Galactitol (BioDeep_00000000454)

 

Secondary id: BioDeep_00000017597, BioDeep_00000399904, BioDeep_00000400429

natural product human metabolite PANOMIX_OTCML-2023 Endogenous blood metabolite


代谢物信息卡片


Galactitol, Pharmaceutical Secondary Standard; Certified Reference Material

化学式: C6H14O6 (182.0790344)
中文名称: 半乳糖醇, 半乳糖醇, 半乳糖醇, 甜醇
谱图信息: 最多检出来源 Homo sapiens(blood) 0.13%

分子结构信息

SMILES: C(C(C(C(C(CO)O)O)O)O)O
InChI: InChI=1S/C6H14O6/c7-1-3(9)5(11)6(12)4(10)2-8/h3-12H,1-2H2

描述信息

Galactitol or dulcitol is a sugar alcohol that is a metabolic breakdown product of galactose. Galactose is derived from lactose in food (such as dairy products). When lactose is broken down by the enzyme lactase it produces glucose and galactose. Galactitol has a slightly sweet taste. It is produced from galactose in a reaction catalyzed by aldose reductase. When present in sufficiently high levels, galactitol can act as a metabotoxin, a neurotoxin, and a hepatotoxin. A neurotoxin is a compound that disrupts or attacks neural cells and neural tissue. A hepatotoxin as a compound that disrupts or attacks liver tissue or liver cells. A metabotoxin is an endogenously produced metabolite that causes adverse health effects at chronically high levels. Chronically high levels of galactitol are associated with at least two inborn errors of metabolism, including galactosemia and galactosemia type II. Galactosemia is a rare genetic metabolic disorder that affects an individuals ability to metabolize the sugar galactose properly. Excess lactose consumption in individuals with galactose intolerance or galactosemia activates aldose reductase to produce galactitol, thus depleting NADPH and leading to lowered glutathione reductase activity. As a result, hydrogen peroxide or other free radicals accumulate causing serious oxidative damage to various cells and tissues. In individuals with galactosemia, the enzymes needed for the further metabolism of galactose (galactose-1-phosphate uridyltransferase) are severely diminished or missing entirely, leading to toxic levels of galactose 1-phosphate, galactitol, and galactonate. High levels of galactitol in infants are specifically associated with hepatomegaly (an enlarged liver), cirrhosis, renal failure, cataracts, vomiting, seizure, hypoglycemia, lethargy, brain damage, and ovarian failure.
Galactitol is an optically inactive hexitol having meso-configuration. It has a role as a metabolite, a human metabolite, an Escherichia coli metabolite and a mouse metabolite.
Galactitol is a metabolite found in or produced by Escherichia coli (strain K12, MG1655).
Galactitol is a natural product found in Elaeodendron croceum, Salacia chinensis, and other organisms with data available.
Galactitol is a naturally occurring product of plants obtained following reduction of galactose. It appears as a white crystalline powder with a slight sweet taste. It may form in excess in the lens of the eye in galactosemias a deficiency of galactokinase.
A naturally occurring product of plants obtained following reduction of GALACTOSE. It appears as a white crystalline powder with a slight sweet taste. It may form in excess in the lens of the eye in GALACTOSEMIAS, a deficiency of GALACTOKINASE.
A naturally occurring product of plants obtained following reduction of galactose. It appears as a white crystalline powder with a slight sweet taste.; Dulcitol (or galactitol) is a sugar alcohol, the reduction product of galactose. Galactitol in the urine is a biomarker for the consumption of milk. Galactitol is found in many foods, some of which are elliotts blueberry, italian sweet red pepper, catjang pea, and green bean.
An optically inactive hexitol having meso-configuration.
COVID info from COVID-19 Disease Map
Corona-virus
Coronavirus
SARS-CoV-2
COVID-19
SARS-CoV
COVID19
SARS2
SARS
Acquisition and generation of the data is financially supported in part by CREST/JST.
Dulcite is a sugar alcohol with a slightly sweet taste which is a metabolic breakdown product of galactose.
Dulcite is a sugar alcohol with a slightly sweet taste which is a metabolic breakdown product of galactose.

同义名列表

36 个代谢物同义名

Galactitol, Pharmaceutical Secondary Standard; Certified Reference Material; Galactitol, United States Pharmacopeia (USP) Reference Standard; Galactitol, European Pharmacopoeia (EP) Reference Standard; LACTITOL MONOHYDRATE IMPURITY D [EP IMPURITY]; rel-(2R,3S,4R,5S)-Hexane-1,2,3,4,5,6-hexaol; (2R,3S,4R,5S)-Hexane-1,2,3,4,5,6-hexaol; Dulcitol, Vetec(TM) reagent grade, 98\\%; (2R,3S,4R,5S)-hexane-1,2,3,4,5,6-hexol; WURCS=2.0/1,1,0/[h2112h]/1/; GALACTITOL [USP-RS]; Dulcitol, puriss.; Dulcitol, >=99\\%; galacto-Hexitol; meso-galactitol; GALACTITOL [MI]; Tox21_111644_1; Tox21_111643_1; L-galactitol; Tox21_111643; Tox21_111644; D-Galactitol; Melampyrite; Melampyrit; Galactitol; Melampyrin; Melampyrum; D-Dulcitol; AI3-19423; Ambap5938; dulcitol; Euonymit; dulcose; dulcite; Hexitol; Galactitol; NSC 1944



