| Record Information |
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| Version | 1.0 |
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| Created at | 2005-11-16 15:48:42 UTC |
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| Updated at | 2020-11-24 22:14:12 UTC |
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| NP-MRD ID | NP0000272 |
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| Secondary Accession Numbers | None |
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| Natural Product Identification |
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| Common Name | Glyceraldehyde |
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| Description | Glyceraldehyde is a triose monosaccharide with chemical formula C3H6O3. It is the simplest of all common aldoses. It is a sweet, colourless crystalline solid that is an intermediate compound in carbohydrate metabolism. The word "glyceraldehyde" comes from combining glycerine and aldehyde, as glyceraldehyde is merely glycerine with one hydroxide changed to an aldehyde. Glyceraldehyde is produced from the action of the enzyme glyceraldehyde dehydrogenase, which converts glycerol to glyceraldehyde using NADP as a cofactor. When present at sufficiently high levels, glyceraldehyde can be a cytotoxin and a mutagen. A cytotoxin is a compound that kills cells. A mutagen is a compound that causes mutations in DNA. Glyceraldehyde is a highly reactive compound that can modify and cross-link proteins. Glyceraldehyde-modified proteins appear to be cytotoxic, depress intracellular glutathione levels, and induce reactive oxygen species (ROS) production (PMID: 14981296 ). Glyceraldehyde has been shown to cause chromosome damage to human cells in culture and is mutagenic in the Ames bacterial test. |
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| Structure | InChI=1S/C3H6O3/c4-1-3(6)2-5/h1,3,5-6H,2H2 |
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| Synonyms | | Value | Source |
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| (+-)-Glyceraldehyde | ChEBI | | 2,3-Dihydroxypropanal | ChEBI | | 2,3-Dihydroxypropionaldehyde | ChEBI | | Aldotriose | ChEBI | | alpha,beta-Dihydroxypropionaldehyde | ChEBI | | DL-Glyceraldehyde | ChEBI | | Gliceraldehido | ChEBI | | Glyceraldehyd | ChEBI | | Glyceric aldehyde | ChEBI | | Glycerinaldehyd | ChEBI | | Glycerinaldehyde | ChEBI | | Glycerinformal | ChEBI | | Glycerose | ChEBI | | Glyzerinaldehyd | ChEBI | | a,b-Dihydroxypropionaldehyde | Generator | | Α,β-dihydroxypropionaldehyde | Generator | | (+/-)-2,3-dihydroxy-propanal | HMDB | | (+/-)-glyceraldehyde | HMDB | | D-(+)-Glyceraldehyde | HMDB | | D-2,3-Dihydroxypropanal | HMDB | | D-2,3-Dihydroxypropionaldehyde | HMDB | | D-Aldotriose | HMDB | | D-Glyceraldehyde | HMDB | | D-Glycerose | HMDB | | delta-(+)-Glyceraldehyde | HMDB | | delta-2,3-Dihydroxypropanal | HMDB | | delta-2,3-Dihydroxypropionaldehyde | HMDB | | delta-Aldotriose | HMDB | | delta-Glyceraldehyde | HMDB | | delta-Glycerose | HMDB | | Dihydroxypropionaldehyde | HMDB |
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| Chemical Formula | C3H6O3 |
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| Average Mass | 90.0779 Da |
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| Monoisotopic Mass | 90.03169 Da |
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| IUPAC Name | 2,3-dihydroxypropanal |
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| Traditional Name | (+/-)-glyceraldehyde |
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| CAS Registry Number | 56-82-6 |
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| SMILES | OCC(O)C=O |
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| InChI Identifier | InChI=1S/C3H6O3/c4-1-3(6)2-5/h1,3,5-6H,2H2 |
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| InChI Key | MNQZXJOMYWMBOU-UHFFFAOYSA-N |
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| Experimental Spectra |
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| | Spectrum Type | Description | Depositor Email | Depositor Organization | Depositor | Deposition Date | View |
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| 1D NMR | 1H NMR Spectrum (1D, 500 MHz, H2O, experimental) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 2D NMR | [1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum |
| | Predicted Spectra |
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| Not Available | | Chemical Shift Submissions |
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| Not Available | | Species |
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| Species of Origin | |
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| Species Where Detected | |
