Nomilin (BioDeep_00000000261)

 

Secondary id: BioDeep_00001867480

human metabolite PANOMIX_OTCML-2023 Endogenous natural product


代谢物信息卡片


(1S,3AS,4AR,4BR,6AR,11S,11AR,11BR,13AS)-11-(ACETYLOXY)-1-(3-FURANYL)DECAHYDRO-4B,7,7,11A,13A-PENTAMETHYLOXIRENO(4,4A)-2-BENZOPYRAN(6,5-G)(2)BENZOXEPIN-3,5,9(3AH,4BH,6H)-TRIONE

化学式: C28H34O9 (514.2203)
中文名称: 诺米林
谱图信息: 最多检出来源 Homo sapiens(otcml) 44.74%

分子结构信息

SMILES: CC(=O)OC1CC(=O)OC(C)(C)C2CC(=O)C3(C)C(CCC4(C)C(c5ccoc5)OC(=O)C5OC543)C12C
InChI: InChI=1S/C28H34O9/c1-14(29)34-19-12-20(31)36-24(2,3)17-11-18(30)27(6)16(26(17,19)5)7-9-25(4)21(15-8-10-33-13-15)35-23(32)22-28(25,27)37-22/h8,10,13,16-17,19,21-22H,7,9,11-12H2,1-6H3/t16-,17+,19+,21+,22-,25+,26-,27+,28-/m1/s1

描述信息

Nomilin is a limonoid.
1-(Acetyloxy)-1,2-dihydroobacunoic acid e-lactone is a natural product found in Citrus latipes, Citrus hystrix, and other organisms with data available.
Constituent of grapefruit (Citrus paradisi). Nomilin is found in lemon, sweet orange, and citrus.
Nomilin is found in citrus. Nomilin is a constituent of grapefruit (Citrus paradisi)
Nomilin is a limonoid compound obtained from the extracts of citrus fruits. Nomilin is an anti-obesity and anti-hyperglycemic agent [1][2].
Nomilin is a limonoid compound obtained from the extracts of citrus fruits. Nomilin is an anti-obesity and anti-hyperglycemic agent [1][2].

同义名列表

19 个代谢物同义名

(1S,3AS,4AR,4BR,6AR,11S,11AR,11BR,13AS)-11-(ACETYLOXY)-1-(3-FURANYL)DECAHYDRO-4B,7,7,11A,13A-PENTAMETHYLOXIRENO(4,4A)-2-BENZOPYRAN(6,5-G)(2)BENZOXEPIN-3,5,9(3AH,4BH,6H)-TRIONE; (1S,3aS,4aR,4bR,6aR,11S,11aR,11bR,13aS)-1-(Furan-3-yl)-4b,7,7,11a,13a-pentamethyl-3,5,9-trioxohexadecahydrooxepino[4,3:3,4]benzo[1,2-f]oxireno[2,3-d]isochromen-11-yl acetate; (1R,2R,4S,7R,8S,11R,12R,13S,18R)-7-(furan-3-yl)-1,8,12,17,17-pentamethyl-5,15,20-trioxo-3,6,16-trioxapentacyclo[9.9.0.0?,?.0?,?.0??,??]icosan-13-yl acetate; 7-(Furan-3-yl)-1,8,12,17,17-pentamethyl-5,15,20-trioxo-3,6,16-trioxapentacyclo[9.9.0.0²,⁴.0²,⁸.0¹²,¹⁸]icosan-13-yl acetic acid; 7-(furan-3-yl)-1,8,12,17,17-pentamethyl-5,15,20-trioxo-3,6,16-trioxapentacyclo[9.9.0.0²,⁴.0²,⁸.0¹²,¹⁸]icosan-13-yl acetate; 1-(Acetyloxy)-1,2-dihydroobacunoic acid .epislon.-lactone; 1-(ACETYLOXY)-1,2-DIHYDROOBACUNOIC ACID .EPSILON.-LACTONE; Obacunoic acid, 1-(acetyloxy)-1,2-dihydro-, eta-lactone; 1-(Acetyloxy)-1,2-dihydroobacunoic acid eta-lactone; 1-(acetyloxy)-1,2-dihydroobacunoic acid e-lactone; (3-furyl-pentamethyl-trioxo-[?]yl) acetate; NOMILIN [MI]; KST-1A9791; AI3-37935; AC1L2HUM; AC1Q6OA3; Nomilin; G3L; Nomilin



