Allose (BioDeep_00000014400)

 

Secondary id: BioDeep_00001868526

human metabolite Endogenous PANOMIX_OTCML-2023


代谢物信息卡片


(3S,4S,5R,6S)-6-(hydroxymethyl)oxane-2,3,4,5-tetrol

化学式: C6H12O6 (180.0633852)
中文名称:
谱图信息: 最多检出来源 Homo sapiens(urine) 1.28%

分子结构信息

SMILES: C(C1C(C(C(C(O1)O)O)O)O)O
InChI: InChI=1S/C6H12O6/c7-1-2-3(8)4(9)5(10)6(11)12-2/h2-11H,1H2/t2-,3-,4-,5-,6?/m0/s1

描述信息

Allose is an aldohexose sugar. Allose is a C-3 epimer of glucose. D-allose is a rare sugar found in nature and, because of its very limited amount and of the high cost associated with its synthesis, its physiological functions remain virtually unknown (PMID 16080505). It is believed to have inhibitory effect on cancer cell proliferation (PMID 16142305), protective effects against ischemia reperfusion injury (PMID 14605979, 16716947), immunosuppressant on allogenic orthotopic liver transplantation (PMID 11120048), neuroprotective effects against retinal ischemia (PMID 16565406), suppress development of salt-induced hypertension (PMID 16148613) and an inhibitory effect on human ovarian carcinoma cells (PMID 16080505). It is a rare monosaccharide that has been isolated from the leaves of the African shrub Protea rubropilosa. It is soluble in water and practically insoluble in methanol.
D-allose is a rare sugar found in nature and, because of its very limited amount and of the high cost associated with its synthesis, its physiological functions remain virtually unknown (PMID 16080505).
D-Allose is an endogenous metabolite.
D-Allose is an endogenous metabolite.

同义名列表

11 个代谢物同义名

(3S,4S,5R,6S)-6-(hydroxymethyl)oxane-2,3,4,5-tetrol; WURCS=2.0/1,1,0/[a1111h-1x_1-5]/1/; beta-delta-Allopyranose; beta-D-Allopyranose; beta-delta-Allose; Beta-D-allose; delta-Allose; (D)-allose; DL-Allose; D-Allose; Allose



数据库引用编号

24 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

8 个相关的代谢反应过程信息。

Reactome(0)

BioCyc(7)

WikiPathways(0)

Plant Reactome(0)

INOH(0)

PlantCyc(0)

COVID-19 Disease Map(0)

PathBank(1)

  • D-Allulose Degradation: Adenosine triphosphate + D-allopyranose + Water ⟶ Adenosine diphosphate + D-allopyranose + Hydrogen Ion + Phosphate

PharmGKB(0)

