Lactopicrin (BioDeep_00001867589)

Main id: BioDeep_00000001041

 

PANOMIX_OTCML-2023


代谢物信息卡片


Benzeneacetic acid, 4-hydroxy-, 2,3,3a,4,5,7,9a,9b-octahydro-9-(hydroxymethyl)-6-methyl-3-methylene-2,7-dioxoazuleno(4,5-b)furan-4-yl ester, (3aR-(3aalpha,4alpha,9aalpha,9bbeta))-

化学式: C23H22O7 (410.1365)
中文名称:
谱图信息: 最多检出来源 () 0%

分子结构信息

SMILES: CC1=C2C(C3C(C(C1)OC(=O)CC4=CC=C(C=C4)O)C(=C)C(=O)O3)C(=CC2=O)CO
InChI: InChI=1S/C23H22O7/c1-11-7-17(29-18(27)8-13-3-5-15(25)6-4-13)20-12(2)23(28)30-22(20)21-14(10-24)9-16(26)19(11)21/h3-6,9,17,20-22,24-25H,2,7-8,10H2,1H3/t17-,20+,21-,22-/m0/s1

描述信息

Lactucopicrin is an azulenofuran, a cyclic terpene ketone, an enone, a member of phenols, a sesquiterpene lactone and a primary alcohol. It has a role as a plant metabolite, a sedative and an antimalarial. It is functionally related to a 4-hydroxyphenylacetic acid and a lactucin.
Lactupicrin is a natural product found in Cichorium endivia, Cichorium spinosum, and other organisms with data available.
Lactupicrin (Lactucopicrin) is a characteristic bitter sesquiterpene lactone that can relieve pain. Lactupicrin exhibits atheroprotective effect[1][2].
Lactupicrin (Lactucopicrin) is a characteristic bitter sesquiterpene lactone that can relieve pain. Lactupicrin exhibits atheroprotective effect[1][2].

同义名列表

9 个代谢物同义名

Benzeneacetic acid, 4-hydroxy-, 2,3,3a,4,5,7,9a,9b-octahydro-9-(hydroxymethyl)-6-methyl-3-methylene-2,7-dioxoazuleno(4,5-b)furan-4-yl ester, (3aR-(3aalpha,4alpha,9aalpha,9bbeta))-; [(3aR,4S,9aS,9bR)-9-(hydroxymethyl)-6-methyl-3-methylidene-2,7-dioxo-4,5,9a,9b-tetrahydro-3aH-azuleno[4,5-b]furan-4-yl] 2-(4-hydroxyphenyl)acetate; 9-(Hydroxymethyl)-6-methyl-3-methylidene-2,7-dioxo-2,3,3a,4,5,7,9a,9b-octahydroazuleno[4,5-b]furan-4-yl (4-hydroxyphenyl)acetate; MEGxp0_000597; ACon1_000375; Lactopicrin; Lactupicrin; Lactucopicrin; Lactupicrin



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)