数据库引用编号

26 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)

47 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 BCL2, CASP3, CASP9, CYP2E1, GPBAR1, HPGDS, MAPK14, MYD88, NQO1, PTGS2, TLR4, VEGFA
Peripheral membrane protein 2 CYP2E1, PTGS2
Endosome membrane 2 MYD88, TLR4
Endoplasmic reticulum membrane 4 BCL2, CYP1A2, CYP2E1, PTGS2
Nucleus 10 BCL2, CASP3, CASP9, GABPA, MAPK14, MYD88, NQO1, NR1H4, NR1I2, VEGFA
cytosol 7 BCL2, CASP3, CASP9, HPGDS, MAPK14, MYD88, NQO1
dendrite 1 NQO1
nuclear body 1 NR1I2
nucleoplasm 6 CASP3, GABPA, HPGDS, MAPK14, NR1H4, NR1I2
RNA polymerase II transcription regulator complex 1 NR1H4
Cell membrane 4 GPBAR1, GPRC5A, TLR4, TNF
Multi-pass membrane protein 2 GPBAR1, GPRC5A
Synapse 1 NQO1
cell surface 4 MYD88, TLR4, TNF, VEGFA
glutamatergic synapse 2 CASP3, MAPK14
Golgi apparatus 1 VEGFA
Golgi membrane 1 INS
mitochondrial inner membrane 1 CYP2E1
neuronal cell body 3 CASP3, NQO1, TNF
Cytoplasm, cytosol 1 NQO1
plasma membrane 5 GPBAR1, GPRC5A, MYD88, TLR4, TNF
Membrane 4 BCL2, NQO1, TLR4, VEGFA
caveola 1 PTGS2
extracellular exosome 1 GPRC5A
endoplasmic reticulum 3 BCL2, PTGS2, VEGFA
extracellular space 3 INS, TNF, VEGFA
perinuclear region of cytoplasm 1 TLR4
adherens junction 1 VEGFA
mitochondrion 3 BCL2, CASP9, MAPK14
protein-containing complex 4 BCL2, CASP9, MYD88, PTGS2
intracellular membrane-bounded organelle 4 CYP1A2, CYP2E1, GPRC5A, HPGDS
Microsome membrane 3 CYP1A2, CYP2E1, PTGS2
postsynaptic density 1 CASP3
Single-pass type I membrane protein 1 TLR4
Secreted 2 INS, VEGFA
extracellular region 4 INS, MAPK14, TNF, VEGFA
Mitochondrion outer membrane 1 BCL2
Single-pass membrane protein 1 BCL2
mitochondrial outer membrane 1 BCL2
transcription regulator complex 1 NR1I2
Nucleus membrane 1 BCL2
Bcl-2 family protein complex 1 BCL2
nuclear membrane 1 BCL2
external side of plasma membrane 2 TLR4, TNF
Secreted, extracellular space, extracellular matrix 1 VEGFA
nucleolus 1 GPRC5A
Early endosome 1 TLR4
recycling endosome 1 TNF
Single-pass type II membrane protein 1 TNF
vesicle 1 GPRC5A
Mitochondrion inner membrane 1 CYP2E1
Membrane raft 1 TNF
pore complex 1 BCL2
extracellular matrix 1 VEGFA
secretory granule 1 VEGFA
nuclear speck 1 MAPK14
Nucleus inner membrane 1 PTGS2
Nucleus outer membrane 1 PTGS2
nuclear inner membrane 1 PTGS2
nuclear outer membrane 1 PTGS2
Cell projection, ruffle 1 TLR4
ruffle 1 TLR4
receptor complex 4 GPBAR1, GPRC5A, NR1H4, TLR4
neuron projection 1 PTGS2
chromatin 3 GABPA, NR1H4, NR1I2
phagocytic cup 2 TLR4, TNF
[Isoform 3]: Nucleus 1 NR1H4
spindle pole 1 MAPK14
endosome lumen 1 INS
Cytoplasmic vesicle membrane 1 GPRC5A
euchromatin 1 NR1H4
myelin sheath 1 BCL2
intermediate filament cytoskeleton 1 NR1I2
lipopolysaccharide receptor complex 1 TLR4
ficolin-1-rich granule lumen 1 MAPK14
secretory granule lumen 2 INS, MAPK14
Golgi lumen 1 INS
endoplasmic reticulum lumen 2 INS, PTGS2
platelet alpha granule lumen 1 VEGFA
transport vesicle 1 INS
Endoplasmic reticulum-Golgi intermediate compartment membrane 1 INS
apoptosome 1 CASP9
[Isoform 2]: Nucleus 1 NR1H4
[Isoform 1]: Nucleus 1 NR1H4
extrinsic component of cytoplasmic side of plasma membrane 1 MYD88
death-inducing signaling complex 1 CASP3
extrinsic component of plasma membrane 1 MYD88
[Isoform 4]: Nucleus 1 NR1H4
[Tumor necrosis factor, soluble form]: Secreted 1 TNF
BAD-BCL-2 complex 1 BCL2
[N-VEGF]: Cytoplasm 1 VEGFA
[VEGFA]: Secreted 1 VEGFA
[Isoform L-VEGF189]: Endoplasmic reticulum 1 VEGFA
[Isoform VEGF121]: Secreted 1 VEGFA
[Isoform VEGF165]: Secreted 1 VEGFA
VEGF-A complex 1 VEGFA
caspase complex 1 CASP9
[C-domain 2]: Secreted 1 TNF
[Tumor necrosis factor, membrane form]: Membrane 1 TNF
[C-domain 1]: Secreted 1 TNF


