Coclaurine (BioDeep_00000000927)

 

Secondary id: BioDeep_00000000890

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 (285.1365)
中文名称: 衡州乌药碱, 乌药碱
谱图信息: 最多检出来源 Homo sapiens(otcml) 28.28%

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

22 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; (S)-Coclaurine; (R)-Coclaurine; Coclaurine



数据库引用编号

28 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(0)

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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)

139 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。

亚细胞结构定位 关联基因列表
Cytoplasm 7 ADRA2C, BCL2L1, ESR1, HSPB1, PTGS1, PTGS2, VEGFA
Peripheral membrane protein 3 ESR1, PTGS1, PTGS2
Endosome membrane 1 ADRB2
Endoplasmic reticulum membrane 2 PTGS1, PTGS2
Mitochondrion membrane 2 BCL2L1, MAOA
Nucleus 5 ADRB2, ESR1, HSPB1, MMP2, VEGFA
cytosol 4 BCL2L1, ESR1, HSPB1, MAOA
dendrite 4 CHRM1, DRD2, HTR2A, MAOB
centrosome 1 BCL2L1
nucleoplasm 1 ESR1
Cell membrane 10 ADRA2C, ADRB2, CHRM1, DRD2, ESR1, GABRA1, HTR2A, KIT, SLC38A5, SLC6A2
Cytoplasmic side 4 BCL2L1, ESR1, MAOA, MAOB
Cell projection, axon 1 HTR2A
Multi-pass membrane protein 9 ADRA2C, ADRB2, CACNA1I, CHRM1, DRD2, GABRA1, HTR2A, SLC38A5, SLC6A2
Golgi apparatus membrane 1 DRD2
Synapse 3 CHRM1, DRD2, GABRA1
cell surface 2 SLC6A2, VEGFA
dendritic shaft 1 HTR2A
glutamatergic synapse 3 CHRM1, DRD2, HTR2A
Golgi apparatus 4 ADRB2, ESR1, PTGS1, VEGFA
Golgi membrane 1 DRD2
mitochondrial inner membrane 1 BCL2L1
neuronal cell body 2 HTR2A, MAOB
postsynapse 1 GABRA1
presynaptic membrane 4 CHRM1, DRD2, HTR2A, SLC6A2
Cytoplasm, cytosol 1 BCL2L1
Lysosome 1 ADRB2
Presynapse 1 HTR2A
acrosomal vesicle 2 DRD2, KIT
endosome 2 ADRA2C, ADRB2
plasma membrane 12 ADRA2C, ADRB2, CACNA1I, CHRM1, DRD2, ESR1, GABRA1, HTR2A, KIT, MMP2, SLC38A5, SLC6A2
synaptic vesicle membrane 3 BCL2L1, DRD2, SLC6A2
Membrane 10 ADRB2, CACNA1I, CHRM1, ESR1, GABRA1, KIT, MAOA, SLC38A5, SLC6A2, VEGFA
apical plasma membrane 1 ADRB2
axon 3 DRD2, HTR2A, SLC6A2
caveola 2 HTR2A, PTGS2
extracellular exosome 3 HSPB1, LYZ, PTGS1
endoplasmic reticulum 3 BCL2L1, PTGS2, VEGFA
extracellular space 5 HSPB1, KIT, LYZ, MMP2, VEGFA
Schaffer collateral - CA1 synapse 1 CHRM1
adherens junction 1 VEGFA
mitochondrion 4 BCL2L1, MAOA, MAOB, MMP2
protein-containing complex 2 ESR1, PTGS2
intracellular membrane-bounded organelle 1 PTGS1
Microsome membrane 2 PTGS1, PTGS2
Single-pass type I membrane protein 1 KIT
Secreted 1 VEGFA
extracellular region 3 LYZ, MMP2, VEGFA
cytoplasmic side of plasma membrane 1 KIT
Mitochondrion outer membrane 3 BCL2L1, MAOA, MAOB
Single-pass membrane protein 2 BCL2L1, MAOA
mitochondrial outer membrane 3 BCL2L1, MAOA, MAOB
neuronal cell body membrane 1 SLC6A2
Mitochondrion matrix 1 BCL2L1
mitochondrial matrix 1 BCL2L1