数据库引用编号

27 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(0)

BioCyc(8)

PlantCyc(0)

代谢反应

19 个相关的代谢反应过程信息。

Reactome(0)

BioCyc(7)

WikiPathways(1)

Plant Reactome(0)

INOH(0)

PlantCyc(0)

COVID-19 Disease Map(2)

PathBank(9)

PharmGKB(0)

207 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

  • Tao Wen, Penghao Xie, C Ryan Penton, Lauren Hale, Linda S Thomashow, Shengdie Yang, Zhexu Ding, Yaqi Su, Jun Yuan, Qirong Shen. Specific metabolites drive the deterministic assembly of diseased rhizosphere microbiome through weakening microbial degradation of autotoxin. Microbiome. 2022 10; 10(1):177. doi: 10.1186/s40168-022-01375-z. [PMID: 36271396]
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  • Yuling Zhang, Hui Wang, Fangjuan Li, Xinxin Xu, Baogui Chen, Tao Zhang. Inhibitory effects of Dulcitol on rat C6 glioma by regulating autophagy pathway. Natural product research. 2020 May; 34(10):1437-1441. doi: 10.1080/14786419.2018.1512994. [PMID: 30445865]
  • Xiao Lin Lin, Kai Li, Zhuo Yang, Baogui Chen, Tao Zhang. Dulcitol suppresses proliferation and migration of hepatocellular carcinoma via regulating SIRT1/p53 pathway. Phytomedicine : international journal of phytotherapy and phytopharmacology. 2020 Jan; 66(?):153112. doi: 10.1016/j.phymed.2019.153112. [PMID: 31786318]
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  • Shuo Yang, Yaya Zhao, Junjing Yu, Zhiqin Fan, Si-Tang Gong, Hong Tang, Lei Pan. Sugar Alcohols of Polyol Pathway Serve as Alarmins to Mediate Local-Systemic Innate Immune Communication in Drosophila. Cell host & microbe. 2019 Aug; 26(2):240-251.e8. doi: 10.1016/j.chom.2019.07.001. [PMID: 31350199]
  • Alina Grama, Ligia Blaga, Alina Nicolescu, Călin Deleanu, Mariela Militaru, Simona Sorana Căinap, Irina Pop, Georgia Tita, Claudia Sîrbe, Otilia Fufezan, Mihaela Adela Vințan, Romana Vulturar, Tudor Lucian Pop. Novel Mutation in GALT Gene in Galactosemia Patient with Group B Streptococcus Meningitis and Acute Liver Failure. Medicina (Kaunas, Lithuania). 2019 Apr; 55(4):. doi: 10.3390/medicina55040091. [PMID: 30987402]
  • Nathalie Vionnet, Linda H Münger, Carola Freiburghaus, Kathryn J Burton, Grégory Pimentel, François P Pralong, René Badertscher, Guy Vergères. Assessment of lactase activity in humans by measurement of galactitol and galactonate in serum and urine after milk intake. The American journal of clinical nutrition. 2019 02; 109(2):470-477. doi: 10.1093/ajcn/nqy296. [PMID: 30721917]
  • Mili Thakur, Faten Shaeib, Sana N Khan, Hamid-Reza Kohan-Ghadr, Roohi Jeelani, Sarah R Aldhaheri, Bernard Gonik, Husam M Abu-Soud. Galactose and its Metabolites Deteriorate Metaphase II Mouse Oocyte Quality and Subsequent Embryo Development by Disrupting the Spindle Structure. Scientific reports. 2017 03; 7(1):231. doi: 10.1038/s41598-017-00159-y. [PMID: 28331195]
  • Byung-Chun Kim, Byoung Seung Jeon, Seil Kim, Hyunook Kim, Youngsoon Um, Byoung-In Sang. Caproiciproducens galactitolivorans gen. nov., sp. nov., a bacterium capable of producing caproic acid from galactitol, isolated from a wastewater treatment plant. International journal of systematic and evolutionary microbiology. 2015 Dec; 65(12):4902-4908. doi: 10.1099/ijsem.0.000665. [PMID: 26474980]
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  • Tetsuya Iizuka, Toshiki Tamura, Hideki Sezutsu, Keisuke Mase, Eiji Okada, Kiyoshi Asaoka. Genetic analysis of the electrophysiological response to salicin, a bitter substance, in a polyphagous strain of the silkworm Bombyx mori. PloS one. 2012; 7(5):e37549. doi: 10.1371/journal.pone.0037549. [PMID: 22649537]
