Record Information |
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Version | 1.0 |
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Creation Date | 2016-05-26 04:30:29 UTC |
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Update Date | 2016-11-09 01:21:01 UTC |
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Accession Number | CHEM033887 |
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Identification |
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Common Name | Polypodoside C |
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Class | Small Molecule |
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Description | The L-enantiomer of aspartic acid. |
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Contaminant Sources | |
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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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(S)-2-Aminobutanedioic acid | ChEBI | (S)-2-Aminosuccinic acid | ChEBI | 2-Aminosuccinic acid | ChEBI | Asp | ChEBI | ASPARTIC ACID | ChEBI | D | ChEBI | L-Asparaginsaeure | ChEBI | L-Asp | Kegg | (S)-2-Aminobutanedioate | Generator | (S)-2-Aminosuccinate | Generator | 2-Aminosuccinate | Generator | ASPARTate | Generator | L-Aspartate | Generator | (+)-Aspartate | HMDB | (+)-Aspartic acid | HMDB | (2S)-Aspartate | HMDB | (2S)-Aspartic acid | HMDB | (L)-Aspartate | HMDB | (L)-Aspartic acid | HMDB | (R)-2-Aminosuccinate | HMDB | (S)-(+)-Aspartate | HMDB | (S)-(+)-Aspartic acid | HMDB | (S)-Amino-butanedioate | HMDB | (S)-Amino-butanedioic acid | HMDB | (S)-Aminobutanedioate | HMDB | (S)-Aminobutanedioic acid | HMDB | (S)-Aspartate | HMDB | (S)-Aspartic acid | HMDB | 2-Amino-3-methylsuccinate | HMDB | 2-Amino-3-methylsuccinic acid | HMDB | alpha-Aminosuccinate | HMDB | alpha-Aminosuccinic acid | HMDB | Aminosuccinate | HMDB | Asparagate | HMDB | Asparagic acid | HMDB | Asparaginate | HMDB | Asparaginic acid | HMDB | Asparatate | HMDB | H-Asp-OH | HMDB | L-(+)-Aspartate | HMDB | L-(+)-Aspartic acid | HMDB | L-Aminosuccinate | HMDB | L-Aminosuccinic acid | HMDB | L-Asparagate | HMDB | L-Asparagic acid | HMDB | L-Asparaginate | HMDB | L-Asparaginic acid | HMDB | (+-)-Aspartic acid | HMDB | (R,S)-Aspartic acid | HMDB | Aspartate, disodium | HMDB | Aspartate, magnesium | HMDB | Aspartate, monopotassium | HMDB | Aspartic acid, dipotassium salt | HMDB | Aspartic acid, hydrobromide | HMDB | Aspartic acid, monopotassium salt | HMDB | Aspartic acid, monosodium salt | HMDB | Aspartic acid, potassium salt | HMDB | L Aspartate | HMDB | MG5Longoral | HMDB | Potassium aspartate | HMDB | Polysuccinimide | HMDB | Ammonium aspartate | HMDB | Aspartate, ammonium | HMDB | Aspartate, calcium | HMDB | Aspartate, monosodium | HMDB | Aspartic acid, calcium salt | HMDB | Aspartic acid, disodium salt | HMDB | Aspartic acid, magnesium (1:1) salt, hydrochloride, trihydrate | HMDB | Dipotassium aspartate | HMDB | Disodium aspartate | HMDB | Hydrochloride, aspartate magnesium | HMDB | Monopotassium aspartate | HMDB | Sodium aspartate | HMDB | Aspartate, dipotassium | HMDB | Aspartic acid, magnesium (2:1) salt | HMDB | Aspartic acid, sodium salt | HMDB | Hydrobromide aspartic acid | HMDB | Magnesium aspartate | HMDB | MG 5 Longoral | HMDB | Monosodium aspartate | HMDB | Aspartate magnesium hydrochloride | HMDB | Aspartate, potassium | HMDB | Aspartate, sodium | HMDB | Aspartic acid, ammonium salt | HMDB | Aspartic acid, hydrochloride | HMDB | Aspartic acid, magnesium-potassium (2:1:2) salt | HMDB | Calcium aspartate | HMDB | Hydrochloride aspartic acid | HMDB | L Aspartic acid | HMDB | Magnesiocard | HMDB | MG-5-Longoral | HMDB | Poly-DL-succinimide | HMDB |