transcription regulator complex 1 ESR1
ciliary membrane 1 DRD2
photoreceptor outer segment 1 PTGS1
Cytoplasm, cytoskeleton, microtubule organizing center, centrosome 1 BCL2L1
Cytoplasmic vesicle, secretory vesicle, synaptic vesicle membrane 1 BCL2L1
Nucleus membrane 1 BCL2L1
Bcl-2 family protein complex 1 BCL2L1
nuclear membrane 1 BCL2L1
external side of plasma membrane 1 KIT
Secreted, extracellular space, extracellular matrix 1 VEGFA
dendritic spine 2 DRD2, GABRA1
perikaryon 1 DRD2
Z disc 1 HSPB1
cytoplasmic vesicle 1 HTR2A
axon cytoplasm 1 HSPB1
Early endosome 1 ADRB2
cell-cell junction 1 KIT
postsynaptic membrane 4 CHRM1, DRD2, GABRA1, HTR2A
Cytoplasm, cytoskeleton, spindle 1 HSPB1
focal adhesion 1 HSPB1
spindle 1 HSPB1
GABA-ergic synapse 2 DRD2, GABRA1
extracellular matrix 2 MMP2, VEGFA
collagen-containing extracellular matrix 1 MMP2
secretory granule 1 VEGFA
lateral plasma membrane 1 DRD2
Nucleus inner membrane 1 PTGS2
Nucleus outer membrane 1 PTGS2
nuclear inner membrane 1 PTGS2
nuclear outer membrane 1 PTGS2
Postsynaptic cell membrane 2 CHRM1, GABRA1
sarcomere 1 MMP2
receptor complex 2 ADRB2, KIT
neuron projection 3 GABRA1, PTGS1, PTGS2
cilium 1 DRD2
chromatin 1 ESR1
cytoskeleton 1 HSPB1
non-motile cilium 1 DRD2
transmembrane transporter complex 1 GABRA1
sperm flagellum 1 DRD2
fibrillar center 1 KIT
Endomembrane system 1 PTGS1
Membrane, caveola 1 HTR2A
chloride channel complex 1 GABRA1
GABA-A receptor complex 1 GABRA1
Cornified envelope 1 HSPB1
Cytoplasmic vesicle membrane 1 GABRA1
cell body fiber 1 HTR2A
Cell projection, dendrite 1 HTR2A
euchromatin 1 ESR1
[Isoform 3]: Cytoplasm 1 KIT
proteasome complex 1 HSPB1
endoplasmic reticulum lumen 1 PTGS2
platelet alpha granule lumen 1 VEGFA
axon terminus 2 CHRM1, DRD2
voltage-gated calcium channel complex 1 CACNA1I
specific granule lumen 1 LYZ
tertiary granule lumen 1 LYZ
endocytic vesicle 1 DRD2
[Isoform 1]: Secreted, extracellular space, extracellular matrix 1 MMP2
azurophil granule lumen 1 LYZ
mitochondrial envelope 1 MAOB
postsynaptic density membrane 1 CHRM1
neuronal dense core vesicle 1 ADRB2
Single-pass type IV membrane protein 2 MAOA, MAOB
neurofilament 1 HTR2A
clathrin-coated endocytic vesicle membrane 1 ADRB2
[Isoform 1]: Nucleus 1 ESR1
postsynaptic specialization membrane 1 GABRA1
dopaminergic synapse 1 DRD2
dendrite membrane 1 GABRA1
GABA receptor complex 1 GABRA1
cholinergic synapse 1 CHRM1
G protein-coupled receptor complex 1 DRD2
[N-VEGF]: Cytoplasm 1 VEGFA
[VEGFA]: Secreted 1 VEGFA
[Isoform L-VEGF189]: Endoplasmic reticulum 1 VEGFA
[Isoform VEGF121]: Secreted 1 VEGFA
[Isoform VEGF165]: Secreted 1 VEGFA
VEGF-A complex 1 VEGFA
G protein-coupled serotonin receptor complex 1 HTR2A
[Isoform Bcl-X(L)]: Mitochondrion inner membrane 1 BCL2L1


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]