Glaucine (BioDeep_00000000937)

 

Secondary id: BioDeep_00000179429, BioDeep_00000396068

natural product PANOMIX_OTCML-2023


代谢物信息卡片


(6aS,11aM)-1,2,9,10-tetramethoxy-6-methyl-5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinoline

化学式: C21H25NO4 (355.1783)
中文名称: 海罌粟鹼, (+)-海罂粟碱, 海罂粟碱
谱图信息: 最多检出来源 Chinese Herbal Medicine(otcml) 53.42%

分子结构信息

SMILES: c1(c2c3c(cc1OC)CCN([C@H]3Cc1c2cc(c(c1)OC)OC)C)OC
InChI: InChI=1/C21H25NO4/c1-22-7-6-12-9-18(25-4)21(26-5)20-14-11-17(24-3)16(23-2)10-13(14)8-15(22)19(12)20/h9-11,15H,6-8H2,1-5H3

描述信息

(S)-glaucine is an aporphine alkaloid that is (S)-1,2,9,10-tetrahydroxy-6-methyl-5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinoline in which the four phenolic hydrogens have been replaced by methyl groups. It has a role as a platelet aggregation inhibitor, a NF-kappaB inhibitor, an antitussive, an antibacterial agent, a muscle relaxant, an antineoplastic agent, a plant metabolite and a rat metabolite. It is an aporphine alkaloid, a polyether, an organic heterotetracyclic compound and a tertiary amino compound. It is a conjugate base of a (S)-glaucine(1+).
Glaucine is a natural product found in Sarcocapnos baetica, Sarcocapnos saetabensis, and other organisms with data available.
An aporphine alkaloid that is (S)-1,2,9,10-tetrahydroxy-6-methyl-5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinoline in which the four phenolic hydrogens have been replaced by methyl groups.
D018373 - Peripheral Nervous System Agents > D001337 - Autonomic Agents > D010276 - Parasympatholytics
D019141 - Respiratory System Agents > D000996 - Antitussive Agents
D020011 - Protective Agents > D000975 - Antioxidants
D002491 - Central Nervous System Agents
Origin: Plant; SubCategory_DNP: Isoquinoline alkaloids, Aporphine alkaloids
Glaucine (O,O-Dimethylisoboldine) is an alkaloid isolated from Glaucium flavum with antitussive, bronchodilation and anti-inflammatory properties. Glaucine is a selective and orally active phosphodiesterase 4 (PDE4) inhibitor with Kis of 3.4 μM in human bronchus and polymorphonuclear leukocytes. Glaucine is also a non-selective α-adrenoceptor antagonist, a Ca2+ entry blocker, and a weak dopamine D1 and D2 receptor antagonist. Glaucine has antioxidative and antiviral activities[1][2][3].
Glaucine (O,O-Dimethylisoboldine) is an alkaloid isolated from Glaucium flavum with antitussive, bronchodilation and anti-inflammatory properties. Glaucine is a selective and orally active phosphodiesterase 4 (PDE4) inhibitor with Kis of 3.4 μM in human bronchus and polymorphonuclear leukocytes. Glaucine is also a non-selective α-adrenoceptor antagonist, a Ca2+ entry blocker, and a weak dopamine D1 and D2 receptor antagonist. Glaucine has antioxidative and antiviral activities[1][2][3].
Glaucine (O,O-Dimethylisoboldine) is an alkaloid isolated from Glaucium flavum with antitussive, bronchodilation and anti-inflammatory properties. Glaucine is a selective and orally active phosphodiesterase 4 (PDE4) inhibitor with Kis of 3.4 μM in human bronchus and polymorphonuclear leukocytes. Glaucine is also a non-selective α-adrenoceptor antagonist, a Ca2+ entry blocker, and a weak dopamine D1 and D2 receptor antagonist. Glaucine has antioxidative and antiviral activities[1][2][3].

