Welcome to DrugBank 4.0! If you prefer, you can still go back to version 3.0.
Identification
NameL-Serine
Accession NumberDB00133  (DB03375, NUTR00053)
Typesmall molecule
Groupsapproved, 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
Synonyms
SynonymLanguageCode
(S)-(−)-serineNot AvailableNot Available
(S)-2-Amino-3-hydroxypropanoic acidNot AvailableNot Available
(S)-alpha-Amino-beta-hydroxypropionic acidNot AvailableNot Available
(S)-SerineNot AvailableNot Available
beta-Hydroxy-L-alanineNot AvailableNot Available
beta-HydroxyalanineNot AvailableNot Available
L-(-)-SerineNot AvailableNot Available
L-(−)-serineNot AvailableNot Available
L-2-Amino-3-hydroxypropionic acidNot AvailableNot Available
L-3-Hydroxy-2-aminopropionic acidNot AvailableNot Available
L-3-Hydroxy-alanineNot AvailableNot Available
L-SerNot AvailableNot Available
L-SerinNot AvailableNot Available
SerNot AvailableNot Available
SerineNot AvailableNot Available
SaltsNot Available
Brand namesNot Available
Brand mixturesNot Available
CategoriesNot Available
CAS number56-45-1
WeightAverage: 105.0926
Monoisotopic: 105.042593095
Chemical FormulaC3H7NO3
InChI KeyInChIKey=MTCFGRXMJLQNBG-REOHCLBHSA-N
InChI
InChI=1S/C3H7NO3/c4-2(1-5)3(6)7/h2,5H,1,4H2,(H,6,7)/t2-/m0/s1
IUPAC Name
(2S)-2-amino-3-hydroxypropanoic acid
SMILES
N[C@@H](CO)C(O)=O
Mass Specshow(8.77 KB)
Taxonomy
KingdomOrganic Compounds
SuperclassOrganic Acids and Derivatives
ClassCarboxylic Acids and Derivatives
SubclassAmino Acids, Peptides, and Analogues
Direct parentAlpha Amino Acids and Derivatives
Alternative parentsBeta Hydroxy Acids and Derivatives; Polyols; Primary Alcohols; Polyamines; Enolates; Carboxylic Acids; Monoalkylamines
Substituentsbeta-hydroxy acid; hydroxy acid; polyol; polyamine; enolate; primary alcohol; carboxylic acid; amine; organonitrogen compound; primary aliphatic amine; alcohol; primary amine
Classification descriptionThis compound belongs to the alpha amino acids and derivatives. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon), or a derivative thereof.
Pharmacology
IndicationUsed as a natural moisturizing agent in some cosmetics and skin care products.
PharmacodynamicsSerine 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 actionL-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.
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
Metabolism
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organisms
  • Humans and other mammals
Pathways
PathwayCategorySMPDB ID
Selenoamino Acid MetabolismMetabolicSMP00029
S-Adenosylhomocysteine (SAH) Hydrolase DeficiencyDiseaseSMP00214
Methionine Adenosyltransferase DeficiencyDiseaseSMP00221
Ammonia RecyclingMetabolicSMP00009
Homocystinuria-megaloblastic anemia due to defect in cobalamin metabolism, cblG complementation typeDiseaseSMP00570
Cystathionine Beta-Synthase DeficiencyDiseaseSMP00177
Homocystinuria, cystathionine beta-synthase deficiencyDiseaseSMP00515
Globoid Cell LeukodystrophyDiseaseSMP00348
Gamma-cystathionase deficiency (CTH)DiseaseSMP00514
Methylenetetrahydrofolate Reductase Deficiency (MTHFRD)DiseaseSMP00340
Glycine N-methyltransferase DeficiencyDiseaseSMP00222
Dimethylglycine Dehydrogenase DeficiencyDiseaseSMP00242
Dihydropyrimidine Dehydrogenase Deficiency (DHPD)DiseaseSMP00179
Homocysteine DegradationMetabolicSMP00455
DimethylglycinuriaDiseaseSMP00484
Gaucher DiseaseDiseaseSMP00349
Fabry diseaseDiseaseSMP00525
Krabbe diseaseDiseaseSMP00526
Glycine and Serine MetabolismMetabolicSMP00004
Non Ketotic HyperglycinemiaDiseaseSMP00223
Hyperglycinemia, non-ketoticDiseaseSMP00485
HypermethioninemiaDiseaseSMP00341
Metachromatic Leukodystrophy (MLD)DiseaseSMP00347
Sphingolipid MetabolismMetabolicSMP00034
Methionine MetabolismMetabolicSMP00033
SarcosinemiaDiseaseSMP00244
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
Property Value Probability
Human Intestinal Absorption + 0.9407
Blood Brain Barrier - 0.6529
Caco-2 permeable - 0.7839
P-glycoprotein substrate Non-substrate 0.7693
P-glycoprotein inhibitor I Non-inhibitor 0.9862
P-glycoprotein inhibitor II Non-inhibitor 0.9877
Renal organic cation transporter Non-inhibitor 0.9436
CYP450 2C9 substrate Non-substrate 0.8673
CYP450 2D6 substrate Non-substrate 0.846
CYP450 3A4 substrate Non-substrate 0.8389
CYP450 1A2 substrate Non-inhibitor 0.9087
CYP450 2C9 substrate Non-inhibitor 0.9512
CYP450 2D6 substrate Non-inhibitor 0.9349
CYP450 2C19 substrate Non-inhibitor 0.945
CYP450 3A4 substrate Non-inhibitor 0.908
CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9914
Ames test Non AMES toxic 0.9088
Carcinogenicity Non-carcinogens 0.82
Biodegradation Ready biodegradable 0.9489
Rat acute toxicity 1.2700 LD50, mol/kg Not applicable
hERG inhibition (predictor I) Weak inhibitor 0.9923
hERG inhibition (predictor II) Non-inhibitor 0.9811
Pharmacoeconomics
ManufacturersNot Available
Packagers
Dosage formsNot Available
Prices
Unit descriptionCostUnit
L-serine powder3.85USDg
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
PatentsNot Available
Properties
Statesolid
Experimental Properties
PropertyValueSource
melting point228 dec °CPhysProp
water solubility4.25E+005 mg/L (at 25 °C)YALKOWSKY,SH & DANNENFELSER,RM (1992)
logP-3.07HANSCH,C ET AL. (1995)
pKa2.21 (at 25 °C)KORTUM,G ET AL (1961)
Predicted Properties
PropertyValueSource
water solubility4.80e+02 g/lALOGPS
logP-3.4ALOGPS
logP-3.9ChemAxon
logS0.66ALOGPS
pKa (strongest acidic)2.03ChemAxon
pKa (strongest basic)8.93ChemAxon
physiological charge0ChemAxon
hydrogen acceptor count4ChemAxon
hydrogen donor count3ChemAxon
polar surface area83.55ChemAxon
rotatable bond count2ChemAxon
refractivity22.04ChemAxon
polarizability9.39ChemAxon
number of rings0ChemAxon
bioavailability1ChemAxon
rule of fiveYesChemAxon
Ghose filterNoChemAxon
Veber's ruleNoChemAxon
MDDR-like ruleNoChemAxon
Spectra
Spectra
References
Synthesis Reference

