Tulipalin_A (BioDeep_00001867578)

Main id: BioDeep_00000000994

 

PANOMIX_OTCML-2023 Chemicals and Drugs


代谢物信息卡片


4-(3-FORMYL-2,5-DIMETHYL-1H-PYRROL-1-YL)BENZENECARBOXYLICACID

化学式: C5H6O2 (98.0368)
中文名称: α-亚甲基-γ-丁内酯, α-亚甲基γ-丁内酯, 郁金香素A
谱图信息: 最多检出来源 () 0%

分子结构信息

SMILES: C=C1CCOC1=O
InChI: InChI=1S/C5H6O2/c1-4-2-3-7-5(4)6/h1-3H2

描述信息

Alpha-methylene gamma-butyrolactone is a butan-4-olide having a methylene group at the 3-position. It has a role as a gastrointestinal drug and an anti-ulcer drug.
alpha-Methylene-gamma-butyrolactone is a natural product found in Tulipa agenensis, Tulipa humilis, and other organisms with data available.
D005765 - Gastrointestinal Agents > D000897 - Anti-Ulcer Agents
Tulipalin A (α-Methylene butyrolactone) is a glycoside. Tulipalin A is a causative allergen that induces Allergic contact dermatitides[1]. Tulipalin A (α-Methylene butyrolactone) at low dose affects the functionality of immune cells, such as Jurkat T cells[2].
Tulipalin A (α-Methylene butyrolactone) is a glycoside. Tulipalin A is a causative allergen that induces Allergic contact dermatitides[1]. Tulipalin A (α-Methylene butyrolactone) at low dose affects the functionality of immune cells, such as Jurkat T cells[2].

同义名列表

40 个代谢物同义名

4-(3-FORMYL-2,5-DIMETHYL-1H-PYRROL-1-YL)BENZENECARBOXYLICACID; 3-METHYLENEDIHYDROFURAN-2(3H)-ONE (STABILIZED WITH 1\\% BHT); alpha-Methylene-gamma-butyrolactone, 97\\%; .alpha.-Methylene-.gamma.-butyrolactone; alpha -Methylene- gamma -butyrolactone; 2(3H)-Furanone, dihydro-3-methylene- (; alpha-methylidene-gamma-butyrolactone; InChI=1/C5H6O2/c1-4-2-3-7-5(4)6/h1-3H; 2(3H)-Furanone, dihydro-3-methylene-; .ALPHA.-METHYLENE BUTYROLACTONE [MI]; alpha-methylene gamma-butyrolactone; alpha-Methylene-gamma-butyrolactone; 3-Methylenedihydro-2(3H)-furanone #; Dihydro-3-methylene-2(3H)-furanone; 3-methylenedihydrofuran-2 (3H)-one; 3-Methylenedihydro-2(3H)-furanone; 3-methylenedihydrofuran-2(3H)-one; dihydro-3-methylene-(3h)-furanone; 3-Methylenedihydro-2(3H)-fuanone; 3-methylenetetrahydrofuran-2-one; METHYLENE BUTYROLACTONE, ALPHA-; .alpha.-Methylene butyrolactone; alpha-Methylene butyrolactone; a-Methylene-g-butyrolactone; a-methylene-y-butyrolactone; 3-methylideneoxolan-2-one; -Methylene butyrolactone; 2-Methylenebutanolactone; a-methyl-y-butyrolactone; 2-methylenebutyrolactone; TULIPALIN A [INCI]; TULIPALIN 98; TULIPALINE A; Tulipalin A; Securolide; AI3-63021; Tulipane; LMSV-6; α-Methylene butyrolactone; alpha-Methylene-gamma-butyrolactone



数据库引用编号

12 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)

