Coclaurine (BioDeep_00000014909)

human metabolite PANOMIX_OTCML-2023

代谢物信息卡片

6-Methoxy-7-hydroxy-1-[(4-hydroxyphenyl)methyl]-1,2,3,4-tetrahydroisoquinoline

化学式: C17H19NO3 (285.13648639999997)
中文名称: 衡州乌药碱
谱图信息: 最多检出来源 () 0%

分子结构信息

SMILES: COC1=C(C=C2C(NCCC2=C1)CC3=CC=C(C=C3)O)O
InChI: InChI=1S/C17H19NO3/c1-21-17-9-12-6-7-18-15(14(12)10-16(17)20)8-11-2-4-13(19)5-3-11/h2-5,9-10,15,18-20H,6-8H2,1H3

描述信息

Coclaurine, also known as (r,s)-coclaurine or machiline, is a member of the class of compounds known as benzylisoquinolines. Benzylisoquinolines are organic compounds containing an isoquinoline to which a benzyl group is attached. Coclaurine is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Coclaurine can be found in custard apple and soursop, which makes coclaurine a potential biomarker for the consumption of these food products. Coclaurine is a nicotinic acetylcholine receptor antagonist which has been isolated from a variety of plant sources including Nelumbo nucifera, Sarcopetalum harveyanum, Ocotea duckei, and others. It belongs to the class of tetrahydroisoquinoline alkaloids. Dimerization of coclaurine leads to the biscoclaurine alkaloids such as cepharanthine .

同义名列表

8 个代谢物同义名

6-Methoxy-7-hydroxy-1-[(4-hydroxyphenyl)methyl]-1,2,3,4-tetrahydroisoquinoline; 1-[(4-hydroxyphenyl)methyl]-6-methoxy-1,2,3,4-tetrahydroisoquinolin-7-ol; (R,S)-Coclaurine; (RS)-coclaurine; (S)-Coclaurine; DL-Coclaurine; Coclaurine; Machiline

数据库引用编号

13 个数据库交叉引用编号

ChEBI: CHEBI:18417
KEGG: C06348
PubChem: 281691
HMDB: HMDB0303359
ChEMBL: CHEMBL453291
KNApSAcK: C00025812
foodb: FDB030166
chemspider: 248088
CAS: 15548-30-8
CAS: 486-39-5
PubChem: 8584
KNApSAcK: C00047850
NIKKAJI: J6.009G

分类词条

Benzylisoquinolines

代谢反应

0 个相关的代谢反应过程信息。

Reactome(0)

BioCyc(0)

WikiPathways(0)

Plant Reactome(0)

INOH(0)

PlantCyc(0)

COVID-19 Disease Map(0)

PathBank(0)

PharmGKB(0)

27 个相关的物种来源信息

203270 - Berberis aquifolium: 10.1016/J.CHROMA.2015.08.015
13601 - Berberis bealei: 10.1016/J.CHROMA.2015.08.015
46963 - Caulophyllum thalictroides: 10.1016/J.JPBA.2011.07.028
461574 - Cocculus diversifolius: 10.1016/0040-4020(80)88040-9
421226 - Cocculus hirsutus: 10.1016/0040-4020(80)88040-9
527501 - Cocculus pendulus: 10.1016/0040-4020(75)80272-9
3442 - Coptis japonica: 10.1074/JBC.M705082200
152372 - Cyclea: 10.1021/NP50101A020
152373 - Cyclea barbata:
2893873 - Cyclea peltata: 10.1021/NP50063A032
1127147 - Delphinium caeruleum: 10.1016/J.PHYTOCHEM.2004.03.017
49817 - Erythrina crista-galli: 10.1016/0040-4020(80)80108-6
9606 - Homo sapiens: -
1679399 - Machilus minutiflora: 10.1021/NP9000653
56857 - Macleaya cordata: 10.1016/J.MOLP.2017.05.007
349509 - Magnolia obovata: 10.1093/CHROMSCI/BMW052
1310093 - Monoon borneense: 10.1021/NP900207Z
1504475 - Phaeanthus ophthalmicus: 10.1021/NP900207Z
1504478 - Polyalthia macropoda: 10.1021/NP900207Z
152363 - Sinomenium acutum: 10.1016/0040-4020(80)88040-9
152367 - Stephania cephalantha: 10.1021/NP50064A031
1501462 - Stephania excentrica:
152366 - Stephania hernandifolia:
461633 - Stephania japonica:
1924984 - Stephania pierrei: 10.1021/NP960381N
425106 - Stephania tetrandra:
295132 - Trepobates: 10.1021/NP960381N

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

Isabel Desgagné-Penix, Morgan F Khan, David C Schriemer, Dustin Cram, Jacek Nowak, Peter J Facchini. Integration of deep transcriptome and proteome analyses reveals the components of alkaloid metabolism in opium poppy cell cultures. BMC plant biology. 2010 Nov; 10(?):252. doi: 10.1186/1471-2229-10-252. [PMID: 21083930]
Ihsan Ergün, M Cenk Akbostanci, Başol Canbakan, Bilge Koçer, Arzu Ensari, Gökhan Nergizoglu, Kenan Keven. Minimal change nephrotic syndrome with stiff-person syndrome: is there a link?. American journal of kidney diseases : the official journal of the National Kidney Foundation. 2005 Jul; 46(1):e11-4. doi: 10.1053/j.ajkd.2005.03.009. [PMID: 15983949]
Yoshiki Kashiwada, Akihiro Aoshima, Yasumasa Ikeshiro, Yuh-Pan Chen, Hiroshi Furukawa, Masataka Itoigawa, Toshihiro Fujioka, Kunihide Mihashi, L Mark Cosentino, Susan L Morris-Natschke, Kuo-Hsiung Lee. Anti-HIV benzylisoquinoline alkaloids and flavonoids from the leaves of Nelumbo nucifera, and structure-activity correlations with related alkaloids. Bioorganic & medicinal chemistry. 2005 Jan; 13(2):443-8. doi: 10.1016/j.bmc.2004.10.020. [PMID: 15598565]
Jürgen Schmidt, Klaus Raith, Chotima Boettcher, Meinhart H Zenk. Analysis of benzylisoquinoline-type alkaloids by electrospray tandem mass spectrometry and atmospheric pressure photoionization. European journal of mass spectrometry (Chichester, England). 2005; 11(3):325-33. doi: 10.1255/ejms.745. [PMID: 16107747]