1 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。



文献列表

  • Ya-Nan OuYang, Lu-Xin Zhou, Yue-Xin Jin, Guo-Feng Hou, Peng-Fei Yang, Meng Chen, Zhongmin Tian. Reconstruction and analysis of correlation networks based on GC-MS metabolomics data for hypercholesterolemia. Biochemical and biophysical research communications. 2021 05; 553(?):1-8. doi: 10.1016/j.bbrc.2021.03.069. [PMID: 33752091]
  • Hiroyuki Yamamoto, Kenji Wada, Jun Toyohara, Tetsuro Tago, Masanobu Ibaraki, Toshibumi Kinoshita, Yuka Yamamoto, Yoshihiro Nishiyama, Nobuyuki Kudomi. Radiosynthesis of 18F-labeled d-allose. Carbohydrate research. 2019 Dec; 486(?):107827. doi: 10.1016/j.carres.2019.107827. [PMID: 31586720]
  • Md Tazul Islam Chowdhury, Hikaru Ando, Ryo C Yanagita, Yasuhiro Kawanami. Syntheses and biological activities of deoxy-d-allose fatty acid ester analogs. Bioscience, biotechnology, and biochemistry. 2016; 80(4):676-81. doi: 10.1080/09168451.2015.1132151. [PMID: 26822163]
  • Akihito Kano, Takeshi Fukumoto, Kouhei Ohtani, Akihide Yoshihara, Toshiaki Ohara, Shigeyuki Tajima, Ken Izumori, Keiji Tanaka, Takeo Ohkouchi, Yutaka Ishida, Yoko Nishizawa, Kazuya Ichimura, Yasuomi Tada, Kenji Gomi, Kazuya Akimitsu. The rare sugar D-allose acts as a triggering molecule of rice defence via ROS generation. Journal of experimental botany. 2013 Nov; 64(16):4939-51. doi: 10.1093/jxb/ert282. [PMID: 24014866]
  • Takeshi Fukumoto, Akihito Kano, Kouhei Ohtani, Megumi Inoue, Akihide Yoshihara, Ken Izumori, Shigeyuki Tajima, Yoshio Shigematsu, Keiji Tanaka, Takeo Ohkouchi, Yutaka Ishida, Yoko Nishizawa, Yasuomi Tada, Kazuya Ichimura, Kenji Gomi, Sang-Dong Yoo, Jen Sheen, Kazuya Akimitsu. Phosphorylation of D-allose by hexokinase involved in regulation of OsABF1 expression for growth inhibition in Oryza sativa L. Planta. 2013 May; 237(5):1379-91. doi: 10.1007/s00425-013-1853-9. [PMID: 23397192]
  • Yuki Miyawaki, Masaaki Ueki, Masaki Ueno, Takehiko Asaga, Masaaki Tokuda, Gotaro Shirakami. D-allose ameliorates cisplatin-induced nephrotoxicity in mice. The Tohoku journal of experimental medicine. 2012 11; 228(3):215-21. doi: 10.1620/tjem.228.215. [PMID: 23064522]
  • Herman Fennell, Abdulquadri Olawin, Rahman M Mizanur, Ken Izumori, Jin-Gui Chen, Hemayet Ullah. Arabidopsis scaffold protein RACK1A modulates rare sugar D-allose regulated gibberellin signaling. Plant signaling & behavior. 2012 Nov; 7(11):1407-10. doi: 10.4161/psb.21995. [PMID: 22951405]
  • Takeshi Fukumoto, Akihito Kano, Kouhei Ohtani, Yumiko Yamasaki-Kokudo, Bong-Gyu Kim, Kouji Hosotani, Miu Saito, Chikage Shirakawa, Shigeyuki Tajima, Ken Izumori, Toshiaki Ohara, Yoshio Shigematsu, Keiji Tanaka, Yutaka Ishida, Yoko Nishizawa, Yasuomi Tada, Kazuya Ichimura, Kenji Gomi, Kazuya Akimitsu. Rare sugar D-allose suppresses gibberellin signaling through hexokinase-dependent pathway in Oryza sativa L. Planta. 2011 Dec; 234(6):1083-95. doi: 10.1007/s00425-011-1463-3. [PMID: 21717189]
  • Akihito Kano, Kouji Hosotani, Kenji Gomi, Yumiko Yamasaki-Kokudo, Chikage Shirakawa, Takeshi Fukumoto, Kouhei Ohtani, Shigeyuki Tajima, Ken Izumori, Keiji Tanaka, Yutaka Ishida, Yoko Nishizawa, Kazuya Ichimura, Yasuomi Tada, Kazuya Akimitsu. D-Psicose induces upregulation of defense-related genes and resistance in rice against bacterial blight. Journal of plant physiology. 2011 Oct; 168(15):1852-7. doi: 10.1016/j.jplph.2011.04.003. [PMID: 21601944]
  • Dakuan Gao, Nobuyuki Kawai, Takashi Tamiya. The anti-inflammatory effects of D-allose contribute to attenuation of cerebral ischemia-reperfusion injury. Medical hypotheses. 2011 Jun; 76(6):911-3. doi: 10.1016/j.mehy.2011.03.007. [PMID: 21440995]
  • U Schnupf, J L Willett, F Momany. DFTMD studies of glucose and epimers: anomeric ratios, rotamer populations, and hydration energies. Carbohydrate research. 2010 Feb; 345(4):503-11. doi: 10.1016/j.carres.2009.12.001. [PMID: 20045509]
