Human Metabolome Database Version 3.5

Showing metabocard for L-Serine (HMDB00187)

Record Information
Version 3.5
Creation Date 2005-11-16 08:48:42 -0700
Update Date 2013-05-29 13:24:58 -0600
HMDB ID HMDB00187
Secondary Accession Numbers
  • HMDB00589
Metabolite Identification
Common Name L-Serine
Description Serine is a nonessential amino acid derived from glycine. Like all the amino acid building blocks of protein and peptides, serine can become essential under certain conditions, and is thus important in maintaining health and preventing disease. Low-average concentration of serine compared to other amino acids is found in muscle. Serine is highly concentrated in all cell membranes. (http://www.dcnutrition.com/AminoAcids/) L-Serine may be derived from four possible sources: dietary intake; biosynthesis from the glycolytic intermediate 3-phosphoglycerate; from glycine ; and by protein and phospholipid degradation. Little data is available on the relative contributions of each of these four sources of l-serine to serine homoeostasis. It is very likely that the predominant source of l-serine will be very different in different tissues and during different stages of human development. In the biosynthetic pathway, the glycolytic intermediate 3-phosphoglycerate is converted into phosphohydroxypyruvate, in a reaction catalyzed by 3-phosphoglycerate dehydrogenase (3- PGDH; EC 1.1.1.95). Phosphohydroxypyruvate is metabolized to phosphoserine by phosphohydroxypyruvate aminotransferase (EC 2.6.1.52) and, finally, phosphoserine is converted into l-serine by phosphoserine phosphatase (PSP; EC 3.1.3.3). In liver tissue, the serine biosynthetic pathway is regulated in response to dietary and hormonal changes. Of the three synthetic enzymes, the properties of 3-PGDH and PSP are the best documented. Hormonal factors such as glucagon and corticosteroids also influence 3-PGDH and PSP activities in interactions dependent upon the diet. L-serine plays a central role in cellular proliferation. L-Serine is the predominant source of one-carbon groups for the de novo synthesis of purine nucleotides and deoxythymidine monophosphate. It has long been recognized that, in cell cultures, L-serine is a conditional essential amino acid, because it cannot be synthesized in sufficient quantities to meet the cellular demands for its utilization. In recent years, L-serine and the products of its metabolism have been recognized not only to be essential for cell proliferation, but also to be necessary for specific functions in the central nervous system. The findings of altered levels of serine and glycine in patients with psychiatric disorders and the severe neurological abnormalities in patients with defects of L-serine synthesis underscore the importance of L-serine in brain development and function. (PMID 12534373 Link_out).
Structure Thumb
Download: MOL | SDF | PDB | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. (-)-Serine
  2. (S)-2-amino-3-hydroxy-Propanoate
  3. (S)-2-amino-3-hydroxy-Propanoic acid
  4. (S)-2-Amino-3-hydroxypropanoate
  5. (S)-2-Amino-3-hydroxypropanoic acid
  6. (S)-a-Amino-b-hydroxypropionate
  7. (S)-a-Amino-b-hydroxypropionic acid
  8. (S)-alpha-Amino-beta-hydroxypropionate
  9. (S)-alpha-Amino-beta-hydroxypropionic acid
  10. (S)-b-Amino-3-hydroxypropionate
  11. (S)-b-Amino-3-hydroxypropionic acid
  12. (S)-beta-Amino-3-hydroxypropionate
  13. (S)-beta-Amino-3-hydroxypropionic acid
  14. (S)-Serine
  15. 2-Amino-3-hydroxypropanoate
  16. 2-Amino-3-hydroxypropanoic acid
  17. 3-Hydroxy-L-Alanine
  18. b-Hydroxy-L-alanine
  19. beta-Hydroxy-L-alanine
  20. beta-Hydroxyalanine
  21. L-(-)-Serine
  22. L-3-Hydroxy-2-aminopropionate
  23. L-3-Hydroxy-2-aminopropionic acid
  24. L-3-Hydroxy-alanine
  25. L-Ser
  26. Serine
Chemical Formula C3H7NO3
Average Molecular Weight 105.0926
Monoisotopic Molecular Weight 105.042593095