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Chemical Formula | C40H64O13 |
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Average Molecular Mass | 752.928 g/mol |
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Monoisotopic Mass | 752.435 g/mol |
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CAS Registry Number | 120015-17-0 |
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IUPAC Name | 14-(1-{6-[(3,5-dihydroxy-4-methoxy-6-methyloxan-2-yl)oxy]-5-methyloxan-2-yl}ethyl)-2,15-dimethyl-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-9-en-8-one |
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Traditional Name | 14-(1-{6-[(3,5-dihydroxy-4-methoxy-6-methyloxan-2-yl)oxy]-5-methyloxan-2-yl}ethyl)-2,15-dimethyl-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-9-en-8-one |
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SMILES | COC1C(O)C(C)OC(OC2OC(CCC2C)C(C)C2CCC3C4=CC(=O)C5CC(CCC5(C)C4CCC23C)OC2OC(CO)C(O)C(O)C2O)C1O |
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InChI Identifier | InChI=1S/C40H64O13/c1-18-7-10-28(51-36(18)53-38-34(47)35(48-6)30(43)20(3)49-38)19(2)23-8-9-24-22-16-27(42)26-15-21(11-13-40(26,5)25(22)12-14-39(23,24)4)50-37-33(46)32(45)31(44)29(17-41)52-37/h16,18-21,23-26,28-38,41,43-47H,7-15,17H2,1-6H3 |
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InChI Key | NDAYDFGEXFEFMC-UHFFFAOYSA-N |
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Chemical Taxonomy |
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Description | belongs to the class of organic compounds known as aspartic acid and derivatives. Aspartic acid and derivatives are compounds containing an aspartic acid or a derivative thereof resulting from reaction of aspartic acid 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 | Aspartic acid and derivatives |
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Alternative Parents | |
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Substituents | - Aspartic acid or derivatives
- Alpha-amino acid
- L-alpha-amino acid
- Dicarboxylic acid or derivatives
- Fatty acid
- Amino acid
- Carboxylic acid
- Organic oxide
- Organopnictogen compound
- Primary amine
- Organooxygen compound
- Organonitrogen compound
- Primary aliphatic amine
- Organic oxygen compound
- Carbonyl group
- Amine
- Organic nitrogen compound
- Hydrocarbon derivative
- 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 LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-01tc-0300490300-edc6224ef96fd393c6e4 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-01t9-0404970000-f748baf58ab62c6e6fd6 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-004i-1403910000-8cf05ee778b5ad688f60 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0ukc-0400290600-6e3d53f5f2317ce571cb | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-07if-2400490200-6f88c511317cf0b107c0 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-05fr-9520570000-0689039c11bec0432ff0 | 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 | DB00128 |
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HMDB ID | HMDB0000191 |
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FooDB ID | FDB012567 |
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Phenol Explorer ID | Not Available |
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KNApSAcK ID | C00001342 |
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BiGG ID | 33663 |
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BioCyc ID | L-ASPARTATE |
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METLIN ID | 5206 |