34 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 12 AIMP2, BCL2, CRYZ, FASN, MSMP, NFKB1, NFKBIA, NLRP3, PMP2, PTGS2, RELA, SRARP
Peripheral membrane protein 1 PTGS2
Endoplasmic reticulum membrane 3 BCL2, HMOX1, PTGS2
Nucleus 11 AIMP2, BCL2, GABPA, HMOX1, NFKB1, NFKBIA, NLRP3, PMP2, RELA, SRARP, TCEA1
cytosol 11 AIMP2, BCL2, CRYZ, FASN, GOLPH3, HMOX1, NFKB1, NFKBIA, NLRP3, PMP2, RELA
trans-Golgi network 1 GOLPH3
nucleoplasm 7 ATP2B1, GABPA, HMOX1, NFKB1, NFKBIA, RELA, TCEA1
Cell membrane 4 ATP2B1, GOLPH3, MAG, TNF
Cytoplasmic side 1 HMOX1
Multi-pass membrane protein 1 ATP2B1
Golgi apparatus membrane 1 NLRP3
Synapse 1 ATP2B1
cell surface 2 ICAM1, TNF
glutamatergic synapse 2 ATP2B1, RELA
Golgi apparatus 2 FASN, GOLPH3
Golgi membrane 2 GOLPH3, NLRP3
neuronal cell body 1 TNF
presynaptic membrane 1 ATP2B1
Cytoplasm, cytosol 2 AIMP2, NLRP3
endosome 1 GOLPH3
plasma membrane 7 ATP2B1, FASN, GOLPH3, ICAM1, MAG, NFKBIA, TNF
synaptic vesicle membrane 1 ATP2B1
Membrane 9 AIMP2, ATP2B1, BCL2, FASN, GOLPH3, HMOX1, ICAM1, MAG, NLRP3
basolateral plasma membrane 1 ATP2B1
caveola 1 PTGS2
extracellular exosome 5 ATP2B1, CRYZ, FASN, ICAM1, PMP2
endoplasmic reticulum 4 BCL2, HMOX1, NLRP3, PTGS2
extracellular space 4 HMOX1, ICAM1, MSMP, TNF
perinuclear region of cytoplasm 1 HMOX1
mitochondrion 5 BCL2, CRYZ, GOLPH3, NFKB1, NLRP3
protein-containing complex 2 BCL2, PTGS2
intracellular membrane-bounded organelle 2 ATP2B1, GOLPH3
Microsome membrane 1 PTGS2
Single-pass type I membrane protein 2 ICAM1, MAG
Secreted 2 MSMP, NLRP3
extracellular region 3 NFKB1, NLRP3, TNF
Mitochondrion outer membrane 1 BCL2
Single-pass membrane protein 2 BCL2, MAG
mitochondrial outer membrane 2 BCL2, HMOX1
transcription regulator complex 2 NFKB1, RELA
Cytoplasmic vesicle, secretory vesicle, synaptic vesicle membrane 1 ATP2B1
Nucleus membrane 1 BCL2
Bcl-2 family protein complex 1 BCL2
nuclear membrane 1 BCL2
external side of plasma membrane 2 ICAM1, TNF
nucleolus 1 TCEA1
recycling endosome 1 TNF
Single-pass type II membrane protein 1 TNF
Membrane raft 3 ICAM1, MAG, TNF
pore complex 1 BCL2
focal adhesion 1 ICAM1
mitochondrial intermembrane space 1 GOLPH3
collagen-containing extracellular matrix 1 ICAM1
lateral plasma membrane 1 ATP2B1
Cytoplasm, cytoskeleton, microtubule organizing center 1 NLRP3
Inflammasome 1 NLRP3
interphase microtubule organizing center 1 NLRP3
NLRP3 inflammasome complex 1 NLRP3
Nucleus inner membrane 1 PTGS2
Nucleus outer membrane 1 PTGS2
nuclear inner membrane 1 PTGS2
nuclear outer membrane 1 PTGS2
neuron projection 1 PTGS2
chromatin 3 GABPA, NFKB1, RELA
cell projection 1 ATP2B1
phagocytic cup 1 TNF
Basolateral cell membrane 1 ATP2B1
Endomembrane system 1 NLRP3
microtubule organizing center 1 NLRP3
Melanosome 1 FASN
Golgi cisterna membrane 1 GOLPH3
Presynaptic cell membrane 1 ATP2B1
myelin sheath 3 BCL2, MAG, PMP2
secretory granule lumen 1 NFKB1
endoplasmic reticulum lumen 1 PTGS2
transcription factor TFIID complex 1 TCEA1
specific granule lumen 1 NFKB1
paranode region of axon 1 MAG
Schmidt-Lanterman incisure 1 MAG
immunological synapse 2 ATP2B1, ICAM1
Single-pass type IV membrane protein 1 HMOX1
Golgi cisterna 1 GOLPH3
aminoacyl-tRNA synthetase multienzyme complex 1 AIMP2
[Tumor necrosis factor, soluble form]: Secreted 1 TNF
compact myelin 1 MAG
myelin sheath adaxonal region 1 MAG
BAD-BCL-2 complex 1 BCL2
photoreceptor ribbon synapse 1 ATP2B1
[Nuclear factor NF-kappa-B p105 subunit]: Cytoplasm 1 NFKB1
[Nuclear factor NF-kappa-B p50 subunit]: Nucleus 1 NFKB1
I-kappaB/NF-kappaB complex 2 NFKB1, NFKBIA
NF-kappaB p50/p65 complex 2 NFKB1, RELA
mesaxon 1 MAG
NF-kappaB complex 1 RELA
glycogen granule 1 FASN
[C-domain 2]: Secreted 1 TNF
[Tumor necrosis factor, membrane form]: Membrane 1 TNF
[C-domain 1]: Secreted 1 TNF