文献列表

  • Yongli Han, Lingling Luo, Hongli Li, Lijun Zhang, Yingxuan Yan, Minglv Fang, Jing Yu, Xiaoyan Gao, Ying Liu, Cheng Huang, Shengjie Fan. Nomilin and its analogue obacunone alleviate NASH and hepatic fibrosis in mice via enhancing antioxidant and anti-inflammation capacity. BioFactors (Oxford, England). 2023 Jul; ?(?):. doi: 10.1002/biof.1987. [PMID: 37401768]
  • Shengjie Fan, Yingxuan Yan, Ying Xia, Zhenyu Zhou, Lingling Luo, Mengnan Zhu, Yongli Han, Deqiang Yao, Lijun Zhang, Minglv Fang, Lina Peng, Jing Yu, Ying Liu, Xiaoyan Gao, Huida Guan, Hongli Li, Changhong Wang, Xiaojun Wu, Huanhu Zhu, Yu Cao, Cheng Huang. Pregnane X receptor agonist nomilin extends lifespan and healthspan in preclinical models through detoxification functions. Nature communications. 2023 Jun; 14(1):3368. doi: 10.1038/s41467-023-39118-9. [PMID: 37291126]
  • Yuting Chen, Song Guo, Guirong Chen, Chang Liu, Mingbo Zhang, Xiaobo Wang. Nomilin attenuates lipopolysaccharide-induced inflammatory response by binding with myeloid differentiation protein-2. Combinatorial chemistry & high throughput screening. 2023 Apr; ?(?):. doi: 10.2174/1386207326666230418112827. [PMID: 37076464]
  • Zhenyu Zhou, Yingxuan Yan, Hongli Li, Yaru Feng, Cheng Huang, Shengjie Fan. Nomilin and Its Analogues in Citrus Fruits: A Review of Its Health Promotion Effects and Potential Application in Medicine. Molecules (Basel, Switzerland). 2022 Dec; 28(1):. doi: 10.3390/molecules28010269. [PMID: 36615463]
  • Maria Laura Bellone, Cesar Muñoz Camero, Maria Giovanna Chini, Fabrizio Dal Piaz, Vanessa Hernandez, Giuseppe Bifulco, Nunziatina De Tommasi, Alessandra Braca. Limonoids from Guarea guidonia and Cedrela odorata: Heat Shock Protein 90 (Hsp90) Modulator Properties of Chisomicine D. Journal of natural products. 2021 03; 84(3):724-737. doi: 10.1021/acs.jnatprod.0c01217. [PMID: 33661631]
  • Yulin Ren, A Douglas Kinghorn. Development of Potential Antitumor Agents from the Scaffolds of Plant-Derived Terpenoid Lactones. Journal of medicinal chemistry. 2020 12; 63(24):15410-15448. doi: 10.1021/acs.jmedchem.0c01449. [PMID: 33289552]
  • Fusheng Wang, Xiaohan Yu, Xiaona Liu, Wanxia Shen, Shiping Zhu, Xiaochun Zhao. Temporal and spatial variations on accumulation of nomilin and limonin in the pummelos. Plant physiology and biochemistry : PPB. 2016 Sep; 106(?):23-9. doi: 10.1016/j.plaphy.2016.04.039. [PMID: 27135815]