IUPAC Name (2S)-2-amino-3-hydroxypropanoic acid
Traditional IUPAC Name L-serine
CAS Registry Number 56-45-1
SMILES N[C@@H](CO)C(O)=O
InChI Identifier InChI=1S/C3H7NO3/c4-2(1-5)3(6)7/h2,5H,1,4H2,(H,6,7)/t2-/m0/s1
InChI Key MTCFGRXMJLQNBG-REOHCLBHSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Amino Acids, Peptides, and Analogues
Class Amino Acids and Derivatives
Sub Class Alpha Amino Acids and Derivatives
Other Descriptors
  • Aliphatic Acyclic Compounds
  • Amino fatty acids(Lipidmaps)
  • amino acid zwitterion(ChEBI)
Substituents
  • 1,2 Aminoalcohol
  • Beta Hydroxy Acid
  • Carboxylic Acid
  • Primary Alcohol
  • Primary Aliphatic Amine (Alkylamine)
Direct Parent Alpha Amino Acids and Derivatives
Ontology
Status Detected and Quantified
Origin
  • Endogenous
Biofunction
  • Component of Aminoacyl-tRNA biosynthesis
  • Component of Cyanoamino acid metabolism
  • Component of Cysteine metabolism
  • Component of Glycine, serine and threonine metabolism
  • Component of Glycosphingolipid metabolism
  • Component of Methane metabolism
  • Component of Methionine metabolism
  • Component of Selenoamino acid metabolism
Application Not Available
Cellular locations
  • Cytoplasm
  • Extracellular
  • Mitochondria
  • Peroxisome
Physical Properties
State Solid
Experimental Properties
Property Value Reference
Melting Point 228 °C Not Available
Boiling Point Not Available Not Available
Water Solubility 425.0 mg/mL Not Available
LogP -3.07 HANSCH,C ET AL. (1995)
Predicted Properties
Property Value Source
Water Solubility 480 g/L ALOGPS
LogP -3.42 ALOGPS
LogP -3.9 ChemAxon
LogS 0.66 ALOGPS
pKa (strongest acidic) 2.03 ChemAxon
pKa (strongest basic) 8.93 ChemAxon
Hydrogen Acceptor Count 4 ChemAxon
Hydrogen Donor Count 3 ChemAxon
Polar Surface Area 83.55 A2 ChemAxon
Rotatable Bond Count 2 ChemAxon
Refractivity 22.04 ChemAxon
Polarizability 9.45 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge 0 ChemAxon
Spectra
Gas-MS Spectrum
1H NMR Spectrum
MS/MS Spectrum Quattro_QQQ 10
MS/MS Spectrum Quattro_QQQ 25
MS/MS Spectrum Quattro_QQQ 40
MS/MS Spectrum LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic)
MS/MS Spectrum LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic)
MS/MS Spectrum LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic)
MS/MS Spectrum LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic)
MS/MS Spectrum LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic)
MS/MS Spectrum LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic)
MS/MS Spectrum LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic)
MS/MS Spectrum LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic)
MS/MS Spectrum LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic)
MS/MS Spectrum LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic)
MS/MS Spectrum LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic)
MS/MS Spectrum LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic)
[1H,1H] 2D NMR Spectrum
[1H,13C] 2D NMR Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Mitochondria
  • Peroxisome
Biofluid Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Urine
Tissue Location
  • All Tissues
  • Prostate
Pathways
Name SMPDB Link KEGG Link
Ammonia Recycling SMP00009 map00910 Link_out
Sphingolipid Metabolism SMP00034 map00500 Link_out
Glycine and Serine Metabolism SMP00004 map00260 Link_out
Methionine Metabolism SMP00033 map00270 Link_out
Homocysteine Degradation SMP00455 Not Available
Normal Concentrations
Biofluid Status Value Age Sex Condition Reference
Blood Detected and Quantified
159.8 +/- 26.6 uM Adult (>18 years old) Not Specified Normal
Blood Detected and Quantified
173.2 +/- 51.3 uM Adult (>18 years old) Not Specified Normal
Blood Detected and Quantified
114.0 (95.0-133.0) uM Adult (>18 years old) Both Normal
Blood Detected and Quantified
134.0 +/- 38.0 uM Newborn (0-30 days old) Not Specified Normal
  • Geigy Scient...
