Showing Metabocard for D-serine (BASm0001930)

Common NameD-serine
DescriptionD-serine is a stereo-isomer of the common amino acid, L-serine. D-serine was only thought to exist in bacteria until relatively recently. D-serine was the second D amino acid discovered to naturally exist in humans. The first one was D-aspartate. D-serine is synthesized from L-serine by serine racemase (SRR), and it is degraded by D-amino acid oxidase (DAO). It is found in high abundance in the brain. D-serine acts on the glycine binding site of the N-methyl-D-aspartate receptor (NMDAR) and modulates glutamate-mediated receptor activation. For the receptor to open, glutamate and either glycine or D-serine must bind to it. In fact, D-serine is a more potent agonist at the glycine site on the NMDAR than glycine itself. The importance of D-serine in mammalian brain function is apparent from extensive investigations reported and reviewed over the past decade, including roles in synaptic plasticity and memory. D-serine is also implicated in the pathophysiology and therapy of several psychiatric and neurological conditions including schizophrenia and glioma. In schizophrenia, there is evidence that D-serine levels are decreased, a deficiency that may contribute to the proposed NMDAR hypofunction of the disorder and that has led to D-serine replenishment as a novel therapeutic strategy.
Structure
Molecular FormulaC3H7NO3
Average Mass105.09260
Monoisotopic Mass105.04259
IUPAC Name(2R)-2-amino-3-hydroxypropanoic acid
Traditional NameD-serine
CAS Registry Number312-84-5
SMILES[NH3+][C@H](CO)C(=O)[O-]
InChI IdentifierInChI=1S/C3H7NO3/c4-2(1-5)3(6)7/h2,5H,1,4H2,(H,6,7)/t2-/m1/s1
InChI KeyMTCFGRXMJLQNBG-UWTATZPHSA-N
CHEBI IDCHEBI:35247
HMDB IDHMDB0003406
Pathways
NameSMPDB/PathBank
Glycine, serine and threonine metabolism
Transcription/Translation
Dihydropyrimidine Dehydrogenase Deficiency (DHPD)
Non Ketotic Hyperglycinemia
Dimethylglycine Dehydrogenase Deficiency
Sarcosinemia
Azithromycin Action Pathway
Clarithromycin Action Pathway
Clindamycin Action Pathway
Erythromycin Action Pathway
Roxithromycin Action Pathway
Telithromycin Action Pathway
Amikacin Action Pathway
Gentamicin Action Pathway
Kanamycin Action Pathway
Neomycin Action Pathway
Netilmicin Action Pathway
Spectinomycin Action Pathway
Streptomycin Action Pathway
Clomocycline Action Pathway
Demeclocycline Action Pathway
Doxycycline Action Pathway
Minocycline Action Pathway
Oxytetracycline Action Pathway
Tetracycline Action Pathway
Lymecycline Action Pathway
Dimethylglycine Dehydrogenase Deficiency
Hyperglycinemia, non-ketotic
Tobramycin Action Pathway
Tigecycline Action Pathway
Arbekacin Action Pathway
Paromomycin Action Pathway
3-Phosphoglycerate dehydrogenase deficiency
Rolitetracycline Action Pathway
Methacycline Action Pathway
Lincomycin Action Pathway
Chloramphenicol Action Pathway
Troleandomycin Action Pathway
Josamycin Action Pathway
StateSolid
Water Solubility4.80e+02 g/l
logP-3.42
logS0.66
pKa (Strongest Acidic)2.03
pKa (Strongest Basic)8.93
Hydrogen Acceptor Count4
Hydrogen Donor Count3
Polar Surface Area83.55 Ų
Rotatable Bond Count2
Physiological Charge0
Formal Charge0
Refractivity22.04 m³·mol⁻¹
Polarizability9.38

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