Vasicinone (BioDeep_00000000813)

   

natural product PANOMIX_OTCML-2023


代谢物信息卡片


NCGC00169472-02_C11H10N2O2_Pyrrolo[2,1-b]quinazolin-9(1H)-one, 2,3-dihydro-3-hydroxy-

化学式: C11H10N2O2 (202.0742)
中文名称: 鸭嘴花酮碱, 鸭嘴花碱酮
谱图信息: 最多检出来源 Viridiplantae(plant) 19.54%

分子结构信息

SMILES: c1ccc2c(c1)c(=O)n1CC[C@@H](c1n2)O
InChI: InChI=1S/C11H10N2O2/c14-9-5-6-13-10(9)12-8-4-2-1-3-7(8)11(13)15/h1-4,9,14H,5-6H2

描述信息

Vasicinone is a member of quinazolines.
Vasicinone is a natural product found in Justicia adhatoda, Anisotes trisulcus, and other organisms with data available.
Vasicinone is a quinazoline alkaloid isolated from the Adhatoda vasica. Vasicinone is a potential agent for Parkinson's disease and possibly other oxidative stress-related neurodegenerative disorders[1].

同义名列表

17 个代谢物同义名

PYRROLO(2,1-.BETA.)QUINAZOLIN-9(1H)-ONE, 2,3-DIHYDRO-3-HYDROXY-, (3S)-; Pyrrolo(2,1-b)quinazolin-9(1H)-one, 2,3-dihydro-3-hydroxy-, (R)-; (3S)-3-hydroxy-2,3-dihydro-1H-pyrrolo[2,1-b]quinazolin-9-one; (3S)-2,3-dihydro-3-hydroxypyrrolo[2,1-b]quinazolin-9(1H)-one; (3R)-3-hydroxy-2,3-dihydro-1H-pyrrolo[2,1-b]quinazolin-9-one; (S)-3-Hydroxy-2,3-dihydropyrrolo[2,1-b]quinazolin-9(1H)-one; (3S)-3-hydroxy-1H,2H,3H,9H-pyrrolo[2,1-b]quinazolin-9-one; 3-hydroxy-2,3-dihydropyrrolo[2,1-b]quinazolin-9(1H)-one; Vasicinone, analytical standard; UNII-G6T5819NXM; (-)-Vasicinone; l-Vasicinone; Vasicinone; G6T5819NXM; AC1L9DON; NCGC00169472-02_C11H10N2O2_Pyrrolo[2,1-b]quinazolin-9(1H)-one, 2,3-dihydro-3-hydroxy-; Vasicinone



数据库引用编号

40 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)

