| Record Information |
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| Version | 1.0 |
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| Creation Date | 2016-09-30 23:04:22 UTC |
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| Update Date | 2020-05-11 20:49:17 UTC |
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| BMDB ID | BMDB0003409 |
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| Secondary Accession Numbers | |
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| Metabolite Identification |
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| Common Name | Berberine |
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| Description | Berberine 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. Based on a literature review a significant number of articles have been published on Berberine. |
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| Structure | |
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| Synonyms | | Value | Source |
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| 7,8,13,13a-Tetradehydro-9,10-dimethoxy-2,3-[methylenebis(oxy)]berbinium | ChEBI | | 9,10-Dimethoxy-2,3-(methylenedioxy)-7,8,13,13a-tetradehydroberbinium | ChEBI | | Berberin | ChEBI | | Coptis rhizome | HMDB |
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| Chemical Formula | C20H18NO4 |
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| Average Molecular Weight | 336.3612 |
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| Monoisotopic Molecular Weight | 336.123583069 |
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| IUPAC Name | 16,17-dimethoxy-5,7-dioxa-13lambda5-azapentacyclo[11.8.0.0^{2,10}.0^{4,8}.0^{15,20}]henicosa-1(21),2,4(8),9,13,15,17,19-octaen-13-ylium |
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| Traditional Name | 16,17-dimethoxy-5,7-dioxa-13lambda5-azapentacyclo[11.8.0.0^{2,10}.0^{4,8}.0^{15,20}]henicosa-1(21),2,4(8),9,13,15,17,19-octaen-13-ylium |
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| CAS Registry Number | 2086-83-1 |
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| SMILES | COC1=CC=C2C=C3C4=CC5=C(OCO5)C=C4CC[N+]3=CC2=C1OC |
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| InChI Identifier | InChI=1S/C20H18NO4/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/h3-4,7-10H,5-6,11H2,1-2H3/q+1 |
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| InChI Key | YBHILYKTIRIUTE-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
- Isoquinoline
- Benzodioxole
- Anisole
- Alkyl aryl ether
- Pyridine
- Pyridinium
- Benzenoid
- Heteroaromatic compound
- Acetal
- Ether
- Oxacycle
- Azacycle
- Organoheterocyclic compound
- Organonitrogen compound
- Hydrocarbon derivative
- Organic nitrogen compound
- Organooxygen compound
- Organic oxygen compound
- Organopnictogen compound
- Organic cation
- 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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| Status | Expected but not Quantified |
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| Origin | |
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| Biofunction | Not Available |
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| Application | Not Available |
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| Cellular locations | |
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| Physical Properties |
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| State | Solid |
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| Experimental Properties | | Property | Value | Reference |
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| Melting Point | 145 °C | Not Available | | Boiling Point | Not Available | Not Available | | Water Solubility | Not Available | Not Available | | LogP | Not Available | Not Available |
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| Predicted Properties | |
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| Spectra |
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| Spectra | |
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