SFG

SINEFUNGIN

Created:	1999-07-08
Last modified:	2020-06-05

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Chemical Details
Formal Charge	0
Atom Count	50
Chiral Atom Count	6
Bond Count	52
Aromatic Bond Count	10

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Chemical Component Summary
Name	SINEFUNGIN
Synonyms	ADENOSYL-ORNITHINE
Systematic Name (OpenEye OEToolkits)	(2S,5S)-6-[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxy-oxolan-2-yl]-2,5-bis(azanyl)hexanoic acid
Formula	C₁₅ H₂₃ N₇ O₅
Molecular Weight	381.387
Type	NON-POLYMER

Chemical Descriptors
Type	Program	Version	Descriptor
SMILES	ACDLabs	12.01	O=C(O)C(N)CCC(N)CC3OC(n2cnc1c(ncnc12)N)C(O)C3O
SMILES	CACTVS	3.370	N[CH](CC[CH](N)C(O)=O)C[CH]1O[CH]([CH](O)[CH]1O)n2cnc3c(N)ncnc23
SMILES	OpenEye OEToolkits	1.7.0	c1nc(c2c(n1)n(cn2)C3C(C(C(O3)CC(CCC(C(=O)O)N)N)O)O)N
Canonical SMILES	CACTVS	3.370	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
Canonical SMILES	OpenEye OEToolkits	1.7.0	c1nc(c2c(n1)n(cn2)[C@H]3[C@@H]([C@@H]([C@H](O3)C[C@H](CC[C@@H](C(=O)O)N)N)O)O)N
InChI	InChI	1.03	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	InChI	1.03	LMXOHSDXUQEUSF-YECHIGJVSA-N

Drug Info: DrugBank

DrugBank ID	DB01910
Name	Sinefungin
Groups	experimental
Description	Sinefungin is a solid. This compound belongs to the purine nucleosides and analogues. These are compounds comprising a purine base attached to a sugar. The proteins that adenosyl-ornithine target include RdmB, modification methylase TaqI, rRNA (adenine-N6-)-methyltransferase, and modification methylase RsrI.
Synonyms	6,9-Diamino-1-(6-amino-9H-purin-9-yl)-1,5,6,7,8,9-hexadeoxydecofuranuronic acid Sinefungin sinefungina Adenosyl-ornithine (2S,5S)-2,5-diamino-6-[(2R,3S,R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxytetrahydrofuran-2-yl]hexanoic acid 6,9-Diamino-1-(6-amino-9H-purin-9-yl)-1,5,6,7,8,9-hexadeoxy-beta-D-ribo-decofuranuronic acid sinefungine sinefunginum
Categories	Anti-Infective Agents Antifungal Agents Antiparasitic Agents Antiprotozoals Heterocyclic Compounds, Fused-Ring Nucleic Acids, Nucleotides, and Nucleosides Nucleosides Purine Nucleosides Purines Ribonucleosides
CAS number	58944-73-3

Drug Targets

Name	Target Sequence	Pharmacological Action
Modification methylase RsrI	MANRSHHNAGHRAMNALRKSGQKHSSESQLGSSEIGTTRHVYDVCDCLDT...	unknown
RdmB	MSSSSPGEPLEPTDQDLDVLLKNLGNLVTPMALRVAATLRLVDHLLAGAD...	unknown
rRNA adenine N-6-methyltransferase	MNEKNIKHSQNFITSKHNIDKIMTNIRLNEHDNIFEIGSGKGHFTLELVQ...	unknown
Modification methylase TaqI	MGLPPLLSLPSNSAPRSLGRVETPPEVVDFMVSLAEAPRGGRVLEPACAH...	unknown

Drug Info/Drug Targets: DrugBank 3.0: a comprehensive resource for 'omics' research on drugs. Knox C, Law V, Jewison T, Liu P, Ly S, Frolkis A, Pon A, Banco K, Mak C, Neveu V, Djoumbou Y, Eisner R, Guo AC, Wishart DS. Nucleic Acids Res. 2011 Jan; 39 (Database issue):D1035-41. | PMID:21059682