Cycasin (BioDeep_00000004688)

 

Secondary id: BioDeep_00000872813, BioDeep_00001028407

human metabolite PANOMIX_OTCML-2023 Toxin


代谢物信息卡片


(Z)-methyl-oxido-[[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethylimino]azanium

化学式: C8H16N2O7 (252.0957)
中文名称: 苏铁苷
谱图信息: 最多检出来源 Chinese Herbal Medicine(otcml) 14.8%

分子结构信息

SMILES: C/[N+](=N/CO[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)O)/[O-]
InChI: 1,4-12,14-21H,2-3H2

描述信息

Cycasin is an alkaloid from seeds of the false sago Cycas circinalis and sago cycas Cycas revoluta (Cycadaceae). Carcinogen of significance in human nutrition; but in practice the toxin is present in the seeds of the plant and the pith is used as a food source.
Isolated from human milk
D009676 - Noxae > D002273 - Carcinogens
D009676 - Noxae > D009498 - Neurotoxins

同义名列表

20 个代谢物同义名

2-(hydroxymethyl)-6-{[(methyl-oxo-λ⁵-azanylidene)amino]methoxy}oxane-3,4,5-triol; (2-Hydroxy-2-methyl-2beta -D-glucosyloxyazoxymethane; beta -D-Glucopyranoside, (methyl-ONN-azoxy)methyl; (Methyl-ONN-azoxy)methyl beta-D-glucopyranoside; beta-D-Glucoside, methylazoxymethanol; Methylazoxymethanol beta -D-glucoside; Methylazoxymethanol beta-D-glucoside; Methylazoxymethanolbeta -D-glucoside; Methylazoxymethanol beta D glucoside; Glucuronate, methylazoxymethanol; Methylazoxymethanol glucuronate; Methylazoxymethanol glucoside; b-D-Glucosyloxyazoxymethane; Cycas revoluta glucoside; Allolactose; Cykazine; cycasin; (Z)-methyl-oxido-[[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethylimino]azanium; Cycasin; Methyl-oxido-[[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethylimino]azanium



数据库引用编号

18 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)

