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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
(2S)-2-amino-3-Hydroxypropanoic acid
(S)-(-)-Serine
(S)-(−)-serine
(S)-2-Amino-3-hydroxypropanoic acid
(S)-alpha-Amino-beta-hydroxypropionic acid
(S)-Serine
beta-Hydroxy-L-alanine
beta-Hydroxyalanine
L-(-)-Serine
L-(−)-serine
L-2-Amino-3-hydroxypropionic acid
L-3-Hydroxy-2-aminopropionic acid
L-3-Hydroxy-alanine
L-Ser
L-Serin
L-Serine
S
Ser
Serine
External Identifiers Not Available
Prescription ProductsNot Available
Generic Prescription ProductsNot Available
Over the Counter ProductsNot Available
International BrandsNot Available
Brand mixtures
NameLabellerIngredients
AminosynHospira, Inc.
Aminosyn 10%Hospira Healthcare Corporation
Aminosyn 5%Hospira Healthcare Corporation
Aminosyn 7%Hospira Healthcare Corporation
Aminosyn 8.5%Hospira Healthcare Corporation
Aminosyn Sulfite FreeHospira, Inc.
Freamine HbcB. Braun Medical Inc.
Freamine IIIB. Braun Medical Inc.
NovamineHospira, Inc.
TravasolBaxter Corporation
Vamin 18 Electrolyte-freeFresenius Kabi Ab
SaltsNot Available
Categories
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
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as d-alpha-amino acids. These are alpha amino acids which have the D-configuration of the alpha-carbon atom.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentD-alpha-amino acids
Alternative Parents
Substituents
  • D-alpha-amino acid
  • Beta-hydroxy acid
  • Hydroxy acid
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Hydrocarbon derivative
  • Primary amine
  • Primary alcohol
  • Organooxygen compound
  • Organonitrogen compound
  • Primary aliphatic amine
  • Carbonyl group
  • Amine
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
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
MetabolismNot Available
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organisms
  • Humans and other mammals
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9407
Blood Brain Barrier-0.6529
Caco-2 permeable-0.7839
P-glycoprotein substrateNon-substrate0.7693
P-glycoprotein inhibitor INon-inhibitor0.9862
P-glycoprotein inhibitor IINon-inhibitor0.9877
Renal organic cation transporterNon-inhibitor0.9436
CYP450 2C9 substrateNon-substrate0.8673
CYP450 2D6 substrateNon-substrate0.846
CYP450 3A4 substrateNon-substrate0.8389
CYP450 1A2 substrateNon-inhibitor0.9087
CYP450 2C9 inhibitorNon-inhibitor0.9512
CYP450 2D6 inhibitorNon-inhibitor0.9349
CYP450 2C19 inhibitorNon-inhibitor0.945
CYP450 3A4 inhibitorNon-inhibitor0.908
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9914
Ames testNon AMES toxic0.9088
CarcinogenicityNon-carcinogens0.82
BiodegradationReady biodegradable0.9489
Rat acute toxicity1.2700 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9923
hERG inhibition (predictor II)Non-inhibitor0.9811
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
ManufacturersNot Available
Packagers
Dosage forms
FormRouteStrength
Injection, solutionintravenous
Injection, solution, concentrateintravenous
Solutionintravenous
Prices
Unit descriptionCostUnit
L-serine powder3.85USD g
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 Solubility480.0 mg/mLALOGPS
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 Area83.55 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity22.04 m3·mol-1ChemAxon
Polarizability9.39 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Download (8.77 KB)
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS)splash10-2zi0000000-59d5e0f76fd204be8110View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS)splash10-2zv0000000-ab49fc3ee88db87d1a16View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)splash10-2z10000000-8e169037bcbe1dcd5de8View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS)splash10-2zs0000000-67271ed235e35c662db5View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS)splash10-zlg0000000-1297bf302358bcf0f1c0View in MoNA
GC-MSGC-MS Spectrum - GC-MS (3 TMS)splash10-4sz0000000-caaa37778f5a4686f5f0View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-z600000000-38f84912ebfc7b4e8339View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-z300000000-89e57995d3ca765a20e8View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-z700000000-f3baf93032cc9f09cf2dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-0z10100000-b6085e53e881cdaa1824View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-z000000000-2e16e9d6f9b3c2688f8aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-z000000000-9857daa028fb3016a7e2View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-000za00000-0617acd25c69bf24ad1fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-0z01000000-823dfcf6229956372e31View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-z000000000-eec63565f8a9fe4bd336View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-z000000000-008412efd202c202d56aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-0zb0000000-932aedc4efb5e1dd5e7bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-1zj5220000-cd0895e475dd50e4934dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-z000000000-15294ba22b153cf5ab5bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-z000000000-48c370acff657443f0e6View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-05z0000000-1bad10ba7388ce0c2249View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-0uza410000-9f2bfe40e4c01044d209View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-z000000000-dfa7aca58cc28303ebc7View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-0z00000000-282f31d8021649afdbe8View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-09z0000000-eeee98e6b0514b08cd63View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-4z00000000-ed66566e27a94ee99f13View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-z700000000-b9f6b4b6ee7c88a9c569View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-z000000000-929aea63ace0e20c6d43View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-z000000000-ba9cd5b3e37ded5d3764View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positivesplash10-pz00000000-5622633ab0a27d2e5360View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positivesplash10-z100000000-3e25ca80e2e62be19ac5View in MoNA
1D NMR1H NMR SpectrumNot Available
2D NMR[1H,1H] 2D NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
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 ReferencesNot Available
External Links
ATC CodesNot Available
AHFS CodesNot Available
PDB Entries
FDA labelNot Available
MSDSDownload (72.9 KB)
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available

Targets

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

Transporters

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

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Drug created on June 13, 2005 07:24 / Updated on September 16, 2013 17:08