1ST14177 (BioDeep_00000229983)

PANOMIX_OTCML-2023

代谢物信息卡片

(1,6)Dioxacyclododecino(2,3,4-gh)pyrrolizine-2,7-dione, 3-ethylidene-3,4,5,6,9,11,13,14,14a,14b-decahydro-6-hydroxy-6-methyl-5-methylene-, (3Z,6R,14aR,14bR)-

化学式: C18H23NO5 (333.1576148)
中文名称: 千屈茶碱-D3, 千里光菲灵碱
谱图信息: 最多检出来源 () 0%

分子结构信息

SMILES: CC=C1CC(=C)C(C(=O)OCC2=CCN3C2C(CC3)OC1=O)(C)O
InChI: InChI=1S/C18H23NO5/c1-4-12-9-11(2)18(3,22)17(21)23-10-13-5-7-19-8-6-14(15(13)19)24-16(12)20/h4-5,14-15,22H,2,6-10H2,1,3H3/b12-4-/t14-,15-,18-/m1/s1

描述信息

Seneciphylline is a white powder. (NTP, 1992)
LSM-2853 is a citraconoyl group.
Seneciphylline is a natural product found in Senecio bollei, Tussilago farfara, and other organisms with data available.
Seneciphylline is a toxic pyrrolizidine alkaloid in Gynura japonica[1]. Seneciphylline significantly increases the activities of epoxide hydrase and glutathione-S-transferase but causes reduction of cytochrome P-450 and related monooxygenase activities[2].

同义名列表

33 个代谢物同义名

(1,6)Dioxacyclododecino(2,3,4-gh)pyrrolizine-2,7-dione, 3-ethylidene-3,4,5,6,9,11,13,14,14a,14b-decahydro-6-hydroxy-6-methyl-5-methylene-, (3Z,6R,14aR,14bR)-; [1,6]Dioxacyclododecino[2,3,4-gh]pyrrolizine-2,7-dione,3-ethylidene-3,4,5,6,9,11,13,14,14a,14b-decahydro-6-hydroxy-6-methyl-5-methylene-, (3Z,6R,14aR,14bR)-; (3Z,6R,14AR,14BR)-3-ETHYLIDENE-3,4,5,6,9,11,13,14,14A,14B-DECAHYDRO-6-HYDROXY-6-METHYL-5-METHYLENE(1,6)DIOXACYCLODODECINO(2,3,4-GH)PYRROLIZINE-2,7-DIONE; (3Z,6R,14aR,14bR)-3-ethylidene-6-hydroxy-6-methyl-5-methylene-3,4,5,6,9,11,13,14,14a,14b-decahydro[1,6]dioxacyclododecino[2,3,4-gh]pyrrolizine-2,7-dione; (6R,9a1R,14aR,Z)-3-ethylidene-6-hydroxy-6-methyl-5-methylene-3,4,5,6,9,9a1,11,13,14,14a-decahydro-[1,6]dioxacyclododecino[2,3,4-gh]pyrrolizine-2,7-dione; Pyrrolizine-2, 3-ethylidene-3,4,5,6,9,11,13,14,14a,14b-decahydro-6-hydroxy-6-methyl-5-methylene(1,6)dioxacyclododecino[2,3,4-gh]-; (1R,4Z,7R,17R)-4-ethylidene-7-hydroxy-7-methyl-6-methylidene-2,9-dioxa-14-azatricyclo[9.5.1.014,17]heptadec-11-ene-3,8-dione; (1R,7R,17R)-4-ethylidene-7-hydroxy-7-methyl-6-methylene-2,9-dioxa-14-azatricyc lo[9.5.1.0<14,17>]heptadec-11-ene-3,8-dione; trans-15-Ethylidene-12beta-hydroxy-12alpha-methyl-13-methylenesenec-1-enine; 2H-Pyran-2-carboxylicacid,5-ethyltetrahydro-2,3-dimethyl-6-oxo-(9ci); Senecionan-11,16-dione, 13,19-didehydro-12-hydroxy-; (Z)-ethylidene-hydroxy-methyl-methylene-[?]dione; 13,19-Didehydro-12-hydroxysenecionan-11,16-dione; Senecionan-11, 13,19-didehydro-12-hydroxy-; seneciphylline, (12 beta,15E)-isomer; Seneciphylline, analytical standard; SENECIPHYLLINE [HSDB]; SENECIPHYLLINE [IARC]; SENECIPHYLLINE [MI]; .ALPHA.-LONGILOBINE; ALPHA-LONGILOBINE; Prestwick3_000599; Prestwick2_000599; Seneciophylline; UNII-0ZYZ9L5454; Seniciphylline; Seneciphylline; Seneciphyllin; BPBio1_000526; Seneciphynine; 0ZYZ9L5454; 1ST14177; Jacodine

