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979-92-0 molecular structure
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(2S)-2-amino-4-({[(2S,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl}sulfanyl)butanoic acid

ChemBase ID: 129344
Molecular Formular: C14H20N6O5S
Molecular Mass: 384.4108
Monoisotopic Mass: 384.12158877
SMILES and InChIs

SMILES:
O=C(O)[C@@H](N)CCSC[C@H]1O[C@@H](n2cnc3c(ncnc23)N)[C@H](O)[C@@H]1O
Canonical SMILES:
OC(=O)[C@H](CCSC[C@H]1O[C@H]([C@@H]([C@@H]1O)O)n1cnc2c1ncnc2N)N
InChI:
InChI=1S/C14H20N6O5S/c15-6(14(23)24)1-2-26-3-7-9(21)10(22)13(25-7)20-5-19-8-11(16)17-4-18-12(8)20/h4-7,9-10,13,21-22H,1-3,15H2,(H,23,24)(H2,16,17,18)/t6-,7+,9+,10+,13+/m0/s1
InChIKey:
ZJUKTBDSGOFHSH-WFMPWKQPSA-N

Cite this record

CBID:129344 http://www.chembase.cn/molecule-129344.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
(2S)-2-amino-4-({[(2S,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl}sulfanyl)butanoic acid
IUPAC Traditional name
S-adenosyl-L-homocysteine
Synonyms
AdoHcy
2-S-adenosyl-L-homocysteine
5'-S-(3-Amino-3-carboxypropyl)-5'-thioadenosineS-adenosylhomocysteine
SAH
S-Adenosyl-L-homocysteine
S-(5'-Deoxyadenosin-5'-yl)-L-homocysteine
L-5'-S-(3-Amino-3-carboxypropyl)-5'-thioadenosine
Adenosyl-L-homocysteine
Adenosylhomocysteine
L-S-Adenosylhomocysteine
S-Adenosyl-L-homocysteine
S-Adenosylhomocysteine
S-(5'-Adenosyl)-L-homocysteine
5′-Deoxy-S-adenosyl-L-homocysteine
S-(5′-Deoxyadenosine-5′)-L-homocysteine
S-(5′-Adenosyl)-L-homocysteine
CAS Number
979-92-0
EC Number
213-560-8
MDL Number
MFCD00037388
Beilstein Number
99188
PubChem SID
24891441
162223638
PubChem CID
439155
CHEBI ID
16680
CHEMBL
418052
Chemspider ID
388301
KEGG ID
C00021
MeSH Name
S-Adenosylhomocysteine
Wikipedia Title
S-Adenosyl-L-homocysteine

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem
Acid pKa 1.8116993  H Acceptors 10 
H Donor LogD (pH = 5.5) -4.137044 
LogD (pH = 7.4) -4.026673  Log P -4.0272307 
Molar Refractivity 92.7235 cm3 Polarizability 36.396317 Å3
Polar Surface Area 182.63 Å2 Rotatable Bonds
Lipinski's Rule of Five true 

PROPERTIES

PROPERTIES

Physical Property Safety Information Product Information Bioassay(PubChem)
Solubility
DMSO expand Show data source
Methanol expand Show data source
Apperance
crystalline expand Show data source
Pale Beige Solid expand Show data source
Melting Point
188-190°C (dec.) expand Show data source
Storage Condition
Refrigerator expand Show data source
MSDS Link
Download expand Show data source
Download expand Show data source
German water hazard class
3 expand Show data source
Personal Protective Equipment
Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter expand Show data source
Storage Temperature
-20°C expand Show data source
Purity
≥98.0% (HPCE) expand Show data source
Certificate of Analysis
Download expand Show data source
Quality Level
PREMIUM expand Show data source
Empirical Formula (Hill Notation)
C14H20N6O5S expand Show data source

DETAILS

DETAILS

Wikipedia Wikipedia Sigma Aldrich Sigma Aldrich TRC TRC
Sigma Aldrich - A9384 external link
包装
10 mg in autosmp vl
Application
S-(5′-Adenosyl)-L-homocysteine (AdoHcy) 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. S-adenosylhomocysteine (AdoHcy) is metabolized by S-adenosylhomocysteine (AdoHcy) hydrolase (AHCY).
Sigma Aldrich - 02090 external link
Other Notes
AdoHcy is a strong inhibitor of most biological transmethylation reactions1
Toronto Research Chemicals - A291500 external link
A novel biomarker for predicting susceptibility of a subject to a mental or neurodegenerative disorder.

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • Chamberlin, M., et al.: J. Clin. Invest., 98, 1021 (1996)
  • • Zoccolella, S., et al.: Neurology, 70, 222 (1996)
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PATENTS

PATENTS

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INTERNET

INTERNET

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