Dihydroxyacetone (BioDeep_00000004393)

 

Secondary id: BioDeep_00000267421, BioDeep_00000863183

human metabolite PANOMIX_OTCML-2023 Endogenous natural product


代谢物信息卡片


Summers brand OF dihydroxyacetone

化学式: C3H6O3 (90.0317)
中文名称: 二羟丙酮, 1,3-二羟基丙酮
谱图信息: 最多检出来源 Homo sapiens(plant) 17.4%

分子结构信息

SMILES: C(C(=O)CO)O
InChI: InChI=1S/C3H6O3/c4-1-3(6)2-5/h4-5H,1-2H2

描述信息

Dihydroxyacetone, also known as 1,3-dihydroxy-2-propanone or glycerone, is a member of the class of compounds known as monosaccharides. Monosaccharides are compounds containing one carbohydrate unit not glycosidically linked to another such unit, and no set of two or more glycosidically linked carbohydrate units. Monosaccharides have the general formula CnH2nOn. Dihydroxyacetone is soluble (in water) and a very weakly acidic compound (based on its pKa). Dihydroxyacetone can be found in a number of food items such as cauliflower, green bell pepper, black cabbage, and sweet basil, which makes dihydroxyacetone a potential biomarker for the consumption of these food products. Dihydroxyacetone can be found primarily in urine, as well as in human muscle and stratum corneum tissues. Dihydroxyacetone exists in all living species, ranging from bacteria to humans. Dihydroxyacetone is primarily used as an ingredient in sunless tanning products. It is often derived from plant sources such as sugar beets and sugar cane, and by the fermentation of glycerin .
Dihydroxyacetone (also known as DHA) is a ketotriose compound. Its addition to blood preservation solutions results in better maintenance of 2,3-diphosphoglycerate levels during storage. It is readily phosphorylated to dihydroxyacetone phosphate by triokinase in erythrocytes. In combination with naphthoquinones, it acts as a sunscreening agent. Dihydroxyacetone is the simplest of all ketoses and, having no chiral centre, is the only one that has no optical activity. Dihydroxyacetone is a simple non-toxic sugar. It is often derived from plant sources such as sugar beets and sugar cane, by the fermentation of glycerin. Dihydroxyacetone is a white crystalline powder which is water soluble.
1,3-Dihydroxyacetone (DHA), the main active ingredient in sunless tanning skin-care preparations and an important precursor for the synthesis of various fine chemicals, is produced on an industrial scale by microbial fermentation of glycerol over Gluconobacter oxydans[1].
1,3-Dihydroxyacetone (DHA), the main active ingredient in sunless tanning skin-care preparations and an important precursor for the synthesis of various fine chemicals, is produced on an industrial scale by microbial fermentation of glycerol over Gluconobacter oxydans[1].

同义名列表

33 个代谢物同义名

Summers brand OF dihydroxyacetone; ICN brand OF dihydroxyacetone; 1,3-Dihydroxydimethyl ketone; alpha,Alpha-dihydroxyacetone; Dihydroxyacetone (glycerone); Bis(hydroxymethyl) ketone; 1,3-Dihydroxypropan-2-one; 1,3-Dihydroxy-2-propanone; 1,3 Dihydroxy 2 propanone; a,Alpha-dihydroxyacetone; Α,alpha-dihydroxyacetone; 1,3-Dihydroxypropanone; 1,3-Propanediol-2-one; 1,3-Dihydroxyacetone; a,A-dihydroxyacetone; Dihydroxy-acetone; Dihydroxyacetone; Aliphatic ketone; Ketochromin; Chromelin; Viticolor; Glycerone; Triulose; Protosol; Oxantin; Dihyxal; Oxatone; Vitadye; Soleal; Otan; DHA; Glycerone; Dihydroxyacetone



数据库引用编号

23 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(0)

BioCyc(6)

PlantCyc(0)