Blood Detected and Quantified
121.0 +/- 25.0 uM Children (1-13 year old) Male Normal
  • Geigy Scient...
Blood Detected and Quantified
127.0 +/- 27.0 uM Children (1-13 year old) Female Normal
  • Geigy Scient...
Blood Detected and Quantified
114.0 +/- 23.0 uM Adult (>18 years old) Male Normal
  • Geigy Scient...
Blood Detected and Quantified
127.0 +/- 29.0 uM Adult (>18 years old) Female Normal
  • Geigy Scient...
Blood Detected and Quantified
121.0 +/- 14.0 uM Children (1-13 year old) Not Specified Normal
  • Geigy Scient...
Blood Detected and Quantified
137.0 +/- 35.0 uM Adult (>18 years old) Male Normal
  • Geigy Scient...
Blood Detected and Quantified
142.0 +/- 35.0 uM Adult (>18 years old) Female Normal
  • Geigy Scient...
Blood Detected and Quantified
70.3 +/- 19.6 uM Adult (>18 years old) Male Normal
Blood Detected and Quantified
236.0 +/- 6.0 uM Adult (>18 years old) Both Normal
Cerebrospinal Fluid (CSF) Detected and Quantified
28.9 (20.7-37.0) uM Adult (>18 years old) Both Normal
Cerebrospinal Fluid (CSF) Detected and Quantified
24.5 +/- 4.4 uM Adult (>18 years old) Both Normal
  • Geigy Scient...
Cerebrospinal Fluid (CSF) Detected and Quantified
42 +/- 18 uM Not Specified Both Normal
Cerebrospinal Fluid (CSF) Detected and Quantified
42.4 +/- 15.1 uM Adult (>18 years old) Not Specified Normal
Cerebrospinal Fluid (CSF) Detected and Quantified
28.1 +/- 4.7 uM Adult (>18 years old) Not Specified Normal
Cerebrospinal Fluid (CSF) Detected and Quantified
30.2 +/- 3.8 uM Adult (>18 years old) Not Specified Normal
Cerebrospinal Fluid (CSF) Detected and Quantified
32.8 +/- 8.6 uM Adult (>18 years old) Not Specified Normal
Cerebrospinal Fluid (CSF) Detected and Quantified
7.6 +/- 0.67 uM Adult (>18 years old) Both Normal
Urine Detected and Quantified
19.0 (10.4-35.8) umol/mmol creatinine Adult (>18 years old) Both Comment Normal
Urine Detected and Quantified
33.6 umol/mmol creatinine Adult (>18 years old) Both Normal
Urine Detected and Quantified
19.04-47.60 umol/mmol creatinine Adult (>18 years old) Both Normal
  • David F. Put...
Urine Detected and Quantified
25.3 (11.6-53.4) umol/mmol creatinine Adult (>18 years old) Both Comment Normal
Urine Detected and Quantified
33.83 umol/mmol creatinine Adult (>18 years old) Male Normal
  • Shaykhutdino...
Urine Detected but not Quantified
Not Applicable Adult (>18 years old) Both Comment Normal
Urine Detected and Quantified
0.0021 - 10.1 umol/mmol creatinine Adult (>18 years old) Both Normal
Urine Detected and Quantified
27.38 +/- 9.54 umol/mmol creatinine Adult (>18 years old) Both Normal
Urine Detected and Quantified
24.5 (12.3-50.2) umol/mmol creatinine Adult (>18 years old) Both Comment Normal
Urine Detected and Quantified
2.6 (0.37-5.0) umol/mmol creatinine Newborn (0-30 days old) Both Normal
  • Geigy Scient...
