Record Information |
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Version | 1.0 |
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Creation Date | 2016-05-22 04:30:12 UTC |
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Update Date | 2016-11-09 01:15:38 UTC |
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Accession Number | CHEM017628 |
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Identification |
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Common Name | D-Serine |
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Class | Small Molecule |
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Description | A non-essential amino acid occurring in natural form as the L-isomer. It is synthesized from GLYCINE or THREONINE. It is involved in the biosynthesis of PURINES; PYRIMIDINES; and other amino acids. |
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Contaminant Sources | - FooDB Chemicals
- HMDB Contaminants - Urine
- ToxCast & Tox21 Chemicals
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Contaminant Type | Not Available |
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Chemical Structure | |
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Synonyms | Value | Source |
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(2R)-2-Amino-3-hydroxypropanoic acid | ChEBI | (R)-2-Amino-3-hydroxy-propionic acid | ChEBI | (R)-2-Amino-3-hydroxypropanoic acid | ChEBI | D-Serin | ChEBI | DSN | ChEBI | (2R)-2-Amino-3-hydroxypropanoate | Generator | (R)-2-Amino-3-hydroxy-propionate | Generator | (R)-2-Amino-3-hydroxypropanoate | Generator | DL-Serine | HMDB | Serine D-form | HMDB |
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Chemical Formula | C3H7NO3 |
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Average Molecular Mass | 105.093 g/mol |
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Monoisotopic Mass | 105.043 g/mol |
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CAS Registry Number | 312-84-5 |
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IUPAC Name | (2R)-2-amino-3-hydroxypropanoic acid |
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Traditional Name | D-serine |
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SMILES | N[C@H](CO)C(O)=O |
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InChI Identifier | InChI=1S/C3H7NO3/c4-2(1-5)3(6)7/h2,5H,1,4H2,(H,6,7)/t2-/m1/s1 |
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InChI Key | MTCFGRXMJLQNBG-UWTATZPHSA-N |
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Chemical Taxonomy |
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Description | belongs to the class of organic compounds known as serine and derivatives. Serine and derivatives are compounds containing serine or a derivative thereof resulting from reaction of serine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom. |
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Kingdom | Organic compounds |
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Super Class | Organic acids and derivatives |
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Class | Carboxylic acids and derivatives |
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Sub Class | Amino acids, peptides, and analogues |
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Direct Parent | Serine and derivatives |
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Alternative Parents | |
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Substituents | - Serine or derivatives
- Alpha-amino acid
- D-alpha-amino acid
- Beta-hydroxy acid
- Hydroxy acid
- Amino acid
- Carboxylic acid
- Monocarboxylic acid or derivatives
- Alcohol
- Primary amine
- Primary alcohol
- Organooxygen compound
- Organonitrogen compound
- Hydrocarbon derivative
- Primary aliphatic amine
- Organic oxide
- Organopnictogen compound
- Carbonyl group
- Organic oxygen compound
- Amine
- Organic nitrogen compound
- Aliphatic acyclic compound
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Molecular Framework | Aliphatic acyclic compounds |
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External Descriptors | |
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Biological Properties |
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Status | Detected and Not Quantified |
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Origin | Not Available |
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Cellular Locations | Not Available |
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Biofluid Locations | Not Available |
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Tissue Locations | Not Available |
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Pathways | Not Available |
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Applications | Not Available |
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Biological Roles | Not Available |
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Chemical Roles | Not Available |
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Physical Properties |
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State | Not Available |
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Appearance | Not Available |
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Experimental Properties | Property | Value |
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Melting Point | Not Available | Boiling Point | Not Available | Solubility | Not Available |
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Predicted Properties | |
