| Identification | Back Directory | [Name]
5'-DEOXY-S-ADENOSYL-L-HOMOCYSTEINE | [CAS]
979-92-0 | [Synonyms]
hpce
ADOHCY
S-(5′
Adenosylhomocysteine
5'-DEOXY-S-ADENOSYL-
s-adenosylhomocysteine
Adenosyl-L-homocysteine
L-S-AdenosylhoMocysteine
HOMOCYSTEINE, S-ADENOSYL
S-Adenosyl-L-homocystein
S-ADENOSYL-L-HOMOCYSTEINE
AdenosylhoMocysteine-13C5
S-(5'-deoxyadenosin-5'-yl)
SAH (S-Adenosylhomocysteine)
Adenosyl-L-hoMocysteine-13C5
L-S-AdenosylhoMocysteine-13C5
S-(5'-ADENOSYL)-L-HOMOCYSTEINE
S-Adenosyl-L-Homocysteine (50 mg)
-Adenosyl)-L-homocysteine
5'-DEOXY-S-ADENOSYL-L-HOMOCYSTEINE
S-(5'-Deoxyadenosine)-L-homocysteine
S-(5'-DEOXYADENOSINE-5')-L-HOMOCYSTEINE
S-(5'-Adenosyl)-L-homocysteine dihydrate
S-(5'-Deoxyadenosin-5'-yl)-L-hoMocysteine
L-Homocysteine, S-(5'-deoxyadenosin-5'-yl)-
5'-DEOXY-S-ADENOSYL-L-HOMOCYSTEINE USP/EP/BP
Ademetionine 1,4-Butanedisulfonate Impurity 1
S-(5'-Deoxyadenosin-5'-yl)-L-hoMocysteine-13C5
S-ADENOSYL-L-HOMOCYSTEINE (ADENOSINE-13C10, 98%)
L-5'-S-(3-AMino-3-carboxypropyl)-
5'-thioadenosine
5-S'-[(S)-3-Amino-3-carboxypropyl]-5'-thioadenosine
(S)-5'-(S)-(3-amino-3-carboxypropyl)-5'-thioadenosine
L-5'-S-(3-AMino-3-carboxypropyl)-
5'-thioadenosine-13C5
( 35 ) -5-( 3-AMINO.-3 CARBOXYPROPYL) THIO ) -5-DEOXYADENOSINE
S-(5'-Adenosyl)-L-homocysteine;AdoHcy;S-(5'-Deoxyadenosine)-L-homocysteine
5μ-Deoxy-S-adenosyl-L-homocysteine, AdoHcy, S-(5μ-Deoxyadenosine-5μ)-L-homocysteine
(2S)-2-amino-4-[[(2S,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxy-oxolan-2-yl]methylsulfanyl]butanoic acid
S-(5′-Adenosyl)-L-homocysteine,5′-Deoxy-S-adenosyl-L-homocysteine, AdoHcy, S-(5′-Deoxyadenosine-5′)-L-homocysteine
(S)-2-amino-4-((((2S,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxytetrahydrofuran-2-yl)methyl)thio)butanoic acid | [EINECS(EC#)]
213-560-8 | [Molecular Formula]
C14H20N6O5S | [MDL Number]
MFCD00037388 | [MOL File]
979-92-0.mol | [Molecular Weight]
384.41 |
| Chemical Properties | Back Directory | [Melting point ]
209-211 °C | [Boiling point ]
787.5±70.0 °C(Predicted) | [density ]
1.91±0.1 g/cm3(Predicted) | [storage temp. ]
-20°C | [solubility ]
1 M HCl: soluble19.60 - 20.40mg/mL, clear to slightly hazy, colorless to faintly yellow | [form ]
crystalline
| [pka]
2.22±0.10(Predicted) | [color ]
Off-White to Brown | [BRN ]
99188 | [InChIKey]
ZJUKTBDSGOFHSH-WFMPWKQPSA-N |
| Hazard Information | Back Directory | [Description]
S-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. | [Chemical Properties]
Pale Beige Solid | [Uses]
A novel biomarker for predicting susceptibility of a subject to a mental or neurodegenerative disorder. | [Definition]
ChEBI: The S-adenosyl derivative of L-homocysteine. | [Biochem/physiol Actions]
S-(5′-Adenosyl)-L-homocysteine (AdoHcy/SAH) is a component of intracellular homocysteine stress. AdoHcy is a competitive inhibitor (versus AdoMet) of DNA methyltransferases (S-adenosyl-L-methionine (AdoMet)-dependent methyltransferases) involved in epigenetics. Consequently, AdoHcy is used in a variety of studies on epigenetics in hyperhomocysteinemic states. AdoHcy is metabolized by S-adenosylhomocysteine hydrolase (AHCY). AdoHcy is the product of enzymatic transmethylation reactions involving S-Adenosylmethionine (SAM). It is reconverted to SAM by its cleavage into adenosine and L-homocysteine, a substrate of thetin-homocysteine S-methyltransferase. The concentration alterations of SAM and SAH in plasma serve as predictors of cellular methylation potential and metabolic alterations. Methylation capacity indicates specific genetic polymorphisms and/or nutritional deficiencies. Methylation is important in epigenetics, reprogramming, and cancer. | [Purification Methods]
It has been recrystallised several times from aqueous EtOH or H2O to give small prisms and has max 260nm in H2O. The picrate has m 170o(dec) from H2O. [Baddiley & Jameison J Chem Soc 1085 1955, de la Haba & Cantoni J Biol Chem 234 603 1959, Borchardt et al. J Org Chem 41 565 1976, NMR: Follmann et al. Eur J Biochem 47 187 1974, Beilstein 26 III/IV 3676.] |
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