  • West Cadwell...
  • Basel, Switz...
Urine Detected and Quantified
8.9 +/- 4.6 umol/mmol creatinine Children (1-13 year old) Female Normal
  • Geigy Scient...
  • West Cadwell...
  • Basel, Switz...
Urine Detected and Quantified
30.0 +/- 13.6 umol/mmol creatinine Adult (>18 years old) Male Normal
  • Geigy Scient...
  • West Cadwell...
  • Basel, Switz...
Urine Detected and Quantified
26.0 +/- 10.0 umol/mmol creatinine Adult (>18 years old) Female Normal
  • Geigy Scient...
  • West Cadwell...
  • Basel, Switz...
Urine Detected and Quantified
28.5 (12.5-44.4) umol/mmol creatinine Adult (>18 years old) Both Normal
Urine Detected and Quantified
74.67 +/- 37.74 umol/mmol creatinine Infant (0-1 year old) Both Normal
Urine Detected and Quantified
31.6 umol/mmol creatinine Adult (>18 years old) Both Normal
Abnormal Concentrations
Biofluid Status Value Age Sex Condition Reference
Blood Detected and Quantified 104.0 (101.0-107.0) uM Adult (>18 years old) Both Refractory localization-related epilepsy (RLE)
Blood Detected and Quantified 140.0 (131.0-148.0) uM Children (1-13 year old) Both Juvenile myoclonic epilepsy (JME)
Blood Detected and Quantified 197.9 +/- 46.4 uM Adult (>18 years old) Both Schizophrenia
Blood Detected and Quantified 0.21 +/- 0.024 uM Elderly (>65 years old) Both Alzheimer's disease
Blood Detected and Quantified 221.0 +/- 8.0 uM Adult (>18 years old) Both Comment Heart failure
Cerebrospinal Fluid (CSF) Detected and Quantified 38.3 +/- 15.5 uM Children (1-13 year old) Not Specified Leukemia
Cerebrospinal Fluid (CSF) Detected and Quantified 31.9 +/- 8.8 uM Children (1-13 year old) Not Specified Comment Leukemia
Cerebrospinal Fluid (CSF) Detected and Quantified 7.5 +/- 0.87 uM Adult (>18 years old) Both Schizophrenia
Urine Detected and Quantified 0.0041 - 0.0122 umol/mmol creatinine Adult (>18 years old) Both ADPKD
Associated Disorders and Diseases
Disease References
Refractory localization-related epilepsy
  • 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. Pubmed: 14992292 Link_out
      Juvenile myoclonic epilepsy
      • 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. Pubmed: 14992292 Link_out
          Leukemia
          • Peng CT, Wu KH, Lan SJ, Tsai JJ, Tsai FJ, Tsai CH: Amino acid concentrations in cerebrospinal fluid in children with acute lymphoblastic leukemia undergoing chemotherapy. Eur J Cancer. 2005 May;41(8):1158-63. Epub 2005 Apr 14. Pubmed: 15911239 Link_out
              Alzheimer's disease
              • Fonteh AN, Harrington RJ, Tsai A, Liao P, Harrington MG: Free amino acid and dipeptide changes in the body fluids from Alzheimer's disease subjects. Amino Acids. 2007 Feb;32(2):213-24. Epub 2006 Oct 10. Pubmed: 17031479 Link_out
                  Heart failure
                  • Norrelund H, Wiggers H, Halbirk M, Frystyk J, Flyvbjerg A, Botker HE, Schmitz O, Jorgensen JO, Christiansen JS, Moller N: Abnormalities of whole body protein turnover, muscle metabolism and levels of metabolic hormones in patients with chronic heart failure. J Intern Med. 2006 Jul;260(1):11-21. Pubmed: 16789974 Link_out
                      Schizophrenia
                      • Hashimoto K, Fukushima T, Shimizu E, Komatsu N, Watanabe H, Shinoda N, Nakazato M, Kumakiri C, Okada S, Hasegawa H, Imai K, Iyo M: Decreased serum levels of D-serine in patients with schizophrenia: evidence in support of the N-methyl-D-aspartate receptor hypofunction hypothesis of schizophrenia. Arch Gen Psychiatry. 2003 Jun;60(6):572-6. Pubmed: 12796220 Link_out
                      • Do KQ, Lauer CJ, Schreiber W, Zollinger M, Gutteck-Amsler U, Cuenod M, Holsboer F: gamma-Glutamylglutamine and taurine concentrations are decreased in the cerebrospinal fluid of drug-naive patients with schizophrenic disorders. J Neurochem. 1995 Dec;65(6):2652-62. Pubmed: 7595563 Link_out
                          Associated OMIM IDs
                          DrugBank ID DB00133 Link_out