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Spectra |
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Spectra | Spectrum Type | Description | Splash Key | View |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | splash10-06sl-9000000000-033631650075b940e0e2 | Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive | splash10-0089-9810000000-06fed7f6e260b107d95a | Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | Not Available | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated) | splash10-03di-9000000000-d33888cff00d0ade0ffe | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated) | splash10-03di-9000000000-f7e50afcb90768dce4a5 | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated) | splash10-0006-9000000000-043951ed5540cce44f4e | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0udi-6900000000-ee98a5a83ffbd434740e | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0uki-9200000000-fa8d04d6ce99a290d187 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-05fu-9000000000-001b18464fb313594dec | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-00di-9100000000-113290360f404e0abfe6 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-00di-9000000000-a5d4e47e8a548414bcb5 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0596-9000000000-45f597b943c27fee51e7 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-08g0-9300000000-dab8446816db786db171 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-03dl-9000000000-1a5aef91299ef3583ca2 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0006-9000000000-b6cfe52e68c644cacfd7 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-03di-9000000000-c00dff763ff1f56fda00 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-03di-9000000000-980e3923ad0861629a12 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0006-9000000000-90338875078d415c5036 | Spectrum | 1D NMR | 1H NMR Spectrum | Not Available | Spectrum | 1D NMR | 13C NMR Spectrum | Not Available | Spectrum | 1D NMR | 1H NMR Spectrum | Not Available | Spectrum | 1D NMR | 13C NMR Spectrum | Not Available | Spectrum | 1D NMR | 1H NMR Spectrum | Not Available | Spectrum | 1D NMR | 13C NMR Spectrum | Not Available | Spectrum | 1D NMR | 1H NMR Spectrum | Not Available | Spectrum | 1D NMR | 13C NMR Spectrum | Not Available | Spectrum | 1D NMR | 1H NMR Spectrum | Not Available | Spectrum | 1D NMR | 13C NMR Spectrum | Not Available | Spectrum | 1D NMR | 1H NMR Spectrum | Not Available | Spectrum | 1D NMR | 13C NMR Spectrum | Not Available | Spectrum | 1D NMR | 1H NMR Spectrum | Not Available | Spectrum | 1D NMR | 13C NMR Spectrum | Not Available | Spectrum | 1D NMR | 1H NMR Spectrum | Not Available | Spectrum | 1D NMR | 13C NMR Spectrum | Not Available | Spectrum | 1D NMR | 1H NMR Spectrum | Not Available | Spectrum | 1D NMR | 13C NMR Spectrum | Not Available | Spectrum | 1D NMR | 1H NMR Spectrum | Not Available | Spectrum | 1D NMR | 13C NMR Spectrum | Not Available | Spectrum | 1D NMR | 1H NMR Spectrum | Not Available | Spectrum | 2D NMR | [1H,1H] 2D NMR Spectrum | Not Available | Spectrum | 2D NMR | [1H,13C] 2D NMR Spectrum | Not Available | Spectrum |
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Toxicity Profile |
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Route of Exposure | Not Available |
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Mechanism of Toxicity | Not Available |
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Metabolism | Not Available |
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Toxicity Values | Not Available |
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Lethal Dose | Not Available |
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Carcinogenicity (IARC Classification) | Not Available |
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Uses/Sources | Not Available |
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Minimum Risk Level | Not Available |
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Health Effects | Not Available |
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Symptoms | Not Available |
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Treatment | Not Available |
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Concentrations |
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| Not Available |
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External Links |
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DrugBank ID | DB03929 |
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HMDB ID | HMDB0003406 |
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FooDB ID | FDB023164 |
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Phenol Explorer ID | Not Available |
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KNApSAcK ID | Not Available |
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BiGG ID | 35846 |
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BioCyc ID | D-SERINE |
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METLIN ID | 6920 |
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PDB ID | Not Available |
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Wikipedia Link | Serine |
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Chemspider ID | 64231 |
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ChEBI ID | 16523 |
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PubChem Compound ID | 71077 |
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Kegg Compound ID | C00740 |