39 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 11 ACE, ALOX5, ANXA5, BCL2, CRNN, MTOR, PARK7, PIK3CA, PTGS1, PTGS2, SNCA
Peripheral membrane protein 6 ACHE, ALOX5, ANXA5, MTOR, PTGS1, PTGS2
Endoplasmic reticulum membrane 4 BCL2, MTOR, PTGS1, PTGS2
Nucleus 6 ACHE, BCL2, MTOR, PARK7, PARP1, SNCA
cytosol 9 ALOX5, ANXA5, BCL2, LIPE, MTOR, PARK7, PARP1, PIK3CA, SNCA
dendrite 1 MTOR
nuclear body 1 PARP1
phagocytic vesicle 1 MTOR
nucleoplasm 5 ALOX5, MTOR, PARK7, PARP1, SP2
Cell membrane 5 ACE, ACHE, IGF1R, LIPE, PARK7
Lipid-anchor 1 PARK7
Cytoplasmic side 1 MTOR
lamellipodium 1 PIK3CA
Cell projection, axon 1 SNCA
Multi-pass membrane protein 1 UCP1
Golgi apparatus membrane 1 MTOR
Synapse 2 ACHE, SNCA
cell cortex 1 SNCA
cell surface 1 ACHE
Golgi apparatus 2 ACHE, PTGS1
Golgi membrane 1 MTOR
growth cone 1 SNCA
lysosomal membrane 1 MTOR
mitochondrial inner membrane 1 UCP1
neuromuscular junction 1 ACHE
neuronal cell body 2 IGF1R, SNCA
postsynapse 1 SNCA
sarcolemma 1 ANXA5
synaptic vesicle 1 PARK7
Cytoplasm, cytosol 3 ALOX5, LIPE, PARP1
Lysosome 3 ACE, MTOR, SNCA
endosome 1 ACE
plasma membrane 7 ACE, ACHE, BCHE, IGF1R, PARK7, PIK3CA, SNCA
synaptic vesicle membrane 1 SNCA
Membrane 11 ACE, ACHE, ANXA5, BCL2, CRNN, IGF1R, LIPE, MTOR, PARK7, PARP1, SNCA
axon 3 IGF1R, PARK7, SNCA
caveola 3 IGF1R, LIPE, PTGS2
extracellular exosome 5 ACE, ANXA5, CRNN, PARK7, PTGS1
Lysosome membrane 1 MTOR
endoplasmic reticulum 3 BCL2, PARK7, PTGS2
extracellular space 5 ACE, ACHE, ALOX5, BCHE, SNCA
perinuclear region of cytoplasm 5 ACHE, ALOX5, PARK7, PIK3CA, SNCA
adherens junction 1 PARK7
intercalated disc 1 PIK3CA
mitochondrion 5 BCL2, PARK7, PARP1, SNCA, UCP1
protein-containing complex 4 BCL2, PARP1, PTGS2, SNCA
intracellular membrane-bounded organelle 2 IGF1R, PTGS1
Microsome membrane 3 MTOR, PTGS1, PTGS2
TORC1 complex 1 MTOR
TORC2 complex 1 MTOR
Single-pass type I membrane protein 2 ACE, IGF1R
Secreted 5 ACE, ACHE, BCHE, MDK, SNCA
extracellular region 8 ACE, ACHE, ALOX5, ANXA5, BCHE, MDK, RLN1, SNCA
Mitochondrion outer membrane 2 BCL2, MTOR
Single-pass membrane protein 1 BCL2
mitochondrial outer membrane 2 BCL2, MTOR
mitochondrial matrix 1 PARK7
Extracellular side 1 ACHE
transcription regulator complex 1 PARP1
photoreceptor outer segment 1 PTGS1
Nucleus membrane 2 ALOX5, BCL2
Bcl-2 family protein complex 1 BCL2
nuclear membrane 2 ALOX5, BCL2
external side of plasma membrane 2 ACE, ANXA5
actin cytoskeleton 1 SNCA
T-tubule 1 IGF1R
nucleolus 1 PARP1
Cytoplasm, perinuclear region 1 ALOX5
Mitochondrion inner membrane 1 UCP1
Membrane raft 1 PARK7
pore complex 1 BCL2
focal adhesion 1 ANXA5
basement membrane 1 ACHE
Nucleus, PML body 1 MTOR
PML body 2 MTOR, PARK7
mitochondrial intermembrane space 1 PARK7
collagen-containing extracellular matrix 1 ANXA5
Nucleus inner membrane 1 PTGS2
Nucleus outer membrane 1 PTGS2
nuclear inner membrane 1 PTGS2
nuclear outer membrane 1 PTGS2
receptor complex 1 IGF1R
Zymogen granule membrane 1 ANXA5
neuron projection 2 PTGS1, PTGS2
chromatin 3 PARK7, PARP1, SP2
supramolecular fiber 1 SNCA
Chromosome 1 PARP1
brush border membrane 1 ACE
Nucleus, nucleolus 1 PARP1
nuclear replication fork 1 PARP1
chromosome, telomeric region 1 PARP1
blood microparticle 1 BCHE
sperm midpiece 1 ACE
Lipid-anchor, GPI-anchor 1 ACHE
site of double-strand break 1 PARP1
nuclear envelope 3 ALOX5, MTOR, PARP1
Nucleus envelope 1 ALOX5
Endomembrane system 2 MTOR, PTGS1
Lipid droplet 1 LIPE
Membrane, caveola 1 LIPE
cell body 1 PARK7
side of membrane 1 ACHE
myelin sheath 1 BCL2
basal plasma membrane 1 ACE
ficolin-1-rich granule lumen 1 ALOX5
secretory granule lumen 1 ALOX5
endoplasmic reticulum lumen 2 BCHE, PTGS2
nuclear matrix 1 ALOX5
axon terminus 1 SNCA
phosphatidylinositol 3-kinase complex 1 PIK3CA
phosphatidylinositol 3-kinase complex, class IA 1 PIK3CA
Nucleus matrix 1 ALOX5
nuclear envelope lumen 2 ALOX5, BCHE
vesicle membrane 1 ANXA5
synaptic cleft 1 ACHE
protein-DNA complex 1 PARP1
Cytoplasmic vesicle, phagosome 1 MTOR
site of DNA damage 1 PARP1
inclusion body 1 SNCA
alphav-beta3 integrin-IGF-1-IGF1R complex 1 IGF1R
insulin receptor complex 1 IGF1R
protein kinase complex 1 IGF1R
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
Nucleus intermembrane space 1 ALOX5
BAD-BCL-2 complex 1 BCL2
[Angiotensin-converting enzyme, soluble form]: Secreted 1 ACE
[Isoform Testis-specific]: Cell membrane 1 ACE
[Isoform H]: Cell membrane 1 ACHE
phosphatidylinositol 3-kinase complex, class IB 1 PIK3CA