13 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 6 APOE, CASP3, CAT, CYP2D6, DST, TARDBP
Peripheral membrane protein 1 GBA1
Endoplasmic reticulum membrane 2 CYP2D6, DST
Nucleus 6 APOE, CASP3, DST, LIG4, MGMT, TARDBP
cytosol 3 CASP3, CAT, DST
dendrite 1 APOE
trans-Golgi network 1 GBA1
nucleoplasm 5 CASP3, DST, LIG4, MGMT, TARDBP
Cell membrane 1 DST
Lipid-anchor 1 DST
Cell projection, axon 1 DST
Multi-pass membrane protein 1 SLC5A1
cell cortex 1 DST
cell junction 1 DST
glutamatergic synapse 2 APOE, CASP3
Golgi apparatus 2 APOE, GBA1
Golgi membrane 1 INS
lysosomal membrane 1 GBA1
neuronal cell body 2 APOE, CASP3
Lysosome 1 GBA1
plasma membrane 4 APOE, BCHE, DST, SLC5A1
Membrane 5 APOE, CAT, CYP2D6, DST, MGMT
apical plasma membrane 1 SLC5A1
axon 1 DST
extracellular exosome 4 APOE, CAT, GBA1, SLC5A1
Lysosome membrane 1 GBA1
Lumenal side 1 GBA1
endoplasmic reticulum 3 APOE, CYP2D6, GBA1
extracellular space 4 APOE, BCHE, COL2A1, INS
lysosomal lumen 1 GBA1
perinuclear region of cytoplasm 1 SLC5A1
mitochondrion 3 CAT, CYP2D6, TARDBP
protein-containing complex 1 CAT
intracellular membrane-bounded organelle 3 CAT, CYP2D6, LIG4
Microsome membrane 1 CYP2D6
postsynaptic density 1 CASP3
Secreted 4 APOE, BCHE, COL2A1, INS
extracellular region 5 APOE, BCHE, CAT, COL2A1, INS
Single-pass membrane protein 2 CYP2D6, DST
mitochondrial matrix 1 CAT
Endosome, multivesicular body 1 APOE
Extracellular vesicle 1 APOE
Secreted, extracellular space, extracellular matrix 2 APOE, COL2A1
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 DST
Z disc 1 DST
cytoplasmic vesicle 1 DST
microtubule cytoskeleton 1 DST
axon cytoplasm 1 DST
Early endosome 2 APOE, SLC5A1
Apical cell membrane 1 SLC5A1
Cytoplasm, cytoskeleton 1 DST
focal adhesion 2 CAT, DST
microtubule 1 DST
extracellular matrix 1 APOE
Peroxisome 1 CAT
basement membrane 2 COL2A1, DST
collagen trimer 1 COL2A1
intracellular vesicle 1 SLC5A1
Peroxisome matrix 1 CAT
peroxisomal matrix 1 CAT
peroxisomal membrane 1 CAT
collagen-containing extracellular matrix 2 APOE, COL2A1
intermediate filament 1 DST
nuclear speck 1 TARDBP
chromatin 1 TARDBP
cell leading edge 1 DST
cell projection 1 DST
cytoskeleton 1 DST
Secreted, extracellular space 1 APOE
brush border membrane 1 SLC5A1
chromosome, telomeric region 1 LIG4
Cytoplasm, cell cortex 1 DST
blood microparticle 2 APOE, BCHE
nuclear envelope 1 DST
Nucleus envelope 1 DST
endosome lumen 1 INS
Melanosome 1 APOE
Cytoplasm, Stress granule 1 TARDBP
cytoplasmic stress granule 1 TARDBP
intermediate filament cytoskeleton 1 DST
stress fiber 1 DST
basal plasma membrane 1 DST
ficolin-1-rich granule lumen 1 CAT
secretory granule lumen 2 CAT, INS
Golgi lumen 1 INS
endoplasmic reticulum lumen 4 APOE, BCHE, COL2A1, INS
transport vesicle 1 INS
Endoplasmic reticulum-Golgi intermediate compartment membrane 1 INS
microtubule plus-end 1 DST
nuclear envelope lumen 1 BCHE
clathrin-coated endocytic vesicle membrane 1 APOE
Cytoplasm, cytoskeleton, stress fiber 1 DST
H zone 1 DST
perichromatin fibrils 1 TARDBP
synaptic cleft 1 APOE
death-inducing signaling complex 1 CASP3
[Isoform 1]: Cytoplasm, cytoskeleton 1 DST
intracellular non-membrane-bounded organelle 1 TARDBP
condensed chromosome 1 LIG4
discoidal high-density lipoprotein particle 1 APOE
endocytic vesicle lumen 1 APOE
collagen type II trimer 1 COL2A1
collagen type XI trimer 1 COL2A1
chylomicron remnant 1 APOE
intermediate-density lipoprotein particle 1 APOE
lipoprotein particle 1 APOE
multivesicular body, internal vesicle 1 APOE
catalase complex 1 CAT
DNA-dependent protein kinase-DNA ligase 4 complex 1 LIG4
nonhomologous end joining complex 1 LIG4
intracellular organelle 1 SLC5A1
hemidesmosome 1 DST
DNA ligase IV complex 1 LIG4
interchromatin granule 1 TARDBP
Cytoplasm, myofibril, sarcomere, H zone 1 DST
[Isoform 2]: Cytoplasm, cytoskeleton 1 DST
[Isoform 6]: Nucleus 1 DST
[Isoform 7]: Cytoplasm, cytoskeleton 1 DST
[Isoform 8]: Cytoplasm, cytoskeleton 1 DST
organelle 1 DST


