Yohimbine (BioDeep_00000398583)

Main id: BioDeep_00000000695

Secondary id: BioDeep_00000866729

natural product PANOMIX_OTCML-2023


代谢物信息卡片


methyl (2S,13bS,14aS,1R,4aR)-2-hydroxy-1,2,3,4,5,8,14,13b,14a,4a-decahydrobenz o[1,2-g]indolo[2,3-a]quinolizinecarboxylate

化学式: C21H26N2O3 (354.1943)
中文名称: 育亨宾
谱图信息: 最多检出来源 Homo sapiens(blood) 23.14%

分子结构信息

SMILES: COC(=O)C1C(CCC2C1CC3C4=C(CCN3C2)C5=CC=CC=C5N4)O
InChI: InChI=1S/C21H26N2O3/c1-26-21(25)19-15-10-17-20-14(13-4-2-3-5-16(13)22-20)8-9-23(17)11-12(15)6-7-18(19)24/h2-5,12,15,17-19,22,24H,6-11H2,1H3/t12-,15-,17-,18-,19+/m0/s1

描述信息

G - Genito urinary system and sex hormones > G04 - Urologicals > G04B - Urologicals > G04BE - Drugs used in erectile dysfunction
C78272 - Agent Affecting Nervous System > C29747 - Adrenergic Agent > C72900 - Adrenergic Antagonist
D018377 - Neurotransmitter Agents > D018663 - Adrenergic Agents > D018674 - Adrenergic Antagonists
D018373 - Peripheral Nervous System Agents > D001337 - Autonomic Agents > D009184 - Mydriatics
D000089162 - Genitourinary Agents > D064804 - Urological Agents
CONFIDENCE Reference Standard (Level 1); INTERNAL_ID 2282
relative retention time with respect to 9-anthracene Carboxylic Acid is 0.556
relative retention time with respect to 9-anthracene Carboxylic Acid is 0.553
Yohimbine is a potent and relatively nonselective alpha 2-adrenergic receptor (AR) antagonist, with IC50 of 0.6 μM. IC50 value: 0.6 uM [1] Target: alpha 2-adrenergic receptor in vitro: Yohimbine inhibits alpha2-receptor antagonist with Ki of 1.05 nM, 1.19 nM, and 1.19 nM for α2A, α2B, α2C, respectively. Yohimbine also inhibits 5-HT1B with Ki of 19.9 nM. Yohimbine acts to block the lowering of cAMP by alpha-2 adrenoceptor agonists. yohimbine actually causes a pronounced lowering of tyrosinase activity. [3] in vivo: Yohimbine is an antagonist at alpha2-noradrenaline receptors with putative panicogenic effects in human subjects, was administered to Swiss-Webster mice at doses of 0.5, 1.0, and 2.0 mg/kg. Yohimbine potentiates active defensive responses to threatening stimuli in Swiss-Webster mice.[2]
Yohimbine is a potent and relatively nonselective alpha 2-adrenergic receptor (AR) antagonist, with IC50 of 0.6 μM. IC50 value: 0.6 uM [1] Target: alpha 2-adrenergic receptor in vitro: Yohimbine inhibits alpha2-receptor antagonist with Ki of 1.05 nM, 1.19 nM, and 1.19 nM for α2A, α2B, α2C, respectively. Yohimbine also inhibits 5-HT1B with Ki of 19.9 nM. Yohimbine acts to block the lowering of cAMP by alpha-2 adrenoceptor agonists. yohimbine actually causes a pronounced lowering of tyrosinase activity. [3] in vivo: Yohimbine is an antagonist at alpha2-noradrenaline receptors with putative panicogenic effects in human subjects, was administered to Swiss-Webster mice at doses of 0.5, 1.0, and 2.0 mg/kg. Yohimbine potentiates active defensive responses to threatening stimuli in Swiss-Webster mice.[2]

同义名列表

3 个代谢物同义名

Yohimbine; methyl (2S,13bS,14aS,1R,4aR)-2-hydroxy-1,2,3,4,5,8,14,13b,14a,4a-decahydrobenz o[1,2-g]indolo[2,3-a]quinolizinecarboxylate; Yohimbine



数据库引用编号

53 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(0)

BioCyc(0)

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)