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PDB ID | Not Available |
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Wikipedia Link | Aspartic acid |
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Chemspider ID | 5745 |
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ChEBI ID | 17053 |
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PubChem Compound ID | 5960 |
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Kegg Compound ID | C00049 |
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YMDB ID | YMDB00896 |
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ECMDB ID | ECMDB00191 |
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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. https://www.ncbi.nlm.nih.gov/pubmed/?term=11568288 | 2. https://www.ncbi.nlm.nih.gov/pubmed/?term=21359215 | 3. https://www.ncbi.nlm.nih.gov/pubmed/?term=22770225 | 4. Pamfil, Maria; Lupescu, Irina; Savoiu, Valeria Gabriela. L-aspartic acid production from fumarate using Escherichia coli whole cells. Rom. (2005), 3pp. | 5. Klein MS, Almstetter MF, Schlamberger G, Nurnberger N, Dettmer K, Oefner PJ, Meyer HH, Wiedemann S, Gronwald W: Nuclear magnetic resonance and mass spectrometry-based milk metabolomics in dairy cows during early and late lactation. J Dairy Sci. 2010 Apr;93(4):1539-50. doi: 10.3168/jds.2009-2563. | 6. Melzer N, Wittenburg D, Hartwig S, Jakubowski S, Kesting U, Willmitzer L, Lisec J, Reinsch N, Repsilber D: Investigating associations between milk metabolite profiles and milk traits of Holstein cows. J Dairy Sci. 2013 Mar;96(3):1521-34. doi: 10.3168/jds.2012-5743. | 7. Mung D, Li L: Development of Chemical Isotope Labeling LC-MS for Milk Metabolomics: Comprehensive and Quantitative Profiling of the Amine/Phenol Submetabolome. Anal Chem. 2017 Apr 18;89(8):4435-4443. doi: 10.1021/acs.analchem.6b03737. Epub 2017 Mar 28. | 8. O'Callaghan TF, Vazquez-Fresno R, Serra-Cayuela A, Dong E, Mandal R, Hennessy D, McAuliffe S, Dillon P, Wishart DS, Stanton C, Ross RP: Pasture Feeding Changes the Bovine Rumen and Milk Metabolome. Metabolites. 2018 Apr 6;8(2). pii: metabo8020027. doi: 10.3390/metabo8020027. | 9. Mung D, Li L: Applying quantitative metabolomics based on chemical isotope labeling LC-MS for detecting potential milk adulterant in human milk. Anal Chim Acta. 2018 Feb 25;1001:78-85. doi: 10.1016/j.aca.2017.11.019. Epub 2017 Nov 14. | 10. Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375?386 | 11. A. Foroutan et al. The Chemical Composition of Commercial Cow's Milk (in preparation) | 12. Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&lang=en | 13. Pamfil, Maria; Lupescu, Irina; Savoiu, Valeria Gabriela. L-aspartic acid production from fumarate using Escherichia coli whole cells. Rom. (2005), 3pp. | 14. Fujii N: D-amino acid in elderly tissues. Biol Pharm Bull. 2005 Sep;28(9):1585-9. | 15. Cynober LA: Plasma amino acid levels with a note on membrane transport: characteristics, regulation, and metabolic significance. Nutrition. 2002 Sep;18(9):761-6. | 16. Grdzelishvili VZ, Smallwood S, Tower D, Hall RL, Hunt DM, Moyer SA: A single amino acid change in the L-polymerase protein of vesicular stomatitis virus completely abolishes viral mRNA cap methylation. J Virol. 2005 Jun;79(12):7327-37. | 17. Rainesalo S, Keranen T, Palmio J, Peltola J, Oja SS, Saransaari P: Plasma and cerebrospinal fluid amino acids in epileptic patients. Neurochem Res. 2004 Jan;29(1):319-24. | 18. Lockridge O: Genetic variants of human serum cholinesterase influence metabolism of the muscle relaxant succinylcholine. Pharmacol Ther. 1990;47(1):35-60. | 19. Franklin RB, Zou J, Yu Z, Costello LC: EAAC1 is expressed in rat and human prostate epithelial cells; functions as a high-affinity L-aspartate transporter; and is regulated by prolactin and testosterone. BMC Biochem. 