文献列表

  • Ann M Bode, Zigang Dong. Toxic phytochemicals and their potential risks for human cancer. Cancer prevention research (Philadelphia, Pa.). 2015 Jan; 8(1):1-8. doi: 10.1158/1940-6207.capr-14-0160. [PMID: 25348854]
  • E Rivadeneyra-Domínguez, J F Rodríguez-Landa. Cycads and their association with certain neurodegenerative diseases. Neurologia (Barcelona, Spain). 2014 Nov; 29(9):517-22. doi: 10.1016/j.nrl.2013.03.005. [PMID: 23725821]
  • O Lolodi, G E Eriyamremu. Effect of methanolic extract of Vernonia amygdalina (common bitter leaf) on lipid peroxidation and antioxidant enzymes in rats exposed to cycasin. Pakistan journal of biological sciences : PJBS. 2013 Jul; 16(13):642-6. doi: 10.3923/pjbs.2013.642.646. [PMID: 24505988]
  • Glen E Kisby, Peter S Spencer. Is neurodegenerative disease a long-latency response to early-life genotoxin exposure?. International journal of environmental research and public health. 2011 10; 8(10):3889-921. doi: 10.3390/ijerph8103889. [PMID: 22073019]
  • Alberto Prado, Julieta Ledezma, Luis Cubilla-Rios, Jacqueline C Bede, Donald M Windsor. Two genera of Aulacoscelinae beetles reflexively bleed azoxyglycosides found in their host cycads. Journal of chemical ecology. 2011 Jul; 37(7):736-40. doi: 10.1007/s10886-011-9977-5. [PMID: 21656034]
  • Zhong-jie Zou, Jun-shan Yang. [Studies on the chemical constituents of the roots of Anemone altaica]. Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials. 2008 Jan; 31(1):49-51. doi: . [PMID: 18589749]
  • Richard Stone. Toxicology. Fruit bats linked to mystery disease. Science (New York, N.Y.). 2002 Apr; 296(5566):241. doi: 10.1126/science.296.5566.241. [PMID: 11951013]
  • Paul Alan Cox, Oliver W Sacks. Cycad neurotoxins, consumption of flying foxes, and ALS-PDC disease in Guam. Neurology. 2002 Mar; 58(6):956-9. doi: 10.1212/wnl.58.6.956. [PMID: 11914415]
  • N Yasuda, T Shimizu. Cycad poisoning in cattle in Japan--studies on spontaneous and experimental cases. The Journal of toxicological sciences. 1998 Jul; 23 Suppl 2(?):126-8. doi: 10.2131/jts.23.supplementii_126. [PMID: 9760447]
  • Y J Choi, C J Kim, G E Ji. A partially purified beta-glucosidase from Bifidobacterium adolescentis converts cycasin to a mutagenic compound. Letters in applied microbiology. 1996 Feb; 22(2):145-8. doi: 10.1111/j.1472-765x.1996.tb01129.x. [PMID: 8936375]
  • D L Eizirik, G E Kisby. Cycad toxin-induced damage of rodent and human pancreatic beta-cells. Biochemical pharmacology. 1995 Jul; 50(3):355-65. doi: 10.1016/0006-2952(95)00150-x. [PMID: 7646537]
  • G E Eriyamremu, V E Osagie, O I Alufa, M O Osaghae, F A Oyibu. Early biochemical events in mice exposed to cycas and fed a Nigerian-like diet. Annals of nutrition & metabolism. 1995; 39(1):42-51. doi: 10.1159/000177841. [PMID: 7872655]
