Heliotrine (BioDeep_00000003965)

   

natural product


代谢物信息卡片


9-Heliotrylheliotridine

化学式: C16H27NO5 (313.1889)
中文名称: 天芥菜碱-D3
谱图信息: 最多检出来源 Viridiplantae(plant) 14.35%

分子结构信息

SMILES: CC(C)C(C(C)OC)(C(=O)OCC1=CCN2C1C(CC2)O)O
InChI: InChI=1S/C16H27NO5/c1-10(2)16(20,11(3)21-4)15(19)22-9-12-5-7-17-8-6-13(18)14(12)17/h5,10-11,13-14,18,20H,6-9H2,1-4H3/t11-,13+,14-,16+/m1/s1

描述信息

Origin: Plant; SubCategory_DNP: Alkaloids derived from ornithine, Pyrrolizidine alkaloids
CONFIDENCE Reference Standard (Level 1); INTERNAL_ID 2319
CONFIDENCE Reference Standard (Level 1); INTERNAL_ID 120
CONFIDENCE Reference Standard (Level 1); INTERNAL_ID 140
CONFIDENCE Reference Standard (Level 1); INTERNAL_ID 160
CONFIDENCE Reference Standard (Level 1); INTERNAL_ID 170
CONFIDENCE Reference Standard (Level 1); INTERNAL_ID 130
CONFIDENCE Reference Standard (Level 1); INTERNAL_ID 110
CONFIDENCE Reference Standard (Level 1); INTERNAL_ID 100
CONFIDENCE Reference Standard (Level 1); INTERNAL_ID 150

同义名列表

4 个代谢物同义名

9-Heliotrylheliotridine; Heliotrine; (7R)-Heliotrine; Heliotrine



数据库引用编号

77 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)