  • Yuepiao Cai, Shuangshuang Zhang, Qiqi Wang, Hao Sun, Mi Zhou, Shuping Hu, Zheng Xiang. A Rapid, Selective and Sensitive UPLC-MS/MS Method for Quantification of Nomilin in Rat Plasma and Its Application in a Pharmacokinetic Study. Planta medica. 2016 Feb; 82(3):224-9. doi: 10.1055/s-0035-1558157. [PMID: 26544116]
  • Cuihua Liu, Fuhua Yan, Huijun Gao, Min He, Zhuang Wang, Yunjiang Cheng, Xiuxin Deng, Juan Xu. Features of citrus terpenoid production as revealed by carotenoid, limonoid and aroma profiles of two pummelos (Citrus maxima) with different flesh color. Journal of the science of food and agriculture. 2015 Jan; 95(1):111-9. doi: 10.1002/jsfa.6689. [PMID: 24723118]
  • Yu Xiang, Jinping Cao, Fenglei Luo, Dengliang Wang, Wei Chen, Xian Li, Chongde Sun, Kunsong Chen. Simultaneous purification of limonin, nomilin and isoobacunoic acid from pomelo fruit (Citrus grandis) segment membrane. Journal of food science. 2014 Oct; 79(10):C1956-63. doi: 10.1111/1750-3841.12581. [PMID: 25212475]
  • Shaojie Li, Zhuang Wang, Fan Ding, Da Sun, Zhaocheng Ma, Yunjiang Cheng, Juan Xu. Content changes of bitter compounds in 'Guoqing No.1' Satsuma mandarin (Citrus unshiu Marc.) during fruit development of consecutive 3 seasons. Food chemistry. 2014 Feb; 145(?):963-9. doi: 10.1016/j.foodchem.2013.09.040. [PMID: 24128570]
  • Ryuichiro Sato. Nomilin as an anti-obesity and anti-hyperglycemic agent. Vitamins and hormones. 2013; 91(?):425-39. doi: 10.1016/b978-0-12-407766-9.00018-3. [PMID: 23374727]
  • Poyil Pratheeshkumar, Tharakan J Raphael, Girija Kuttan. Nomilin inhibits metastasis via induction of apoptosis and regulates the activation of transcription factors and the cytokine profile in B16F-10 cells. Integrative cancer therapies. 2012 Mar; 11(1):48-60. doi: 10.1177/1534735411403307. [PMID: 21665879]
  • Poyil Pratheeshkumar, Girija Kuttan. Nomilin inhibits tumor-specific angiogenesis by downregulating VEGF, NO and proinflammatory cytokine profile and also by inhibiting the activation of MMP-2 and MMP-9. European journal of pharmacology. 2011 Oct; 668(3):450-8. doi: 10.1016/j.ejphar.2011.07.029. [PMID: 21839074]
  • Eri Ono, Jun Inoue, Tsutomu Hashidume, Makoto Shimizu, Ryuichiro Sato. Anti-obesity and anti-hyperglycemic effects of the dietary citrus limonoid nomilin in mice fed a high-fat diet. Biochemical and biophysical research communications. 2011 Jul; 410(3):677-81. doi: 10.1016/j.bbrc.2011.06.055. [PMID: 21693102]