                          DrugBank Metabolite ID Not Available
                          Phenol Explorer Compound ID Not Available
                          Phenol Explorer Metabolite ID Not Available
                          FoodDB ID FDB012739
                          KNApSAcK ID C00001393 Link_out
                          Chemspider ID 5736 Link_out
                          KEGG Compound ID C00065 Link_out
                          BioCyc ID SER Link_out
                          BiGG ID 33717 Link_out
                          Wikipedia Link L-Serine Link_out
                          NuGOwiki Link HMDB00187 Link_out
                          Metagene Link HMDB00187 Link_out
                          METLIN ID 5203 Link_out
                          PubChem Compound 5951 Link_out
                          PDB ID SER Link_out
                          ChEBI ID 17115 Link_out
                          References
                          Synthesis Reference Qin, Wei-min; Cao, Fei; Zhou, Hua; Li, Zhen-jiang; Wei, Ping. Asymmetric synthesis of D- and L-serine with "Glycine equivalent" method. Huaxue Shiji (2005), 27(11), 643-644, 670.
                          Material Safety Data Sheet (MSDS) Download (PDF)
                          General References
                          1. Furuya S, Watanabe M: Novel neuroglial and glioglial relationships mediated by L-serine metabolism. Arch Histol Cytol. 2003 May;66(2):109-21. Pubmed: 12846552 Link_out
                          2. Peng CT, Wu KH, Lan SJ, Tsai JJ, Tsai FJ, Tsai CH: Amino acid concentrations in cerebrospinal fluid in children with acute lymphoblastic leukemia undergoing chemotherapy. Eur J Cancer. 2005 May;41(8):1158-63. Epub 2005 Apr 14. Pubmed: 15911239 Link_out
                          3. Kaumeyer JF, Polazzi JO, Kotick MP: The mRNA for a proteinase inhibitor related to the HI-30 domain of inter-alpha-trypsin inhibitor also encodes alpha-1-microglobulin (protein HC). Nucleic Acids Res. 1986 Oct 24;14(20):7839-50. Pubmed: 2430261 Link_out
                          4. Haas W, Grabe K, Geis C, Pach T, Stoll K, Fuchs M, Haberl B, Loy C: Recognition and invasion of human skin by Schistosoma mansoni cercariae: the key-role of L-arginine. Parasitology. 2002 Feb;124(Pt 2):153-67. Pubmed: 11860033 Link_out
                          5. Cynober LA: Plasma amino acid levels with a note on membrane transport: characteristics, regulation, and metabolic significance. Nutrition. 2002 Sep;18(9):761-6. Pubmed: 12297216 Link_out
                          6. 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. Pubmed: 14992292 Link_out
                          7. Hashimoto K, Engberg G, Shimizu E, Nordin C, Lindstrom LH, Iyo M: Reduced D-serine to total serine ratio in the cerebrospinal fluid of drug naive schizophrenic patients. Prog Neuropsychopharmacol Biol Psychiatry. 2005 Jun;29(5):767-9. Pubmed: 15939521 Link_out
                          8. Castedo M, Ferri KF, Blanco J, Roumier T, Larochette N, Barretina J, Amendola A, Nardacci R, Metivier D, Este JA, Piacentini M, Kroemer G: Human immunodeficiency virus 1 envelope glycoprotein complex-induced apoptosis involves mammalian target of rapamycin/FKBP12-rapamycin-associated protein-mediated p53 phosphorylation. J Exp Med. 2001 Oct 15;194(8):1097-110. Pubmed: 11602639 Link_out
                          9. Liu T, Zhu E, Wang L, Okada T, Yamaguchi A, Okada N: Abnormal expression of Rb pathway-related proteins in salivary gland acinic cell carcinoma. Hum Pathol. 2005 Sep;36(9):962-70. Pubmed: 16153458 Link_out
                          10. Franchi-Gazzola R, Gazzola GC, Dall'Asta V, Guidotti GG: The transport of alanine, serine, and cysteine in cultured human fibroblasts. J Biol Chem. 1982 Aug 25;257(16):9582-7. Pubmed: 6809740 Link_out