数据库引用编号

15 个数据库交叉引用编号

ChEBI: CHEBI:181715
ChEBI: CHEBI:92677
ChEBI: CHEBI:9108
KEGG: C10391
PubChem: 5281750
ChEMBL: CHEMBL523911
MeSH: seneciphylline
ChemIDplus: 0000480819
KNApSAcK: C00002117
CAS: 480-81-9
medchemexpress: HY-N1282
MetaboLights: MTBLC9108
PubChem: 12577
3DMET: B03804
NIKKAJI: J15.536E

分类词条

生物碱

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)

46 个相关的物种来源信息

1346275 - Adenostyles alliariae:
1395540 - Adenostyles glabra: 10.1002/ARDP.19843170202
3829 - Crotalaria juncea: 10.1021/JA01590A040
76228 - Danaus genutia: 10.1007/BF01951680
13037 - Danaus plexippus: 10.1007/BF01951680
189226 - Jacobaea adonidifolia: 10.1016/J.PHYTOCHEM.2005.04.015
189227 - Jacobaea alpina: 10.1016/S0176-1617(86)80085-2
189228 - Jacobaea ambigua: 10.1016/J.PHYTOCHEM.2005.04.015
189230 - Jacobaea aquatica:
186967 - Jacobaea argunensis: 10.1016/S0031-9422(00)95221-X
189245 - Jacobaea arnautorum: 10.1016/J.PHYTOCHEM.2005.04.015
214893 - Jacobaea boissieri: 10.1016/J.PHYTOCHEM.2005.04.015
189232 - Jacobaea cannabifolia: 10.1016/J.PHYTOCHEM.2005.04.015
189240 - Jacobaea carniolica: 10.1016/J.PHYTOCHEM.2005.04.015
214896 - Jacobaea delphiniifolia: 10.1016/J.PHYTOCHEM.2005.04.015
214897 - Jacobaea gigantea: 10.1016/J.PHYTOCHEM.2005.04.015
214898 - Jacobaea gnaphalioides: 10.1016/J.PHYTOCHEM.2005.04.015
189239 - Jacobaea incana:
214900 - Jacobaea leucophylla:
189241 - Jacobaea minuta: 10.1016/J.PHYTOCHEM.2005.04.015
214901 - Jacobaea othonnae: 10.1016/J.PHYTOCHEM.2005.04.015
214902 - Jacobaea persoonii:
189250 - Jacobaea subalpina:
214899 - Jacobaea uniflora:
186954 - Ligularia fischeri: 10.1038/106503D0
52725 - Melampyrum pratense: 10.1002/NT.2620010108
278673 - Petasites hybridus: 10.1055/S-2006-957875
33090 - Plants: -
1129149 - Senecio bollei: 10.1038/106503D0
183623 - Senecio brasiliensis: 10.1021/JA01601A044
98721 - Senecio eremophilus: 10.1021/JA01601A044
462528 - Senecio fistulosus: 10.1021/NP50045A025
98720 - Senecio flaccidus var. douglasii:
121546 - Senecio glaucus: 10.1055/S-2007-971305
58524 - Senecio inaequidens:
82364 - Senecio pterophorus: 10.1016/S0031-9422(00)90859-8
1268588 - Senecio racemosus: 10.1038/106503D0
121552 - Senecio rodriguezii: 10.1002/NT.2620010407
1886452 - Senecio rosmarinifolius: 10.1139/CJR39B-002
121553 - Senecio rupestris: 10.1016/S0176-1617(86)80085-2
1896791 - Senecio ruwenzoriensis: 10.1016/0031-9422(93)85124-A
462557 - Senecio sarracenicus: 10.1135/CCCC19732658
93496 - Senecio vernalis:
85882 - Senecio viscosus: 10.1016/S0176-1617(86)80085-2
76276 - Senecio vulgaris:
118778 - Tussilago farfara: 10.1007/978-3-642-49340-9_21