同义名列表

75 个代谢物同义名

(6aS,11aM)-1,2,9,10-tetramethoxy-6-methyl-5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinoline; 4H-Dibenzo(de,g)quinoline, 5,6,6a,7-tetrahydro-1,2,9,10-tetramethoxy-6-methyl-, (S)-; (6AS)-5,6,6A,7-TETRAHYDRO-1,2,9,10-TETRAMETHOXY-6-METHYL-4H-DIBENZO(DE,G)QUINOLINE; (6aS)-1,2,9,10-tetramethoxy-6-methyl-5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinoline; (S)-1,2,9,10-tetramethoxy-6-methyl-5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinoline; (S)-5,6,6a,7-Tetrahydro-1,2,9,10-tetramethoxy-6-methyl-4H-dibenzo(de,g)quinoline; (S)-5,6,6a7-Tetrahydro-1,2,9,10-tetramethoxy-6-methyl-4H-dibenzo(de,g)quinoline; 4H-Dibenzo[de, 5,6,6a,7-tetrahydro-1,2,9,10-tetramethoxy-6-methyl-, (S)-; 6a-alpha-APORPHINE, 1,2,9,10-TETRAMETHOXY-; 6aalpha-Aporphine, 1,2,9,10-tetramethoxy-; 1,2,9,10-Tetramethoxy-6a-alpha-aporphine; 6a.alpha.-Aporphine,2,9,10-tetramethoxy-; (s)-(+)-1,2,9,10-tetramethoxyaporphine; glaucine phosphate (5:7), (+-)-isomer; glaucine phosphate (2:3), (+-)-isomer; glaucine phosphate (5:8), (+-)-isomer; glaucine phosphate (2:3), (S)-isomer; glaucine tartrate (1:1), (+-)-isomer; glaucine phosphate (2:3), (R)-isomer; glaucine tartrate (1:1), (S)-isomer; glaucine tartrate (1:1), (R)-isomer; glaucine hydrochloride, (+-)-isomer; glaucine hydrobromide, (+-)-isomer; glaucine hydrochloride, (S)-isomer; glaucine hydrochloride, (R)-isomer; glaucine hydrobromide, (R)-isomer; glaucine hydrobromide, (S)-isomer; glaucine hydroiodide, (R)-isomer; glaucine hydroiodide, (S)-isomer; glaucine sulphate, (+-)-isomer; glaucine tartrate, (+-)-isomer; glaucine phosphate, (S)-isomer; 1,2,9,10-tetramethoxyaporphine; glaucine mesylate, (+-)-isomer; glaucine tosylate, (R)-isomer; glaucine maleate, (+-)-isomer; glaucine acetate, (+-)-isomer; glaucine tartrate, (R)-isomer; glaucine tartrate, (S)-isomer; glaucine citrate, (+-)-isomer; RUZIUYOSRDWYQF-HNNXBMFYSA-N; Glaucine; S-(+)-Glaucine; Boldine dimethyl ether; glaucine, (R)-isomer; glaucine, (S)-isomer; glaucine phosphate; Glaucine fumarate; GLAUCINE [WHO-DD]; GLAUCINE [MART.]; GLAUCINE [INCI]; S-(+)-Glaucine; GLAUCINE [MI]; Bromcholitin; tussiglaucin; Tusidil (TN); (+)-Glaucine; GLAUCINE,(D); (S)-glaucine; Glaucine, d; d-Glaucine; Glaucine; Glauvent; 08V; 4H-Dibenzo[de,g]quinoline, 5,6,6a,7-tetrahydro-1,2,9,10-tetramethoxy-6-methyl-, (S)-; 6a.alpha.-Aporphine, 1,2,9,10-tetramethoxy-; AIDS-011385; BB_NC-0833; AIDS011385; 475-81-0; NSC34396; C09446; 1,2,9,10-Tetramethoxy-6-methyl-5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinoline; O,O-Dimethylisoboldine; NSC 34396; Glaucine



数据库引用编号

29 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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PlantCyc(0)

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)