  • Sayani Banerjee, Pratip Chakraborty, Piyali Saha, Soma Aditya Bandyopadhyay, Sutapa Banerjee, Syed N Kabir. Ovotoxic effects of galactose involve attenuation of follicle-stimulating hormone bioactivity and up-regulation of granulosa cell p53 expression. PloS one. 2012; 7(2):e30709. doi: 10.1371/journal.pone.0030709. [PMID: 22319579]
  • Hong Mei Li, Jin Kyu Kim, Jai Man Jang, Sang Oh Kwon, Cheng Bi Cui, Soon Sung Lim. The inhibitory effect of Prunella vulgaris L. on aldose reductase and protein glycation. Journal of biomedicine & biotechnology. 2012; 2012(?):928159. doi: 10.1155/2012/928159. [PMID: 23091363]
  • Jieping Qin, Jun Feng, Yaohua Li, Kefeng Mo, Shiying Lu. Ultrasonic-assisted liquid-liquid extraction and HILIC-ELSD analysis of ginsenoside Rb(1), astragaloside IV and dulcitol in sugar-free "Fufangfufangteng Heji". Journal of pharmaceutical and biomedical analysis. 2011 Dec; 56(4):836-40. doi: 10.1016/j.jpba.2011.07.033. [PMID: 21840664]
  • Djalma Menezes-de-Oliveira, Maria-Isabel Aguilar, Beatriz King-Díaz, Sidney Augusto Vieira-Filho, Lucinier Pains-Duarte, Grácia-Divina de Fátima Silva, Blas Lotina-Hennsen. The triterpenes 3β-lup-20(29)-en-3-ol and 3β-lup-20(29)-en-3-yl acetate and the carbohydrate 1,2,3,4,5,6-hexa-O-acetyl-dulcitol as photosynthesis light reactions inhibitors. Molecules (Basel, Switzerland). 2011 Dec; 16(12):9939-56. doi: 10.3390/molecules16129939. [PMID: 22134400]
  • K Krabbi, M-L Uudelepp, K Joost, R Zordania, K Õunap. Long-term complications in Estonian galactosemia patients with a less strict lactose-free diet and metabolic control. Molecular genetics and metabolism. 2011 Jul; 103(3):249-53. doi: 10.1016/j.ymgme.2011.03.023. [PMID: 21501963]
  • Tomiko Kuhara, Morimasa Ohse, Yoshito Inoue, Arthur J L Cooper. A GC/MS-based metabolomic approach for diagnosing citrin deficiency. Analytical and bioanalytical chemistry. 2011 Jun; 400(7):1881-94. doi: 10.1007/s00216-011-4766-0. [PMID: 21365350]
  • Julia B Hennermann, Peter Schadewaldt, Barbara Vetter, Yoon S Shin, Eberhard Mönch, Jeannette Klein. Features and outcome of galactokinase deficiency in children diagnosed by newborn screening. Journal of inherited metabolic disease. 2011 Apr; 34(2):399-407. doi: 10.1007/s10545-010-9270-8. [PMID: 21290184]
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  • Katerina I Kalliampakou, Evangelia D Kouri, Haralabia Boleti, Ourania Pavli, Laurence Maurousset, Michael K Udvardi, Panagiotis Katinakis, Rémi Lemoine, Emmanouil Flemetakis. Cloning and functional characterization of LjPLT4, a plasma membrane xylitol H(+)- symporter from Lotus japonicus. Molecular membrane biology. 2011 Jan; 28(1):1-13. doi: 10.3109/09687688.2010.500626. [PMID: 21219252]
  • Jia Liu, Lawrence Litt, Mark R Segal, Mark J S Kelly, Jeffrey G Pelton, Myungwon Kim. Metabolomics of oxidative stress in recent studies of endogenous and exogenously administered intermediate metabolites. International journal of molecular sciences. 2011; 12(10):6469-501. doi: 10.3390/ijms12106469. [PMID: 22072900]
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  • Hui Sun, Alla Lapidus, Matt Nolan, Susan Lucas, Tijana Glavina Del Rio, Hope Tice, Jan-Fang Cheng, Roxane Tapia, Cliff Han, Lynne Goodwin, Sam Pitluck, Ioanna Pagani, Natalia Ivanova, Konstantinos Mavromatis, Natalia Mikhailova, Amrita Pati, Amy Chen, Krishna Palaniappan, Miriam Land, Loren Hauser, Yun-Juan Chang, Cynthia D Jeffries, Olivier Duplex Ngatchou Djao, Manfred Rohde, Johannes Sikorski, Markus Göker, Tanja Woyke, James Bristow, Jonathan A Eisen, Victor Markowitz, Philip Hugenholtz, Nikos C Kyrpides, Hans-Peter Klenk. Complete genome sequence of Nocardiopsis dassonvillei type strain (IMRU 509). Standards in genomic sciences. 2010 Nov; 3(3):325-36. doi: 10.4056/sigs.1363462. [PMID: 21304737]
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