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Identification
NameD-Serine
Accession NumberDB03929  (EXPT01275)
TypeSmall Molecule
GroupsExperimental
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
SynonymsNot Available
Prescription ProductsNot Available
Generic Prescription ProductsNot Available
Over the Counter ProductsNot Available
International BrandsNot Available
Brand mixturesNot Available
SaltsNot Available
CategoriesNot Available
CAS number312-84-5
WeightAverage: 105.0926
Monoisotopic: 105.042593095
Chemical FormulaC3H7NO3
InChI KeyMTCFGRXMJLQNBG-UWTATZPHSA-N
InChI
InChI=1S/C3H7NO3/c4-2(1-5)3(6)7/h2,5H,1,4H2,(H,6,7)/t2-/m1/s1
IUPAC Name
(2R)-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
IndicationNot Available
PharmacodynamicsNot Available
Mechanism of actionNot Available
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
MetabolismNot Available
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organismsNot Available
Pathways
PathwayCategorySMPDB ID
Clomocycline Action PathwayDrug actionSMP00262
Clarithromycin Action PathwayDrug actionSMP00248
Kanamycin Action PathwayDrug actionSMP00255
Demeclocycline Action PathwayDrug actionSMP00290
Minocycline Action PathwayDrug actionSMP00292
Troleandomycin Action PathwayDrug actionSMP00730
Roxithromycin Action PathwayDrug actionSMP00251
Amikacin Action PathwayDrug actionSMP00253
Spectinomycin Action PathwayDrug actionSMP00258
Lymecycline Action PathwayDrug actionSMP00295
Lincomycin Action PathwayDrug actionSMP00728
Azithromycin Action PathwayDrug actionSMP00247
Gentamicin Action PathwayDrug actionSMP00254
Streptomycin Action PathwayDrug actionSMP00259
Chloramphenicol Action PathwayDrug actionSMP00729
Clindamycin Action PathwayDrug actionSMP00249
Neomycin Action PathwayDrug actionSMP00256
Doxycycline Action PathwayDrug actionSMP00291
Oxytetracycline Action PathwayDrug actionSMP00293
Tobramycin Action PathwayDrug actionSMP00711
Arbekacin Action PathwayDrug actionSMP00713
Rolitetracycline Action PathwayDrug actionSMP00726
Josamycin Action PathwayDrug actionSMP00731
Erythromycin Action PathwayDrug actionSMP00250
Telithromycin Action PathwayDrug actionSMP00252
Netilmicin Action PathwayDrug actionSMP00257
Tetracycline Action PathwayDrug actionSMP00294
Tigecycline Action PathwayDrug actionSMP00712
Paromomycin Action PathwayDrug actionSMP00714
Methacycline Action PathwayDrug actionSMP00727
SarcosinemiaDiseaseSMP00244
Hyperglycinemia, non-ketoticDiseaseSMP00485
Dimethylglycine Dehydrogenase DeficiencyDiseaseSMP00242
Glycine and Serine MetabolismMetabolicSMP00004
Dimethylglycine Dehydrogenase DeficiencyDiseaseSMP00484
3-Phosphoglycerate dehydrogenase deficiencyDiseaseSMP00721
Dihydropyrimidine Dehydrogenase Deficiency (DHPD)DiseaseSMP00179
Non Ketotic HyperglycinemiaDiseaseSMP00223
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 substrateNon-inhibitor0.9512
CYP450 2D6 substrateNon-inhibitor0.9349
CYP450 2C19 substrateNon-inhibitor0.945
CYP450 3A4 substrateNon-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
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point229 dec °CPhysProp
water solubility3.64E+005 mg/L (at 20 °C)BEILSTEIN
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)Not Available
SpectraMS/MS1D NMR2D NMR
References
Synthesis Reference

Edward J. J. Grabowski, Paul J. Reider, “Preparation of 2-Deutero-D-serine.” U.S. Patent US4582931, issued June, 1978.

US4582931
General Reference
  1. Hatanaka T, Huang W, Nakanishi T, Bridges CC, Smith SB, Prasad PD, Ganapathy ME, Ganapathy V: Transport of D-serine via the amino acid transporter ATB expressed in the colon. Biochem Biophys Res Commun. 2002 Feb 22;291(2):291-5. Pubmed
External Links
ATC CodesNot Available
AHFS CodesNot Available
PDB Entries
FDA labelNot Available
MSDSNot Available
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available

Targets

1. Glutamate receptor ionotropic, NMDA 1

Kind: protein

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details
Glutamate receptor ionotropic, NMDA 1 Q05586 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. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. Pubmed

2. Glycine receptor subunit alpha-1

Kind: protein

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details
Glycine receptor subunit alpha-1 P23415 Details

References:

  1. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. Pubmed

3. Serpin B3

Kind: protein

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details
Serpin B3 P29508 Details

References:

  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. Pubmed

4. Head decoration protein

Kind: protein

Organism: Bacteriophage 21

Pharmacological action: unknown

Components

Name UniProt ID Details
Head decoration protein P36275 Details

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

2. Sodium- and chloride-dependent neutral and basic amino acid transporter B(0+)

Kind: protein

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details
Sodium- and chloride-dependent neutral and basic amino acid transporter B(0+) Q9UN76 Details

References:

  1. Hatanaka T, Huang W, Nakanishi T, Bridges CC, Smith SB, Prasad PD, Ganapathy ME, Ganapathy V: Transport of D-serine via the amino acid transporter ATB expressed in the colon. Biochem Biophys Res Commun. 2002 Feb 22;291(2):291-5. Pubmed

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Drug created on June 13, 2005 07:24 / Updated on September 16, 2013 17:23