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。

文献列表

Feng Long, Jie Ji, Xin Wang, Lili Wang, Ting Chen. LC-MS/MS method for determination of seneciphylline and its metabolite, seneciphylline N-oxide in rat plasma, and its application to a rat pharmacokinetic study. Biomedical chromatography : BMC. 2021 Sep; 35(9):e5145. doi: 10.1002/bmc.5145. [PMID: 33886121]
Lukas Rutz, Lan Gao, Jan-Heiner Küpper, Dieter Schrenk. Structure-dependent genotoxic potencies of selected pyrrolizidine alkaloids in metabolically competent HepG2 cells. Archives of toxicology. 2020 12; 94(12):4159-4172. doi: 10.1007/s00204-020-02895-z. [PMID: 32910235]
Weiqian Wang, Xiao Yang, Yan Chen, Xuanling Ye, Kaiyuan Jiang, Aizhen Xiong, Li Yang, Zhengtao Wang. Seneciphylline, a main pyrrolizidine alkaloid in Gynura japonica, induces hepatotoxicity in mice and primary hepatocytes via activating mitochondria-mediated apoptosis. Journal of applied toxicology : JAT. 2020 11; 40(11):1534-1544. doi: 10.1002/jat.4004. [PMID: 32618019]
Xiaojie Liu, Peter G L Klinkhamer, Klaas Vrieling. The effect of structurally related metabolites on insect herbivores: A case study on pyrrolizidine alkaloids and western flower thrips. Phytochemistry. 2017 Jun; 138(?):93-103. doi: 10.1016/j.phytochem.2017.02.027. [PMID: 28267991]
Reuel A Field, Bryan L Stegelmeier, Steven M Colegate, Ammon W Brown, Benedict T Green. An in vitro comparison of the cytotoxic potential of selected dehydropyrrolizidine alkaloids and some N-oxides. Toxicon : official journal of the International Society on Toxinology. 2015 Apr; 97(?):36-45. doi: 10.1016/j.toxicon.2015.02.001. [PMID: 25666399]
Jia-Yin Han, Yan Yi, Ai-Hua Liang, Yu-Shi Zhang, Chun-Ying Li, Yong Zhao, Hong-Yu Cui, Yu-Ting Lu. [Embryotoxicity of Senecionis Scandentis Hebra on in vitro cultured mouse embryos]. Yao xue xue bao = Acta pharmaceutica Sinica. 2014 Sep; 49(9):1267-72. doi: . [PMID: 25518325]
Tri R Nuringtyas, Robert Verpoorte, Peter G L Klinkhamer, Monique M van Oers, Kirsten A Leiss. Toxicity of pyrrolizidine alkaloids to Spodoptera exigua using insect cell lines and injection bioassays. Journal of chemical ecology. 2014 Jun; 40(6):609-16. doi: 10.1007/s10886-014-0459-4. [PMID: 24981118]
M T Skaanild, C Friis, L Brimer. Interplant alkaloid variation and Senecio vernalis toxicity in cattle. Veterinary and human toxicology. 2001 Jun; 43(3):147-51. doi: . [PMID: 11383654]
M Noorwala, F V Mohammad, V U Ahmad, B Sener, F Ergun, D Deliorman. Pyrrolizidine alkaloids from Senecio lorenthii. Fitoterapia. 2000 Sep; 71(5):618-20. doi: 10.1016/s0367-326x(00)00194-5. [PMID: 11449528]
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]
U Candrian, J Lüthy, C Schlatter. In vivo covalent binding of retronecine-labelled [3H]seneciphylline and [3H]senecionine to DNA of rat liver, lung and kidney. Chemico-biological interactions. 1985 Jun; 54(1):57-69. doi: 10.1016/s0009-2797(85)80152-6. [PMID: 4017105]
D F Eastman, G P Dimenna, H J Segall. Covalent binding of two pyrrolizidine alkaloids, senecionine and seneciphylline, to hepatic macromolecules and their distribution, excretion, and transfer into milk of lactating mice. Drug metabolism and disposition: the biological fate of chemicals. 1982 May; 10(3):236-40. doi: . [PMID: 6179729]