Coclaurine (BioDeep_00000000927)

natural product PANOMIX_OTCML-2023

代谢物信息卡片

(1S)-1-[(4-hydroxyphenyl)methyl]-6-methoxy-1,2,3,4-tetrahydroisoquinolin-7-ol

化学式: C17H19NO3 (285.13648639999997)
中文名称: 衡州乌药碱, 乌药碱
谱图信息: 最多检出来源 Macaca mulatta(otcml) 0.19%

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

(S)-coclaurine is the (S)-enantiomer of coclaurine. It is a conjugate base of a (S)-coclaurinium. It is an enantiomer of a (R)-coclaurine.
Coclaurine is a natural product found in Delphinium pentagynum, Damburneya salicifolia, and other organisms with data available.
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

19 个代谢物同义名

(1S)-1-[(4-hydroxyphenyl)methyl]-6-methoxy-1,2,3,4-tetrahydroisoquinolin-7-ol; (1S)-1,2,3,4-TETRAHYDRO-1-((4-HYDROXYPHENYL)METHYL)-6-METHOXY-7-ISOQUINOLINOL; (S)-1,2,3,4-Tetrahydro-1-[(4-hydroxyphenyl)methyl]-6-methoxy-7-isoquinolinol; 1-(p-Hydroxybenzyl)-6-methoxy-7-hydroxy-1,2,3,4-tetrahydroisoquinoline; (1S)-1-(4-hydroxybenzyl)-6-methoxy-1,2,3,4-tetrahydroisoquinolin-7-ol; 1,2,3,4-Tetrahydro-1-(p-hydroxybenzyl)-6-methoxy-7-isoquinolinol; coclaurine, (+-)-isomer; coclaurine, (R)-isomer; COCLAURINE [MI]; 1(R)-coclaurine; (-)-Coclaurine; (S)-Coclaurine; Coclaurine; Coclaurin; Machiline; (+)-Coclaurine; (S)-1,2,3,4-Tetrahydro-1-[(4-hydroxyphenyl)methyl]-6-methoxy-7- isoquinolinol; 1-(p-Hydroxybenzyl)-6-methoxy-7-hydroxy-1,2,3,4- tetrahydroisoquinoline; (RS)-coclaurine

数据库引用编号

21 个数据库交叉引用编号

ChEBI: CHEBI:15950
KEGG: C06161
PubChem: 160487
PubChem: 281691
Metlin: METLIN64367
ChEMBL: CHEMBL446211
Wikipedia: Coclaurine
MeSH: coclaurine
ChemIDplus: 0000486395
MetaCyc: S-COCLAURINE
foodb: FDB011812
CAS: 486-39-5
CAS: 2196-60-3
MoNA: CCMSLIB00005436045
MoNA: PM010803
medchemexpress: HY-N3610
PMhub: MS000011133
PubChem: 8417
KNApSAcK: C00025812
3DMET: B01978
NIKKAJI: J6.009G

分类词条

异喹啉生物碱

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)

54 个相关的物种来源信息

2803977 - Aniba canelilla: 10.1139/V93-149
13337 - Annona muricata: 10.1007/S10600-011-9921-5
12948 - Aristolochia gigantea: 10.3390/MOLECULES15129462
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
1857144 - Clematis parviloba: 10.1007/S12272-009-1111-7
461574 - Cocculus diversifolius: 10.1016/0040-4020(80)88040-9
421226 - Cocculus hirsutus: 10.1016/0040-4020(80)88040-9
421226 - Cocculus hirsutus: 10.1080/10575639308043793
152359 - Cocculus laurifolius:
527501 - Cocculus pendulus: 10.1016/0040-4020(75)80272-9
3442 - Coptis japonica: 10.1074/JBC.M106405200
3442 - Coptis japonica: 10.1074/JBC.M705082200
666371 - Cryptocarya concinna: 10.1248/YAKUSHI1947.86.4_296
152372 - Cyclea: 10.1021/NP50101A020
152373 - Cyclea barbata:
152373 - Cyclea barbata: 10.1021/NP50101A020
2893873 - Cyclea peltata: 10.1021/NP50063A032
128651 - Damburneya salicifolia: 10.1021/NP960195H
1127147 - Delphinium caeruleum: 10.1016/J.PHYTOCHEM.2004.03.017
1127184 - Delphinium pentagynum: 10.1016/J.PHYTOCHEM.2004.03.017
49817 - Erythrina crista-galli: 10.1016/0040-4020(80)80108-6
49817 - Erythrina crista-galli: 10.1016/S0031-9422(99)00230-7
1464625 - Fumaria parviflora:
367484 - Fumaria vaillantii:
3381 - Gnetum montanum: 10.1021/NP200700F
1679399 - Machilus minutiflora: 10.1021/NP9000653
56857 - Macleaya cordata: 10.1016/J.MOLP.2017.05.007
349509 - Magnolia obovata: 10.1093/CHROMSCI/BMW052
3411 - Magnolia salicifolia: 10.1055/S-2007-969493
493334 - Monodora junodii: 10.1016/J.PHYTOCHEM.2006.07.011
1310093 - Monoon borneense: 10.1016/0031-9422(90)85344-F
1310093 - Monoon borneense: 10.1021/NP900207Z
2592295 - Ocotea fasciculata: 10.1016/S0305-1978(02)00024-8
461616 - Pachygone ovata:
1504475 - Phaeanthus ophthalmicus: 10.1016/0031-9422(90)85344-F
1504475 - Phaeanthus ophthalmicus: 10.1021/NP900207Z
1504478 - Polyalthia macropoda: 10.1016/0031-9422(90)85344-F
1504478 - Polyalthia macropoda: 10.1021/NP900207Z
56862 - Romneya coulteri: 10.1016/S0031-9422(98)00745-6
152363 - Sinomenium acutum: 10.1016/0040-4020(80)88040-9
152367 - Stephania cephalantha: 10.1021/NP50064A031
1501462 - Stephania excentrica:
1501462 - Stephania excentrica: 10.1021/NP960371M
152366 - Stephania hernandifolia:
461633 - Stephania japonica:
1924984 - Stephania pierrei: 10.1021/NP50064A031
1924984 - Stephania pierrei: 10.1021/NP960381N
425106 - Stephania tetrandra:
295132 - Trepobates: 10.1021/NP50064A031
295132 - Trepobates: 10.1021/NP960381N
992813 - Xylopia parviflora: 10.1016/J.PHYTOCHEM.2003.12.010
326968 - Ziziphus jujuba:

