D-Serin
D-Serine
Grundinformationen
- CAS
312-84-5- Standard-SMILES
N[C@H](CO)C(=O)O- InChIKey
MTCFGRXMJLQNBG-UWTATZPHSA-N- Summenformel
- C3H7NO3
- Durchschnittliche Molmasse
- 105,09 g/mol
- Monoisotopische Masse
- 105,04259308
Überblick
D-serine is the R-enantiomer of serine. It has a role as a NMDA receptor agonist, an Escherichia coli metabolite and a human metabolite. It is a D-alpha-amino acid and a serine. It is a conjugate base of a D-serinium. It is a conjugate acid of a D-serinate. It is an enantiomer of a L-serine. It is a tautomer of a D-serine zwitterion.
Namen und Bezeichner
- Bevorzugter Name
- D-Serine
- IUPAC
- (2R)-2-amino-3-hydroxypropanoic acid
- Lokaler Name
- D-Serin
- Englischer Name
- D-Serine
- Summenformel
- C3H7NO3
- Molmasse
- 105.09
Namen und Synonyme
D-serine312-84-5(R)-Serine(R)-2-amino-3-hydroxypropanoic acid(2R)-2-amino-3-hydroxypropanoic acidSerine D-formSerine, D-D-SerinDTXSID9041021EINECS 206-229-4NSC 77689AI3-18476
Weitere Namen anzeigen
H-D-SER-OH2-AMINO-3-HYDROXYPROPANOIC ACIDβ-Hydroxyalanine(R)-2-AMINO-3-HYDROXYPROPIONIC ACIDMethyl (2R)-3-hydroxy-2-(2,2,2-trifluoroacetaMido)propanoateDW75P1010
1K77H2Z9B1(D)-SERINESERINE D-FORM [MI]DTXCID7021021CHEBI:16523NSC77689NSC-77689(R)-2-Amino-3-hydroxy-propionic acid
Datenbank-Bezeichner
- CAS
312-84-5- PubChem CID
- 71077
- DTXSID
DTXSID9041021- ChEMBL
CHEMBL285123- ChEBI
CHEBI:16523- UNII
Eigenschaften
Berechnete Struktureigenschaften
- XLogP
- -3,1
- Polarare Oberfläche (TPSA)
- 83,6 Ų
- H-Brücken-Donoren
- 3
- H-Brücken-Akzeptoren
- 4
- Frei drehbare Bindungen
- 2
- Schwere Atome
- 7
- Formalladung
- 0
- Komplexität
- 72,6
Experimentelle und physikochemische Eigenschaften
Solubility364 mg/mL at 20 °C
Melting Point229 °C
Physical DescriptionSolid
Physikochemische Eigenschaften
- Schmelzpunkt
- 220 °C · 220 °C
- Siedepunkt
- 197.09 °C · 197.09°C (rough estimate)
- Dichte
- 1.3895 · 1.3895 (rough estimate)
- Brechungsindex
- 1.4368 · 1.4368 (estimate)
- storage temp.
- Keep in dark place,Inert atmosphere,Room temperature
- Löslichkeit
- 2 O: · H2O: 0.1 g/mL, clear, colorless
- pka
- 2.16 · 2.16±0.10(Predicted)
- Aggregatzustand
- Crystalline Powder
- Farbe
- White
- Wasserlöslichkeit
- 346 g/L · 346 g/L (20 ºC)
Sicherheit und Regulatorisches
Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.
GHS-Klassifizierung
GHS Classification
This chemical does not meet GHS hazard criteria for 90% (18 of 20) of all reports.
Warning
H315 (10%): Causes skin irritation [Warning Skin corrosion/irritation]
P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 20 reports by companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Gefahrenhinweise
Regulatory Information
Status: Active Update: 19-02-2021 https://echa.europa.eu/registration-dossier/-/registered-dossier/21814
D-Serine: Does not have an individual approval but may be used under an appropriate group standard
Hazard Classes and CategoriesSkin Irrit. 2 (10%)
Sicherheitsdaten
- wgk
- 3
- tsca
- TSCA listed
- hs_code
- 29225000
- RTECS-Nr.
- VT8200000
- risk_code
- 36/37/38
- hazard_code
- Xi
- safety_code
- 24/25-36-26
- Speicherklasse
- 11 - Combustible Solids
Chemie und Industrie
Pharmakologische Informationen
Tissue LocationsAdipose Tissue
Cellular LocationsExtracellular
Metabolite Pathways3-Phosphoglycerate dehydrogenase deficiency
Verwendung und Herstellung
UsesUse (kg; approx.) in Germany (2009): >10000
General Manufacturing InformationD-Serine: ACTIVE
Anwendungen
BeschreibungSerine is one of the 20 naturally-occurring amino acids used by all organisms in the biosynthesis of proteins. Having a single chiral center, serine can exist as one of two stereoisomers (L-Serine and D-Serine).D-serine is categorized as a nootropic. It is an amino acid found in the brain and is produced primarily in astrocytes; the conversion of L-serine to D-serine is catalyzed by the serine racemase enzyme. D-serine acts as a co-agonist of glutamate NMDA receptors and binds at the glycine site. NMDA receptors mediate synaptic plasticity, synaptogenesis, excitotoxicity, memory acquisition, and learning. Schizophrenia is characterized by reduced NMDA receptor signaling and therefore, D-serine supplementation has been tested extensively in patients with schizophrenia. It is thought to improve cognitive symptoms in this population. It is worth noting that in Alzheimer’s disease, there is excess glutamate receptor activation. Memantine, one of the drugs used to treat Alzheimer’s disease, is an NMDA receptor antagonist.
VerwendenD-Serine is involved in the biosynthesis of purines, pyrimidines, and other amino acids. D-Serine also is an agonist of glycine site of the NMDA-type glutamate receptor. It also acts as Lacosamide intermediate.
Vor- und nachgelagerte Produkte
Zugehörige Reaktionen
73
Notizen zur Verbindung
Wird geladen…