Narcissin (BioDeep_00000000158)

 

Secondary id: BioDeep_00000018466

natural product PANOMIX_OTCML-2023


代谢物信息卡片


5,7-Dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-3-(((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-((((2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)methyl)tetrahydro-2H-pyran-2-yl)oxy)-4H-chromen-4-one

化学式: C28H32O16 (624.169)
中文名称: 水仙甙, 水仙苷
谱图信息: 最多检出来源 Viridiplantae(plant) 21.86%

分子结构信息

SMILES: c1(cc(c2c(c1)oc(c(c2=O)O[C@H]1[C@H]([C@@H]([C@H]([C@H](O1)CO[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)C)O)O)O)O)O)O)c1ccc(c(c1)OC)O)O)O
InChI: InChI=1/C28H32O16/c1-9-18(32)21(35)23(37)27(41-9)40-8-16-19(33)22(36)24(38)28(43-16)44-26-20(34)17-13(31)6-11(29)7-15(17)42-25(26)10-3-4-12(30)14(5-10)39-2/h3-7,9,16,18-19,21-24,27-33,35-38H,8H2,1-2H3/t9-,16+,18-,19+,21+,22-,23+,24+,27+,28-/m0/s1

描述信息

Isorhamnetin-3-O-rutinoside is a disaccharide derivative, a glycosyloxyflavone, a monomethoxyflavone and a trihydroxyflavone.
Narcissoside is a natural product found in Phoenix canariensis, Scolymus hispanicus, and other organisms with data available.
See also: Ginkgo (part of); Calendula Officinalis Flower (part of).
Acquisition and generation of the data is financially supported in part by CREST/JST.
Narcissin (Narcissoside), a flavonol glycoside, exhibits evident scavenging activity against both authentic ONOO-?and SIN-1-derived ONOO- with IC50s?of 3.5 and 9.6 μM, respectively[1].
Narcissin (Narcissoside), a flavonol glycoside, exhibits evident scavenging activity against both authentic ONOO-?and SIN-1-derived ONOO- with IC50s?of 3.5 and 9.6 μM, respectively[1].

同义名列表

41 个代谢物同义名

5,7-Dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-3-(((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-((((2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)methyl)tetrahydro-2H-pyran-2-yl)oxy)-4H-chromen-4-one; 5,7-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-3-((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(((2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyltetrahydro-2H-pyran-2-yloxy)methyl)tetrahydro-2H-pyran-2-yloxy)-4H-chromen-4-one; 5,7-dihydroxy-2-(4-hydroxy-3-methoxy-phenyl)-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyl-tetrahydropyran-2-yl]oxymethyl]tetrahydropyran-2-yl]oxy-chromen-4-one; 5,7-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-3-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-({[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}methyl)oxan-2-yl]oxy}-4H-chromen-4-one; 5,7-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxymethyl]oxan-2-yl]oxychromen-4-one; 5,7-Dihydroxy-2-(4-hydroxy-3-methoxy-phenyl)-3-[3,4,5-trihydroxy-6-(3,4,5-trihydroxy-6-methyl-tetrahydro-pyran-2-yloxymethyl)-tetrahydro-pyran-2-yloxy]-1-benzopyran-4-one; 4H-1-BENZOPYRAN-4-ONE, 3-996-O-(6-DEOXY-.ALPHA.-L-MANNOPYRANOSYL)-.BETA.-D-GLUCOPYRANOSYL)OXY)-5,7-DIHYDROXY-2-(4-HYDROXY-3-METHOXYPHENYL)-; 4H-1-Benzopyran-4-one, 3-((6-O-(6-deoxy-alpha-L-mannopyranosyl)-beta-D-glucopyranosyl)oxy)-5,7-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-; 4H-1-BENZOPYRAN-4-ONE, 3-996-O-(6-DEOXY-alpha-L-MANNOPYRANOSYL)-beta-D-GLUCOPYRANOSYL)OXY)-5,7-DIHYDROXY-2-(4-HYDROXY-3-METHOXYPHENYL)-; 4H-Benzopyran-4-one, 3-((6-O-(6-deoxy-alpha-L-mannopyranosyl)-beta-D-glucopyranosyl)oxy)-5,7-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-; 4H-1-Benzopyran-4-one,3-[[6-O-(6-deoxy-a-L-mannopyranosyl)-b-D-glucopyranosyl]oxy]-5,7-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-; ISORHAMNETIN 3-O-.BETA.-D-(6-O-.ALPHA.-L-RHAMNOSYL)GLUCOSIDE; ISORHAMNETIN-3-O-RUTINOSIDE (CONSTITUENT OF GINKGO) [DSC]; ISORHAMNETIN-3-O-RUTINOSIDE (CONSTITUENT OF GINKGO); ISORHAMNETIN-3-O-RUTINOSIDE (USP-RS); ISORHAMNETIN-3-O-RUTINOSIDE [USP-RS]; ISORHAMENTIN-3-O-.BETA.-D-RUTINOSIDE; ISORHAMNETIN 3-O-.BETA.-RUTINOSIDE; ISORHAMNETIN 3-.BETA.-O-RUTINOSIDE; ISORHAMNETIN 3-O-beta-RUTINOSIDE; ISORHAMNETIN 3-beta-O-RUTINOSIDE; 3-O-METHYLQUERCETIN 3-RUTINOSIDE; Isorhamnetin 3-rhamnoglucoside; Isorhamnetin 3-O-rutinoside; Isorhamnetin-3-O-rutinoside; Isorhamnetin-3-rutinoside; Isorhamnetin 3-rutinoside; Isprhamnetin-3-rutinoside; 3-O-RUTINOSYLISORHAMNETIN; Isorhamnetin3-rutinoside; narcissin flavonol; UNII-N4AX11L1TF; Defensin beta-2; Narcissoside; N4AX11L1TF; C28H32O16; Narcissin; Isorhamnetin-3-O-beta-D-rutinoside; 3-O-Rutinosyl-isorhamnetin; 3- [ [ 6-O- (6-Deoxy-alpha-L-mannopyranosyl) -beta-D-glucopyranosyl ] oxy ] -5,7-dihydroxy-2- (4-hydroxy-3-methoxyphenyl) -4H-1-benzopyran-4-one; Isorhamnetin-3-O-hexoside



