Sinefungin

Identification

Name
Sinefungin
Accession Number
DB01910  (EXPT02890)
Type
Small Molecule
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.

Structure
Thumb
Synonyms
  • (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
  • 6,9-Diamino-1-(6-amino-9H-purin-9-yl)-1,5,6,7,8,9-hexadeoxydecofuranuronic acid
  • Adenosyl-ornithine
  • sinefungina
  • sinefungine
  • sinefunginum
External IDs
A 9145 / Antibiotic A 9145 / LILLY 57926 / LY-57926
Categories
UNII
W2U467CIIL
CAS number
58944-73-3
Weight
Average: 381.387
Monoisotopic: 381.176066881
Chemical Formula
C15H23N7O5
InChI Key
LMXOHSDXUQEUSF-YECHIGJVSA-N
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
IUPAC Name
(2S,5S)-2,5-diamino-6-[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]hexanoic acid
SMILES
[H][C@](N)(CC[C@]([H])(N)C(O)=O)C[C@@]1([H])O[C@@]([H])(N2C=NC3=C(N)N=CN=C23)[C@]([H])(O)[C@]1([H])O

Pharmacology

Indication
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
URdmBNot AvailableStreptomyces purpurascens
UrRNA adenine N-6-methyltransferaseNot AvailableBacillus subtilis
UModification methylase TaqINot AvailableThermus aquaticus
UModification methylase RsrINot AvailableRhodobacter sphaeroides
Absorption
Not Available
Volume of distribution
Not Available
Protein binding
Not Available
Metabolism
Not Available
Route of elimination
Not Available
Half life
Not Available
Clearance
Not Available
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not Available

References

General References
Not Available
External Links
KEGG Drug
D05846
PubChem Compound
65482
PubChem Substance
46508037
ChemSpider
58931
BindingDB
50378739
ChEBI
45453
ChEMBL
CHEMBL1214186
HET
SFG
PDB Entries
1aqj / 1nw6 / 1qaq / 1xdu / 1yfl / 2h2j / 2hv9 / 2xva / 2xyr / 2y1w
show 67 more

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility4.63 mg/mLALOGPS
logP-3ALOGPS
logP-5.1ChemAxon
logS-1.9ALOGPS
pKa (Strongest Acidic)1.95ChemAxon
pKa (Strongest Basic)10.18ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count11ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area208.65 Å2ChemAxon
Rotatable Bond Count7ChemAxon
Refractivity92.68 m3·mol-1ChemAxon
Polarizability37.69 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.8761
Blood Brain Barrier+0.5494
Caco-2 permeable-0.8305
P-glycoprotein substrateSubstrate0.5
P-glycoprotein inhibitor INon-inhibitor0.9415
P-glycoprotein inhibitor IINon-inhibitor0.9378
Renal organic cation transporterNon-inhibitor0.9402
CYP450 2C9 substrateNon-substrate0.866
CYP450 2D6 substrateNon-substrate0.8329
CYP450 3A4 substrateNon-substrate0.5259
CYP450 1A2 substrateNon-inhibitor0.8975
CYP450 2C9 inhibitorNon-inhibitor0.93
CYP450 2D6 inhibitorNon-inhibitor0.9419
CYP450 2C19 inhibitorNon-inhibitor0.9085
CYP450 3A4 inhibitorNon-inhibitor0.8717
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9296
Ames testNon AMES toxic0.7312
CarcinogenicityNon-carcinogens0.9336
BiodegradationNot ready biodegradable0.9707
Rat acute toxicity2.3802 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9855
hERG inhibition (predictor II)Non-inhibitor0.9144
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

Description
This compound belongs to the class of organic compounds known as 5'-deoxyribonucleosides. These are nucleosides in which the oxygen atom at the 5'position of the ribose moiety has been replaced by another atom. The nucleobases here are limited to purine, pyrimidine, and pyridine derivatives.
Kingdom
Organic compounds
Super Class
Nucleosides, nucleotides, and analogues
Class
5'-deoxyribonucleosides
Sub Class
Not Available
Direct Parent
5'-deoxyribonucleosides
Alternative Parents
Glycosylamines / 6-aminopurines / Pentoses / L-alpha-amino acids / Medium-chain fatty acids / Amino fatty acids / Aminopyrimidines and derivatives / Heterocyclic fatty acids / Hydroxy fatty acids / N-substituted imidazoles
show 15 more
Substituents
5'-deoxyribonucleoside / N-glycosyl compound / Glycosyl compound / Pentose monosaccharide / 6-aminopurine / L-alpha-amino acid / Alpha-amino acid or derivatives / Alpha-amino acid / Imidazopyrimidine / Purine
show 38 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
adenosines, non-proteinogenic alpha-amino acid (CHEBI:45453)

Targets

Kind
Protein
Organism
Streptomyces purpurascens
Pharmacological action
Unknown
General Function
Not Available
Specific Function
Not Available
Gene Name
rdmB
Uniprot ID
Q54527
Uniprot Name
Aclacinomycin 10-hydroxylase RdmB
Molecular Weight
39796.525 Da
Kind
Protein
Organism
Bacillus subtilis
Pharmacological action
Unknown
General Function
Rrna (adenine-n6,n6-)-dimethyltransferase activity
Specific Function
This protein produces a dimethylation of the adenine residue at position 2085 in 23S rRNA, resulting in reduced affinity between ribosomes and macrolide-lincosamide-streptogramin B antibiotics.
Gene Name
ermC'
Uniprot ID
P13956
Uniprot Name
rRNA adenine N-6-methyltransferase
Molecular Weight
28907.235 Da
Kind
Protein
Organism
Thermus aquaticus
Pharmacological action
Unknown
General Function
Site-specific dna-methyltransferase (adenine-specific) activity
Specific Function
This methylase recognizes the double-stranded sequence TCGA, causes specific methylation on A-4 on both strands and protects the DNA from cleavage by the TaqI endonuclease.
Gene Name
taqIM
Uniprot ID
P14385
Uniprot Name
Modification methylase TaqI
Molecular Weight
47861.91 Da
Kind
Protein
Organism
Rhodobacter sphaeroides
Pharmacological action
Unknown
General Function
Site-specific dna-methyltransferase (adenine-specific) activity
Specific Function
This methylase recognizes the double-stranded sequence GAATTC, causes specific methylation on A-? on both strands, and protects the DNA from cleavage by the RsrI endonuclease.
Gene Name
rsrIM
Uniprot ID
P14751
Uniprot Name
Modification methylase RsrI
Molecular Weight
35654.88 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423]

Drug created on June 13, 2005 07:24 / Updated on November 02, 2018 05:08