  • B Hirayama, A Hazama, D F Loo, E M Wright, G E Kisby. Transport of cycasin by the intestinal Na+/glucose cotransporter. Biochimica et biophysica acta. 1994 Jul; 1193(1):151-4. doi: 10.1016/0005-2736(94)90344-1. [PMID: 8038185]
  • R Osborne, A Grove, P Oh, T J Mabry, J C Ng, A A Seawright. The magical and medicinal usage of Stangeria eriopus in South Africa. Journal of ethnopharmacology. 1994 Jul; 43(2):67-72. doi: 10.1016/0378-8741(94)90005-1. [PMID: 7967657]
  • P S Spencer, G E Kisby, A C Ludolph. Long-latency neurodegenerative disease in the western Pacific. Geriatrics. 1991 Aug; 46 Suppl 1(?):37-42. doi: . [PMID: 1894143]
  • P S Spencer, G E Kisby, A C Ludolph. Slow toxins, biologic markers, and long-latency neurodegenerative disease in the western Pacific region. Neurology. 1991 May; 41(5 Suppl 2):62-6; discussion 66. doi: 10.1212/wnl.41.5_suppl_2.62. [PMID: 2041595]
  • ". A poison tree. Lancet (London, England). 1987 Oct; 2(8565):947-8. doi: ". [PMID: 2889865]
  • R Fukunishi, A Kadota, A Yoshida, N Hirota. Induction of tumors with cycasin in newborn and preweanling rats. Journal of the National Cancer Institute. 1985 Jun; 74(6):1275-81. doi: . [PMID: 2987594]
  • G L Laqueur, H Matsumoto, R S Yamamoto. Comparison of the carcinogenicity of methylazoxymethanol-beta-D-glucosiduronic acid in conventional and germfree Sprague-Dawley rats. Journal of the National Cancer Institute. 1981 Nov; 67(5):1053-5. doi: NULL. [PMID: 6946247]
  • H Matsumoto, R H Takata, H Ishizaki. Determination of the carcinogen methylazoxymethyl-beta-D-glucosiduronic acid in rat bile and urine. Journal of chromatography. 1981 Jul; 211(3):403-8. doi: 10.1016/s0021-9673(00)83072-1. [PMID: 7263796]
  • I Hirono. Natural carcinogenic products of plant origin. Critical reviews in toxicology. 1981 Jun; 8(3):235-77. doi: 10.3109/10408448109109659. [PMID: 7018839]
  • I Hirono. [Occurrence of neoplasms in the large intestine and role of intestinal bacteria]. Nihon rinsho. Japanese journal of clinical medicine. 1981 May; 39(5):2028-31. doi: NULL. [PMID: 7026830]
  • E Uchida, I Hirono. Effect of phenobarbital on the development of neoplastic lesions in the liver of cycasin-treated rats. Journal of cancer research and clinical oncology. 1981; 100(3):231-8. doi: 10.1007/bf00410683. [PMID: 6115862]
  • W Gusek. [Classification, histochemistry and ultrastructure of experimental renal tumors (author's transl)]. Der Urologe. Ausg. A. 1980 Jul; 19(4):242-9. doi: . [PMID: 7414773]
  • M Cavanna, S Parodi, M Taningher, C Bolognesi, L Sciabà, G Brambilla. DNA fragmentation in some organs of rats and mice treated with cycasin. British journal of cancer. 1979 Apr; 39(4):383-90. doi: 10.1038/bjc.1979.70. [PMID: 444396]
  • S Parodi, M Taningher, L Santi, M Cavanna, L Sciaba, A Maura, G Brambilla. A practical procedure for testing DNA damage in vivo, proposed for a pre-screening of chemical carcinogens. Mutation research. 1978 Aug; 54(1):39-46. doi: 10.1016/0165-1161(78)90133-4. [PMID: 672928]