数据库引用编号

52 个数据库交叉引用编号

分类词条

相关代谢途径

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代谢反应

0 个相关的代谢反应过程信息。

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BioCyc(0)

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INOH(0)

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250 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 8 ABCB1, AIMP2, CASP3, CASP8, KEAP1, MAPK8, PPARG, TYR
Peripheral membrane protein 1 ACHE
Endoplasmic reticulum membrane 1 HMOX1
Nucleus 10 ACHE, AIMP2, CASP3, CASP8, GABPA, HMOX1, KEAP1, MAPK8, PARP1, PPARG
cytosol 8 AIMP2, CASP3, CASP8, HMOX1, KEAP1, MAPK8, PARP1, PPARG
nuclear body 1 PARP1
nucleoplasm 8 CASP3, CASP8, GABPA, HMOX1, KEAP1, MAPK8, PARP1, PPARG
RNA polymerase II transcription regulator complex 1 PPARG
Cell membrane 4 ABCB1, ACHE, TNF, TRPV1
Cytoplasmic side 1 HMOX1
lamellipodium 1 CASP8
Multi-pass membrane protein 2 ABCB1, TRPV1
Synapse 2 ACHE, MAPK8
cell surface 3 ABCB1, ACHE, TNF
glutamatergic synapse 1 CASP3
Golgi apparatus 1 ACHE
Golgi membrane 1 INS
lysosomal membrane 1 GAA
neuromuscular junction 1 ACHE
neuronal cell body 3 CASP3, TNF, TRPV1
Cytoplasm, cytosol 2 AIMP2, PARP1
Lysosome 2 GAA, TYR
plasma membrane 5 ABCB1, ACHE, GAA, TNF, TRPV1
Membrane 7 ABCB1, ACHE, AIMP2, GAA, HMOX1, PARP1, TRPV1
apical plasma membrane 1 ABCB1
axon 1 MAPK8
extracellular exosome 2 ABCB1, GAA
Lysosome membrane 1 GAA
endoplasmic reticulum 2 HMOX1, KEAP1
extracellular space 7 ACHE, HMOX1, IL2, IL6, INS, PNLIP, TNF
lysosomal lumen 1 GAA
perinuclear region of cytoplasm 4 ACHE, HMOX1, PPARG, TYR
mitochondrion 2 CASP8, PARP1
protein-containing complex 2 CASP8, PARP1
intracellular membrane-bounded organelle 3 GAA, PPARG, TYR
postsynaptic density 1 CASP3
Single-pass type I membrane protein 1 TYR
Secreted 6 ACHE, GAA, IL2, IL6, INS, PNLIP
extracellular region 7 ACHE, GAA, IL2, IL6, INS, PNLIP, TNF
mitochondrial outer membrane 2 CASP8, HMOX1
Extracellular side 1 ACHE
transcription regulator complex 1 PARP1
centriolar satellite 1 KEAP1
external side of plasma membrane 2 TNF, TRPV1
nucleolus 1 PARP1
Melanosome membrane 1 TYR
midbody 1 KEAP1
Golgi-associated vesicle 1 TYR
recycling endosome 1 TNF
Single-pass type II membrane protein 1 TNF
postsynaptic membrane 1 TRPV1
Apical cell membrane 1 ABCB1
Cell projection, lamellipodium 1 CASP8
Membrane raft 1 TNF
GABA-ergic synapse 1 TRPV1
basement membrane 1 ACHE
Postsynaptic cell membrane 1 TRPV1
receptor complex 1 PPARG
Cell projection, neuron projection 1 TRPV1
chromatin 3 GABPA, PARP1, PPARG
phagocytic cup 1 TNF
Chromosome 1 PARP1
cytoskeleton 1 CASP8
Nucleus, nucleolus 1 PARP1
nuclear replication fork 1 PARP1
chromosome, telomeric region 1 PARP1
actin filament 1 KEAP1
Lipid-anchor, GPI-anchor 1 ACHE
site of double-strand break 1 PARP1
Cul3-RING ubiquitin ligase complex 1 KEAP1
nuclear envelope 1 PARP1
endosome lumen 1 INS
tertiary granule membrane 1 GAA
Melanosome 1 TYR
cell body 1 CASP8
side of membrane 1 ACHE
secretory granule lumen 1 INS
Golgi lumen 1 INS
endoplasmic reticulum lumen 2 IL6, INS
transport vesicle 1 INS
azurophil granule membrane 1 GAA
Endoplasmic reticulum-Golgi intermediate compartment membrane 1 INS
Single-pass type IV membrane protein 1 HMOX1
synaptic cleft 1 ACHE
protein-DNA complex 1 PARP1
ficolin-1-rich granule membrane 1 GAA
external side of apical plasma membrane 1 ABCB1
basal dendrite 1 MAPK8
CD95 death-inducing signaling complex 1 CASP8
death-inducing signaling complex 2 CASP3, CASP8
ripoptosome 1 CASP8
aminoacyl-tRNA synthetase multienzyme complex 1 AIMP2
site of DNA damage 1 PARP1
Cell projection, dendritic spine membrane 1 TRPV1
dendritic spine membrane 1 TRPV1
[Tumor necrosis factor, soluble form]: Secreted 1 TNF
inclusion body 1 KEAP1
interleukin-6 receptor complex 1 IL6
[Poly [ADP-ribose] polymerase 1, processed N-terminus]: Chromosome 1 PARP1
[Poly [ADP-ribose] polymerase 1, processed C-terminus]: Cytoplasm 1 PARP1
autolysosome lumen 1 GAA
[Isoform H]: Cell membrane 1 ACHE
[C-domain 2]: Secreted 1 TNF
[Tumor necrosis factor, membrane form]: Membrane 1 TNF
[C-domain 1]: Secreted 1 TNF