                          11. Fontaine M, Porchet N, Largilliere C, Marrakchi S, Lhermitte M, Aubert JP, Degand P: Biochemical contribution to diagnosis and study of a new case of D-glyceric acidemia/aciduria. Clin Chem. 1989 Oct;35(10):2148-51. Pubmed: 2551543 Link_out
                          12. Yamamoto T, Nishizaki I, Nukada T, Kamegaya E, Furuya S, Hirabayashi Y, Ikeda K, Hata H, Kobayashi H, Sora I, Yamamoto H: Functional identification of ASCT1 neutral amino acid transporter as the predominant system for the uptake of L-serine in rat neurons in primary culture. Neurosci Res. 2004 May;49(1):101-11. Pubmed: 15099708 Link_out
                          13. Mackie S, Aitken A: Novel brain 14-3-3 interacting proteins involved in neurodegenerative disease. FEBS J. 2005 Aug;272(16):4202-10. Pubmed: 16098201 Link_out
                          14. Kobza K, Camporeale G, Rueckert B, Kueh A, Griffin JB, Sarath G, Zempleni J: K4, K9 and K18 in human histone H3 are targets for biotinylation by biotinidase. FEBS J. 2005 Aug;272(16):4249-59. Pubmed: 16098205 Link_out
                          15. Whittemore AS, Cirillo PM, Feldman D, Cohn BA: Prostate specific antigen levels in young adulthood predict prostate cancer risk: results from a cohort of Black and White Americans. J Urol. 2005 Sep;174(3):872-6; discussion 876. Pubmed: 16093978 Link_out
                          16. Schulz I, Zeitschel U, Rudolph T, Ruiz-Carrillo D, Rahfeld JU, Gerhartz B, Bigl V, Demuth HU, Rossner S: Subcellular localization suggests novel functions for prolyl endopeptidase in protein secretion. J Neurochem. 2005 Aug;94(4):970-9. Pubmed: 16092940 Link_out
                          17. 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. Pubmed: 6696735 Link_out
                          18. 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. Pubmed: 12834252 Link_out
                          19. 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. Pubmed: 6198473 Link_out
                          20. 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. Pubmed: 19212411 Link_out
                          21. de Koning TJ, Snell K, Duran M, Berger R, Poll-The BT, Surtees R: L-serine in disease and development. Biochem J. 2003 May 1;371(Pt 3):653-61. Pubmed: 12534373 Link_out

                          Enzymes
                          Name: Serine--tRNA ligase, mitochondrial
                          Reactions:
                          Adenosine triphosphate + L-Serine + tRNA(Ser) unknown Adenosine monophosphate + Pyrophosphate + L-seryl-tRNA(Ser) details
                          Adenosine triphosphate + L-Serine + tRNA(Sec) unknown Adenosine monophosphate + Pyrophosphate + L-seryl-tRNA(Sec) details
                          Adenosine triphosphate + L-Serine + tRNA(Ser) unknown Adenosine monophosphate + Pyrophosphate + L-Seryl-tRNA(Ser) details
                          Adenosine triphosphate + L-Serine + tRNA(Sec) unknown Adenosine monophosphate + Pyrophosphate + L-Seryl-tRNA(Sec) details
                          Gene Name: SARS2
                          Uniprot ID: Q9NP81 Link_out
                          Protein Sequence: FASTA
                          Gene Sequence: FASTA
                          Name: Serine--tRNA ligase, cytoplasmic
                          Reactions:
                          Adenosine triphosphate + L-Serine + tRNA(Ser) unknown Adenosine monophosphate + Pyrophosphate + L-seryl-tRNA(Ser) details
                          Adenosine triphosphate + L-Serine + tRNA(Sec) unknown Adenosine monophosphate + Pyrophosphate + L-seryl-tRNA(Sec) details
                          Adenosine triphosphate + L-Serine + tRNA(Ser) unknown Adenosine monophosphate + Pyrophosphate + L-Seryl-tRNA(Ser) details
                          Adenosine triphosphate + L-Serine + tRNA(Sec) unknown Adenosine monophosphate + Pyrophosphate + L-Seryl-tRNA(Sec) details
                          Gene Name: SARS
                          Uniprot ID: P49591 Link_out