文献列表

  • Hong-Wei He, Dan Xu, Ke-Huan Wu, Zheng-Yi Lu, Xili Liu, Gong Xu. Discovery of novel salicylaldehyde derivatives incorporating an α-methylene-γ-butyrolactone moiety as fungicidal agents. Pest management science. 2023 Dec; 79(12):5015-5028. doi: 10.1002/ps.7703. [PMID: 37544900]
  • Luwei Li, Deyou Yang, Heng Li, Guangyou Chen, Peng Lei, Yanqing Gao, Juntao Feng. Heterocycle-Substituted α-Methylene-γ-Butyrolactones Derivatives Synthesis, Antifungal Activity, and 3D-QSAR. Journal of agricultural and food chemistry. 2023 Jul; ?(?):. doi: 10.1021/acs.jafc.3c02117. [PMID: 37432089]
  • Hong-Wei He, Fei-Yu Wang, Danyang Zhang, Cai-Yun Chen, Dan Xu, Huan Zhou, Xili Liu, Gong Xu. Discovery of Novel α-Methylene-γ-Butyrolactone Derivatives Containing Vanillin Moieties as Antiviral and Antifungal Agents. Journal of agricultural and food chemistry. 2022 Aug; 70(33):10316-10325. doi: 10.1021/acs.jafc.2c03632. [PMID: 35960686]
  • Xue Li, Lingmei Kong, Qihong Yang, Aizhu Duan, Xiaoman Ju, Bicheng Cai, Lin Chen, Tao An, Yan Li. Parthenolide inhibits ubiquitin-specific peptidase 7 (USP7), Wnt signaling, and colorectal cancer cell growth. The Journal of biological chemistry. 2020 03; 295(11):3576-3589. doi: 10.1074/jbc.ra119.011396. [PMID: 32029476]
  • Taiji Nomura, Shinjiro Ogita, Yasuo Kato. One-Step Enzymatic Synthesis of 1-Tuliposide A Using Tuliposide-Converting Enzyme. Applied biochemistry and biotechnology. 2019 May; 188(1):12-28. doi: 10.1007/s12010-018-2903-3. [PMID: 30284210]
  • Iffat Hassan, Farhan Rasool, Saniya Akhtar, Afifa Kamili, Parvaiz Rather, Raihana Kanth, Yasmeen Bhat, Shagufta Rather, Syed Mubashir, Atiya Yaseen, Safia Bashir. Contact dermatitis caused by tulips: identification of contact sensitizers in tulip workers of Kashmir Valley in North India. Contact dermatitis. 2018 Jan; 78(1):64-69. doi: 10.1111/cod.12870. [PMID: 28940507]
  • Yongling Wu, Delong Wang, Yanqing Gao, Juntao Feng, Xing Zhang. New α-Methylene-γ-Butyrolactone Derivatives as Potential Fungicidal Agents: Design, Synthesis and Antifungal Activities. Molecules (Basel, Switzerland). 2016 Jan; 21(2):130. doi: 10.3390/molecules21020130. [PMID: 26805804]
  • Camille Debeuckelaere, Valérie Berl, Karim Elbayed, François-Marie Moussallieh, Izzie-Jacques Namer, J-P Lepoittevin. Matrix Effect of Human Reconstructed Epidermis on the Chemoselectivity of a Skin Sensitizing α-Methylene-γ-Butyrolactone: Consequences for the Development of in Chemico Alternative Methods. Chemical research in toxicology. 2015 Nov; 28(11):2192-8. doi: 10.1021/acs.chemrestox.5b00363. [PMID: 26496248]
  • Pierluigi Caboni, Laura Tronci, Barbara Liori, Graziella Tocco, Nicola Sasanelli, Andrea Diana. Tulipaline A: structure-activity aspects as a nematicide and V-ATPase inhibitor. Pesticide biochemistry and physiology. 2014 Jun; 112(?):33-9. doi: 10.1016/j.pestbp.2014.05.002. [PMID: 24974115]
  • Feng Jun-Tao, Wang De-Long, Wu Yong-Ling, Yan He, Zhang Xing. New antifungal scaffold derived from a natural pharmacophore: synthesis of α-methylene-γ-butyrolactone derivatives and their antifungal activity against Colletotrichum lagenarium. Bioorganic & medicinal chemistry letters. 2013 Aug; 23(15):4393-7. doi: 10.1016/j.bmcl.2013.05.073. [PMID: 23777779]
  • Jihoon Shin, Youngmin Lee, William B Tolman, Marc A Hillmyer. Thermoplastic elastomers derived from menthide and tulipalin A. Biomacromolecules. 2012 Nov; 13(11):3833-40. doi: 10.1021/bm3012852. [PMID: 23062206]
  • Quan Zhang, Yaxin Lu, Yahui Ding, Jiadai Zhai, Qing Ji, Weiwei Ma, Ming Yang, Hongxia Fan, Jing Long, Zhongsheng Tong, Yehui Shi, Yongsheng Jia, Bin Han, Wenpeng Zhang, Chuanjiang Qiu, Xiaoyan Ma, Qiuying Li, Qianqian Shi, Haoliang Zhang, Dongmei Li, Jing Zhang, Jianping Lin, Lu-Yuan Li, Yingdai Gao, Yue Chen. Guaianolide sesquiterpene lactones, a source to discover agents that selectively inhibit acute myelogenous leukemia stem and progenitor cells. Journal of medicinal chemistry. 2012 Oct; 55(20):8757-69. doi: 10.1021/jm301064b. [PMID: 22985027]
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  • Anil Pareek, Manish Suthar, Garvendra S Rathore, Vijay Bansal. Feverfew (Tanacetum parthenium L.): A systematic review. Pharmacognosy reviews. 2011 Jan; 5(9):103-10. doi: 10.4103/0973-7847.79105. [PMID: 22096324]
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