文献列表

  • Shuo Gao, Chaoyi Zhou, Linhua Hou, Kuo Xu, Yun Zhang, Xue Wang, Jianheng Li, Kechun Liu, Qing Xia. Narcissin induces developmental toxicity and cardiotoxicity in zebrafish embryos via Nrf2/HO-1 and calcium signaling pathways. Journal of applied toxicology : JAT. 2023 Sep; ?(?):. doi: 10.1002/jat.4545. [PMID: 37718569]
  • Mun Seok Jo, Seoyoung Lee, Jae Sik Yu, Su Cheol Baek, Young-Chang Cho, Ki Hyun Kim. Megastigmane Derivatives from the Cladodes of Opuntia humifusa and Their Nitric Oxide Inhibitory Activities in Macrophages. Journal of natural products. 2020 03; 83(3):684-692. doi: 10.1021/acs.jnatprod.9b01120. [PMID: 32118424]
  • Zhi-Gang Wu, Wei Wei, Hai-Yan Xu, Lin-Lin Zheng, Chao-Mei Ma, Ying-Chun Wang. Constituents from the Leaves of Tetraena mongolica and Their Protective Activity in HEK 293t Cells Damaged by CdCl2. Journal of natural products. 2019 10; 82(10):2707-2712. doi: 10.1021/acs.jnatprod.9b00212. [PMID: 31593459]
  • Gen Wang, Qi Cui, Lu-Jun Yin, Xue Zheng, Ming-Zhu Gao, Yao Meng, Wei Wang. Efficient extraction of flavonoids from Flos Sophorae Immaturus by tailored and sustainable deep eutectic solvent as green extraction media. Journal of pharmaceutical and biomedical analysis. 2019 Jun; 170(?):285-294. doi: 10.1016/j.jpba.2018.12.032. [PMID: 30951994]
  • Di Zhou, Hongyan Wei, Zhe Jiang, Xuezheng Li, Kun Jiao, Xiaoguang Jia, Yue Hou, Ning Li. Natural potential neuroinflammatory inhibitors from Alhagi sparsifolia Shap. Bioorganic & medicinal chemistry letters. 2017 02; 27(4):973-978. doi: 10.1016/j.bmcl.2016.12.075. [PMID: 28073678]
  • Ning Li, Ying Wang, Xuezheng Li, Hong Zhang, Di Zhou, Wenli Wang, Wei Li, Xiangrong Zhang, Xinyu Li, Yue Hou, Dali Meng. Bioactive phenols as potential neuroinflammation inhibitors from the leaves of Xanthoceras sorbifolia Bunge. Bioorganic & medicinal chemistry letters. 2016 10; 26(20):5018-5023. doi: 10.1016/j.bmcl.2016.08.094. [PMID: 27623545]
  • Le Duc Dat, Nguyen Phuong Thao, Bui Huu Tai, Bui Thi Thuy Luyen, Sohyun Kim, Jung Eun Koo, Young Sang Koh, Nguyen The Cuong, Nguyen Van Thanh, Nguyen Xuan Cuong, Nguyen Hoai Nam, Phan Van Kiem, Chau Van Minh, Young Ho Kim. Chemical constituents from Kandelia candel with their inhibitory effects on pro-inflammatory cytokines production in LPS-stimulated bone marrow-derived dendritic cells (BMDCs). Bioorganic & medicinal chemistry letters. 2015 Apr; 25(7):1412-6. doi: 10.1016/j.bmcl.2015.02.048. [PMID: 25769817]