  • Miyuki Kobayashi, Mariko Ueda, Toshio Furumoto, Yasuhiro Kawanami. Retarding activity of 6-O-acyl-D-alloses against plant growth. Bioscience, biotechnology, and biochemistry. 2010; 74(1):216-7. doi: 10.1271/bbb.90713. [PMID: 20057117]
  • Akihito Kano, Kenji Gomi, Yumiko Yamasaki-Kokudo, Masaru Satoh, Takeshi Fukumoto, Kouhei Ohtani, Shigeyuki Tajima, Ken Izumori, Keiji Tanaka, Yutaka Ishida, Yasuomi Tada, Yoko Nishizawa, Kazuya Akimitsu. A rare sugar, d-allose, confers resistance to rice bacterial blight with upregulation of defense-related genes in Oryza sativa. Phytopathology. 2010 Jan; 100(1):85-90. doi: 10.1094/phyto-100-1-0085. [PMID: 19968553]
  • Masaaki Ueki, Takehiko Asaga, Kousuke Chujo, Junichiro Ono, Yasuyuki Iwanaga, Satoshi Taie. D-allose protects against endotoxemic acute renal injury. Journal of bioscience and bioengineering. 2008 May; 105(5):481-5. doi: 10.1263/jbb.105.481. [PMID: 18558338]
  • Masanao Yokohira, Kyoko Hosokawa, Keiko Yamakawa, Kousuke Saoo, Yoko Matsuda, Yu Zeng, Toshiya Kuno, Katsumi Imaida. Potential inhibitory effects of D-allose, a rare sugar, on liver preneoplastic lesion development in F344 rat medium-term bioassay. Journal of bioscience and bioengineering. 2008 May; 105(5):545-53. doi: 10.1263/jbb.105.545. [PMID: 18558347]
  • Jongjit Rangsansarid, Nopparat Cheetangdee, Naomi Kinoshita, Kazuhiro Fukuda. Bovine serum albumin-sugar conjugates through the maillard reaction: effects on interfacial behavior and emulsifying ability. Journal of oleo science. 2008; 57(10):539-47. doi: 10.5650/jos.57.539. [PMID: 18781054]
  • Masaaki Ueki, Satoshi Taie, Kousuke Chujo, Takehiko Asaga, Yasuyuki Iwanaga, Nobuhiro Maekawa. Inhibitory effect of d-allose on neutrophil activation after rat renal ischemia/reperfusion. Journal of bioscience and bioengineering. 2007 Oct; 104(4):304-8. doi: 10.1263/jbb.104.304. [PMID: 18023804]
  • Udo Schnupf, J L Willett, Wayne B Bosma, Frank A Momany. DFT study of alpha- and beta-D-allopyranose at the B3LYP/6-311++G ** level of theory. Carbohydrate research. 2007 Feb; 342(2):196-216. doi: 10.1016/j.carres.2006.12.006. [PMID: 17204259]
  • Ghanwa Afach, Yasuhiro Kawanami, Hisashi Kato-Noguchi, Ken Izumori. Practical production of 6-O-octanoyl-D-allose and its biological activity on plant growth. Bioscience, biotechnology, and biochemistry. 2006 Aug; 70(8):2010-2. doi: 10.1271/bbb.60150. [PMID: 16926519]
  • Anna Maria Serrilli, Alessia Ramunno, Francesco Piccioni, Mauro Serafini, Mauro Ballero, Armandodoriano Bianco. Monoterpenoids from Stachys glutinosa L. Natural product research. 2006 May; 20(6):648-52. doi: 10.1080/14786410600636635. [PMID: 16835100]
  • Shoji Kimura, Guo-Xing Zhang, Akira Nishiyama, Yukiko Nagai, Toshitaka Nakagawa, Hiroshi Miyanaka, Yoshihide Fujisawa, Akira Miyatake, Tsubasa Nagai, Masaaki Tokuda, Youichi Abe. D-allose, an all-cis aldo-hexose, suppresses development of salt-induced hypertension in Dahl rats. Journal of hypertension. 2005 Oct; 23(10):1887-94. doi: 10.1097/01.hjh.0000182523.29193.e3. [PMID: 16148613]
  • T Warashina, T Noro. Steroidal glycosides from the aerial part of Asclepias incarnata L. II. Chemical & pharmaceutical bulletin. 2000 Jan; 48(1):99-107. doi: 10.1248/cpb.48.99. [PMID: 10705484]
  • T Baykal, T Panayir, D Tasdemir, O Sticher, I Calis. Triterpene saponins from Scabiosa rotata. Phytochemistry. 1998 Jul; 48(5):867-73. doi: 10.1016/s0031-9422(97)00982-5. [PMID: 9664710]
  • S E Pratt, S Colby-Germinario, S Manuel, R J Germinario. Evidence that modulation of glucose transporter intrinsic activity is the mechanism involved in the allose-mediated depression of hexose transport in mammalian cells. Journal of cellular physiology. 1994 Dec; 161(3):580-8. doi: 10.1002/jcp.1041610322. [PMID: 7962139]