52 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 ABCB1, CRY1, CYP1A1, MAPK8, NR1H2, NUPR1, SREBF1, SREBF2, TP53
Peripheral membrane protein 2 CYP1A1, MGLL
Endoplasmic reticulum membrane 4 CYP1A1, MGLL, SREBF1, SREBF2
Nucleus 10 CBX5, CRY1, MAPK8, NR1H2, NUPR1, POLH, PPARA, SREBF1, SREBF2, TP53
cytosol 8 LIPE, MAPK8, MGLL, NR1H2, POLH, SREBF1, SREBF2, TP53
centrosome 1 TP53
nucleoplasm 9 CBX5, MAPK8, NR1H2, NUPR1, POLH, PPARA, SREBF1, SREBF2, TP53
RNA polymerase II transcription regulator complex 1 NR1H2
Cell membrane 2 ABCB1, LIPE
Multi-pass membrane protein 3 ABCB1, SREBF1, SREBF2
Golgi apparatus membrane 2 SREBF1, SREBF2
Synapse 1 MAPK8
cell surface 1 ABCB1
Golgi apparatus 3 ATRN, POLH, TAS1R3
Golgi membrane 3 INS, SREBF1, SREBF2
mitochondrial inner membrane 1 CYP1A1
Cytoplasm, cytosol 2 LIPE, MGLL
plasma membrane 4 ABCB1, ATRN, MGLL, TAS1R3
Membrane 5 ABCB1, LIPE, MGLL, TAS1R3, TP53
apical plasma membrane 1 ABCB1
axon 1 MAPK8
caveola 1 LIPE
extracellular exosome 3 ABCB1, AMY2A, ATRN
endoplasmic reticulum 3 SREBF1, SREBF2, TP53
extracellular space 4 AMY2A, ATRN, COL2A1, INS
perinuclear region of cytoplasm 1 NUPR1
mitochondrion 3 CRY1, CYP1A1, TP53
protein-containing complex 3 CBX5, SREBF1, TP53
intracellular membrane-bounded organelle 2 CYP1A1, SREBF2
Microsome membrane 1 CYP1A1
pericentric heterochromatin 1 CBX5
Single-pass type I membrane protein 1 ATRN
Secreted 2 COL2A1, INS
extracellular region 3 AMY2A, COL2A1, INS
[Isoform 2]: Secreted 1 ATRN
Mitochondrion matrix 1 TP53
mitochondrial matrix 1 TP53
transcription regulator complex 1 TP53
Cytoplasm, cytoskeleton, microtubule organizing center, centrosome 1 TP53
Secreted, extracellular space, extracellular matrix 1 COL2A1
nucleolus 3 CBX5, PANO1, TP53
Apical cell membrane 1 ABCB1
Cytoplasm, perinuclear region 1 NUPR1
Mitochondrion inner membrane 1 CYP1A1
heterochromatin 1 CBX5
Cytoplasm, cytoskeleton 1 TP53
mitochondrial nucleoid 1 POLH
basement membrane 1 COL2A1
collagen trimer 1 COL2A1
Nucleus, PML body 1 TP53
PML body 1 TP53
collagen-containing extracellular matrix 1 COL2A1
chromatin 5 NR1H2, PPARA, SREBF1, SREBF2, TP53
Chromosome 2 CBX5, POLH
Nucleus, nucleolus 1 PANO1
chromosome, telomeric region 1 CBX5
site of double-strand break 2 POLH, TP53
[Isoform 3]: Secreted 1 ATRN
intercellular bridge 1 NUPR1
nuclear envelope 2 CBX5, SREBF1
endosome lumen 1 INS
Lipid droplet 1 LIPE
Membrane, caveola 1 LIPE
Chromosome, centromere 1 CBX5
Cytoplasmic vesicle membrane 1 SREBF1
germ cell nucleus 1 TP53
replication fork 2 POLH, TP53
secretory granule lumen 1 INS
Golgi lumen 1 INS
endoplasmic reticulum lumen 2 COL2A1, INS
histone methyltransferase complex 1 CBX5
nuclear matrix 1 TP53
transcription repressor complex 2 CBX5, TP53
kinetochore 1 CBX5
histone deacetylase complex 1 CBX5
transport vesicle 1 INS
Endoplasmic reticulum-Golgi intermediate compartment membrane 1 INS
ER to Golgi transport vesicle membrane 2 SREBF1, SREBF2
ribonucleoprotein complex 1 CBX5
[Isoform 1]: Nucleus 1 TP53
protein-DNA complex 1 NUPR1
external side of apical plasma membrane 1 ABCB1
basal dendrite 1 MAPK8
SREBP-SCAP-Insig complex 1 SREBF2
[Isoform 1]: Cell membrane 1 ATRN
chromocenter 1 CBX5
Cytoplasmic vesicle, COPII-coated vesicle membrane 2 SREBF1, SREBF2
site of DNA damage 2 CBX5, POLH
collagen type II trimer 1 COL2A1
collagen type XI trimer 1 COL2A1
[Sterol regulatory element-binding protein 1]: Endoplasmic reticulum membrane 1 SREBF1
[Processed sterol regulatory element-binding protein 1]: Nucleus 1 SREBF1
[Isoform SREBP-1aDelta]: Nucleus 1 SREBF1
[Isoform SREBP-1cDelta]: Nucleus 1 SREBF1
[Sterol regulatory element-binding protein 2]: Endoplasmic reticulum membrane 1 SREBF2
[Processed sterol regulatory element-binding protein 2]: Nucleus 1 SREBF2
sweet taste receptor complex 1 TAS1R3


