Basic information
- CAS
58944-73-3- Standard SMILES
Nc1ncnc2c1ncn2[C@@H]1O[C@H](C[C@@H](N)CC[C@H](N)C(=O)O)[C@@H](O)[C@H]1O- InChIKey
LMXOHSDXUQEUSF-YECHIGJVSA-N- Molecular formula
- C15H23N7O5
- Average molar mass
- 381.39 g/mol
- Monoisotopic mass
- 381.17606686
Overview
Sinefungin is an adenosine that is the the delta-(5'-adenosyl) derivative of ornithine. It has a role as an antimicrobial agent and an antifungal agent. It is a member of adenosines and a non-proteinogenic alpha-amino acid. It is functionally related to a L-ornithine.
Names & identifiers
- Preferred name
- Sinefungin
- IUPAC
- (2S,5S)-2,5-diamino-6-[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]hexanoic acid
- English name
- SINEFUNGIN
- Molecular formula
- C15H23N7O5
- Molecular weight
- 381.39
Names & synonyms
sinefungin58944-73-3SinefungineSinefunginaAntibiotic A 9145ADENOSYL-ORNITHINECompound 57926SinefunginumAdenosylornithineA 9145LILLY 579266,9-Diamino-1-(6-amino-9H-purin-9-yl)-1,5,6,7,8,9-hexadeoxydecofuranuronic acid
Show more names
SFDCUAFPHHSHEP7A-9145DFNA69DFNB39rp3223232232RP
W2U467CIIL6,9-Diamino-1-(6-amino-9H-purin-9-yl)-1,5,6,7,8,9-hexadeoxy-beta-D-ribo-decofuranuronic acid(2S,5S)-2,5-diamino-6-[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]hexanoic acidLY-57926DTXSID10207689Decofuranuronic acid, 6,9-diamino-1-(6-amino-9H-purin-9-yl)-1,5,6,7,8,9-hexadeoxy-CHEBI:45453(2S,5S)-2,5-diamino-6-[(2R,3S,R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxytetrahydrofuran-2-yl]hexanoic acid
Database identifiers
- CAS
58944-73-3- PubChem CID
- 65482
- DTXSID
DTXSID10207689
Properties
Computed structural properties
- XLogP
- -4.3
- Topological polar surface area
- 209 Ų
- Hydrogen bond donors
- 6
- Hydrogen bond acceptors
- 11
- Rotatable bonds
- 7
- Heavy atoms
- 27
- Formal charge
- 0
- Complexity
- 529
Experimental & physicochemical properties
DrugsPharmaceuticals -> Listed in ZINC15
Physicochemical properties
- alpha
- 25 · D25 -2.61° (c = 5 in water); D23 +12 ±2° (c = 0.227 in water)
- Boiling point
- 783.2 · 783.2±70.0 °C(Predicted)
- Density
- 1.91 · 1.91±0.1 g/cm3(Predicted)
- storage temp.
- 2 · 2-8°C
- solubility
- 2 O: · H2O: soluble
- form
- powder
- pka
- pKa (66% DMF): 2.9, 3.9, 8.9, 10.2(at 25℃)
- color
- white to yellow
- biological source
- rat
- Stability
- 2 years · Stable for 2 years from date of purchase as supplied. Solutions in distilled water may be stored at -20°C for up to 1 month.
- InChIKey
- LMXOHSDXUQEUSF-YECHIGJVSA-N
- SMILES
- N[C@@H](CC[C@H](N)C(O)=O)C[C@H]1O[C@H]([C@H](O)[C@@H]1O)n2cnc3c(N)ncnc23
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Warning
H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]
P264, P270, P301+P317, P330, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 68 reports by companies from 2 notifications to the ECHA C&L Inventory.
Hazard information
Hazard Classes and CategoriesAcute Tox. 4 (100%)
Safety data
- PPE
- dust mask type N95 (US), Eyeshields, Gloves
- wgk
- 3
- rtecs
- HE3140000
- hs_code
- 29419090
- Toxicity
- LD50 s.c. in mice: 185 mg/kg (Hamill, Hoehn, J. Antibiot.)
- risk_code
- 22
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- hazard_code
- Xn
- safety_code
- 36
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H302-H315-H319-H335
- Precautionary statements
- P261-P280-P301+P312-P302+P352-P305+P351+P338
Chemistry & industry
Pharmacology
MeSH Pharmacological Classification
Substances that destroy fungi by suppressing their ability to grow or reproduce. They differ from FUNGICIDES, INDUSTRIAL because they defend against fungi present in human or animal tissues.
Agents used in the treatment of malaria. They are usually classified on the basis of their action against plasmodia at different stages in their life cycle in the human. (From AMA, Drug Evaluations Annual, 1992, p1585)
Substances that are destructive to protozoans.
Applications
DescriptionSinefungin (58944-73-3) is a nucleoside S-adenosyl-1-methionine analog. Potent, competitive methyltransferase (protein, DNA, and RNA methyltransferases) inhibitor.1,2IC50< 1.0 and 2.5 μM for PRMT1 and SET7/9, respectively.3Sinefungin binds with greater affinity to the adenine-specific DNA methyltransferase M.TaqI than S-adenosyl-L-homocysteine.4Inhibits biofilm formation byStreptococcus pneumoniae.5
UsesSinefungin, a polar nucleoside antifungal active with broad biological activity, was isolated from a number of species of Streptomyces in the early 1970s. Sinefungin acts by inhibiting a wide range of methyltransferases, including the methylation of bases in DNA and RNA which alters cytosine deamination and gene expression. Sinefungin is widely used as a bioprobe to block methyltransferase-dependent pathways.
UsesSinefungin is a natural nucleoside analog of S-adenosylmethionine and inhibits Streptococcus pneumoniae biofilm growth. Its derivatives can be used as inhibitors and structure probes for human protein lysine methyltransferase SETD2.
General DescriptionChemical structure: nucleoside
Suppliers64 total
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
湖北万得化工有限公司
Related reactions
4 records
Compound notes
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