  • Zhisheng Xie, Yongjiang Sun, Shingchung Lam, Mingqian Zhao, Zhikun Liang, Xiaoxue Yu, Depo Yang, Xinjun Xu. Extraction and isolation of flavonoid glycosides from Flos Sophorae Immaturus using ultrasonic-assisted extraction followed by high-speed countercurrent chromatography. Journal of separation science. 2014 Apr; 37(8):957-65. doi: 10.1002/jssc.201301340. [PMID: 24515421]
  • Jun Lee, Yun Mi Lee, Byong Won Lee, Joo-Hwan Kim, Jin Sook Kim. Chemical constituents from the aerial parts of Aster koraiensis with protein glycation and aldose reductase inhibitory activities. Journal of natural products. 2012 Feb; 75(2):267-70. doi: 10.1021/np200646e. [PMID: 22264115]
  • Li Liu, Hongyue Ma, Yuping Tang, Wenxing Chen, Yin Lu, Jianming Guo, Jin-Ao Duan. Discovery of estrogen receptor α modulators from natural compounds in Si-Wu-Tang series decoctions using estrogen-responsive MCF-7 breast cancer cells. Bioorganic & medicinal chemistry letters. 2012 Jan; 22(1):154-63. doi: 10.1016/j.bmcl.2011.11.041. [PMID: 22137340]
  • Anastasia Karioti, Anastasia Protopappa, Nikolaos Megoulas, Helen Skaltsa. Identification of tyrosinase inhibitors from Marrubium velutinum and Marrubium cylleneum. Bioorganic & medicinal chemistry. 2007 Apr; 15(7):2708-14. doi: 10.1016/j.bmc.2007.01.035. [PMID: 17287127]
  • Wei Wang, Hong Liang, Bin Wang, Guang-zhong Tu, Hu-biao Chen, Yu-ying Zhao. [A new natural product from the roots of Hedysarum multijugum]. Beijing da xue xue bao. Yi xue ban = Journal of Peking University. Health sciences. 2005 Oct; 37(5):532-5. doi: . [PMID: 16224530]
  • Maria-Teresa Gutierrez-Lugo, Yuehong Wang, Scott G Franzblau, Enrique Suarez, Barbara N Timmermann. Antitubercular sterols from Thalia multiflora Horkel ex Koernicke. Phytotherapy research : PTR. 2005 Oct; 19(10):876-80. doi: 10.1002/ptr.1731. [PMID: 16261518]
  • A Dini, L Rastrelli, P Saturnino, O Schettino. Minor components in food plants--Note I. Flavonol glycosides from Ullucus tuberosus. Bollettino della Societa italiana di biologia sperimentale. 1991 Dec; 67(12):1053-8. doi: ". [PMID: 1840797]
  • Q Liu, Y Gao, C Li. [Chemical constituents of Bupleurum Longicaule Wall. ex DC. var. giraldii Wolff]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 1990 Jun; 15(6):358-60, 384. doi: ". [PMID: 2206389]
  • C C Hsu, R H Dobberstein, A S Bingel, H H Fong, N R Farnsworth, J F Morton. Biological and phytochemical investigation of plants XVI: Strumpfia maritima (Rubiaceae). Journal of pharmaceutical sciences. 1981 Jun; 70(6):682-3. doi: 10.1002/jps.2600700628. [PMID: 7252817]