Proazulene (BioDeep_00000227700)

Main id: BioDeep_00000007418

 

human metabolite PANOMIX_OTCML-2023 natural product


代谢物信息卡片


(3S,3aR,4S,9R,9aS,9bS)-9-hydroxy-3,6,9-trimethyl-2-oxo-2H,3H,3aH,4H,5H,9H,9aH,9bH-azuleno[4,5-b]furan-4-yl acetate

化学式: C17H22O5 (306.1467)
中文名称:
谱图信息: 最多检出来源 () 0%

分子结构信息

SMILES: CC(=O)O[C@H]1CC(C)=C2C=C[C@@](C)(O)[C@@H]2[C@H]2OC(=O)[C@@H](C)[C@H]12
InChI: InChI=1S/C17H22O5/c1-8-7-12(21-10(3)18)13-9(2)16(19)22-15(13)14-11(8)5-6-17(14,4)20/h5-6,9,12-15,20H,7H2,1-4H3/t9-,12-,13+,14-,15-,17+/m0/s1

描述信息

Proazulene, also known as matricine, is a member of the class of compounds known as gamma butyrolactones. Gamma butyrolactones are compounds containing a gamma butyrolactone moiety, which consists of an aliphatic five-member ring with four carbon atoms, one oxygen atom, and bears a ketone group on the carbon adjacent to the oxygen atom. Thus, proazulene is considered to be an isoprenoid lipid molecule. Proazulene is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Proazulene can be found in anise, which makes proazulene a potential biomarker for the consumption of this food product. Chamazulene, a blue-violet derivative of azulene, found in a variety of plants including in chamomile (Matricaria chamomilla), wormwood (Artemisia absinthium) and yarrow (Achillea millefolium) is biosynthesized from matricin .

同义名列表

5 个代谢物同义名

(3S,3aR,4S,9R,9aS,9bS)-9-hydroxy-3,6,9-trimethyl-2-oxo-2H,3H,3aH,4H,5H,9H,9aH,9bH-azuleno[4,5-b]furan-4-yl acetate; Proazulene; Matricine; Matricin; Matricin



数据库引用编号

17 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)

44 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 ANXA5, BCL2, BCL2L1, ENO2, MTOR, PIK3CA, PTGS1, PTGS2, S100B
Peripheral membrane protein 4 ANXA5, MTOR, PTGS1, PTGS2
Endoplasmic reticulum membrane 4 BCL2, MTOR, PTGS1, PTGS2
Mitochondrion membrane 1 BCL2L1
Nucleus 3 BCL2, MTOR, S100B
cytosol 7 ANXA5, BCL2, BCL2L1, ENO2, MTOR, PIK3CA, S100B
dendrite 1 MTOR
phagocytic vesicle 1 MTOR
centrosome 1 BCL2L1
nucleoplasm 2 MTOR, S100B
Cell membrane 3 ENO2, ITGAM, TNF
Cytoplasmic side 2 BCL2L1, MTOR
lamellipodium 1 PIK3CA
Golgi apparatus membrane 1 MTOR
cell surface 3 BMP2, ITGAM, TNF
Golgi apparatus 1 PTGS1
Golgi membrane 1 MTOR
lysosomal membrane 1 MTOR
mitochondrial inner membrane 1 BCL2L1
neuronal cell body 2 S100B, TNF
sarcolemma 1 ANXA5
Cytoplasm, cytosol 1 BCL2L1
Lysosome 1 MTOR
plasma membrane 6 BMP2, ENO2, F2, ITGAM, PIK3CA, TNF
synaptic vesicle membrane 1 BCL2L1
Membrane 5 ANXA5, BCL2, ENO2, ITGAM, MTOR
apical plasma membrane 1 IGFBP2
caveola 1 PTGS2
extracellular exosome 8 ANXA5, BMP3, COMP, ENO2, F2, IGFBP2, ITGAM, PTGS1
Lysosome membrane 1 MTOR
endoplasmic reticulum 3 BCL2, BCL2L1, PTGS2
extracellular space 11 BMP2, BMP3, COMP, ENO2, F2, IGF2, IGFBP2, IL6, ITGAM, S100B, TNF
perinuclear region of cytoplasm 2 PIK3CA, S100B
intercalated disc 1 PIK3CA
mitochondrion 2 BCL2, BCL2L1
protein-containing complex 3 BCL2, COMP, PTGS2
intracellular membrane-bounded organelle 3 BMP2, PTGS1, S100B
Microsome membrane 3 MTOR, PTGS1, PTGS2
TORC1 complex 1 MTOR
TORC2 complex 1 MTOR
Single-pass type I membrane protein 1 ITGAM
Secreted 7 BMP2, BMP3, F2, IGF2, IGFBP2, IL6, S100B
extracellular region 11 ANXA5, BMP2, BMP3, COMP, ELN, F2, IGF2, IGFBP2, IL6, S100B, TNF
Mitochondrion outer membrane 3 BCL2, BCL2L1, MTOR
Single-pass membrane protein 2 BCL2, BCL2L1
mitochondrial outer membrane 3 BCL2, BCL2L1, MTOR
Mitochondrion matrix 1 BCL2L1
mitochondrial matrix 1 BCL2L1
photoreceptor inner segment 1 ENO2
photoreceptor outer segment 1 PTGS1
Cytoplasm, cytoskeleton, microtubule organizing center, centrosome 1 BCL2L1
Cytoplasmic vesicle, secretory vesicle, synaptic vesicle membrane 1 BCL2L1
Nucleus membrane 2 BCL2, BCL2L1
Bcl-2 family protein complex 2 BCL2, BCL2L1
nuclear membrane 2 BCL2, BCL2L1
external side of plasma membrane 3 ANXA5, ITGAM, TNF
Secreted, extracellular space, extracellular matrix 2 COMP, ELN
perikaryon 1 ENO2
recycling endosome 1 TNF
Single-pass type II membrane protein 1 TNF
Membrane raft 2 ITGAM, TNF
pore complex 1 BCL2
focal adhesion 1 ANXA5
extracellular matrix 2 COMP, ELN
Nucleus, PML body 1 MTOR
PML body 1 MTOR
collagen-containing extracellular matrix 4 ANXA5, COMP, ELN, F2
Nucleus inner membrane 1 PTGS2
Nucleus outer membrane 1 PTGS2
nuclear inner membrane 1 PTGS2
nuclear outer membrane 1 PTGS2
ruffle 1 S100B
Zymogen granule membrane 1 ANXA5
neuron projection 2 PTGS1, PTGS2
phagocytic cup 1 TNF
blood microparticle 1 F2
nuclear envelope 1 MTOR
Endomembrane system 2 MTOR, PTGS1
specific granule membrane 1 ITGAM
tertiary granule membrane 1 ITGAM
myelin sheath 1 BCL2
plasma membrane raft 1 ITGAM
Golgi lumen 1 F2
endoplasmic reticulum lumen 3 F2, IL6, PTGS2
platelet alpha granule lumen 1 IGF2
phosphatidylinositol 3-kinase complex 1 PIK3CA
phosphatidylinositol 3-kinase complex, class IA 1 PIK3CA
vesicle membrane 1 ANXA5
Cytoplasmic vesicle, phagosome 1 MTOR
integrin complex 1 ITGAM
elastic fiber 1 ELN
[Tumor necrosis factor, soluble form]: Secreted 1 TNF
integrin alphaM-beta2 complex 1 ITGAM
interleukin-6 receptor complex 1 IL6
phosphopyruvate hydratase complex 1 ENO2
endothelial microparticle 1 ANXA5
BAD-BCL-2 complex 1 BCL2
BMP receptor complex 1 BMP2
phosphatidylinositol 3-kinase complex, class IB 1 PIK3CA
[Isoform Bcl-X(L)]: Mitochondrion inner membrane 1 BCL2L1
[C-domain 2]: Secreted 1 TNF
[Tumor necrosis factor, membrane form]: Membrane 1 TNF
[C-domain 1]: Secreted 1 TNF


