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Record Information |
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Version | 4.0 |
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Status | Detected and Quantified |
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Creation Date | 2006-05-22 14:17:53 UTC |
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Update Date | 2019-01-11 19:17:05 UTC |
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HMDB ID | HMDB0002453 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | 4-Deoxythreonic acid |
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Description | 4-Deoxythreonic acid is a normally occurring carboxylic acid in human. (PMID: 3829393 , 6725493 ). Metabolic profiling of urinary organic acids from patients with juvenile-onset (Type 1) diabetes mellitus have revealed significantly elevated levels of 4-deoxythreonic acid. (PMID: 2947647 ). The normal urinary constituent 4-deoxythreonic acid was found to diminish in urine incubated with E. coli. (PMID: 3910670 ). |
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Structure | |
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Synonyms | Value | Source |
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(+/-)-erythro-2,3-dihydroxybutyrate | HMDB | (+/-)-erythro-2,3-dihydroxybutyric acid | HMDB | (2R,3S)-Rel-2,3-dihydroxy--butanoate | HMDB | (2R,3S)-Rel-2,3-dihydroxy--butanoic acid | HMDB | (R*,s*)-2,3-dihydroxybutanoate | HMDB | (R*,s*)-2,3-dihydroxybutanoic acid | HMDB | 2,3-threo-Dihydroxybutyrate | HMDB | 2,3-threo-Dihydroxybutyric acid | HMDB | 4-Deoxy-threonate | HMDB | 4-Deoxy-threonic acid | HMDB | 4-Deoxythreonate | HMDB | erythro-2,3-Dihydroxybutyrate | HMDB | erythro-2,3-Dihydroxybutyric acid | HMDB |
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Chemical Formula | C4H8O4 |
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Average Molecular Weight | 120.1039 |
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Monoisotopic Molecular Weight | 120.042258744 |
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IUPAC Name | (2S,3R)-2,3-dihydroxybutanoic acid |
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Traditional Name | 4-deoxythreonic acid |
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CAS Registry Number | 5057-93-2 |
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SMILES | C[C@@H](O)[C@H](O)C(O)=O |
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InChI Identifier | InChI=1S/C4H8O4/c1-2(5)3(6)4(7)8/h2-3,5-6H,1H3,(H,7,8)/t2-,3+/m1/s1 |
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InChI Key | LOUGYXZSURQALL-GBXIJSLDSA-N |
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Chemical Taxonomy |
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Description | This compound belongs to the class of organic compounds known as sugar acids and derivatives. These are compounds containing a saccharide unit which bears a carboxylic acid group. |
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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 | Sugar acids and derivatives |
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Alternative Parents | |
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Substituents | - Beta-hydroxy acid
- Short-chain hydroxy acid
- Sugar acid
- Monosaccharide
- Hydroxy acid
- Alpha-hydroxy acid
- Fatty acid
- Secondary alcohol
- 1,2-diol
- Monocarboxylic acid or derivatives
- Carboxylic acid
- Carboxylic acid derivative
- Alcohol
- Carbonyl group
- Hydrocarbon derivative
- Organic oxide
- Aliphatic acyclic compound
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Molecular Framework | Aliphatic acyclic compounds |
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External Descriptors | |
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Ontology |
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Disposition | Source: Biological location: |
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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 | Not Available | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | Not Available | Not Available | LogP | Not Available | Not Available |
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Predicted Properties | |
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Spectra | |
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Biological Properties |
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Cellular Locations | - Cytoplasm (predicted from logP)
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Biospecimen Locations | |
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Tissue Locations | Not Available |
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Pathways | |
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Normal Concentrations |
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Blood | Expected but not Quantified | | Not Available | Not Available | Normal | | details | Urine | Detected and Quantified | 12.3 (4.4-19.8) umol/mmol creatinine | Adult (>18 years old) | Both | Normal | | details | Urine | Detected but not Quantified | | Adult (>18 years old) | Both | Normal | | details | Urine | Detected and Quantified | 14.0 +/- 7.0 umol/mmol creatinine | Newborn (0-30 days old) | Both | Normal | | details | Urine | Detected and Quantified | 25.0 +/- 10.0 umol/mmol creatinine | Adult (>18 years old) | Both | Normal | | details | Urine | Detected and Quantified | 18.2 (5.6-23.9) umol/mmol creatinine | Adult (>18 years old) | Both | Normal | | details | Urine | Detected and Quantified | 307.674 +/- 224.458 umol/mmol creatinine | Children (1 - 13 years old) | Not Specified | Normal | | details |
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Abnormal Concentrations |
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Urine | Detected and Quantified | 442.222 +/- 291.319 umol/mmol creatinine | Children (1 - 13 years old) | Not Specified | Eosinophilic esophagitis | | details | Urine | Detected and Quantified | 765.086 +/- 469.712 umol/mmol creatinine | Children (1 - 13 years old) | Not Specified | Gastroesophageal reflux disease | | details |
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Associated Disorders and Diseases |
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Disease References | Eosinophilic esophagitis |
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- (). Mordechai, Hien, and David S. Wishart. .
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Associated OMIM IDs | - 610247 (Eosinophilic esophagitis)
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External Links |
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DrugBank ID | Not Available |
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Phenol Explorer Compound ID | Not Available |
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FoodDB ID | FDB023007 |
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KNApSAcK ID | Not Available |
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Chemspider ID | 9139682 |
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KEGG Compound ID | Not Available |
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BioCyc ID | Not Available |
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BiGG ID | Not Available |
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Wikipedia Link | Not Available |
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METLIN ID | 6686 |
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PubChem Compound | 10964471 |
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PDB ID | Not Available |
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ChEBI ID | 86391 |
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References |
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Synthesis Reference | Sakai, Takashi; Nakamura, Toshiki; Fukuda, Katsuyoshi; Amano, Eiichiro; Utaka, Masanori; Takeda, Akira. Highly enantioselective reduction of ethyl 2-acyloxy-3-oxobutanoate with immobilized bakers' yeast. Bulletin of the Chemical Society of Japan (1986), 59(10), 3185-8. |
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Material Safety Data Sheet (MSDS) | Not Available |
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General References | - Kassel DB, Martin M, Schall W, Sweeley CC: Urinary metabolites of L-threonine in type 1 diabetes determined by combined gas chromatography/chemical ionization mass spectrometry. Biomed Environ Mass Spectrom. 1986 Oct;13(10):535-40. [PubMed:2947647 ]
- Chamberlin BA, Sweeley CC: Metabolic profiles of urinary organic acids recovered from absorbent filter paper. Clin Chem. 1987 Apr;33(4):572-6. [PubMed:3829393 ]
- Tuchman M, Bowers LD, Fregien KD, Crippin PJ, Krivit W: Capillary gas chromatographic separation of urinary organic acids. Retention indices of 101 urinary acids on a 5% phenylmethyl silicone capillary column. J Chromatogr Sci. 1984 May;22(5):198-202. [PubMed:6725493 ]
- Maeda K, Shiraishi S, Sakamoto N, Ohki T, Hosoi M, Ohta K, Yamanaka N: Identification of Escherichia coli by detection of hydroquinone and uracil in the urine system. J Chromatogr. 1985 Nov 29;345(1):11-8. [PubMed:3910670 ]
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