(S)-5'-(S)-(3-Amino-3-carboxypropyl)-5'-thioadenosin
5'-S-[(3S)-3-azaniumyl-3-carboxylatopropyl]-5'-thioadenosine
Grundinformationen
- CAS
979-92-0- Standard-SMILES
Nc1ncnc2c1ncn2[C@@H]1O[C@H](CSCC[C@H]([NH3+])C(=O)[O-])[C@@H](O)[C@H]1O- InChIKey
ZJUKTBDSGOFHSH-WFMPWKQPSA-N- Summenformel
- C14H20N6O5S
- Durchschnittliche Molmasse
- 384,41 g/mol
- Monoisotopische Masse
- 384,12158893
Überblick
S-adenosyl-L-homocysteine zwitterion is zwitterionic form of S-adenosyl-L-homocysteine arising from migration of a proton from the carboxy group to the alpha-amino group; major species at pH 7.3. It is a tautomer of a S-adenosyl-L-homocysteine.
Namen und Bezeichner
- Bevorzugter Name
- 5'-S-[(3S)-3-azaniumyl-3-carboxylatopropyl]-5'-thioadenosine
- IUPAC
- (2S)-4-[[(2S,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methylsulfanyl]-2-azaniumylbutanoate
- Lokaler Name
- (S)-5'-(S)-(3-Amino-3-carboxypropyl)-5'-thioadenosin
- Englischer Name
- 5'-Deoxy-S-adenosyl-L-homocysteine
- Summenformel
- C14H20N6O5S
- Molmasse
- 384.41
Namen und Synonyme
5'-S-[(3S)-3-azaniumyl-3-carboxylatopropyl]-5'-thioadenosineS-adenosyl-homocysteine2qbu3lcu3qox3ujb2wr83p2e3pb3CHEBI:578563u81S-adenosyl-L-homocysteine zwitterion
Weitere Namen anzeigen
S-ADENOSYL-L-HOMOCYSTEINEs-adenosylhomocysteineADOHCYAdenosylhomocysteineS-(5'-Adenosyl)-L-homocysteinehpceS-Adenosyl-L-homocysteinS-(5′-Adenosyl)-L-homocysteineSAH, 10 mM in DMSO5'-DEOXY-S-ADENOSYL-
Datenbank-Bezeichner
- CAS
979-92-0
Eigenschaften
Berechnete Struktureigenschaften
- XLogP
- -2,9
- Polarare Oberfläche (TPSA)
- 212 Ų
- H-Brücken-Donoren
- 4
- H-Brücken-Akzeptoren
- 10
- Frei drehbare Bindungen
- 6
- Schwere Atome
- 26
- Formalladung
- 0
- Komplexität
- 499
Experimentelle und physikochemische Eigenschaften
Melting Point209 - 211 °C
Physical DescriptionSolid
Physikochemische Eigenschaften
- Schmelzpunkt
- 209 · 209-211 °C
- Siedepunkt
- 787.5 · 787.5±70.0 °C(Predicted)
- Dichte
- 1.91 · 1.91±0.1 g/cm3(Predicted)
- storage temp.
- -20 °C · -20°C
- Löslichkeit
- 1 M · 1 M HCl: soluble19.60 - 20.40mg/mL, clear to slightly hazy, colorless to faintly yellow
- Aggregatzustand
- crystalline
- pka
- 2.22 · 2.22±0.10(Predicted)
- Farbe
- Off-White to Brown
- BRN
- 99188 · 99188
- Stabilität
- Hygroscopic
- Major Application
- pharmaceutical (small molecule)
Sicherheit und Regulatorisches
Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.
Sicherheitsdaten
- F
- 8-10-23
- wgk
- 3
- hs_code
- 2934990002
- Speicherklasse
- 11 - Combustible Solids
Chemie und Industrie
Pharmakologische Informationen
Tissue LocationsKidney
Cellular LocationsEndoplasmic reticulum
Metabolite Pathways3-Phosphoglycerate dehydrogenase deficiency
Anwendungen
BeschreibungS-Adenosyl-L-homocysteine (SAH) is an amino acid derivative and an intermediate, by-product, or modulator of several metabolic pathways, including the activated methyl cycle and cysteine biosynthesis. It is also a product of S-adenosyl-methionine (SAM)-dependent methylation of biological molecules, including DNA, RNA, and histones and other proteins. SAH is a risk factor for many diseases, including cancer and neurodegenerative diseases. In addition, inhibitors that block its hydrolysis are being developed as anti-viral, anti-parasitic, anti-arthritic and immunosuppressive agents.
VerwendenA novel biomarker for predicting susceptibility of a subject to a mental or neurodegenerative disorder.
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