83 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 9 ABCB1, ADRA1A, CNR1, GJA1, JAK2, TLR2, TLR4, TLR9, XDH
Peripheral membrane protein 2 JAK2, USO1
Endosome membrane 2 TLR4, TLR9
Endoplasmic reticulum membrane 3 DRD1, GJA1, TLR9
Nucleus 4 ADRA1A, DRD1, GJA1, JAK2
cytosol 7 ACP5, ADRA1A, GJA1, JAK2, PRKCQ, USO1, XDH
dendrite 2 HTR2A, HTR2C
phagocytic vesicle 1 TLR9
nucleoplasm 4 ADRA1A, ATP2B1, GJA1, JAK2
Cell membrane 10 ABCB1, ADRA1A, ATP2B1, CNR1, DRD1, GJA1, HTR2A, HTR2C, TLR4, TNF
Cell projection, axon 2 CNR1, HTR2A
Early endosome membrane 1 TLR9
Multi-pass membrane protein 9 ABCB1, ADRA1A, ATP2B1, CACNA1I, CNR1, DRD1, GJA1, HTR2A, HTR2C
Golgi apparatus membrane 2 TLR9, USO1
Synapse 2 ATP2B1, HTR2C
cell junction 1 GJA1
cell surface 4 ABCB1, TLR2, TLR4, TNF
dendritic shaft 1 HTR2A
glutamatergic synapse 5 ATP2B1, CNR1, DRD1, HTR2A, JAK2
Golgi apparatus 3 GJA1, TLR2, USO1
Golgi membrane 3 GJA1, TLR9, USO1
growth cone 1 CNR1
neuronal cell body 2 HTR2A, TNF
postsynapse 1 JAK2
presynaptic membrane 4 ATP2B1, CNR1, DRD1, HTR2A
Cytoplasm, cytosol 1 USO1
Lysosome 2 ACP5, TLR9
Presynapse 2 CNR1, HTR2A
endosome 1 TLR9
plasma membrane 16 ABCB1, ADRA1A, ATP2B1, BCHE, CACNA1I, CNR1, DRD1, GJA1, HTR2A, HTR2C, JAK2, PRKCQ, TLR2, TLR4, TLR9, TNF
synaptic vesicle membrane 1 ATP2B1
Membrane 9 ABCB1, ACP5, ATP2B1, CACNA1I, JAK2, TLR2, TLR4, TLR9, USO1
apical plasma membrane 3 ABCB1, GJA1, TLR9
axon 2 CNR1, HTR2A
basolateral plasma membrane 2 ATP2B1, TLR9
caveola 3 ADRA1A, HTR2A, JAK2
extracellular exosome 2 ABCB1, ATP2B1
endoplasmic reticulum 3 GJA1, TLR9, USO1
extracellular space 4 BCHE, IL10, TNF, XDH
perinuclear region of cytoplasm 2 TLR4, USO1
gap junction 1 GJA1
intercalated disc 1 GJA1
mitochondrion 1 GJA1
intracellular membrane-bounded organelle 3 ADRA1A, ATP2B1, GJA1
Single-pass type I membrane protein 3 TLR2, TLR4, TLR9
Secreted 2 BCHE, IL10
extracellular region 4 BCHE, IL10, TLR9, TNF
cytoplasmic side of plasma membrane 1 JAK2
Mitochondrion outer membrane 1 CNR1
mitochondrial outer membrane 1 CNR1
centriolar satellite 1 PRKCQ
ciliary membrane 1 DRD1
Cytoplasmic vesicle, secretory vesicle, synaptic vesicle membrane 1 ATP2B1
Nucleus membrane 1 ADRA1A
nuclear membrane 1 ADRA1A
external side of plasma membrane 2 TLR4, TNF
actin cytoskeleton 1 CNR1
dendritic spine 1 DRD1
cytoplasmic vesicle 1 HTR2A
Early endosome 1 TLR4
recycling endosome 1 TNF
Single-pass type II membrane protein 1 TNF
postsynaptic membrane 2 DRD1, HTR2A
Apical cell membrane 1 ABCB1
Membrane raft 5 CNR1, GJA1, JAK2, TLR2, TNF
focal adhesion 2 GJA1, JAK2
GABA-ergic synapse 2 CNR1, DRD1
Peroxisome 1 XDH
sarcoplasmic reticulum 1 XDH
Cell projection, dendritic spine 1 DRD1
Cell junction, gap junction 1 GJA1
connexin complex 1 GJA1
contractile muscle fiber 1 GJA1
fascia adherens 1 GJA1
