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 18:04:24 UTC |
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Update Date | 2022-03-07 02:53:40 UTC |
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HMDB ID | HMDB0033357 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | Laurelliptine |
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Description | Laurelliptine belongs to the class of organic compounds known as aporphines. These are quinoline alkaloids containing the dibenzo[de,g]quinoline ring system or a dehydrogenated derivative thereof. Laurelliptine has been detected, but not quantified in, fruits. This could make laurelliptine a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Laurelliptine. |
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Structure | COC1=C(O)C=C2CC3NCCC4=CC(OC)=C(O)C(C2=C1)=C34 InChI=1S/C18H19NO4/c1-22-14-8-11-10(6-13(14)20)5-12-16-9(3-4-19-12)7-15(23-2)18(21)17(11)16/h6-8,12,19-21H,3-5H2,1-2H3 |
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Synonyms | Value | Source |
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(+)-Laurelliptine | HMDB | (+)-N-Norisoboldine | HMDB | 1,9-Dihydroxy-2,10-dimethoxynoraporphine | HMDB | Norisoboldine | HMDB |
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Chemical Formula | C18H19NO4 |
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Average Molecular Weight | 313.3478 |
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Monoisotopic Molecular Weight | 313.131408101 |
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IUPAC Name | 4,15-dimethoxy-10-azatetracyclo[7.7.1.0²,⁷.0¹³,¹⁷]heptadeca-1(17),2,4,6,13,15-hexaene-5,16-diol |
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Traditional Name | 4,15-dimethoxy-10-azatetracyclo[7.7.1.0²,⁷.0¹³,¹⁷]heptadeca-1(17),2,4,6,13,15-hexaene-5,16-diol |
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CAS Registry Number | 23599-69-1 |
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SMILES | COC1=C(O)C=C2CC3NCCC4=CC(OC)=C(O)C(C2=C1)=C34 |
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InChI Identifier | InChI=1S/C18H19NO4/c1-22-14-8-11-10(6-13(14)20)5-12-16-9(3-4-19-12)7-15(23-2)18(21)17(11)16/h6-8,12,19-21H,3-5H2,1-2H3 |
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InChI Key | HORZNQYQXBFWNZ-UHFFFAOYSA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as aporphines. These are quinoline alkaloids containing the dibenzo[de,g]quinoline ring system or a dehydrogenated derivative thereof. |
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Kingdom | Organic compounds |
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Super Class | Alkaloids and derivatives |
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Class | Aporphines |
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Sub Class | Not Available |
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Direct Parent | Aporphines |
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Alternative Parents | |
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Substituents | - Aporphine
- Benzoquinoline
- Phenanthrene
- 1-naphthol
- Naphthalene
- Quinoline
- Tetrahydroisoquinoline
- Anisole
- Alkyl aryl ether
- 1-hydroxy-2-unsubstituted benzenoid
- Aralkylamine
- Benzenoid
- Azacycle
- Ether
- Secondary aliphatic amine
- Secondary amine
- Organoheterocyclic compound
- Organic nitrogen compound
- Organooxygen compound
- Organonitrogen compound
- Hydrocarbon derivative
- Organopnictogen compound
- Organic oxygen compound
- Amine
- 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 | 190 - 192 °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 | | Show more...
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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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Laurelliptine,1TMS,isomer #1 | COC1=CC2=C(C=C1O[Si](C)(C)C)CC1NCCC3=C1C2=C(O)C(OC)=C3 | 3032.1 | Semi standard non polar | 33892256 | Laurelliptine,1TMS,isomer #2 | COC1=CC2=C(C=C1O)CC1NCCC3=C1C2=C(O[Si](C)(C)C)C(OC)=C3 | 3037.6 | Semi standard non polar | 33892256 | Laurelliptine,1TMS,isomer #3 | COC1=CC2=C(C=C1O)CC1C3=C(C=C(OC)C(O)=C23)CCN1[Si](C)(C)C | 2909.0 | Semi standard non polar | 33892256 | Laurelliptine,2TMS,isomer #1 | COC1=CC2=C(C=C1O[Si](C)(C)C)CC1NCCC3=C1C2=C(O[Si](C)(C)C)C(OC)=C3 | 2937.1 | Semi standard non polar | 33892256 | Laurelliptine,2TMS,isomer #2 | COC1=CC2=C(C=C1O[Si](C)(C)C)CC1C3=C(C=C(OC)C(O)=C23)CCN1[Si](C)(C)C | 2834.6 | Semi standard non polar | 33892256 | Laurelliptine,2TMS,isomer #3 | COC1=CC2=C(C=C1O)CC1C3=C(C=C(OC)C(O[Si](C)(C)C)=C23)CCN1[Si](C)(C)C | 2869.4 | Semi standard non polar | 33892256 | Laurelliptine,3TMS,isomer #1 | COC1=CC2=C(C=C1O[Si](C)(C)C)CC1C3=C(C=C(OC)C(O[Si](C)(C)C)=C23)CCN1[Si](C)(C)C | 2857.5 | Semi standard non polar | 33892256 | Laurelliptine,3TMS,isomer #1 | COC1=CC2=C(C=C1O[Si](C)(C)C)CC1C3=C(C=C(OC)C(O[Si](C)(C)C)=C23)CCN1[Si](C)(C)C | 3011.8 | Standard non polar | 33892256 | Laurelliptine,1TBDMS,isomer #1 | COC1=CC2=C(C=C1O[Si](C)(C)C(C)(C)C)CC1NCCC3=C1C2=C(O)C(OC)=C3 | 3296.0 | Semi standard non polar | 33892256 | Laurelliptine,1TBDMS,isomer #2 | COC1=CC2=C(C=C1O)CC1NCCC3=C1C2=C(O[Si](C)(C)C(C)(C)C)C(OC)=C3 | 3270.3 | Semi standard non polar | 33892256 | Laurelliptine,1TBDMS,isomer #3 | COC1=CC2=C(C=C1O)CC1C3=C(C=C(OC)C(O)=C23)CCN1[Si](C)(C)C(C)(C)C | 