                          Protein Sequence: FASTA
                          Gene Sequence: FASTA
                          Name: L-serine dehydratase/L-threonine deaminase
                          Reactions:
                          L-Serine unknown Pyruvic acid + Ammonia details
                          L-Serine unknown 2-Aminoacrylic acid + Water details
                          Gene Name: SDS
                          Uniprot ID: P20132 Link_out
                          Protein Sequence: FASTA
                          Gene Sequence: FASTA
                          Name: Cystathionine beta-synthase
                          Reactions:
                          L-Serine + Homocysteine unknown L-Cystathionine + Water details
                          L-Serine + Hydrogen sulfide unknown L-Cysteine + Water details
                          L-Serine + Selenohomocysteine unknown Selenocystathionine + Water details
                          Gene Name: CBS
                          Uniprot ID: P35520 Link_out
                          Protein Sequence: FASTA
                          Gene Sequence: FASTA
                          Name: Serine--pyruvate aminotransferase
                          Reactions:
                          L-Serine + Pyruvic acid unknown Hydroxypyruvic acid + L-Alanine details
                          L-Serine + Glyoxylic acid unknown Hydroxypyruvic acid + Glycine details
                          Gene Name: AGXT
                          Uniprot ID: P21549 Link_out
                          Protein Sequence: FASTA
                          Gene Sequence: FASTA
                          Name: Serine hydroxymethyltransferase, mitochondrial
                          Reactions:
                          5,10-Methylene-THF + Glycine + Water unknown Tetrahydrofolic acid + L-Serine details
                          L-Serine + 5,6,7,8-Tetrahydromethanopterin unknown 5,10-Methylenetetrahydromethanopterin + Glycine + Water details
                          Gene Name: SHMT2
                          Uniprot ID: P34897 Link_out
                          Protein Sequence: FASTA
                          Gene Sequence: FASTA
                          Name: Serine hydroxymethyltransferase, cytosolic
                          Reactions:
                          5,10-Methylene-THF + Glycine + Water unknown Tetrahydrofolic acid + L-Serine details
                          L-Serine + 5,6,7,8-Tetrahydromethanopterin unknown 5,10-Methylenetetrahydromethanopterin + Glycine + Water details
                          Gene Name: SHMT1
                          Uniprot ID: P34896 Link_out
                          Protein Sequence: FASTA
                          Gene Sequence: FASTA
                          Name: Serine palmitoyltransferase 1
                          Reactions:
                          hexadecanoyl-CoA + L-Serine unknown Coenzyme A + 3-Dehydrosphinganine + CO(2) details
                          hexadecanoyl-CoA + L-Serine unknown 3-Dehydrosphinganine + Coenzyme A + Carbon dioxide details
                          Gene Name: SPTLC1
                          Uniprot ID: O15269 Link_out
                          Protein Sequence: FASTA
                          Gene Sequence: FASTA
                          Name: Phosphoserine phosphatase
                          Reactions:
                          Phosphoserine + Water unknown L-Serine + Phosphoric acid details
                          Gene Name: PSPH
                          Uniprot ID: P78330 Link_out
                          Protein Sequence: FASTA
                          Gene Sequence: FASTA
                          Name: Serine palmitoyltransferase 2
                          Reactions:
                          hexadecanoyl-CoA + L-Serine unknown Coenzyme A + 3-Dehydrosphinganine + CO(2) details
                          hexadecanoyl-CoA + L-Serine unknown 3-Dehydrosphinganine + Coenzyme A + Carbon dioxide details