  • W Gusek. [Histology, fine structure and differentiation of experimental Wilms tumors (author's transl)]. Klinische Padiatrie. 1978 Jan; 190(1):44-53. doi: . [PMID: 204826]
  • NULL. Cycasin. IARC monographs on the evaluation of the carcinogenic risk of chemicals to man. 1976; 10(?):121-38. doi: NULL. [PMID: 791794]
  • A M Clark. Naturally occuring mutagens. Mutation research. 1976; 32(3-4):361-74. doi: 10.1016/0165-1110(76)90006-3. [PMID: 958226]
  • L M Fonshteĭn, A A Shapiro, S K Abilev. [Microorganisms as indicators of the mutagenic activity of chemical compounds and their metabolites]. Izvestiia Akademii nauk SSSR. Seriia biologicheskaia. 1975 Sep; ?(5):671-81. doi: NULL. [PMID: 1100704]
  • K Watanabe, H Yoshii, H Iwashita, K Muta, Y Hamada. Intestinal tumors of rats by gastric or intestinal administration of cycad extract and cycasin. Gan. 1975 Aug; 66(4):449-53. doi: . [PMID: 1183779]
  • J M Hamilton. Renal carcinogenesis. Advances in cancer research. 1975; 22(?):1-56. doi: 10.1016/s0065-230x(08)60175-x. [PMID: 175645]
  • O Mickelsen, M G Yang. Naturally occurring toxicants in foods. Federation proceedings. 1966 Jan; 25(1):104-23. doi: ". [PMID: 5006560]
  • H J TEAS, H SAX, K SAX. CYCASIN: RADIOMIMETIC EFFECT. Science (New York, N.Y.). 1965 Jul; 149(3683):541-2. doi: 10.1126/science.149.3683.541. [PMID: 14325155]
  • J N WILLIAMS, G L LAQUEUR. RESPONSE OF LIVER NUCLEIC ACIDS AND LIPIDS IN RATS FED CYCAS CIRCINALIS L. ENDOSPERM OR CYCASIN. Proceedings of the Society for Experimental Biology and Medicine. Society for Experimental Biology and Medicine (New York, N.Y.). 1965 Jan; 118(?):1-4. doi: 10.3181/00379727-118-29740. [PMID: 14254546]
  • G L LAQUEUR. CARCINOGENIC EFFECTS OF CYCAD MEAL AND CYCASIN, METHYLAZOXYMETHANOL GLYCOSIDE, IN RATS AND EFFECTS OF CYCASIN IN GERMFREE RATS. Federation proceedings. 1964 Nov; 23(?):1386-8. doi: NULL. [PMID: 14236160]
  • M RECHCIGL. RATES AND KINETICS OF CATALASE SYNTHESIS AND DESTRUCTION IN RATS FED CYCAD AND CYCASIN IN VIVO. Federation proceedings. 1964 Nov; 23(?):1376-7. doi: . [PMID: 14236156]
  • A KOBAYASHI, H MATSUMOTO. METHYLAZOXYMETHANOL, THE AGLYCONE OF CYCASIN. Federation proceedings. 1964 Nov; 23(?):1354-6. doi: NULL. [PMID: 14236148]
  • J N WILLIAMS. EFFECT OF CYCAD AND CYCASIN FEEDING ON LIVER RNA, DNA, SUCCINIC OXIDASE, AND LIPIDS IN THE RAT. Federation proceedings. 1964 Nov; 23(?):1374-5. doi: ". [PMID: 14236155]
  • W H ORGELL, G L LAQUEUR. EFFECT OF INGESTED CYCASIN ON RAT BLOOD PLASMA CHOLINESTERASE. Federation proceedings. 1964 Nov; 23(?):1578-80. doi: . [PMID: 14236161]
  • C I LEVENE, S DUBAN, R H HUGHES. EFFECTS OF CYCASIN AND CYCAD MEAL. Federation proceedings. 1964 Nov; 23(?):1366-7. doi: ". [PMID: 14236152]
  • M SPATZ. EFFECTS OF CYCAD MEAL AND CYCASIN ON HISTOCHEMICALLY DEMONSTRABLE LIVER PHOSPHATASES AND NON SPECIFIC ESTERASES. Federation proceedings. 1964 Nov; 23(?):1381-2. doi: ". [PMID: 14236157]