3176.2 | Semi standard non polar | 33892256 | Laurelliptine,2TBDMS,isomer #1 | COC1=CC2=C(C=C1O[Si](C)(C)C(C)(C)C)CC1NCCC3=C1C2=C(O[Si](C)(C)C(C)(C)C)C(OC)=C3 | 3351.1 | Semi standard non polar | 33892256 | Laurelliptine,2TBDMS,isomer #2 | COC1=CC2=C(C=C1O[Si](C)(C)C(C)(C)C)CC1C3=C(C=C(OC)C(O)=C23)CCN1[Si](C)(C)C(C)(C)C | 3322.6 | Semi standard non polar | 33892256 | Laurelliptine,2TBDMS,isomer #3 | COC1=CC2=C(C=C1O)CC1C3=C(C=C(OC)C(O[Si](C)(C)C(C)(C)C)=C23)CCN1[Si](C)(C)C(C)(C)C | 3338.2 | Semi standard non polar | 33892256 | Laurelliptine,3TBDMS,isomer #1 | COC1=CC2=C(C=C1O[Si](C)(C)C(C)(C)C)CC1C3=C(C=C(OC)C(O[Si](C)(C)C(C)(C)C)=C23)CCN1[Si](C)(C)C(C)(C)C | 3496.4 | Semi standard non polar | 33892256 | Laurelliptine,3TBDMS,isomer #1 | COC1=CC2=C(C=C1O[Si](C)(C)C(C)(C)C)CC1C3=C(C=C(OC)C(O[Si](C)(C)C(C)(C)C)=C23)CCN1[Si](C)(C)C(C)(C)C | 3657.8 | Standard non 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 - Laurelliptine GC-MS (Non-derivatized) - 70eV, Positive | splash10-000t-0090000000-7be9419b5a22d4d6f971 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Laurelliptine GC-MS (2 TMS) - 70eV, Positive | splash10-0006-2019800000-88e399791df065edbf6c | 2017-10-06 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Laurelliptine GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Laurelliptine GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Laurelliptine GC-MS (TMS_1_1) - 70eV, Positive | Not Available | 2021-11-04 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Laurelliptine GC-MS (TMS_1_2) - 70eV, Positive | Not Available | 2021-11-04 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Laurelliptine GC-MS (TMS_1_3) - 70eV, Positive | Not Available | 2021-11-04 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Laurelliptine GC-MS (TMS_2_2) - 70eV, Positive | Not Available | 2021-11-04 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Laurelliptine GC-MS (TMS_2_3) - 70eV, Positive | Not Available | 2021-11-04 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Laurelliptine GC-MS (TBDMS_1_1) - 70eV, Positive | Not Available | 2021-11-04 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Laurelliptine GC-MS (TBDMS_1_2) - 70eV, Positive | Not Available | 2021-11-04 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Laurelliptine GC-MS (TBDMS_1_3) - 70eV, Positive | Not Available | 2021-11-04 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Laurelliptine GC-MS (TBDMS_2_1) - 70eV, Positive | Not Available | 2021-11-04 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Laurelliptine GC-MS (TBDMS_2_2) - 70eV, Positive | Not Available | 2021-11-04 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Laurelliptine GC-MS (TBDMS_2_3) - 70eV, Positive | Not Available | 2021-11-04 | 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 - Laurelliptine 10V, Negative-QTOF | splash10-03di-0009000000-cdeeadd31b672c74e70c | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Laurelliptine 20V, Negative-QTOF | splash10-03di-0069000000-15c5e41431c9a09ac687 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Laurelliptine 40V, Negative-QTOF | splash10-014m-0090000000-66c2435bbd59fb6c1c57 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Laurelliptine 10V, Negative-QTOF | splash10-03di-0009000000-5cd9c8e6e0b2900b51af | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Laurelliptine 20V, Negative-QTOF | splash10-03di-0029000000-9d8cbac2bda936817445 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Laurelliptine 40V, Negative-QTOF | splash10-03di-0096000000-5f437699acff38283db0 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Laurelliptine 10V, Positive-QTOF | splash10-03di-0019000000-27f714314b7bb0538937 | 2016-08-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Laurelliptine 20V, Positive-QTOF | splash10-03di-0096000000-471c6840d0fade25e1c6 | 2016-08-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Laurelliptine 40V, Positive-QTOF | splash10-00ou-0290000000-9d3ff39edda0ffd8494d | 2016-08-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Laurelliptine 10V, Positive-QTOF | splash10-03di-0009000000-7a1d998903fa1bad0b1e | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Laurelliptine 20V, Positive-QTOF | splash10-03di-0009000000-4045b3500554ed2bae36 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Laurelliptine 40V, Positive-QTOF | splash10-0gxx-0191000000-12c69080f4fd0d2db982 | 2021-09-22 | Wishart Lab | View Spectrum |
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Biological Properties |
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Cellular Locations | |
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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 | FDB011385 |
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KNApSAcK ID | C00025962 |
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Chemspider ID | 15035486 |
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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 | 14539910 |
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PDB ID | Not Available |
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ChEBI ID | Not Available |
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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 | - (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
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