2006 Mar 27;7:10. | 20. Advani SJ, Hagglund R, Weichselbaum RR, Roizman B: Posttranslational processing of infected cell proteins 0 and 4 of herpes simplex virus 1 is sequential and reflects the subcellular compartment in which the proteins localize. J Virol. 2001 Sep;75(17):7904-12. | 21. Wang M, Meng Z, Fu J: Synthesis and biodistribution of six novel 99mTc complexes of 2-hydroxybenzaldehyde-amino acid Schiff bases. Appl Radiat Isot. 2006 Feb;64(2):235-40. | 22. Fisher G, Lopez S, Peterson K, Goff T, Philip I, Gaviria R, Lorenzo N, Tsesarskaia M: Is there a correlation between age and D: -aspartic acid in human knee cartilage? Amino Acids. 2006 Jun 1;. | 23. Baslow MH: Brain N-acetylaspartate as a molecular water pump and its role in the etiology of Canavan disease: a mechanistic explanation. J Mol Neurosci. 2003;21(3):185-90. | 24. Shao B, Belaaouaj A, Verlinde CL, Fu X, Heinecke JW: Methionine sulfoxide and proteolytic cleavage contribute to the inactivation of cathepsin G by hypochlorous acid: an oxidative mechanism for regulation of serine proteinases by myeloperoxidase. J Biol Chem. 2005 Aug 12;280(32):29311-21. Epub 2005 Jun 20. | 25. Silwood CJ, Lynch E, Claxson AW, Grootveld MC: 1H and (13)C NMR spectroscopic analysis of human saliva. J Dent Res. 2002 Jun;81(6):422-7. | 26. Rose CH, Thigpen BD, Bofill JA, Cushman J, May WL, Martin JN Jr: Obstetric implications of antepartum corticosteroid therapy for HELLP syndrome. Obstet Gynecol. 2004 Nov;104(5 Pt 1):1011-4. | 27. Chiara F, Goumans MJ, Forsberg H, Ahgren A, Rasola A, Aspenstrom P, Wernstedt C, Hellberg C, Heldin CH, Heuchel R: A gain of function mutation in the activation loop of platelet-derived growth factor beta-receptor deregulates its kinase activity. J Biol Chem. 2004 Oct 8;279(41):42516-27. Epub 2004 Jul 28. | 28. Bhende PM, Seaman WT, Delecluse HJ, Kenney SC: BZLF1 activation of the methylated form of the BRLF1 immediate-early promoter is regulated by BZLF1 residue 186. J Virol. 2005 Jun;79(12):7338-48. | 29. Nicholson JK, O'Flynn MP, Sadler PJ, Macleod AF, Juul SM, Sonksen PH: Proton-nuclear-magnetic-resonance studies of serum, plasma and urine from fasting normal and diabetic subjects. Biochem J. 1984 Jan 15;217(2):365-75. | 30. Engelborghs S, Marescau B, De Deyn PP: Amino acids and biogenic amines in cerebrospinal fluid of patients with Parkinson's disease. Neurochem Res. 2003 Aug;28(8):1145-50. | 31. Burman P, Hetta J, Wide L, Mansson JE, Ekman R, Karlsson FA: Growth hormone treatment affects brain neurotransmitters and thyroxine [see comment]. Clin Endocrinol (Oxf). 1996 Mar;44(3):319-24. | 32. Butterworth RF: Pathophysiology of hepatic encephalopathy: a new look at ammonia. Metab Brain Dis. 2002 Dec;17(4):221-7. | 33. Hagenfeldt L, Bjerkenstedt L, Edman G, Sedvall G, Wiesel FA: Amino acids in plasma and CSF and monoamine metabolites in CSF: interrelationship in healthy subjects. J Neurochem. 1984 Mar;42(3):833-7. | 34. Sreekumar A, Poisson LM, Rajendiran TM, Khan AP, Cao Q, Yu J, Laxman B, Mehra R, Lonigro RJ, Li Y, Nyati MK, Ahsan A, Kalyana-Sundaram S, Han B, Cao X, Byun J, Omenn GS, Ghosh D, Pennathur S, Alexander DC, Berger A, Shuster JR, Wei JT, Varambally S, Beecher C, Chinnaiyan AM: Metabolomic profiles delineate potential role for sarcosine in prostate cancer progression. Nature. 2009 Feb 12;457(7231):910-4. doi: 10.1038/nature07762. |
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