Record Information |
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Version | 5.0 |
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Status | Expected but not Quantified |
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Creation Date | 2012-09-11 17:36:08 UTC |
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Update Date | 2022-03-07 02:52:30 UTC |
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HMDB ID | HMDB0030327 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | Perlolyrine |
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Description | Perlolyrine, also known as substance ys, belongs to the class of organic compounds known as harmala alkaloids. Harmala alkaloids are compounds with a structure based on harmaline, harmine, harmalol, harman or a derivative of those parents. These parents are beta-carbolines, consisting of a pyrimidine fused to the pyrrole moiety of an indole to form a pyrido[3,4-b]indole. Perlolyrine has been detected, but not quantified in, a few different foods, such as herbs and spices, saffrons (Crocus sativus), and soy beans (Glycine max). This could make perlolyrine a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on Perlolyrine. |
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Structure | OCC1=CC=C(O1)C1=NC=CC2=C1NC1=CC=CC=C21 InChI=1S/C16H12N2O2/c19-9-10-5-6-14(20-10)16-15-12(7-8-17-16)11-3-1-2-4-13(11)18-15/h1-8,18-19H,9H2 |
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Synonyms | Value | Source |
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Substance ys | MeSH | Yellow substance ys | MeSH | 2-(b-Carbolin-1-yl)-5-hydroxymethylfuran | HMDB | 2-Dehydrocarbonylflazin | HMDB | 5-(9H-pyrido(3,4-b)indol-1-yl)-2-Furanmethanol | HMDB | 5-(9H-pyrido[3,4-b]indol-1-yl)-2-Furanmethanol, 9ci | HMDB | Alkaloid ys | HMDB | [5-(9H-beta-Carbolin-1-yl)-2-furyl]methanol | HMDB |
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Chemical Formula | C16H12N2O2 |
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Average Molecular Weight | 264.2787 |
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Monoisotopic Molecular Weight | 264.089877638 |
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IUPAC Name | (5-{9H-pyrido[3,4-b]indol-1-yl}furan-2-yl)methanol |
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Traditional Name | perlolyrine |
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CAS Registry Number | 29700-20-7 |
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SMILES | OCC1=CC=C(O1)C1=NC=CC2=C1NC1=CC=CC=C21 |
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InChI Identifier | InChI=1S/C16H12N2O2/c19-9-10-5-6-14(20-10)16-15-12(7-8-17-16)11-3-1-2-4-13(11)18-15/h1-8,18-19H,9H2 |
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InChI Key | KFUCYPGCMLPUMT-UHFFFAOYSA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as harmala alkaloids. Harmala alkaloids are compounds with a structure based on harmaline, harmine, harmalol, harman or a derivative of those parents. These parents are beta-carbolines, consisting of a pyrimidine fused to the pyrrole moiety of an indole to form a pyrido[3,4-b]indole. |
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Kingdom | Organic compounds |
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Super Class | Alkaloids and derivatives |
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Class | Harmala alkaloids |
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Sub Class | Not Available |
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Direct Parent | Harmala alkaloids |
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Alternative Parents | |
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Substituents | - Harman
- Beta-carboline
- Pyridoindole
- Indole
- Indole or derivatives
- Benzenoid
- Pyridine
- Heteroaromatic compound
- Pyrrole
- Furan
- Oxacycle
- Azacycle
- Organoheterocyclic compound
- Hydrocarbon derivative
- Primary alcohol
- Organooxygen compound
- Organonitrogen compound
- Alcohol
- Organic oxygen compound
- Organopnictogen compound
- Organic nitrogen compound
- Aromatic alcohol
- 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 | 183 °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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Perlolyrine,1TMS,isomer #1 | C[Si](C)(C)OCC1=CC=C(C2=NC=CC3=C2[NH]C2=CC=CC=C23)O1 | 2864.2 | Semi standard non polar | 33892256 | Perlolyrine,1TMS,isomer #2 | C[Si](C)(C)N1C2=CC=CC=C2C2=CC=NC(C3=CC=C(CO)O3)=C21 | 2844.0 | Semi standard non polar | 33892256 | Perlolyrine,2TMS,isomer #1 | C[Si](C)(C)OCC1=CC=C(C2=NC=CC3=C2N([Si](C)(C)C)C2=CC=CC=C32)O1 | 2844.7 | Semi standard non polar | 33892256 | Perlolyrine,2TMS,isomer #1 | C[Si](C)(C)OCC1=CC=C(C2=NC=CC3=C2N([Si](C)(C)C)C2=CC=CC=C32)O1 | 2744.8 | Standard non polar | 33892256 | Perlolyrine,1TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)OCC1=CC=C(C2=NC=CC3=C2[NH]C2=CC=CC=C23)O1 | 3096.4 | Semi standard non polar | 33892256 | Perlolyrine,1TBDMS,isomer #2 | CC(C)(C)[Si](C)(C)N1C2=CC=CC=C2C2=CC=NC(C3=CC=C(CO)O3)=C21 | 3039.4 | Semi standard non polar | 33892256 | Perlolyrine,2TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)OCC1=CC=C(C2=NC=CC3=C2N([Si](C)(C)C(C)(C)C)C2=CC=CC=C32)O1 | 3248.2 | Semi standard non polar | 33892256 | Perlolyrine,2TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)OCC1=CC=C(C2=NC=CC3=C2N([Si](C)(C)C(C)(C)C)C2=CC=CC=C32)O1 | 3146.3 | 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 - Perlolyrine GC-MS (Non-derivatized) - 70eV, Positive | splash10-000b-0190000000-366a1478638155f0b62d | 2017-07-27 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Perlolyrine GC-MS (1 TMS) - 70eV, Positive | splash10-00dj-9263000000-7f547b2cb0cea39ddfb4 | 2017-10-06 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Perlolyrine GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Perlolyrine 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 - Perlolyrine 10V, Positive-QTOF | splash10-014i-0090000000-5aae234b5117054b9b0e | 2015-04-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Perlolyrine 20V, Positive-QTOF | splash10-014j-0090000000-c544b87c4bab088505c9 | 2015-04-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Perlolyrine 40V, Positive-QTOF | splash10-014i-4960000000-89238e7378563fe9e333 | 2015-04-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Perlolyrine 10V, Negative-QTOF | splash10-03di-0090000000-4022863ec611eb08878d | 2015-04-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Perlolyrine 20V, Negative-QTOF | splash10-01qa-0190000000-05b5aa6ed9c4bfaf6e90 | 2015-04-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Perlolyrine 40V, Negative-QTOF | splash10-0gb9-3490000000-2bf143ea0acfda8a07a2 | 2015-04-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Perlolyrine 10V, Negative-QTOF | splash10-03e9-0090000000-5db7fd9219b8a82d732a | 2021-09-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Perlolyrine 20V, Negative-QTOF | splash10-03di-0090000000-3ba2386f41e0df1e8c34 | 2021-09-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Perlolyrine 40V, Negative-QTOF | splash10-0006-2920000000-e2eeb6b2f419c48d29aa | 2021-09-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Perlolyrine 10V, Positive-QTOF | splash10-014i-0090000000-e6e22b9224f216c1ee62 | 2021-09-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Perlolyrine 20V, Positive-QTOF | splash10-014i-0290000000-021deff5c273a5c42dc8 | 2021-09-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Perlolyrine 40V, Positive-QTOF | splash10-05n0-0490000000-5349405c626001a3e473 | 2021-09-25 | Wishart Lab | View Spectrum |
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