代谢反应

34 个相关的代谢反应过程信息。

Reactome(0)

BioCyc(25)

WikiPathways(0)

Plant Reactome(0)

INOH(0)

PlantCyc(7)

COVID-19 Disease Map(1)

PathBank(1)

PharmGKB(0)

32 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 10 CAT, GAPDH, GCK, GK, GLO1, GPD1, NLN, PARVA, PC, PKM
Peripheral membrane protein 3 GCK, HSD17B6, SORD
Endoplasmic reticulum membrane 1 TKT
Mitochondrion membrane 1 SORD
Nucleus 5 GAPDH, GCK, GK, PARVA, PKM
cytosol 14 CAT, GAPDH, GCK, GK, GLO1, GPD1, NLN, PARVA, PC, PKM, PRKCQ, SORD, SST, TKT
mitochondrial membrane 1 SORD
nuclear body 1 TKT
nucleoplasm 3 GCK, GLO1, TKT
Cell membrane 1 TKT
lamellipodium 1 PARVA
Early endosome membrane 1 HSD17B6
Golgi apparatus membrane 1 GCK
cell surface 1 EPO
Golgi membrane 2 GCK, INS
neuronal cell body 1 SST
Cytoplasm, cytosol 3 GAPDH, GK, NLN
plasma membrane 8 F2, GAPDH, GCG, GLO1, NLN, PARVA, PRKCQ, TKT
Membrane 3 CAT, GAPDH, SORD
apical plasma membrane 1 TKT
basolateral plasma membrane 1 GCK
extracellular exosome 11 CAT, EPO, F2, GAPDH, GK, GLO1, GPD1, GPX3, PKM, SORD, TKT
Lumenal side 1 HSD17B6
endoplasmic reticulum 1 HSD17B6
extracellular space 7 EPO, F2, GCG, GPX3, INS, SORD, SST
perinuclear region of cytoplasm 1 GAPDH
mitochondrion 6 CAT, GCK, GK, NLN, PC, PKM
protein-containing complex 1 CAT
intracellular membrane-bounded organelle 3 CAT, GAPDH, HSD17B6
Microsome membrane 1 HSD17B6
Single-pass type I membrane protein 1 TKT
Secreted 6 EPO, F2, GCG, GPX3, INS, SST
extracellular region 9 CAT, EPO, F2, GCG, GPX3, INS, NLN, PKM, SST
Mitochondrion outer membrane 1 GK
Single-pass membrane protein 1 GK
mitochondrial outer membrane 1 GK
Mitochondrion matrix 1 PC
mitochondrial matrix 2 CAT, PC
centriolar satellite 1 PRKCQ
motile cilium 1 SORD
nuclear membrane 1 GAPDH
Extracellular vesicle 1 PKM
actin cytoskeleton 2 PARVA, TKT
Z disc 1 PARVA
microtubule cytoskeleton 1 GAPDH
vesicle 3 GAPDH, PKM, TKT
Cytoplasm, perinuclear region 1 GAPDH
Cell junction, focal adhesion 1 PARVA
Cytoplasm, cytoskeleton 2 GAPDH, PARVA
focal adhesion 3 CAT, PARVA, TKT
GABA-ergic synapse 1 SST
Peroxisome 2 CAT, TKT
Peroxisome matrix 1 CAT
peroxisomal matrix 1 CAT
peroxisomal membrane 1 CAT
Mitochondrion intermembrane space 1 NLN
mitochondrial intermembrane space 1 NLN
collagen-containing extracellular matrix 2 F2, PKM
receptor complex 1 TKT
cilium 1 PKM
cytoskeleton 1 GAPDH
blood microparticle 1 F2
Cell projection, cilium, flagellum 1 SORD
Basolateral cell membrane 1 GCK
endosome lumen 1 INS
Lipid droplet 1 GAPDH
cell body 1 EPO
Cytoplasm, myofibril, sarcomere, Z line 1 PARVA
[Isoform 4]: Cytoplasm, cytosol 1 GK
ficolin-1-rich granule lumen 2 CAT, PKM
secretory granule lumen 5 CAT, EPO, GCG, INS, PKM
Golgi lumen 2 F2, INS
endoplasmic reticulum lumen 3 F2, GCG, INS
transport vesicle 1 INS
Endoplasmic reticulum-Golgi intermediate compartment membrane 1 INS
immunological synapse 1 PRKCQ
neuronal dense core vesicle 1 SST
aggresome 1 PRKCQ
ribonucleoprotein complex 1 GAPDH
Rough endoplasmic reticulum 1 PKM
GAIT complex 1 GAPDH
[Glucagon-like peptide 1]: Secreted 1 GCG
catalase complex 1 CAT
[Isoform M2]: Cytoplasm 1 PKM
[Isoform M1]: Cytoplasm 1 PKM
[Isoform 3]: Mitochondrion outer membrane 1 GK


