(S)-scoulerine (BioDeep_00000003728)

 

Secondary id: BioDeep_00000361468, BioDeep_00000403162

natural product human metabolite PANOMIX_OTCML-2023


代谢物信息卡片


(13aS)-5,8,13,13a-Tetrahydro-3,10-dimethoxy-6H- dibenzo[a,g]quinolizine-2,9-diol

化学式: C19H21NO4 (327.14705060000006)
中文名称: 金黄紫堇碱
谱图信息: 最多检出来源 Viridiplantae(plant) 1.31%

分子结构信息

SMILES: COC1=C(C2=C(CC3C4=CC(=C(C=C4CCN3C2)OC)O)C=C1)O
InChI: InChI=1S/C19H21NO4/c1-23-17-4-3-11-7-15-13-9-16(21)18(24-2)8-12(13)5-6-20(15)10-14(11)19(17)22/h3-4,8-9,15,21-22H,5-7,10H2,1-2H3

描述信息

(s)-scoulerine, also known as discretamine or aequaline, belongs to protoberberine alkaloids and derivatives class of compounds. Those 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 (s)-scoulerine is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). (s)-scoulerine can be found in a number of food items such as rice, lemon grass, chinese bayberry, and sea-buckthornberry, which makes (s)-scoulerine a potential biomarker for the consumption of these food products.

同义名列表

15 个代谢物同义名

(13aS)-5,8,13,13a-Tetrahydro-3,10-dimethoxy-6H- dibenzo[a,g]quinolizine-2,9-diol; (13AS)-5,8,13,13a-tetrahydro-3,10-dimethoxy-6H-dibenzo[a,g]quinolizine-2,9-diol; (12bS)-3,10-dimethoxy-7,8,12b,13-tetrahydro-5H-6-azatetraphene-4,11-diol; discretamine, hydrochloride, (S)-isomer; discretamine, (+-)-isomer; discretamine, (R)-isomer; discretamine, (S)-isomer; scoulerine, (S)-isomer; aequaline, (S)-isomer; (S)-scoulerine; (-)-scoulerine; discretamine; Scoulerine; Scoulerin; aequaline



数据库引用编号

30 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(0)

BioCyc(2)

PlantCyc(0)

代谢反应

25 个相关的代谢反应过程信息。

Reactome(0)

BioCyc(5)

WikiPathways(0)

Plant Reactome(0)

INOH(0)

PlantCyc(20)

COVID-19 Disease Map(0)

PathBank(0)

PharmGKB(0)

197 个相关的物种来源信息

在这里通过桑基图来展示出与当前的这个代谢物在我们的BioDeep知识库中具有相关联信息的其他代谢物。在这里进行关联的信息来源主要有：

  • PubMed: 来源于PubMed文献库中的文献信息，我们通过自然语言数据挖掘得到的在同一篇文献中被同时提及的相关代谢物列表，这个列表按照代谢物同时出现的文献数量降序排序，取前10个代谢物作为相关研究中关联性很高的代谢物集合展示在桑基图中。
  • NCBI Taxonomy: 通过文献数据挖掘，得到的代谢物物种来源信息关联。这个关联信息同样按照出现的次数降序排序，取前10个代谢物作为高关联度的代谢物集合展示在桑吉图上。
  • Chemical Taxonomy: 在物质分类上处于同一个分类集合中的其他代谢物
  • Chemical Reaction: 在化学反应过程中，存在为当前代谢物相关联的生化反应过程中的反应底物或者反应产物的关联代谢物信息。

点击图上的相关代谢物的名称，可以跳转到相关代谢物的信息页面。



文献列表

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  • Limei Chang, Jillian M Hagel, Peter J Facchini. Isolation and Characterization of O-methyltransferases Involved in the Biosynthesis of Glaucine in Glaucium flavum. Plant physiology. 2015 Oct; 169(2):1127-40. doi: 10.1104/pp.15.01240. [PMID: 26297140]
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  • Thu-Thuy T Dang, Peter J Facchini. Characterization of three O-methyltransferases involved in noscapine biosynthesis in opium poppy. Plant physiology. 2012 Jun; 159(2):618-31. doi: 10.1104/pp.112.194886. [PMID: 22535422]
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  • Tomoya Takemura, Nobuhiro Ikezawa, Kinuko Iwasa, Fumihiko Sato. Metabolic diversification of benzylisoquinoline alkaloid biosynthesis through the introduction of a branch pathway in Eschscholzia californica. Plant & cell physiology. 2010 Jun; 51(6):949-59. doi: 10.1093/pcp/pcq063. [PMID: 20427510]
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  • Andreas Winkler, Martin Puhl, Hansjörg Weber, Toni M Kutchan, Karl Gruber, Peter Macheroux. Berberine bridge enzyme catalyzes the six electron oxidation of (S)-reticuline to dehydroscoulerine. Phytochemistry. 2009 Jun; 70(9):1092-1097. doi: 10.1016/j.phytochem.2009.06.005. [PMID: 19570558]
  • Hiromichi Minami, Ju-Sung Kim, Nobuhiro Ikezawa, Tomoya Takemura, Takane Katayama, Hidehiko Kumagai, Fumihiko Sato. Microbial production of plant benzylisoquinoline alkaloids. Proceedings of the National Academy of Sciences of the United States of America. 2008 May; 105(21):7393-8. doi: 10.1073/pnas.0802981105. [PMID: 18492807]
  • David K Liscombe, Peter J Facchini. Molecular cloning and characterization of tetrahydroprotoberberine cis-N-methyltransferase, an enzyme involved in alkaloid biosynthesis in opium poppy. The Journal of biological chemistry. 2007 May; 282(20):14741-51. doi: 10.1074/jbc.m611908200. [PMID: 17389594]
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