文献列表

  • Yueyang Pan, Jiang Ma, Hui Zhao, Peter P Fu, Ge Lin. Hepatotoxicity screening and ranking of structurally different pyrrolizidine alkaloids in zebrafish. Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association. 2023 Jun; 178(?):113903. doi: 10.1016/j.fct.2023.113903. [PMID: 37390955]
  • Julia Buchmueller, Heike Sprenger, Johanna Ebmeyer, Josef Daniel Rasinger, Otto Creutzenberg, Dirk Schaudien, Jan G Hengstler, Georgia Guenther, Albert Braeuning, Stefanie Hessel-Pras. Pyrrolizidine alkaloid-induced transcriptomic changes in rat lungs in a 28-day subacute feeding study. Archives of toxicology. 2021 08; 95(8):2785-2796. doi: 10.1007/s00204-021-03108-x. [PMID: 34185104]
  • Jean-François Picron, Florian Philippe, Nelly Dubrulle, Els Van Hoeck, Nicole Giraud, Séverine Goscinny, Céline Vanhee. Targeted LC-MS/MS combined with multilocus DNA metabarcoding as a combinatory approach to determine the amount and the source of pyrrolizidine alkaloids contamination in popular cooking herbs, seeds, spices and leafy vegetables. Food additives & contaminants. Part A, Chemistry, analysis, control, exposure & risk assessment. 2021 Jun; 38(6):962-977. doi: 10.1080/19440049.2021.1889043. [PMID: 33780325]
  • 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]
  • Johanna Ebmeyer, Josef Daniel Rasinger, Jan G Hengstler, Dirk Schaudien, Otto Creutzenberg, Alfonso Lampen, Albert Braeuning, Stefanie Hessel-Pras. Hepatotoxic pyrrolizidine alkaloids induce DNA damage response in rat liver in a 28-day feeding study. Archives of toxicology. 2020 05; 94(5):1739-1751. doi: 10.1007/s00204-020-02779-2. [PMID: 32419051]
  • Johanna Ebmeyer, Jessica Behrend, Mario Lorenz, Georgia Günther, Raymond Reif, Jan G Hengstler, Albert Braeuning, Alfonso Lampen, Stefanie Hessel-Pras. Pyrrolizidine alkaloid-induced alterations of prostanoid synthesis in human endothelial cells. Chemico-biological interactions. 2019 Jan; 298(?):104-111. doi: 10.1016/j.cbi.2018.11.007. [PMID: 30465738]
  • Julia Waizenegger, Albert Braeuning, Markus Templin, Alfonso Lampen, Stefanie Hessel-Pras. Structure-dependent induction of apoptosis by hepatotoxic pyrrolizidine alkaloids in the human hepatoma cell line HepaRG: Single versus repeated exposure. Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association. 2018 Apr; 114(?):215-226. doi: 10.1016/j.fct.2018.02.036. [PMID: 29458164]
  • Claudia Luckert, Stefanie Hessel, Dido Lenze, Alfonso Lampen. Disturbance of gene expression in primary human hepatocytes by hepatotoxic pyrrolizidine alkaloids: A whole genome transcriptome analysis. Toxicology in vitro : an international journal published in association with BIBRA. 2015 Oct; 29(7):1669-82. doi: 10.1016/j.tiv.2015.06.021. [PMID: 26100227]
  • 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]
  • Stefanie Hessel, Christoph Gottschalk, Dania Schumann, Anja These, Angelika Preiss-Weigert, Alfonso Lampen. Structure-activity relationship in the passage of different pyrrolizidine alkaloids through the gastrointestinal barrier: ABCB1 excretes heliotrine and echimidine. Molecular nutrition & food research. 2014 May; 58(5):995-1004. doi: 10.1002/mnfr.201300707. [PMID: 24375927]
  • Dandan Cheng, Heather Kirk, Klaas Vrieling, Patrick P J Mulder, Peter G L Klinkhamer. The relationship between structurally different pyrrolizidine alkaloids and western flower thrips resistance in F(2) hybrids of Jacobaea vulgaris and Jacobaea aquatica. Journal of chemical ecology. 2011 Oct; 37(10):1071-80. doi: 10.1007/s10886-011-0021-6. [PMID: 21969251]
  • Devita Surjana, Gary M Halliday, Diona L Damian. Role of nicotinamide in DNA damage, mutagenesis, and DNA repair. Journal of nucleic acids. 2010 Jul; 2010(?):. doi: 10.4061/2010/157591. [PMID: 20725615]
  • Heather Kirk, Klaas Vrieling, Eddy Van Der Meijden, Peter G L Klinkhamer. Species by environment interactions affect pyrrolizidine alkaloid expression in Senecio jacobaea, Senecio aquaticus, and their hybrids. Journal of chemical ecology. 2010 Apr; 36(4):378-87. doi: 10.1007/s10886-010-9772-8. [PMID: 20309618]
