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targets (7) transporters (1)
for drugs
Identification
Name L-Serine
Accession Number DB00133 (DB03375, NUTR00053)
Type small molecule
Groups approved, nutraceutical
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. [PubChem]
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
(-)-Serine
(S)-2-Amino-3-hydroxypropanoic acid
(S)-a-Amino-b-hydroxypropionic acid
(S)-Serine
2-Amino-3-hydroxypropionic acid
3-Hydroxyalanine
b-Hydroxy-L-alanine
L-(-)-Serine
L-3-Hydroxy-2-aminopropionic acid
L-Ser
Serine
First Prev Next Last
Salts Not Available
Brand names Not Available
Brand mixtures Not Available
Categories
  • Dietary supplement
  • Micronutrient
  • Non-Essential Amino Acids
CAS number 56-45-1
Weight Average: 105.0926
Monoisotopic: 105.042593095
Chemical Formula C3H7NO3
InChI Key InChIKey=MTCFGRXMJLQNBG-REOHCLBHSA-N
InChI
InChI=1S/C3H7NO3/c4-2(1-5)3(6)7/h2,5H,1,4H2,(H,6,7)/t2-/m0/s1
Plain Text
IUPAC Name
(2S)-2-amino-3-hydroxypropanoic acid
SMILES
N[C@@H](CO)C(O)=O
Plain Text
Mass Spec show (8.77 KB)
Taxonomy
Kingdom Organic
Classes
  • Amino Acids
Substructures
  • Amino Acids
  • Hydroxy Compounds
  • Acetates
  • Aliphatic and Aryl Amines
  • Carboxylic Acids and Derivatives
  • Alcohols and Polyols
  • Amino Alcohols
Pharmacology
Indication Used as a natural moisturizing agent in some cosmetics and skin care products.
Pharmacodynamics Serine is classified as a nutritionally non-essential amino acid. Serine is critical for the production of the body's proteins, enzymes and muscle tissue. Serine is needed for the proper metabolism of fats and fatty acids. It also helps in the production of antibodies. Serine is used as a natural moisturizing agent in some cosmetics and skin care products. The main source of essential amino acids is from the diet, non-essential amino acids are normally synthesize by humans and other mammals from common intermediates.
Mechanism of action L-Serine plays a role in cell growth and development (cellular proliferation). The conversion of L-serine to glycine by serine hydroxymethyltransferase results in the formation of the one-carbon units necessary for the synthesis of the purine bases, adenine and guanine. These bases when linked to the phosphate ester of pentose sugars are essential components of DNA and RNA and the end products of energy producing metabolic pathways, ATP and GTP. In addition, L-serine conversion to glycine via this same enzyme provides the one-carbon units necessary for production of the pyrimidine nucleotide, deoxythymidine monophosphate, also an essential component of DNA.
Absorption Not Available
Volume of distribution Not Available
Protein binding Not Available
Metabolism
Not Available
Route of elimination Not Available
Half life Not Available
Clearance Not Available
Toxicity Not Available
Affected organisms
  • Humans and other mammals
Pathways Not Available
Pharmacoeconomics
Manufacturers Not Available
Packagers
Dosage forms Not Available
Prices
Unit description Cost Unit
L-serine powder 3.85 USD g
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents Not Available
Properties
State solid
Experimental Properties
Property Value Source
melting point 228 dec °C PhysProp
water solubility 4.25E+005 mg/L (at 25 °C) YALKOWSKY,SH & DANNENFELSER,RM (1992)
logP -3.07 HANSCH,C ET AL. (1995)
pKa 2.21 (at 25 °C) KORTUM,G ET AL (1961)
Predicted Properties
Property Value Source
water solubility 4.80e+02 g/l ALOGPS
logP -3.4 ALOGPS
logP -3.9 ChemAxon
logS 0.66 ALOGPS
pKa (strongest acidic) 2.03 ChemAxon
pKa (strongest basic) 8.93 ChemAxon
physiological charge 0 ChemAxon
hydrogen acceptor count 4 ChemAxon
hydrogen donor count 3 ChemAxon
polar surface area 83.55 ChemAxon
rotatable bond count 2 ChemAxon
refractivity 22.04 ChemAxon
polarizability 9.43 ChemAxon
References
Synthesis Reference Not Available
General Reference Not Available
External Links
Resource Link
KEGG Drug D00016 Link_out
KEGG Compound C00065 Link_out
PubChem Compound 5951 Link_out
PubChem Substance 46506450 Link_out
ChemSpider 5736 Link_out
ChEBI 17115 Link_out
ChEMBL 17115 Link_out
PharmGKB PA451330 Link_out
IUPHAR 726 Link_out
Guide to Pharmacology 726 Link_out
HET SER Link_out
Wikipedia http://en.wikipedia.org/wiki/Serine Link_out
ATC Codes Not Available
AHFS Codes Not Available
PDB Entries
FDA label Not Available
MSDS show (72.9 KB)
Interactions
Drug Interactions Not Available
Food Interactions Not Available
Targets

1. Cystathionine beta-synthase

Pharmacological action: unknown
Organism class: human
UniProt ID: P35520 Link_out
Gene: CBS Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Sen S, Banerjee R: A pathogenic linked mutation in the catalytic core of human cystathionine beta-synthase disrupts allosteric regulation and allows kinetic characterization of a full-length dimer. Biochemistry. 2007 Apr 3;46(13):4110-6. Epub 2007 Mar 13. Pubmed
  2. Qu K, Lee SW, Bian JS, Low CM, Wong PT: Hydrogen sulfide: Neurochemistry and neurobiology. Neurochem Int. 2007 Jun 8;. Pubmed