78 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 8 ADRA1A, ADRA2A, AXIN2, CYP2D6, DBH, POMC, PRL, TH
Endoplasmic reticulum membrane 1 CYP2D6
Nucleus 5 ADRA1A, AXIN2, FOS, PRL, TH
cytosol 5 ADRA1A, ADRA2B, AXIN2, FOS, TH
dendrite 4 DRD2, HTR1A, HTR2A, TH
centrosome 1 AXIN2
nucleoplasm 3 ADRA1A, FOS, PRL
RNA polymerase II transcription regulator complex 2 FOS, PRL
Cell membrane 9 ADRA1A, ADRA2A, ADRA2B, ADRB3, DRD2, HTR1A, HTR2A, OPRD1, TNF
Cell projection, axon 2 HTR2A, TH
Multi-pass membrane protein 8 ADRA1A, ADRA2A, ADRA2B, ADRB3, DRD2, HTR1A, HTR2A, OPRD1
Golgi apparatus membrane 1 DRD2
Synapse 4 CRH, DBH, DRD2, HTR1A
cell surface 2 ADRA2B, TNF
dendritic shaft 1 HTR2A
glutamatergic synapse 3 ADRA2A, DRD2, HTR2A
Golgi apparatus 1 NPY
Golgi membrane 2 DRD2, INS
neuronal cell body 3 ADRA2A, HTR2A, TNF
presynaptic membrane 3 DRD2, HTR2A, OPRD1
smooth endoplasmic reticulum 1 TH
synaptic vesicle 1 TH
Presynapse 1 HTR2A
acrosomal vesicle 1 DRD2
plasma membrane 11 ADRA1A, ADRA2A, ADRA2B, ADRB3, AXIN2, DRD2, GCG, HTR1A, HTR2A, OPRD1, TNF
synaptic vesicle membrane 2 DRD2, OPRD1
terminal bouton 1 TH
Membrane 3 CYP2D6, DBH, OPRD1
axon 3 DRD2, HTR2A, TH
basolateral plasma membrane 1 ADRA2A
caveola 2 ADRA1A, HTR2A
endoplasmic reticulum 3 CYP2D6, DBH, FOS
extracellular space 8 CRH, DBH, GCG, INS, NPY, POMC, PRL, TNF
perinuclear region of cytoplasm 1 TH
mitochondrion 2 CYP2D6, TH
intracellular membrane-bounded organelle 4 ADRA1A, ADRA2B, CYP2D6, DBH
Microsome membrane 1 CYP2D6
Secreted 7 CRH, DBH, GCG, INS, NPY, POMC, PRL
extracellular region 8 CRH, DBH, GCG, INS, NPY, POMC, PRL, TNF
cytoplasmic side of plasma membrane 1 TH
Single-pass membrane protein 1 CYP2D6
centriolar satellite 1 DBH
ciliary membrane 1 DRD2
Nucleus membrane 1 ADRA1A
nuclear membrane 1 ADRA1A
external side of plasma membrane 1 TNF
varicosity 1 CRH
dendritic spine 1 DRD2
neuronal dense core vesicle lumen 1 CRH
perikaryon 3 CRH, DRD2, TH
beta-catenin destruction complex 1 AXIN2
cytoplasmic vesicle 2 HTR2A, TH
Melanosome membrane 1 TH
recycling endosome 1 TNF
Single-pass type II membrane protein 2 DBH, TNF
postsynaptic membrane 2 DRD2, HTR2A
presynaptic active zone membrane 1 ADRA2A
Cytoplasm, perinuclear region 1 TH
Membrane raft 1 TNF
GABA-ergic synapse 3 ADRA2A, DRD2, NPY
secretory granule 1 POMC
lateral plasma membrane 1 DRD2
receptor complex 2 ADRA2A, ADRB3
neuron projection 2 OPRD1, TH
cilium 1 DRD2
chromatin 2 FOS, PRL
phagocytic cup 1 TNF
non-motile cilium 1 DRD2
sperm flagellum 1 DRD2
endosome lumen 2 INS, PRL
Membrane, caveola 2 ADRA1A, HTR2A
cell body fiber 1 HTR2A
Cell projection, dendrite 2 HTR1A, HTR2A
secretory granule lumen 4 DBH, GCG, INS, POMC
secretory granule membrane 1 DBH
Golgi lumen 1 INS
endoplasmic reticulum lumen 2 GCG, INS
nuclear matrix 1 FOS
axon terminus 3 ADRA2A, DRD2, OPRD1
endocytic vesicle 1 DRD2
transport vesicle 1 INS
Endoplasmic reticulum-Golgi intermediate compartment membrane 1 INS
postsynaptic density membrane 2 ADRA2A, OPRD1
neuronal dense core vesicle 2 NPY, OPRD1
neurofilament 1 HTR2A
protein-DNA complex 1 FOS
dopaminergic synapse 2 ADRA2A, DRD2
dendrite membrane 1 OPRD1
Cytoplasmic vesicle, secretory vesicle membrane 1 DBH
transcription factor AP-1 complex 1 FOS
Cytoplasmic vesicle, secretory vesicle, chromaffin granule lumen 1 DBH
chromaffin granule lumen 1 DBH
[Glucagon-like peptide 1]: Secreted 1 GCG
Cytoplasmic vesicle, secretory vesicle, neuronal dense core vesicle 1 NPY
[Tumor necrosis factor, soluble form]: Secreted 1 TNF
transport vesicle membrane 1 DBH
Cytoplasmic vesicle, secretory vesicle, synaptic vesicle 1 TH
[Soluble dopamine beta-hydroxylase]: Cytoplasmic vesicle, secretory vesicle lumen 1 DBH
Cytoplasmic vesicle, secretory vesicle, chromaffin granule membrane 1 DBH
chromaffin granule membrane 1 DBH
G protein-coupled receptor complex 1 DRD2
G protein-coupled serotonin receptor complex 1 HTR2A
spine apparatus 1 OPRD1
[C-domain 2]: Secreted 1 TNF
[Tumor necrosis factor, membrane form]: Membrane 1 TNF
[C-domain 1]: Secreted 1 TNF


文献列表

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  • Yani Zhao, Yan Zhang, Yao Li, Min Yang, Jiani Yuan, Yu Cao, Lu Xu, Xuexinyu Ma, Sisong Lin, Junming An, Siwang Wang. Yohimbine hydrochloride inhibits benign prostatic hyperplasia by downregulating steroid 5α-reductase type 2. European journal of pharmacology. 2021 Oct; 908(?):174334. doi: 10.1016/j.ejphar.2021.174334. [PMID: 34265299]
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