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YMDB ID | YMDB00284 |
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ECMDB ID | ECMDB03406 |
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References |
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Synthesis Reference | Not Available |
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MSDS | Not Available |
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General References | 1. Zhu, Yanxin; Yuan, Minglong; Yuan, Mingwei; Du, Bilin; Zheng, Ling. Preparation of D-serine from acetylglycine. Faming Zhuanli Shenqing Gongkai Shuomingshu (2006), 4pp. | 2. Zhu, Yanxin; Yuan, Minglong; Yuan, Mingwei; Du, Bilin; Zheng, Ling. Preparation of D-serine from acetylglycine. Faming Zhuanli Shenqing Gongkai Shuomingshu (2006), 4pp. | 3. Hansson L, Stromqvist M, Backman A, Wallbrandt P, Carlstein A, Egelrud T: Cloning, expression, and characterization of stratum corneum chymotryptic enzyme. A skin-specific human serine proteinase. J Biol Chem. 1994 Jul 29;269(30):19420-6. | 4. Jones CM, Smith M, Henderson MJ: Reference data for cerebrospinal fluid and the utility of amino acid measurement for the diagnosis of inborn errors of metabolism. Ann Clin Biochem. 2006 Jan;43(Pt 1):63-6. | 5. Shafqat S, Tamarappoo BK, Kilberg MS, Puranam RS, McNamara JO, Guadano-Ferraz A, Fremeau RT Jr: Cloning and expression of a novel Na(+)-dependent neutral amino acid transporter structurally related to mammalian Na+/glutamate cotransporters. J Biol Chem. 1993 Jul 25;268(21):15351-5. | 6. Deshpande RV, Goust JM, Hogan EL, Banik NL: Calpain secreted by activated human lymphoid cells degrades myelin. J Neurosci Res. 1995 Oct 1;42(2):259-65. | 7. Metzner L, Kottra G, Neubert K, Daniel H, Brandsch M: Serotonin, L-tryptophan, and tryptamine are effective inhibitors of the amino acid transport system PAT1. FASEB J. 2005 Sep;19(11):1468-73. | 8. Nagata Y, Higashi M, Ishii Y, Sano H, Tanigawa M, Nagata K, Noguchi K, Urade M: The presence of high concentrations of free D-amino acids in human saliva. Life Sci. 2006 Mar 6;78(15):1677-81. Epub 2006 Feb 9. | 9. 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Pfundt R, van Ruissen F, van Vlijmen-Willems IM, Alkemade HA, Zeeuwen PL, Jap PH, Dijkman H, Fransen J, Croes H, van Erp PE, Schalkwijk J: Constitutive and inducible expression of SKALP/elafin provides anti-elastase defense in human epithelia. J Clin Invest. 1996 Sep 15;98(6):1389-99. | 21. Strauss JF 3rd, Kallen CB, Christenson LK, Watari H, Devoto L, Arakane F, Kiriakidou M, Sugawara T: The steroidogenic acute regulatory protein (StAR): a window into the complexities of intracellular cholesterol trafficking. Recent Prog Horm Res. 1999;54:369-94; discussion 394-5. | 22. Kim JK, Fillmore JJ, Sunshine MJ, Albrecht B, Higashimori T, Kim DW, Liu ZX, Soos TJ, Cline GW, O'Brien WR, Littman DR, Shulman GI: PKC-theta knockout mice are protected from fat-induced insulin resistance. J Clin Invest. 2004 Sep;114(6):823-7. | 23. Olive PL, Banath JP, Sinnott LT: Phosphorylated histone H2AX in spheroids, tumors, and tissues of mice exposed to etoposide and 3-amino-1,2,4-benzotriazine-1,3-dioxide. Cancer Res. 2004 Aug 1;64(15):5363-9. | 24. Hinek A, Smith AC, Cutiongco EM, Callahan JW, Gripp KW, Weksberg R: Decreased elastin deposition and high proliferation of fibroblasts from Costello syndrome are related to functional deficiency in the 67-kD elastin-binding protein. Am J Hum Genet. 2000 Mar;66(3):859-72. | 25. Lavker RM, Risse B, Brown H, Ginsburg D, Pearson J, Baker MS, Jensen PJ: Localization of plasminogen activator inhibitor type 2 (PAI-2) in hair and nail: implications for terminal differentiation. J Invest Dermatol. 1998 Jun;110(6):917-22. | 26. Paju A, Bjartell A, Zhang WM, Nordling S, Borgstrom A, Hansson J, Stenman UH: Expression and characterization of trypsinogen produced in the human male genital tract. Am J Pathol. 2000 Dec;157(6):2011-21. | 27. Schultess J, Danielewski O, Smolenski AP: Rap1GAP2 is a new GTPase-activating protein of Rap1 expressed in human platelets. Blood. 2005 Apr 15;105(8):3185-92. Epub 2005 Jan 4. | 28. Alvarez JV, Greulich H, Sellers WR, Meyerson M, Frank DA: Signal transducer and activator of transcription 3 is required for the oncogenic effects of non-small-cell lung cancer-associated mutations of the epidermal growth factor receptor. Cancer Res. 2006 Mar 15;66(6):3162-8. | 29. Hayes GM, Carrigan PE, Beck AM, Miller LJ: Targeting the RNA splicing machinery as a novel treatment strategy for pancreatic carcinoma. Cancer Res. 2006 Apr 1;66(7):3819-27. | 30. Roesch PL, Redford P, Batchelet S, Moritz RL, Pellett S, Haugen BJ, Blattner FR, Welch RA: Uropathogenic Escherichia coli use d-serine deaminase to modulate infection of the murine urinary tract. Mol Microbiol. 2003 Jul;49(1):55-67. | 31. Amberger VR, Hensel T, Ogata N, Schwab ME: Spreading and migration of human glioma and rat C6 cells on central nervous system myelin in vitro is correlated with tumor malignancy and involves a metalloproteolytic activity. Cancer Res. 1998 Jan 1;58(1):149-58. | 32. 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Zhu L, Wigle D, Hinek A, Kobayashi J, Ye C, Zuker M, Dodo H, Keeley FW, Rabinovitch M: The endogenous vascular elastase that governs development and progression of monocrotaline-induced pulmonary hypertension in rats is a novel enzyme related to the serine proteinase adipsin. J Clin Invest. 1994 Sep;94(3):1163-71. | 36. Boehning D, Snyder SH: Novel neural modulators. 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