CHEBI:45453 - sinefungin

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ChEBI Name sinefungin
ChEBI ID CHEBI:45453
Definition An adenosine that is the the δ-(5'-adenosyl) derivative of ornithine.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
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Formula C15H23N7O5
Net Charge 0
Average Mass 381.38700
Monoisotopic Mass 381.17607
InChI InChI=1S/C15H23N7O5/c16-6(1-2-7(17)15(25)26)3-8-10(23)11(24)14(27-8)22-5-21-9-12(18)19-4-20-13(9)22/h4-8,10-11,14,23-24H,1-3,16-17H2,(H,25,26)(H2,18,19,20)/t6-,7-,8+,10+,11+,14+/m0/s1
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)n1cnc2c(N)ncnc12
Roles Classification
Chemical Role(s): Bronsted base
A molecular entity capable of accepting a hydron from a donor (Bronsted acid).
(via organic amino compound )
Bronsted acid
A molecular entity capable of donating a hydron to an acceptor (Bronsted base).
(via oxoacid )
Biological Role(s): antifungal agent
An antimicrobial agent that destroys fungi by suppressing their ability to grow or reproduce.
antimicrobial agent
A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing sinefungin (CHEBI:45453) has functional parent L-ornithine (CHEBI:15729)
sinefungin (CHEBI:45453) has role antifungal agent (CHEBI:35718)
sinefungin (CHEBI:45453) has role antimicrobial agent (CHEBI:33281)
sinefungin (CHEBI:45453) is a adenosines (CHEBI:22260)
sinefungin (CHEBI:45453) is a non-proteinogenic α-amino acid (CHEBI:83925)
IUPAC Name
(5S)-5-amino-6-[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxytetrahydrofuran-2-yl]-L-norleucine
INNs Sources
sinefungin KEGG DRUG
sinefungina ChemIDplus
sinefungine ChemIDplus
sinefunginum ChemIDplus
Synonyms Sources
(2S,5S)-2,5-diamino-6-[(2R,3S,R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxytetrahydrofuran-2-yl]hexanoic acid PDBeChem
6,9-Diamino-1-(6-amino-9H-purin-9-yl)-1,5,6,7,8,9-hexadeoxy-beta-D-ribo-decofuranuronic acid ChemIDplus
6,9-Diamino-1-(6-amino-9H-purin-9-yl)-1,5,6,7,8,9-hexadeoxydecofuranuronic acid ChemIDplus
A 9145 ChemIDplus
ADENOSYL-ORNITHINE PDBeChem
Antibiotic A 9145 ChemIDplus
Manual Xrefs Databases
D05846 KEGG DRUG
SFG PDBeChem
SINEFUNGIN MetaCyc
US3758681 Patent
US5872104 Patent
View more database links
Registry Numbers Types Sources
3574678 Reaxys Registry Number Reaxys
58944-73-3 CAS Registry Number ChemIDplus
58944-73-3 CAS Registry Number KEGG DRUG
Citations Waiting for Citations Types Sources
20347768 PubMed citation Europe PMC
20859291 PubMed citation Europe PMC
21738746 PubMed citation Europe PMC
21781040 PubMed citation Europe PMC
22342622 PubMed citation Europe PMC
22362751 PubMed citation Europe PMC
22965231 PubMed citation Europe PMC
Last Modified
26 March 2015