Hirsuteine (BioDeep_00000000229)

 

Secondary id: BioDeep_00000408401

PANOMIX_OTCML-2023 natural product


代谢物信息卡片


INDOLO(2,3-A)QUINOLIZINE-2-ACETIC ACID, 3-ETHENYL-1,2,3,4,6,7,12,12B-OCTAHYDRO-.ALPHA.-(METHOXYMETHYLENE)-, METHYL ESTER, (.ALPHA.E,2S,3R,12BS)-

化学式: C22H26N2O3 (366.1943)
中文名称: 去氢毛钩藤碱, DELTA18-毛钩藤碱
谱图信息: 最多检出来源 Viridiplantae(plant) 15.87%

分子结构信息

SMILES: C=CC1CN2CCc3c([nH]c4ccccc34)C2CC1C(=COC)C(=O)OC
InChI: InChI=1S/C22H26N2O3/c1-4-14-12-24-10-9-16-15-7-5-6-8-19(15)23-21(16)20(24)11-17(14)18(13-26-2)22(25)27-3/h4-8,13-14,17,20,23H,1,9-12H2,2-3H3

描述信息

Corynantheine is a monoterpenoid indole alkaloid.
Corynantheine is a natural product found in Corynanthe pachyceras, Uncaria rhynchophylla, and other organisms with data available.
Hirsuteine is an alkaloid.
Hirsuteine is a natural product found in Uncaria tomentosa, Mitragyna hirsuta, and other organisms with data available.
See also: Cats Claw (part of).
Annotation level-1
Hirsuteine is an indole alkaloid extracted from Uncaria rhynchophylla. Hirsuteine non-competitively antagonizes nicotine-mediated dopamine release by blocking ion permeation through nicotinic receptor channel complexes[1].

同义名列表

29 个代谢物同义名

INDOLO(2,3-A)QUINOLIZINE-2-ACETIC ACID, 3-ETHENYL-1,2,3,4,6,7,12,12B-OCTAHYDRO-.ALPHA.-(METHOXYMETHYLENE)-, METHYL ESTER, (.ALPHA.E,2S,3R,12BS)-; (.ALPHA.E,2S,3R,12BS)-3-ETHENYL-1,2,3,4,6,7,12,12B-OCTAHYDRO-.ALPHA.-(METHOXYMETHYLENE)INDOLO(2,3-A)QUINOLIZINE-2-ACETIC ACID METHYL ESTER; methyl (E)-2-[(2S,3R,12bS)-3-ethenyl-1,2,3,4,6,7,12,12b-octahydroindolo[2,3-a]quinolizin-2-yl]-3-methoxyprop-2-enoate; Methyl (E)-3-methoxy-2-((2S,3R,12bS)-3-vinyl-1,2,3,4,6,7,12,12b-octahydroindolo[2,3-a]quinolizin-2-yl)acrylate; 17,18-Secoyohimban-16-carboxylic acid, 16,17,18,19-tetradehydro-17-methoxy-, methyl ester, (E)-; 4-25-00-01255 (Beilstein Handbook Reference); hirsuteine, (R-(R*,R*))-tartrate (1:1) salt; hirsuteine, (3beta,16E)-isomer; hirsuteine hydrochloride; CORYNANTHEINE [MI]; (+)-Corynantheine; Corynantheine; Hirsuteine; INDOLO(2,3-A)QUINOLIZINE-2-ACETIC ACID, 3-ETHENYL-1,2,3,4,6,7,12,12B-OCTAHYDRO-.ALPHA.-(METHOXYMETHYLENE)-, METHYL ESTER, (.ALPHA.E,2S,3R,12BR)-; INDOLO(2,3-A)QUINOLIZINE-2-ACETIC ACID, 3-ETHENYL-1,2,3,4,6,7,12,12B-OCTAHYDRO-alpha-(METHOXYMETHYLENE)-, METHYL ESTER, (alphaE,2S,3R,12BR)-; methyl (E)-2-[(2S,3R,12bR)-3-ethenyl-1,2,3,4,6,7,12,12b-octahydroindolo[2,3-a]quinolizin-2-yl]-3-methoxyprop-2-enoate; CORYNAN-16-CARBOXYLIC ACID, 16,17,18,19-TETRADEHYDRO-17-METHOXY-, METHYL ESTER, (3.BETA.,16E)-; Corynan-16-carboxylic acid, 16,17,18,19-tetradehydro-17-methoxy-, methyl ester, (3-beta,16E)-; CORYNAN-16-CARBOXYLIC ACID, 16,17,18,19-TETRADEHYDRO-17-METHOXY-, METHYL ESTER, (3beta,16E)-; Corynan-16-carboxylic acid, 16,17,18,19-tetrahydro-17-methoxy-, methyl ester, (3beta,16E)-; (3-beta,16E)-16,17,18,19-Tetradehydro-17-methoxy-corynan-16-carboxylic acid methyl ester; (3beta,16E)-16,17,18,19-Tetradehydro-17-methoxycorynan-16-carboxylic acid methyl ester; methyl (3beta,16E)-16-(methoxymethylidene)coryn-18-en-17-oate; 18,19-Didehydrohirsutine; delta(sup 18)-Hirsutine; 3-Epicorynantheine; UNII-43X9C2G2W5; 43X9C2G2W5; Hirsuteine