2. L-serine dehydratase

Pharmacological action: unknown
Organism class: human
UniProt ID: P20132 Link_out
Gene: SDS Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. Pubmed
  3. Velayudhan J, Jones MA, Barrow PA, Kelly DJ: L-serine catabolism via an oxygen-labile L-serine dehydratase is essential for colonization of the avian gut by Campylobacter jejuni. Infect Immun. 2004 Jan;72(1):260-8. Pubmed
  4. Snell K, Walker DG: Regulation of hepatic L-serine dehydratase and L-serine-pyruvate aminotransferase in the developing neonatal rat. Biochem J. 1974 Dec;144(3):519-31. Pubmed
  5. Wong HC, Lessie TG: Hydroxy amino acid metabolism in Pseudomonas cepacia: role of L-serine deaminase in dissimilation of serine, glycine, and threonine. J Bacteriol. 1979 Oct;140(1):240-5. Pubmed

3. Serine racemase

Pharmacological action: unknown

Catalyzes the synthesis of D-serine from L-serine

Organism class: human
UniProt ID: Q9GZT4 Link_out
Gene: SRR Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Fujitani Y, Horiuchi T, Ito K, Sugimoto M: Serine racemases from barley, Hordeum vulgare L., and other plant species represent a distinct eukaryotic group: gene cloning and recombinant protein characterization. Phytochemistry. 2007 Jun;68(11):1530-6. Epub 2007 May 17. Pubmed
  2. Ying-Luan Z, Zhao YL, Mori H: [Role of D-serine in the mammalian brain] Brain Nerve. 2007 Jul;59(7):725-30. Pubmed

4. Serine palmitoyltransferase 2

Pharmacological action: unknown
Organism class: human
UniProt ID: O15270 Link_out
Gene: SPTLC2 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Yard BA, Carter LG, Johnson KA, Overton IM, Dorward M, Liu H, McMahon SA, Oke M, Puech D, Barton GJ, Naismith JH, Campopiano DJ: The structure of serine palmitoyltransferase; gateway to sphingolipid biosynthesis. J Mol Biol. 2007 Jul 27;370(5):870-86. Epub 2007 May 10. Pubmed

5. Serine palmitoyltransferase 1

Pharmacological action: unknown
Organism class: human
UniProt ID: O15269 Link_out
Gene: SPTLC1 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Yard BA, Carter LG, Johnson KA, Overton IM, Dorward M, Liu H, McMahon SA, Oke M, Puech D, Barton GJ, Naismith JH, Campopiano DJ: The structure of serine palmitoyltransferase; gateway to sphingolipid biosynthesis. J Mol Biol. 2007 Jul 27;370(5):870-86. Epub 2007 May 10. Pubmed

6. Seryl-tRNA synthetase, cytoplasmic

Pharmacological action: unknown
Organism class: human
UniProt ID: P49591 Link_out
Gene: SARS Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. Pubmed
  3. Zhang Y, Cui J, Zhang R, Wang Y, Hong M: A novel fibrinolytic serine protease from the polychaete Nereis (Neanthes) virens (Sars): purification and characterization. Biochimie. 2007 Jan;89(1):93-103. Epub 2006 Aug 22. Pubmed
  4. Follis KE, York J, Nunberg JH: Serine-scanning mutagenesis studies of the C-terminal heptad repeats in the SARS coronavirus S glycoprotein highlight the important role of the short helical region. Virology. 2005 Oct 10;341(1):122-9. Pubmed
  5. McClendon CL, Vaidehi N, Kam VW, Zhang D, Goddard WA 3rd: Fidelity of seryl-tRNA synthetase to binding of natural amino acids from HierDock first principles computations. Protein Eng Des Sel. 2006 May;19(5):195-203. Epub 2006 Mar 3. Pubmed

7. Serine--pyruvate aminotransferase

Pharmacological action: unknown
Organism class: human
UniProt ID: P21549 Link_out
Gene: AGXT Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Ikushiro H, Islam MM, Tojo H, Hayashi H: Molecular characterization of membrane-associated soluble serine palmitoyltransferases from Sphingobacterium multivorum and Bdellovibrio stolpii. J Bacteriol. 2007 Aug;189(15):5749-61. Epub 2007 Jun 8. Pubmed
  2. Cowart LA, Hannun YA: Selective substrate supply in the regulation of yeast de novo sphingolipid synthesis. J Biol Chem. 2007 Apr 20;282(16):12330-40. Epub 2007 Feb 23. Pubmed
  3. Son JH, Yoo HH, Kim DH: Activation of de novo synthetic pathway of ceramides is responsible for the initiation of hydrogen peroxide-induced apoptosis in HL-60 cells. J Toxicol Environ Health A. 2007 Aug;70(15-16):1310-8. Pubmed
  4. Yard BA, Carter LG, Johnson KA, Overton IM, Dorward M, Liu H, McMahon SA, Oke M, Puech D, Barton GJ, Naismith JH, Campopiano DJ: The structure of serine palmitoyltransferase; gateway to sphingolipid biosynthesis. J Mol Biol. 2007 Jul 27;370(5):870-86. Epub 2007 May 10. Pubmed
Transporters

1. Monocarboxylate transporter 10

Actions: inhibitor

Sodium-independent transporter that mediates the update of aromatic acid. Can function as a net efflux pathway for aromatic amino acids in the basosolateral epithelial cells (By similarity)

UniProt ID: Q8TF71 Link_out
Gene: SLC16A10 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Kim DK, Kanai Y, Chairoungdua A, Matsuo H, Cha SH, Endou H: Expression cloning of a Na+-independent aromatic amino acid transporter with structural similarity to H+/monocarboxylate transporters. J Biol Chem. 2001 May 18;276(20):17221-8. Epub 2001 Feb 20. Pubmed
Comments
Drug created on June 13, 2005 07:24 / Updated on February 08, 2013 16:19