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| Chemical Taxonomy |
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| Description | Belongs to the class of organic 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. |
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| Kingdom | Organic compounds |
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| Super Class | Organic oxygen compounds |
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| Class | Organooxygen compounds |
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| Sub Class | Carbohydrates and carbohydrate conjugates |
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| Direct Parent | Monosaccharides |
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| Alternative Parents | |
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| Substituents | - Monosaccharide
- Alpha-hydroxyaldehyde
- Secondary alcohol
- 1,2-diol
- Organic oxide
- Hydrocarbon derivative
- Short-chain aldehyde
- Primary alcohol
- Carbonyl group
- Aldehyde
- Alcohol
- Aliphatic acyclic compound
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| Molecular Framework | Aliphatic acyclic compounds |
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| External Descriptors | |
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| Physical Properties |
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| State | Solid |
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| Experimental Properties | | Property | Value | Reference |
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| Melting Point | 145 °C | Not Available | | Boiling Point | Not Available | Not Available | | Water Solubility | 17 mg/mL | Not Available | | LogP | Not Available | Not Available |
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| Predicted Properties | |
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| General References | - Gugliucci A: A practical method to study functional impairment of proteins by glycation and effects of inhibitors using current coagulation/fibrinolysis reagent kits. Clin Biochem. 2003 Mar;36(2):155-8. [PubMed:12633766 ]
- Beard KM, Shangari N, Wu B, O'Brien PJ: Metabolism, not autoxidation, plays a role in alpha-oxoaldehyde- and reducing sugar-induced erythrocyte GSH depletion: relevance for diabetes mellitus. Mol Cell Biochem. 2003 Oct;252(1-2):331-8. [PubMed:14577607 ]
- Iwata H, Ukeda H, Maruyama T, Fujino T, Sawamura M: Effect of carbonyl compounds on red blood cells deformability. Biochem Biophys Res Commun. 2004 Aug 27;321(3):700-6. [PubMed:15358163 ]
- Zakrzewska I, Prokopowicz J, Worowski K, Skrzydlewska E, Puchalski Z, Piotrowski Z: Low molecular organic inactivators in differentiating organ origin of alpha-amylase in humans. Part I. Mater Med Pol. 1989 Oct-Dec;21(4):274-6. [PubMed:2518736 ]
- Phillipou G, Seaborn CJ, Phillips PJ: Re-evaluation of the fructosamine reaction. Clin Chem. 1988 Aug;34(8):1561-4. [PubMed:3402055 ]
- Fujita T, Funako T, Hayashi H: 8-Hydroxydaidzein, an aldose reductase inhibitor from okara fermented with Aspergillus sp. HK-388. Biosci Biotechnol Biochem. 2004 Jul;68(7):1588-90. [PubMed:15277768 ]
- Haraguchi H, Hayashi R, Ishizu T, Yagi A: A flavone from Manilkara indica as a specific inhibitor against aldose reductase in vitro. Planta Med. 2003 Sep;69(9):853-5. [PubMed:14598214 ]
- Yamagishi S, Nakamura K, Inoue H, Kikuchi S, Takeuchi M: Serum or cerebrospinal fluid levels of glyceraldehyde-derived advanced glycation end products (AGEs) may be a promising biomarker for early detection of Alzheimer's disease. Med Hypotheses. 2005;64(6):1205-7. [PubMed:15823718 ]
- Choei H, Sasaki N, Takeuchi M, Yoshida T, Ukai W, Yamagishi S, Kikuchi S, Saito T: Glyceraldehyde-derived advanced glycation end products in Alzheimer's disease. Acta Neuropathol. 2004 Sep;108(3):189-93. Epub 2004 Jun 17. [PubMed:15221334 ]
- Jonas AJ, Lin SN, Conley SB, Schneider JA, Williams JC, Caprioli RC: Urine glyceraldehyde excretion is elevated in the renal Fanconi syndrome. Kidney Int. 1989 Jan;35(1):99-104. [PubMed:2709665 ]
- Takeuchi M, Yamagishi S: Alternative routes for the formation of glyceraldehyde-derived AGEs (TAGE) in vivo. Med Hypotheses. 2004;63(3):453-5. [PubMed:15288367 ]
- Nagaraj RH, Oya-Ito T, Padayatti PS, Kumar R, Mehta S, West K, Levison B, Sun J, Crabb JW, Padival AK: Enhancement of chaperone function of alpha-crystallin by methylglyoxal modification. Biochemistry. 2003 Sep 16;42(36):10746-55. [PubMed:12962499 ]
- Usui T, Shizuuchi S, Watanabe H, Hayase F: Cytotoxicity and oxidative stress induced by the glyceraldehyde-related Maillard reaction products for HL-60 cells. Biosci Biotechnol Biochem. 2004 Feb;68(2):333-40. [PubMed:14981296 ]
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