文献列表

  • Syeda Tehreem, Saeedur Rahman, Muhammad Salman Bhatti, Reaz Uddin, Muhammad Noman Khan, Saba Tauseef, Hesham R El-Seedi, Abdullatif Bin Muhsinah, Jalal Uddin, Syed Ghulam Musharraf. A UPLC-DAD-Based Bio-Screening Assay for the Evaluation of the Angiotensin Converting Enzyme Inhibitory Potential of Plant Extracts and Compounds: Pyrroquinazoline Alkaloids from Adhatoda vasica as a Case Study. Molecules (Basel, Switzerland). 2021 Nov; 26(22):. doi: 10.3390/molecules26226971. [PMID: 34834066]
  • Da-Tong Ju, Kalaiselvi Sivalingam, Wei-Wen Kuo, Tsung-Jung Ho, Ruey-Lin Chang, Li-Chin Chung, Cecilia Hsuan Day, Vijaya Padma Viswanadha, Po-Hsiang Liao, Chih-Yang Huang. Effect of Vasicinone against Paraquat-Induced MAPK/p53-Mediated Apoptosis via the IGF-1R/PI3K/AKT Pathway in a Parkinson's Disease-Associated SH-SY5Y Cell Model. Nutrients. 2019 Jul; 11(7):. doi: 10.3390/nu11071655. [PMID: 31331066]
  • Bharat Singh, Pooran M Sahu, Ram A Sharma. Effect of elicitors on the production of pyrroloquinazoline alkaloids by stimulating anthranilate synthase activity in Adhatoda vasica Nees cell cultures. Planta. 2017 Dec; 246(6):1125-1137. doi: 10.1007/s00425-017-2757-x. [PMID: 28819874]
  • Wei Liu, Yongli Wang, Dan-dan He, Shu-ping Li, Yu-dan Zhu, Bo Jiang, Xue-mei Cheng, Zheng--tao Wang, Chang-hong Wang. Antitussive, expectorant, and bronchodilating effects of quinazoline alkaloids (±)-vasicine, deoxyvasicine, and (±)-vasicinone from aerial parts of Peganum harmala L. Phytomedicine : international journal of phytotherapy and phytopharmacology. 2015 Nov; 22(12):1088-95. doi: 10.1016/j.phymed.2015.08.005. [PMID: 26547531]
  • Chaitali Sarkar, Sankhadip Bose, Sugato Banerjee. Evaluation of hepatoprotective activity of vasicinone in mice. Indian journal of experimental biology. 2014 Jul; 52(7):705-11. doi: ". [PMID: 25059038]
  • Bharat Singh, Ram Avtar Sharma. Anti-inflammatory and antimicrobial properties of pyrroloquinazoline alkaloids from Adhatoda vasica Nees. Phytomedicine : international journal of phytotherapy and phytopharmacology. 2013 Mar; 20(5):441-5. doi: 10.1016/j.phymed.2012.12.015. [PMID: 23357363]
  • Deepak Kumar Jha, Likun Panda, P Lavanya, Sudha Ramaiah, Anand Anbarasu. Detection and confirmation of alkaloids in leaves of Justicia adhatoda and bioinformatics approach to elicit its anti-tuberculosis activity. Applied biochemistry and biotechnology. 2012 Nov; 168(5):980-90. doi: 10.1007/s12010-012-9834-1. [PMID: 22899014]
  • Bin Liu. [Study on chemical constituents of Peganum multisectum]. Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials. 2011 Nov; 34(11):1719-21. doi: . [PMID: 22506396]
  • Adil Astulla, Kazumasa Zaima, Yosuke Matsuno, Yusuke Hirasawa, Wiwied Ekasari, Aty Widyawaruyanti, Noor Cholies Zaini, Hiroshi Morita. Alkaloids from the seeds of Peganum harmala showing antiplasmodial and vasorelaxant activities. Journal of natural medicines. 2008 Oct; 62(4):470-2. doi: 10.1007/s11418-008-0259-7. [PMID: 18523842]
  • B Avula, S Begum, S Ahmed, M I Choudhary, I A Khan. Quantitative determination of vasicine and vasicinone in Adhatoda vasica by high performance capillary electrophoresis. Die Pharmazie. 2008 Jan; 63(1):20-2. doi: . [PMID: 18271297]
  • Chaitali Das, Rajlakshmi Poi, Ashim Chowdhury. HPTLC determination of vasicine and vasicinone in Adhatoda vasica. Phytochemical analysis : PCA. 2005 Mar; 16(2):90-2. doi: 10.1002/pca.817. [PMID: 15881115]
  • D S Samiulla, V V Vaidyanathan, P C Arun, G Balan, M Blaze, S Bondre, G Chandrasekhar, A Gadakh, R Kumar, G Kharvi, H O Kim, S Kumar, J A Malikayil, M Moger, M K Mone, P Nagarjuna, C Ogbu, D Pendhalkar, A V S Raja Rao, G Venkateshwar Rao, V K Sarma, S Shaik, G V R Sharma, S Singh, C Sreedhar, R Sonawane, U Timmanna, L W Hardy. Rational selection of structurally diverse natural product scaffolds with favorable ADME properties for drug discovery. Molecular diversity. 2005; 9(1-3):131-9. doi: 10.1007/s11030-005-1297-7. [PMID: 15789560]