Record Information |
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Version | 5.0 |
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Status | Detected but not Quantified |
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Creation Date | 2012-09-11 18:15:44 UTC |
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Update Date | 2022-09-22 18:34:25 UTC |
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HMDB ID | HMDB0033524 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | Lambertine |
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Description | Lambertine, also known as dihydroberberine, belongs to the class of organic compounds known as protoberberine alkaloids and derivatives. These are alkaloids with a structure based on a protoberberine moiety, which consists of a 5,6-dihydrodibenzene moiety fused to a quinolizinium and forming 5,6-Dihydrodibenzo(a,g)quinolizinium skeleton. Lambertine is a strong basic compound (based on its pKa). Outside of the human body, lambertine has been detected, but not quantified in, fruits and tea. This could make lambertine a potential biomarker for the consumption of these foods. |
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Structure | COC1=CC=C2C=C3N(CCC4=CC5=C(OCO5)C=C34)CC2=C1OC InChI=1S/C20H19NO4/c1-22-17-4-3-12-7-16-14-9-19-18(24-11-25-19)8-13(14)5-6-21(16)10-15(12)20(17)23-2/h3-4,7-9H,5-6,10-11H2,1-2H3 |
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Synonyms | Value | Source |
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Dihydroberberine | HMDB | Dihydroberberine hydrochloride | HMDB |
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Chemical Formula | C20H19NO4 |
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Average Molecular Weight | 337.3692 |
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Monoisotopic Molecular Weight | 337.131408101 |
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IUPAC Name | 16,17-dimethoxy-5,7-dioxa-13-azapentacyclo[11.8.0.0²,¹⁰.0⁴,⁸.0¹⁵,²⁰]henicosa-1(21),2,4(8),9,15,17,19-heptaene |
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Traditional Name | 16,17-dimethoxy-5,7-dioxa-13-azapentacyclo[11.8.0.0²,¹⁰.0⁴,⁸.0¹⁵,²⁰]henicosa-1(21),2,4(8),9,15,17,19-heptaene |
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CAS Registry Number | 120834-89-1 |
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SMILES | COC1=CC=C2C=C3N(CCC4=CC5=C(OCO5)C=C34)CC2=C1OC |
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InChI Identifier | InChI=1S/C20H19NO4/c1-22-17-4-3-12-7-16-14-9-19-18(24-11-25-19)8-13(14)5-6-21(16)10-15(12)20(17)23-2/h3-4,7-9H,5-6,10-11H2,1-2H3 |
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InChI Key | FZAGOOYMTPGPGF-UHFFFAOYSA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as protoberberine alkaloids and derivatives. These are alkaloids with a structure based on a protoberberine moiety, which consists of a 5,6-dihydrodibenzene moiety fused to a quinolizinium and forming 5,6-Dihydrodibenzo(a,g)quinolizinium skeleton. |
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Kingdom | Organic compounds |
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Super Class | Alkaloids and derivatives |
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Class | Protoberberine alkaloids and derivatives |
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Sub Class | Not Available |
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Direct Parent | Protoberberine alkaloids and derivatives |
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Alternative Parents | |
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Substituents | - Protoberberine skeleton
- Tetrahydroisoquinoline
- Benzodioxole
- Anisole
- Alkyl aryl ether
- Aralkylamine
- Benzenoid
- Tertiary aliphatic amine
- Tertiary amine
- Acetal
- Organoheterocyclic compound
- Oxacycle
- Azacycle
- Enamine
- Ether
- Hydrocarbon derivative
- Organonitrogen compound
- Organooxygen compound
- Organic oxygen compound
- Organic nitrogen compound
- Amine
- Organopnictogen compound
- 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 | 163 - 164 °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 IndicesUnderivatized |
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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 - Lambertine GC-MS (Non-derivatized) - 70eV, Positive | splash10-00dr-0937000000-0c51681a533aea1542e8 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Lambertine 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 - Lambertine 10V, Positive-QTOF | splash10-000i-0009000000-71e9dc30e119186620ae | 2016-06-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Lambertine 20V, Positive-QTOF | splash10-000i-0109000000-811a0237d57b2724db6b | 2016-06-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Lambertine 40V, Positive-QTOF | splash10-002g-0891000000-70473923c1a156f45883 | 2016-06-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Lambertine 10V, Negative-QTOF | splash10-000i-0009000000-a4fa7b371323f46c26ef | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Lambertine 20V, Negative-QTOF | splash10-000i-0019000000-f71cc29f31c9f8419066 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Lambertine 40V, Negative-QTOF | splash10-0fdo-0092000000-a15fa22a545766a000f5 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Lambertine 10V, Negative-QTOF | splash10-000i-0009000000-e425d548b88b81358192 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Lambertine 20V, Negative-QTOF | splash10-000i-0009000000-875cb50d577bc475b166 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Lambertine 40V, Negative-QTOF | splash10-0076-0093000000-545328ff2003bc0bf8bd | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Lambertine 10V, Positive-QTOF | splash10-000i-0009000000-195152c9499dc2b0f3dd | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Lambertine 20V, Positive-QTOF | splash10-000i-0009000000-177debf6280ad456cbfd | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Lambertine 40V, Positive-QTOF | splash10-000i-0369000000-0a5b23cfa362b926caa0 | 2021-09-23 | Wishart Lab | View Spectrum |
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