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

Thitima Rukachaisirikul, Sittisak Kumjun, Parichat Suebsakwong, Nuttapon Apiratikul, Apichart Suksamrarn. A new pyrrole alkaloid from the roots of Cissampelos pareira. Natural product research. 2021 Jan; 35(1):80-87. doi: 10.1080/14786419.2019.1614576. [PMID: 31135214]
Yu-Feng Huang, Fan He, Can-Jian Wang, Ying Xie, Yan-Yu Zhang, Zhen Sang, Ping Qiu, Pei Luo, Sheng-Yuan Xiao, Jing Li, Fei-Ci Wu, Liang Liu, Hua Zhou. Discovery of chemical markers for improving the quality and safety control of Sinomenium acutum stem by the simultaneous determination of multiple alkaloids using UHPLC-QQQ-MS/MS. Scientific reports. 2020 08; 10(1):14182. doi: 10.1038/s41598-020-71133-4. [PMID: 32843671]
Gang Fan, Qi Li, Hai-Jiao Li, Yun-Sen Zhang, Xin-Mei Xu, Gang Fang, Yi-Man Ge, Lei-Lei Du. Active Ingredients and Anti-Arthritic Mechanisms of Ba-Wei-Long-Zuan Granule Revealed by 1 H-NMR-Based Metabolomics Combined with Network Pharmacology Analysis. Chemistry & biodiversity. 2020 Jun; 17(6):e2000122. doi: 10.1002/cbdv.202000122. [PMID: 32274851]
Arjen Lommen, Abdurzag Elaradi, Ariadni Vonaparti, Marco Blokland, Michel W Nielen, Khadija Ali Saad, Wadha Masoud Abushreeda, Peter Horvatovich, Amal Essa Al-Muraikhi, Mohammed Al-Maadheed, Costas Georgakopoulos. Ultra-fast retroactive processing of liquid chromatography high-resolution full-scan Orbitrap mass spectrometry data in anti-doping screening of human urine. Rapid communications in mass spectrometry : RCM. 2019 Oct; 33(20):1578-1588. doi: 10.1002/rcm.8507. [PMID: 31240795]
Masato Okano, Mitsuhiko Sato, Shinji Kageyama. Determination of higenamine and coclaurine levels in human urine after the administration of a throat lozenge containing Nandina domestica fruit. Drug testing and analysis. 2017 Nov; 9(11-12):1788-1793. doi: 10.1002/dta.2258. [PMID: 28801989]
I-Chi Hung, Su-Sen Chang, Pei-Chun Chang, Cheng-Chun Lee, Calvin Yu-Chian Chen. Memory enhancement by traditional Chinese medicine?. Journal of biomolecular structure & dynamics. 2013 Dec; 31(12):1411-39. doi: 10.1080/07391102.2012.741052. [PMID: 23249175]
Ayu Afiqah Nasrullah, Azeana Zahari, Jamaludin Mohamad, Khalijah Awang. Antiplasmodial alkaloids from the bark of Cryptocarya nigra (Lauraceae). Molecules (Basel, Switzerland). 2013 Jul; 18(7):8009-17. doi: 10.3390/molecules18078009. [PMID: 23884132]
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]
I Kimura, L H Chui, K Fujitani, T Kikuchi, M Kimura. Inotropic effects of (+/-)-higenamine and its chemically related components, (+)-R-coclaurine and (+)-S-reticuline, contained in the traditional sino-Japanese medicines "bushi" and "shin-i" in isolated guinea pig papillary muscle. Japanese journal of pharmacology. 1989 May; 50(1):75-8. doi: 10.1254/jjp.50.75. [PMID: 2724702]
H Watanabe, M Ikeda, K Watanabe, T Kikuchi. Effects on central dopaminergic systems of d-coclaurine and d-reticuline, extracted from Magnolia salicifolia. Planta medica. 1981 Jul; 42(3):213-22. doi: 10.1055/s-2007-971630. [PMID: 7280087]
M Sano. Subcellular localizations of guanylate cyclase and 3',5'-cyclic nucleotide phosphodiesterase in sea urchin sperm. Biochimica et biophysica acta. 1976 Apr; 428(2):525-31. doi: 10.1016/0304-4165(76)90061-1. [PMID: 6049]