  • Faizullah Kakar, Zarif Akbarian, Toby Leslie, Mir Lais Mustafa, John Watson, Hans P van Egmond, Mohammad Fahim Omar, Jawad Mofleh. An outbreak of hepatic veno-occlusive disease in Western afghanistan associated with exposure to wheat flour contaminated with pyrrolizidine alkaloids. Journal of toxicology. 2010; 2010(?):313280. doi: 10.1155/2010/313280. [PMID: 20652038]
  • Tim C Thoden, Michael Boppré, Johannes Hallmann. Effects of pyrrolizidine alkaloids on the performance of plant-parasitic and free-living nematodes. Pest management science. 2009 Jul; 65(7):823-30. doi: 10.1002/ps.1764. [PMID: 19378265]
  • V N Syrov, Z A Khushbaktova, A S Komarin, A B Abidov, T V Pechenitsina, F A Aripkhodzhaeva. [Experimental and clinical evaluation of the efficacy of ecdysten in the treatment of hepatitis]. Eksperimental'naia i klinicheskaia farmakologiia. 2004 Sep; 67(5):56-9. doi: . [PMID: 15559639]
  • Brian T Schaneberg, Russell J Molyneux, Ikhlas A Khan. Evaporative light scattering detection of pyrrolizidine alkaloids. Phytochemical analysis : PCA. 2004 Jan; 15(1):36-9. doi: 10.1002/pca.715. [PMID: 14979525]
  • H Eröksüz, Y Eröksüz, H Ozer, A O Ceribasi, F Tosun, U Tamer, C Akyüz Kizilay. Toxicity of dietary Heliotropium circinatum to rats. Veterinary and human toxicology. 2003 Aug; 45(4):198-201. doi: . [PMID: 12882490]
  • Mirka Macel, Klaas Vrieling. Pyrrolizidine alkaloids as oviposition stimulants for the cinnabar moth, Tyria jacobaeae. Journal of chemical ecology. 2003 Jun; 29(6):1435-46. doi: 10.1023/a:1024269621284. [PMID: 12918926]
  • T Hartmann, C Theuring, L Witte, S Schulz, J M Pasteels. Biochemical processing of plant acquired pyrrolizidine alkaloids by the neotropical leaf-beetle Platyphora boucardi. Insect biochemistry and molecular biology. 2003 May; 33(5):515-23. doi: 10.1016/s0965-1748(03)00026-2. [PMID: 12706631]
  • Jeannette T Hovermale, A Morrie Craig. Metabolism of pyrrolizidine alkaloids by Peptostreptococcus heliotrinreducens and a mixed culture derived from ovine ruminal fluid. Biophysical chemistry. 2002 Dec; 101-102(?):387-99. doi: 10.1016/s0301-4622(02)00152-7. [PMID: 12488016]
  • L M Fesenko, O A Arkhipov. [Correction of the lipid composition of the liver plasma membranes during heliotrine intoxication]. Klinicheskaia laboratornaia diagnostika. 2001 Aug; ?(8):36-8. doi: . [PMID: 11582672]
  • Y Eröksüz, H Eröksüz, H Ozer, B Sener, F Tosun, C Akyüz. Toxicity of dietary Heliotropium dolosum seed to mice. Veterinary and human toxicology. 2001 Jun; 43(3):152-5. doi: . [PMID: 11383655]
  • O V Dobrynina, S Z Shatinina, A I Archakov. [Reparation of the hepatocyte plasma membrane using phosphatidylcholine liposomes]. Biulleten' eksperimental'noi biologii i meditsiny. 1990 Jul; 110(7):94-6. doi: . [PMID: 2171698]
  • O V Dobrynina, S Z Shatinina, A I Archakov. [Phosphatidylcholine-induced repair of damaged hepatocyte membranes in heliotrine poisoning]. Biulleten' eksperimental'noi biologii i meditsiny. 1987 Apr; 103(4):413-5. doi: . [PMID: 3032300]
  • F M Hammouda, A M Rizk, S I Ismail, S Z Atteya, H A Ghaleb, M K Madkour, A E Pohland, G Wood. Poisonous plants contaminating edible ones and toxic substances in plant foods. Part 3. Pyrrolizidine alkaloids from Heliotropium digynum Forssk. (= H. luteum, Poir.). Die Pharmazie. 1984 Oct; 39(10):703-5. doi: . [PMID: 6522451]
  • L N Iuldasheva, R G Sulmanov. [State of oxidizing processes in rat liver in chronic heliotrine hepatitis]. Voprosy meditsinskoi khimii. 1983 Jan; 29(1):81-5. doi: . [PMID: 6836964]
  • I G Savin, G I Bachmanova, I I Karuzina, E D Skotselias, G N Anmonova. [Influence of heliotrin on the rat liver microsomal oxidation system]. Voprosy meditsinskoi khimii. 1983 Jan; 29(1):49-52. doi: . [PMID: 6836959]
  • R Schoental, K N Frayn. The effects of the pyrrolizidine alkaloid, heliotrine, and nicotinamide on the concentration of plasma insulin and blood glucose in the rat. Biochemical Society transactions. 1976; 4(4):649-50. doi: 10.1042/bst0040649. [PMID: 137152]