Kenichi Ishiwata, Nobuyoshi Makiguichi, Hideki Kawashima, Tadashi Suzuki, Masami Imadegawa, “Method of producing L-serine.” U.S. Patent US4782021, issued August, 1973.

US4782021
General ReferenceNot Available
External Links
ResourceLink
KEGG DrugD00016
KEGG CompoundC00065
ChEBI17115
ChEMBLCHEMBL11298
PharmGKBPA451330
IUPHAR726
Guide to Pharmacology726
HETSER
WikipediaSerine
ATC CodesNot Available
AHFS CodesNot Available
PDB Entries
FDA labelNot Available
MSDSshow(72.9 KB)
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available

1. Cystathionine beta-synthase

Kind: protein

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details
Cystathionine beta-synthase P35520 Details

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/L-threonine deaminase

Kind: protein

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details
L-serine dehydratase/L-threonine deaminase P20132 Details

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

Kind: protein

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details
Serine racemase Q9GZT4 Details

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

Kind: protein

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details
Serine palmitoyltransferase 2 O15270 Details

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

Kind: protein

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details
Serine palmitoyltransferase 1 O15269 Details

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. Serine--tRNA ligase, cytoplasmic

Kind: protein

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details
Serine--tRNA ligase, cytoplasmic P49591 Details

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

Kind: protein

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details
Serine--pyruvate aminotransferase P21549 Details

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

1. Monocarboxylate transporter 10

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details
Monocarboxylate transporter 10 Q8TF71 Details

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 September 16, 2013 17:08