文献列表

  • Ella R P Grierson, Amali H Thrimawithana, John W van Klink, David H Lewis, Ignacio Carvajal, Jason Shiller, Poppy Miller, Simon C Deroles, Michael J Clearwater, Kevin M Davies, David Chagné, Kathy E Schwinn. A phosphatase gene is linked to nectar dihydroxyacetone accumulation in mānuka (Leptospermum scoparium). The New phytologist. 2024 Jun; 242(5):2270-2284. doi: 10.1111/nph.19714. [PMID: 38532557]
  • Maoxiang Zhao, Toshiyuki Nakamura, Yoshimasa Nakamura, Shintaro Munemasa, Izumi C Mori, Yoshiyuki Murata. The effect of exogenous dihydroxyacetone and methylglyoxal on growth, anthocyanin accumulation, and the glyoxalase system in Arabidopsis. Bioscience, biotechnology, and biochemistry. 2023 Aug; ?(?):. doi: 10.1093/bbb/zbad109. [PMID: 37553179]
  • Zhen Yuan, Hai Liu, Yimin Wang, Yihu Ke. Biosynthesis of Au/CuO catalyst with Syringa oblata Lindl. leaf extract for efficient selective oxidation of glycerol to 1,3-dihydroxyacetone. Nanotechnology. 2023 Jun; ?(?):. doi: 10.1088/1361-6528/acdd7c. [PMID: 37307796]
  • Sylvester A Obeng-Darko, Jean Sloan, Rachel M Binks, Peter R Brooks, Erik J Veneklaas, Patrick M Finnegan. Dihydroxyacetone in the Floral Nectar of Ericomyrtus serpyllifolia (Turcz.) Rye (Myrtaceae) and Verticordia chrysantha Endl. (Myrtaceae) Demonstrates That This Precursor to Bioactive Honey Is Not Restricted to the Genus Leptospermum (Myrtaceae). Journal of agricultural and food chemistry. 2023 May; 71(20):7703-7709. doi: 10.1021/acs.jafc.3c00673. [PMID: 37191313]
  • Igor Rafael Sousa Costa, Francisco Lucas Pacheco Cavalcante, Fábio Rossi Cavalcanti, Cleberson de Freitas Fernandes, Enéas Gomes-Filho, Kirley Marques Canuto, Humberto Henrique de Carvalho. Metabolomic exhibits different profiles and potential biomarkers of Vitis sp co-cultivated with Fusarium oxysporum for short, medium, and long times. Physiologia plantarum. 2023 Apr; ?(?):e13918. doi: 10.1111/ppl.13918. [PMID: 37087574]
  • Sylvester A Obeng-Darko, Peter R Brooks, Erik J Veneklaas, Patrick M Finnegan. Sugar and dihydroxyacetone ratios in floral nectar suggest continuous exudation and reabsorption in Leptospermum polygalifolium Salisb. Plant science : an international journal of experimental plant biology. 2022 Oct; 323(?):111378. doi: 10.1016/j.plantsci.2022.111378. [PMID: 35842059]
  • Juan Matías Viecenz, Patricia Andrea Garavaglia, Laura Mónica Tasso, Cristina Graciela Maidana, Joaquín Juan Bautista Cannata, Gabriela Andrea García. Identification and biochemical characterization of an ATP-dependent dihydroxyacetone kinase from Trypanosoma cruzi. Experimental parasitology. 2021 Dec; 231(?):108178. doi: 10.1016/j.exppara.2021.108178. [PMID: 34767777]