数据库引用编号

51 个数据库交叉引用编号

分类词条

相关代谢途径

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代谢反应

0 个相关的代谢反应过程信息。

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BioCyc(0)

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INOH(0)

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22 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 14 ABCB1, ANXA5, APAF1, BCL2, CASP3, CCNB1, CDK1, CDK2, MDM2, MSMP, PIK3CA, S1PR1, SPHK1, SPTB
Peripheral membrane protein 3 ACHE, ANXA5, SPHK1
Endosome membrane 1 SPHK1
Endoplasmic reticulum membrane 2 BCL2, CDK1
Nucleus 10 ACHE, APAF1, BCL2, CASP3, CCNB1, CDK1, CDK2, MDM2, PARP1, SPHK1
cytosol 12 ANXA5, APAF1, BCL2, CASP3, CCNB1, CDK1, CDK2, MDM2, PARP1, PIK3CA, SPHK1, SPTB
nuclear body 1 PARP1
centrosome 3 CCNB1, CDK1, CDK2
nucleoplasm 8 CASP3, CCNB1, CDK1, CDK2, MDM2, PARP1, S1PR1, SPHK1
Cell membrane 6 ABCB1, ACHE, HTR3A, HTR3B, S1PR1, SPHK1
Cleavage furrow 1 HTR3A
lamellipodium 1 PIK3CA
Early endosome membrane 1 SPHK1
Multi-pass membrane protein 4 ABCB1, HTR3A, HTR3B, S1PR1
Synapse 4 ACHE, HTR3A, HTR3B, SPHK1
cell junction 1 SPTB
cell surface 4 ABCB1, ACHE, HTR3B, SPTB
glutamatergic synapse 3 CASP3, MDM2, SPTB
Golgi apparatus 1 ACHE
neuromuscular junction 1 ACHE
neuronal cell body 1 CASP3
postsynapse 2 HTR3A, SPTB
sarcolemma 1 ANXA5
Cytoplasm, cytosol 1 PARP1
Presynapse 2 S1PR1, SPHK1
endosome 2 CDK2, S1PR1
plasma membrane 9 ABCB1, ACHE, HTR3A, HTR3B, MDM2, PIK3CA, S1PR1, SPHK1, SPTB
Membrane 12 ABCB1, ACHE, ANXA5, APAF1, BCL2, CCNB1, CDK1, HTR3A, HTR3B, PARP1, SPHK1, SPTB
apical plasma membrane 1 ABCB1
axon 1 CCK
extracellular exosome 4 ABCB1, ANXA5, APAF1, CDK1
endoplasmic reticulum 1 BCL2
extracellular space 3 ACHE, CCK, MSMP
perinuclear region of cytoplasm 2 ACHE, PIK3CA
intercalated disc 1 PIK3CA
mitochondrion 3 BCL2, CDK1, PARP1
protein-containing complex 5 APAF1, BCL2, MDM2, PARP1, SPTB
intracellular membrane-bounded organelle 2 S1PR1, SPHK1
postsynaptic density 2 CASP3, MDM2
Secreted 3 ACHE, CCK, MSMP
extracellular region 4 ACHE, ANXA5, APAF1, CCK
cytoplasmic side of plasma membrane 1 SPTB
Mitochondrion outer membrane 1 BCL2
Single-pass membrane protein 1 BCL2
mitochondrial outer membrane 1 BCL2
mitochondrial matrix 2 CCNB1, CDK1
Extracellular side 1 ACHE
transcription regulator complex 2 CDK2, PARP1
Cytoplasm, cytoskeleton, microtubule organizing center, centrosome 2 CDK1, CDK2
Nucleus membrane 1 BCL2
Bcl-2 family protein complex 1 BCL2
