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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
SaltsNot Available
Brand namesNot Available
Brand mixturesNot 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
Mass SpecNot Available
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
IndicationNot Available
PharmacodynamicsNot Available
Mechanism of actionNot Available
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
Metabolism
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organismsNot Available
PathwaysNot Available
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
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 Solubility480.0ALOGPS
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 FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
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
ResourceLink
KEGG CompoundC00740
BindingDB23167
ChEBI16523
ChEMBL
Therapeutic Targets DatabaseDCL000784
HETDSN
ATC CodesNot Available
AHFS CodesNot Available
PDB Entries
FDA labelNot Available
MSDSNot Available
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available

Targets

1. 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

2. 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

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