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 ADAM17, ANXA5, APOE, BCL2, BDNF, CASP3, CDK2, EIF2AK3, SQSTM1
Peripheral membrane protein 2 ANXA5, GORASP1
Endoplasmic reticulum membrane 2 BCL2, EIF2AK3
Cytoplasmic vesicle, autophagosome 1 SQSTM1
Nucleus 8 APOE, ATF1, BCL2, CASP3, CDK2, EIF2AK3, PARP1, SQSTM1
autophagosome 1 SQSTM1
cytosol 9 ADAM17, ANXA5, BCL2, CASP3, CDK2, EIF2AK3, NGF, PARP1, SQSTM1
dendrite 4 APOE, BDNF, CHRM1, NGF
nuclear body 1 PARP1
centrosome 1 CDK2
nucleoplasm 5 ATF1, CASP3, CDK2, PARP1, SQSTM1
RNA polymerase II transcription regulator complex 1 ATF1
Cell membrane 3 ADAM17, CHRM1, VCAM1
Cytoplasmic side 1 GORASP1
Multi-pass membrane protein 1 CHRM1
Golgi apparatus membrane 1 GORASP1
Synapse 1 CHRM1
cell surface 3 ADAM17, ICAM1, VCAM1
glutamatergic synapse 4 APOE, CASP3, CHRM1, SQSTM1
Golgi apparatus 3 APOE, GORASP1, VCAM1
Golgi membrane 2 ADAM17, GORASP1
mitochondrial inner membrane 1 HADHA
neuronal cell body 2 APOE, CASP3
presynaptic membrane 1 CHRM1
sarcolemma 2 ANXA5, VCAM1
synaptic vesicle 2 BDNF, NGF
Cytoplasm, cytosol 2 PARP1, SQSTM1
Lysosome 1 SQSTM1
endosome 1 CDK2
plasma membrane 5 ADAM17, APOE, CHRM1, ICAM1, VCAM1
Membrane 10 ADAM17, ANXA5, APOE, BCL2, BDNF, CHRM1, EIF2AK3, ICAM1, PARP1, VCAM1
apical plasma membrane 1 ADAM17
axon 2 BDNF, NGF
extracellular exosome 5 ANXA5, APOE, ICAM1, SQSTM1, VCAM1
endoplasmic reticulum 5 APOE, BCL2, EIF2AK3, SQSTM1, VCAM1
extracellular space 7 APOE, BDNF, ICAM1, IL10, IL4, NGF, VCAM1
perinuclear region of cytoplasm 2 BDNF, EIF2AK3
Schaffer collateral - CA1 synapse 1 CHRM1
mitochondrion 4 BCL2, HADHA, PARP1, SQSTM1
protein-containing complex 2 BCL2, PARP1
intracellular membrane-bounded organelle 1 SQSTM1
filopodium 1 VCAM1
postsynaptic density 1 CASP3
Single-pass type I membrane protein 4 ADAM17, EIF2AK3, ICAM1, VCAM1
Secreted 5 APOE, BDNF, IL10, IL4, NGF
extracellular region 6 ANXA5, APOE, BDNF, IL10, IL4, NGF
Mitochondrion outer membrane 1 BCL2
Single-pass membrane protein 1 BCL2
mitochondrial outer membrane 1 BCL2
transcription regulator complex 2 CDK2, PARP1
Cytoplasm, cytoskeleton, microtubule organizing center, centrosome 1 CDK2
Nucleus membrane 1 BCL2
Bcl-2 family protein complex 1 BCL2
nuclear membrane 1 BCL2
external side of plasma membrane 3 ANXA5, ICAM1, VCAM1
Endosome, multivesicular body 1 APOE
Extracellular vesicle 1 APOE
Secreted, extracellular space, extracellular matrix 1 APOE
chylomicron 1 APOE
high-density lipoprotein particle 1 APOE
low-density lipoprotein particle 1 APOE
multivesicular body 1 APOE
very-low-density lipoprotein particle 1 APOE
actin cytoskeleton 1 ADAM17
cytoplasmic vesicle 1 SQSTM1
nucleolus 1 PARP1
P-body 1 SQSTM1
Early endosome 2 APOE, VCAM1
apical part of cell 1 VCAM1
postsynaptic membrane 1 CHRM1
Mitochondrion inner membrane 1 HADHA
Membrane raft 2 ADAM17, ICAM1
pore complex 1 BCL2
focal adhesion 2 ANXA5, ICAM1
cis-Golgi network 1 GORASP1
extracellular matrix 1 APOE
mitochondrial nucleoid 1 HADHA
Nucleus, PML body 1 SQSTM1
PML body 1 SQSTM1
collagen-containing extracellular matrix 3 ANXA5, APOE, ICAM1
Postsynaptic cell membrane 1 CHRM1
Cytoplasm, myofibril, sarcomere 1 SQSTM1
Late endosome 1 SQSTM1
sarcomere 1 SQSTM1
Zymogen granule membrane 1 ANXA5
chromatin 2 ATF1, PARP1
Chromosome 1 PARP1
podosome 1 VCAM1
Secreted, extracellular space 1 APOE
Nucleus, nucleolus 1 PARP1
nuclear replication fork 1 PARP1
chromosome, telomeric region 2 CDK2, PARP1
blood microparticle 1 APOE
sperm midpiece 1 SQSTM1
site of double-strand break 1 PARP1
nuclear envelope 2 CDK2, PARP1
endosome lumen 1 NGF
microvillus 1 VCAM1
phagophore assembly site 1 SQSTM1
Melanosome 1 APOE
myelin sheath 1 BCL2
Golgi lumen 1 NGF
endoplasmic reticulum lumen 3 ADAM17, APOE, BDNF
male germ cell nucleus 1 CDK2
axon terminus 1 CHRM1
mitochondrial fatty acid beta-oxidation multienzyme complex 1 HADHA
Endoplasmic reticulum-Golgi intermediate compartment membrane 1 GORASP1
postsynaptic density membrane 1 CHRM1
immunological synapse 1 ICAM1
aggresome 1 SQSTM1
Golgi apparatus, cis-Golgi network membrane 1 GORASP1
vesicle membrane 1 ANXA5
clathrin-coated endocytic vesicle membrane 1 APOE
Cajal body 1 CDK2
synaptic cleft 1 APOE
protein-DNA complex 1 PARP1
death-inducing signaling complex 1 CASP3
intracellular non-membrane-bounded organelle 1 SQSTM1
condensed chromosome 1 CDK2
Lewy body 1 SQSTM1
Nucleus, Cajal body 1 CDK2
Preautophagosomal structure 1 SQSTM1
X chromosome 1 CDK2
Y chromosome 1 CDK2
site of DNA damage 1 PARP1
cyclin-dependent protein kinase holoenzyme complex 1 CDK2
discoidal high-density lipoprotein particle 1 APOE
cholinergic synapse 1 CHRM1
cyclin E1-CDK2 complex 1 CDK2
cyclin E2-CDK2 complex 1 CDK2
endocytic vesicle lumen 1 APOE
chylomicron remnant 1 APOE
intermediate-density lipoprotein particle 1 APOE
lipoprotein particle 1 APOE
multivesicular body, internal vesicle 1 APOE
Autolysosome 1 SQSTM1
inclusion body 1 SQSTM1
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
ATF4-CREB1 transcription factor complex 1 ATF1
ATF1-ATF4 transcription factor complex 1 ATF1
[Vascular cell adhesion protein 1]: Cell membrane 1 VCAM1
[Soluble Vascular Cell Adhesion Molecule-1]: Secreted 1 VCAM1
alpha9-beta1 integrin-vascular cell adhesion molecule-1 complex 1 VCAM1
cyclin A2-CDK2 complex 1 CDK2
[Neurotrophic factor BDNF precursor form]: Secreted 1 BDNF
cyclin A1-CDK2 complex 1 CDK2
amphisome 1 SQSTM1