nuclear membrane 1 BCL2
external side of plasma membrane 2 ANXA5, S1PR1
actin cytoskeleton 1 SPTB
nucleolus 2 MDM2, PARP1
midbody 1 CDK1
Membrane, clathrin-coated pit 1 SPHK1
clathrin-coated pit 1 SPHK1
postsynaptic membrane 2 HTR3A, HTR3B
Apical cell membrane 1 ABCB1
Membrane raft 1 S1PR1
pore complex 1 BCL2
Cytoplasm, cytoskeleton 1 SPTB
focal adhesion 1 ANXA5
basement membrane 1 ACHE
collagen-containing extracellular matrix 1 ANXA5
Postsynaptic cell membrane 2 HTR3A, HTR3B
Zymogen granule membrane 1 ANXA5
neuron projection 2 HTR3A, HTR3B
chromatin 1 PARP1
cell projection 1 SPTB
mitotic spindle 1 CDK1
Chromosome 1 PARP1
Nucleus, nucleolus 2 MDM2, PARP1
spindle pole 1 CCNB1
nuclear replication fork 1 PARP1
chromosome, telomeric region 3 CDK1, CDK2, PARP1
serotonin-activated cation-selective channel complex 2 HTR3A, HTR3B
transmembrane transporter complex 2 HTR3A, HTR3B
Lipid-anchor, GPI-anchor 1 ACHE
site of double-strand break 1 PARP1
nuclear envelope 2 CDK2, PARP1
Nucleus, nucleoplasm 1 MDM2
side of membrane 1 ACHE
myelin sheath 1 BCL2
ficolin-1-rich granule lumen 1 APAF1
secretory granule lumen 1 APAF1
transcription repressor complex 1 MDM2
male germ cell nucleus 1 CDK2
cortical actin cytoskeleton 1 SPTB
phosphatidylinositol 3-kinase complex 1 PIK3CA
phosphatidylinositol 3-kinase complex, class IA 1 PIK3CA
endocytic vesicle membrane 1 MDM2
endocytic vesicle 1 SPHK1
apoptosome 1 APAF1
outer kinetochore 1 CCNB1
vesicle membrane 1 ANXA5
Cajal body 1 CDK2
spectrin 1 SPTB
synaptic cleft 1 ACHE
protein-DNA complex 1 PARP1
spindle microtubule 1 CDK1
external side of apical plasma membrane 1 ABCB1
death-inducing signaling complex 1 CASP3
condensed chromosome 1 CDK2
Nucleus, Cajal body 1 CDK2
X chromosome 1 CDK2
Y chromosome 1 CDK2
site of DNA damage 1 PARP1
cyclin-dependent protein kinase holoenzyme complex 2 CDK1, CDK2
cyclin E1-CDK2 complex 1 CDK2
cyclin E2-CDK2 complex 1 CDK2
spectrin-associated cytoskeleton 1 SPTB
cyclin A1-CDK1 complex 1 CDK1
cyclin A2-CDK1 complex 1 CDK1
cyclin B1-CDK1 complex 2 CCNB1, CDK1
endothelial microparticle 1 ANXA5
[Poly [ADP-ribose] polymerase 1, processed N-terminus]: Chromosome 1 PARP1
[Poly [ADP-ribose] polymerase 1, processed C-terminus]: Cytoplasm 1 PARP1
BAD-BCL-2 complex 1 BCL2
cyclin A2-CDK2 complex 1 CDK2
[Isoform H]: Cell membrane 1 ACHE
cyclin A1-CDK2 complex 1 CDK2
phosphatidylinositol 3-kinase complex, class IB 1 PIK3CA
organelle 1 SPTB