文献列表

  • Kaifeng Fang, Li Wang, LuJia Chen, Tao Liu, Zhi Fang. Antiproliferative Effects of Matricine in Gemcitabine-Resistant Human Pancreatic Carcinoma Cells Are Mediated via Mitochondrial-Mediated Apoptosis, Inhibition of Cell Migration, Invasion Suppression, and Mammalian Target of Rapamycin (mTOR)-TOR/PI3K/AKT Signalling Pathway. Medical science monitor : international medical journal of experimental and clinical research. 2019 04; 25(?):2943-2949. doi: 10.12659/msm.914244. [PMID: 31005960]
  • Mehdi Sharifi-Rad, Jolanta Nazaruk, Letizia Polito, Maria Flaviana Bezerra Morais-Braga, Janaína Esmeraldo Rocha, Henrique Douglas Melo Coutinho, Bahare Salehi, Giulia Tabanelli, Chiara Montanari, María Del Mar Contreras, Zubaida Yousaf, William N Setzer, Deepa R Verma, Miquel Martorell, Antoni Sureda, Javad Sharifi-Rad. Matricaria genus as a source of antimicrobial agents: From farm to pharmacy and food applications. Microbiological research. 2018 Oct; 215(?):76-88. doi: 10.1016/j.micres.2018.06.010. [PMID: 30172312]
  • Frances Watkins, Barbara Pendry, Olivia Corcoran, Alberto Sanchez-Medina. Anglo-Saxon pharmacopoeia revisited: a potential treasure in drug discovery. Drug discovery today. 2011 Dec; 16(23-24):1069-75. doi: 10.1016/j.drudis.2011.07.002. [PMID: 21782968]
  • Cheryl Lans, Nancy Turner, Tonya Khan, Gerhard Brauer, Willi Boepple. Ethnoveterinary medicines used for ruminants in British Columbia, Canada. Journal of ethnobiology and ethnomedicine. 2007 Feb; 3(?):11. doi: 10.1186/1746-4269-3-11. [PMID: 17324258]
  • Mai Ramadan, Susanne Goeters, Bernhard Watzer, Eva Krause, Klaus Lohmann, Rudolf Bauer, Bernd Hempel, Peter Imming. Chamazulene carboxylic acid and matricin: a natural profen and its natural prodrug, identified through similarity to synthetic drug substances. Journal of natural products. 2006 Jul; 69(7):1041-5. doi: 10.1021/np0601556. [PMID: 16872141]
  • C S Kaiser, H Römpp, P C Schmidt. Supercritical carbon dioxide extraction of chamomile flowers: extraction efficiency, stability, and in-line inclusion of chamomile-carbon dioxide extract in beta-cyclodextrin. Phytochemical analysis : PCA. 2004 Jul; 15(4):249-56. doi: 10.1002/pca.775. [PMID: 15311845]
  • S Goeters, P Imming, G Pawlitzki, B Hempel. On the absolute configuration of matricin. Planta medica. 2001 Apr; 67(3):292-4. doi: 10.1055/s-2001-11998. [PMID: 11345709]