erythrina velutina, induced sleep on normal mice. Bioorg Med Chem Lett. 2008 Jul 15;18(14):3992-4. doi: 10.1016/j.bmcl.2008.06.002. Epub 2008 Jun 6. [PubMed:18571406 ]
- Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]
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