  • Jose L Perez, Guddarangavvanahally K Jayaprakasha, Adriana Cadena, Elvia Martinez, Hassan Ahmad, Bhimanagouda S Patil. In vivo induction of phase II detoxifying enzymes, glutathione transferase and quinone reductase by citrus triterpenoids. BMC complementary and alternative medicine. 2010 Sep; 10(?):51. doi: 10.1186/1472-6882-10-51. [PMID: 20846448]
  • Anne Plotto, Elizabeth Baldwin, Greg McCollum, John Manthey, Jan Narciso, Mike Irey. Effect of Liberibacter infection (huanglongbing or 'greening' disease) of citrus on orange juice flavor quality by sensory evaluation. Journal of food science. 2010 May; 75(4):S220-30. doi: 10.1111/j.1750-3841.2010.01580.x. [PMID: 20546425]
  • Lucia Battinelli, Fabio Mengoni, Miriam Lichtner, Gabriela Mazzanti, Antonina Saija, Claudio Maria Mastroianni, Vincenzo Vullo. Effect of limonin and nomilin on HIV-1 replication on infected human mononuclear cells. Planta medica. 2003 Oct; 69(10):910-3. doi: 10.1055/s-2003-45099. [PMID: 14648393]
  • Giuseppe Ruberto, Agatino Renda, Corrado Tringali, Edoardo M Napoli, Monique S J Simmonds. Citrus limonoids and their semisynthetic derivatives as antifeedant agents against Spodoptera frugiperda larvae. A structure-activity relationship study. Journal of agricultural and food chemistry. 2002 Nov; 50(23):6766-74. doi: 10.1021/jf020607u. [PMID: 12405773]
  • Q Tian, E G Miller, H Ahmad, L Tang, B S Patil. Differential inhibition of human cancer cell proliferation by citrus limonoids. Nutrition and cancer. 2001; 40(2):180-4. doi: 10.1207/s15327914nc402_15. [PMID: 11962254]
  • F Castelli, N Giuffrida, C Tringali, G Ruberto. Calorimetric evidence of differentiated transport of limonin and nomilin through biomembranes. Journal of agricultural and food chemistry. 2000 Sep; 48(9):4123-7. doi: 10.1021/jf991282t. [PMID: 10995325]
  • G T Tan, J M Pezzuto, A D Kinghorn, S H Hughes. Evaluation of natural products as inhibitors of human immunodeficiency virus type 1 (HIV-1) reverse transcriptase. Journal of natural products. 1991 Jan; 54(1):143-54. doi: 10.1021/np50073a012. [PMID: 1710653]
  • E G Miller, R Fanous, F Rivera-Hidalgo, W H Binnie, S Hasegawa, L K Lam. The effect of citrus limonoids on hamster buccal pouch carcinogenesis. Carcinogenesis. 1989 Aug; 10(8):1535-7. doi: 10.1093/carcin/10.8.1535. [PMID: 2502323]
  • R Geigy, L Jenni, M Kauffmann, R J Onyango, N Weiss. Identification of T. brucei-subgroup strains isolated from game. Acta tropica. 1975; 32(3):190-205. doi: NULL. [PMID: 1983]