  • Michael J Clearwater, Stevie T Noe, Merilyn Manley-Harris, Georgia-Leigh Truman, Stephen Gardyne, Jessica Murray, Sylvester A Obeng-Darko, Sarah J Richardson. Nectary photosynthesis contributes to the production of mānuka (Leptospermum scoparium) floral nectar. The New phytologist. 2021 11; 232(4):1703-1717. doi: 10.1111/nph.17632. [PMID: 34287899]
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  • Sara Yazdi, David J Chen, David Putnam. Microparticle fabricated from a series of symmetrical lipids based on dihydroxyacetone form textured architectures. Journal of controlled release : official journal of the Controlled Release Society. 2021 02; 330(?):1071-1079. doi: 10.1016/j.jconrel.2020.11.012. [PMID: 33188826]
  • David M Perrin. A hypothesis for examining dihydroxyacetone, the active component in sunless tanning products, as a topical prophylactic against SARS-COV-2 transmission. Medical hypotheses. 2020 Nov; 144(?):110280. doi: 10.1016/j.mehy.2020.110280. [PMID: 33254584]
  • Jose M Orozco, Patrycja A Krawczyk, Sonia M Scaria, Andrew L Cangelosi, Sze Ham Chan, Tenzin Kunchok, Caroline A Lewis, David M Sabatini. Dihydroxyacetone phosphate signals glucose availability to mTORC1. Nature metabolism. 2020 09; 2(9):893-901. doi: 10.1038/s42255-020-0250-5. [PMID: 32719541]
  • Lili Zhang, Chaojie Wang, Yongang Yu, Yamin Zhang, Yulong Song, Zheng Li, Shuping Wang, Yanfang Zhang, Xiaofeng Guo, Dan Liu, Ziliang Li, Shoucai Ma, Jinjuan Zheng, Huiyan Zhao, Gaisheng Zhang. Cyclin-Dependent Kinase Inhibitor Gene TaICK1 acts as a Potential Contributor to Wheat Male Sterility induced by a Chemical Hybridizing Agent. International journal of molecular sciences. 2020 Apr; 21(7):. doi: 10.3390/ijms21072468. [PMID: 32252420]
  • Gaofeng Wang, Yunhe Wang, Hazem Abdelnabby, Xueqiong Xiao, Wenkun Huang, Deliang Peng, Yannong Xiao. Dihydroxyacetone of wheat root exudates serves as an attractant for Heterodera avenae. PloS one. 2020; 15(7):e0236317. doi: 10.1371/journal.pone.0236317. [PMID: 32702002]
  • Simon D Williams, Linda Pappalardo, Josiah Bishop, Peter R Brooks. Dihydroxyacetone Production in the Nectar of Australian Leptospermum Is Species Dependent. Journal of agricultural and food chemistry. 2018 Oct; 66(42):11133-11140. doi: 10.1021/acs.jafc.8b04363. [PMID: 30289260]
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  • Xi Lin, Sha Liu, Guangrong Xie, Jing Chen, Penghua Li, Jianhua Chen. Enhancement of 1,3-Dihydroxyacetone Production from Gluconobacter oxydans by Combined Mutagenesis. Journal of microbiology and biotechnology. 2016 Nov; 26(11):1908-1917. doi: 10.4014/jmb.1604.04019. [PMID: 27876710]
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