文献列表

  • Yilizere Aibaidula, Mutalifu Aimaiti, Huiwen Tan, Bingting Chen, Jian Yang, Xiaoli Ma. Lactucin & Lactucopicrin ameliorates FFA-induced steatosis in HepG2 cells via modulating lipid metabolism. Journal of pharmacological sciences. 2022 Oct; 150(2):110-122. doi: 10.1016/j.jphs.2022.07.007. [PMID: 36055749]
  • Qing Li, Xiuping Liu, Xu Zhang, Yushi Du, Guanyu Chen, Panyin Xiang, Wenhua Ling, Dongliang Wang. Terpene Lactucopicrin Limits Macrophage Foam Cell Formation by a Reduction of Lectin-Like Oxidized Low-Density Lipoprotein Receptor-1 in Lipid Rafts. Molecular nutrition & food research. 2022 02; 66(4):e2100905. doi: 10.1002/mnfr.202100905. [PMID: 34932892]
  • Luanying He, Hui Weng, Qing Li, Guojun Shi, Xiuping Liu, Yushi Du, Jiakun Zheng, Wenhua Ling, Dongliang Wang. Lactucopicrin Inhibits Cytoplasmic Dynein-Mediated NF-κB Activation in Inflammated Macrophages and Alleviates Atherogenesis in Apolipoprotein E-Deficient Mice. Molecular nutrition & food research. 2021 02; 65(4):e2000989. doi: 10.1002/mnfr.202000989. [PMID: 33377310]
  • Carlos J García, David Beltrán, Francisco A Tomás-Barberán. Human Gut Microbiota Metabolism of Dietary Sesquiterpene Lactones: Untargeted Metabolomics Study of Lactucopicrin and Lactucin Conversion In Vitro and In Vivo. Molecular nutrition & food research. 2020 11; 64(21):e2000619. doi: 10.1002/mnfr.202000619. [PMID: 32970341]
  • Hyo-Won Kim, Hyung Joo Suh, Hyeon-Son Choi, Ki-Bae Hong, Kyungae Jo. Effectiveness of the Sleep Enhancement by Green Romaine Lettuce (Lactuca sativa) in a Rodent Model. Biological & pharmaceutical bulletin. 2019; 42(10):1726-1732. doi: 10.1248/bpb.b19-00454. [PMID: 31582660]
  • A Wesołowska, A Nikiforuk, K Michalska, W Kisiel, E Chojnacka-Wójcik. Analgesic and sedative activities of lactucin and some lactucin-like guaianolides in mice. Journal of ethnopharmacology. 2006 Sep; 107(2):254-8. doi: 10.1016/j.jep.2006.03.003. [PMID: 16621374]
  • G SCHENCK, H LOTH, W REUBERT. [Research on the preparation of lactucin and lactucopicrin from Lactuca virosa plants. 15. On the enzymatic and non-enzymatic oxidation of therapeutically active plant substances]. Archiv der Pharmazie und Berichte der Deutschen Pharmazeutischen Gesellschaft. 1961 Jan; 294/66(?):17-24. doi: 10.1002/ardp.19612940105. [PMID: 13747469]