文献列表

  • Adam Yasgar, Danielle Bougie, Richard T Eastman, Ruili Huang, Misha Itkin, Jennifer Kouznetsova, Caitlin Lynch, Crystal McKnight, Mitch Miller, Deborah K Ngan, Tyler Peryea, Pranav Shah, Paul Shinn, Menghang Xia, Xin Xu, Alexey V Zakharov, Anton Simeonov. Quantitative Bioactivity Signatures of Dietary Supplements and Natural Products. ACS pharmacology & translational science. 2023 May; 6(5):683-701. doi: 10.1021/acsptsci.2c00194. [PMID: 37200814]
  • Ye Liu, Heng-Yi Yu, Hong-Zhe Xu, Jun-Jun Liu, Xiang-Gao Meng, Ming Zhou, Han-Li Ruan. Alkaloids with Immunosuppressive Activity from the Bark of Pausinystalia yohimbe. Journal of natural products. 2018 08; 81(8):1841-1849. doi: 10.1021/acs.jnatprod.8b00324. [PMID: 30059216]
  • Hiroyuki Kitagawa, Masaya Munekage, Kengo Ichikawa, Ian Fukudome, Eri Munekage, Yuka Takezaki, Takashi Matsumoto, Yasushi Igarashi, Haruo Hanyu, Kazuhiro Hanazaki. Pharmacokinetics of Active Components of Yokukansan, a Traditional Japanese Herbal Medicine after a Single Oral Administration to Healthy Japanese Volunteers: A Cross-Over, Randomized Study. PloS one. 2015; 10(7):e0131165. doi: 10.1371/journal.pone.0131165. [PMID: 26151135]
  • Wen Qi, Si-Jia Yue, Jia-Hong Sun, James W Simpkins, Lin Zhang, Dan Yuan. Alkaloids from the hook-bearing branch of Uncariarhynchophylla and their neuroprotective effects against glutamate-induced HT22 cell death. Journal of Asian natural products research. 2014; 16(8):876-83. doi: 10.1080/10286020.2014.918109. [PMID: 24899363]
  • Takahiro Nakazawa, Koh-ichi Banba, Kazumasa Hata, Yutaka Nihei, Ayumi Hoshikawa, Keisuke Ohsawa. Metabolites of hirsuteine and hirsutine, the major indole alkaloids of Uncaria rhynchophylla, in rats. Biological & pharmaceutical bulletin. 2006 Aug; 29(8):1671-7. doi: 10.1248/bpb.29.1671. [PMID: 16880624]
  • Y Ozaki. [Vasodilative effects of indole alkaloids obtained from domestic plants, Uncaria rhynchophylla Miq. and Amsonia elliptica Roem. et Schult]. Nihon yakurigaku zasshi. Folia pharmacologica Japonica. 1990 Feb; 95(2):47-54. doi: 10.1254/fpj.95.2_47. [PMID: 2328929]