                          Gene Name: SPTLC2
                          Uniprot ID: O15270 Link_out
                          Protein Sequence: FASTA
                          Gene Sequence: FASTA
                          Name: Phosphatidylserine synthase 1
                          Reactions:
                          L-1-phosphatidylethanolamine + L-Serine unknown L-1-phosphatidylserine + Ethanolamine details
                          Gene Name: PTDSS1
                          Uniprot ID: P48651 Link_out
                          Protein Sequence: FASTA
                          Gene Sequence: FASTA
                          Name: Phosphatidylserine synthase 2
                          Reactions:
                          L-1-phosphatidylethanolamine + L-Serine unknown L-1-phosphatidylserine + Ethanolamine details
                          Gene Name: PTDSS2
                          Uniprot ID: Q9BVG9 Link_out
                          Protein Sequence: FASTA
                          Gene Sequence: FASTA
                          Name: Neutral amino acid transporter A
                          Reactions: Not Available
                          Gene Name: SLC1A4
                          Uniprot ID: P43007 Link_out
                          Protein Sequence: FASTA
                          Gene Sequence: FASTA
                          Name: Serine dehydratase-like
                          Reactions:
                          L-Serine unknown Pyruvic acid + Ammonia details
                          Gene Name: SDSL
                          Uniprot ID: Q96GA7 Link_out
                          Protein Sequence: FASTA
                          Gene Sequence: FASTA
                          Name: Serine palmitoyltransferase 3
                          Reactions:
                          hexadecanoyl-CoA + L-Serine unknown Coenzyme A + 3-Dehydrosphinganine + CO(2) details
                          hexadecanoyl-CoA + L-Serine unknown 3-Dehydrosphinganine + Coenzyme A + Carbon dioxide details
                          Gene Name: SPTLC3
                          Uniprot ID: Q9NUV7 Link_out
                          Protein Sequence: FASTA
                          Gene Sequence: FASTA
                          Name: Serine racemase
                          Reactions:
                          L-Serine unknown D-Serine details
                          L-Serine unknown Pyruvic acid + Ammonia details
                          Gene Name: SRR
                          Uniprot ID: Q9GZT4 Link_out
                          Protein Sequence: FASTA
                          Gene Sequence: FASTA
                          Name: Serine hydroxymethyltransferase
                          Reactions: Not Available
                          Gene Name: SHMT1
                          Uniprot ID: A8MYA6 Link_out
                          Protein Sequence: FASTA
                          Gene Sequence: FASTA
                          Name: Serine hydroxymethyltransferase
                          Reactions: Not Available
                          Gene Name: SHMT2
                          Uniprot ID: Q5BJF5 Link_out
                          Protein Sequence: FASTA
                          Gene Sequence: FASTA
                          Name: Serine incorporator 1
                          Reactions: Not Available
                          Gene Name: SERINC1
                          Uniprot ID: Q9NRX5 Link_out
                          Protein Sequence: FASTA
                          Gene Sequence: FASTA
                          Transporters
                          Name: Monocarboxylate transporter 10
                          Reactions: Not Available
                          Gene Name: SLC16A10
                          Uniprot ID: Q8TF71 Link_out
                          Protein Sequence: FASTA
                          Gene Sequence: FASTA