intermediate filament 1 GJA1
lateral plasma membrane 2 ATP2B1, GJA1
Cell projection, ruffle 1 TLR4
ruffle 1 TLR4
receptor complex 2 TLR2, TLR4
cilium 1 DRD1
Cytoplasmic vesicle, phagosome membrane 1 TLR2
cell projection 2 ATP2B1, TLR2
phagocytic cup 2 TLR4, TNF
phagocytic vesicle membrane 1 TLR2
cytoskeleton 1 JAK2
blood microparticle 1 BCHE
non-motile cilium 1 DRD1
Basolateral cell membrane 1 ATP2B1
fibrillar center 1 USO1
Endomembrane system 1 JAK2
endosome lumen 1 JAK2
Membrane, caveola 2 ADRA1A, HTR2A
microtubule organizing center 1 USO1
cell body fiber 1 HTR2A
Cell projection, dendrite 2 DRD1, HTR2A
Golgi-associated vesicle membrane 1 GJA1
euchromatin 1 JAK2
Presynaptic cell membrane 1 ATP2B1
cell body 1 TLR2
Golgi stack 1 USO1
lipopolysaccharide receptor complex 1 TLR4
secretory granule membrane 1 TLR2
endoplasmic reticulum lumen 1 BCHE
voltage-gated calcium channel complex 1 CACNA1I
transport vesicle 1 USO1
tight junction 1 GJA1
immunological synapse 2 ATP2B1, PRKCQ
aggresome 1 PRKCQ
ER to Golgi transport vesicle membrane 1 USO1
nuclear envelope lumen 1 BCHE
neurofilament 1 HTR2A
extrinsic component of cytoplasmic side of plasma membrane 1 JAK2
external side of apical plasma membrane 1 ABCB1
endolysosome membrane 1 TLR9
early phagosome 1 TLR9
Cytoplasmic vesicle, phagosome 1 TLR9
Toll-like receptor 1-Toll-like receptor 2 protein complex 1 TLR2
Toll-like receptor 2-Toll-like receptor 6 protein complex 1 TLR2
extrinsic component of plasma membrane 1 JAK2
granulocyte macrophage colony-stimulating factor receptor complex 1 JAK2
interleukin-12 receptor complex 1 JAK2
interleukin-23 receptor complex 1 JAK2
Cell projection, cilium membrane 1 DRD1
cell-cell contact zone 1 GJA1
[Tumor necrosis factor, soluble form]: Secreted 1 TNF
photoreceptor ribbon synapse 1 ATP2B1
G protein-coupled receptor complex 1 DRD1
endolysosome 1 TLR9
G protein-coupled serotonin receptor complex 2 HTR2A, HTR2C
[C-domain 2]: Secreted 1 TNF
[Tumor necrosis factor, membrane form]: Membrane 1 TNF
[C-domain 1]: Secreted 1 TNF


文献列表

  • Joanne E Haughan, Jaclyn R Missanelli, Youwen You, Darko Stefanovski, Lawrence R Soma, Mary A Robinson. Pharmacokinetics of glaucine after intravenous and oral administrations and detection of systemic aporphine alkaloids after ingestion of tulip poplar shavings in horses. Journal of veterinary pharmacology and therapeutics. 2022 May; 45(3):273-282. doi: 10.1111/jvp.13057. [PMID: 35394081]
  • Gonzalo Fuentes-Barros, Sebastián Castro-Saavedra, Leonel Liberona, Williams Acevedo-Fuentes, Cristian Tirapegui, César Mattar, Bruce K Cassels. Variation of the alkaloid content of Peumus boldus (boldo). Fitoterapia. 2018 Jun; 127(?):179-185. doi: 10.1016/j.fitote.2018.02.020. [PMID: 29454020]
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