Sinefungin
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Identification
- Generic Name
- Sinefungin
- DrugBank Accession Number
- DB01910
- Background
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.
- Type
- Small Molecule
- Groups
- Experimental
- Structure
- Weight
- Average: 381.387
Monoisotopic: 381.176066881 - Chemical Formula
- C15H23N7O5
- 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
- Sinefungin
- sinefungina
- sinefungine
- sinefunginum
- External IDs
- A 9145
- Antibiotic A 9145
- LILLY 57926
- LY-57926
Pharmacology
- Indication
Not Available
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- Pharmacodynamics
Not Available
- Mechanism of action
Target Actions Organism UModification methylase RsrI Not Available Rhodobacter sphaeroides URdmB Not Available Streptomyces purpurascens UrRNA adenine N-6-methyltransferase Not Available Bacillus subtilis UModification methylase TaqI Not Available Thermus aquaticus - 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
- Adverse Effects
- Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.
- Toxicity
Not Available
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Integrate drug-drug
interactions in your softwareAcenocoumarol The therapeutic efficacy of Acenocoumarol can be increased when used in combination with Sinefungin. Dicoumarol The therapeutic efficacy of Dicoumarol can be increased when used in combination with Sinefungin. Fluindione The therapeutic efficacy of Fluindione can be increased when used in combination with Sinefungin. Phenindione The therapeutic efficacy of Phenindione can be increased when used in combination with Sinefungin. Phenprocoumon The therapeutic efficacy of Phenprocoumon can be increased when used in combination with Sinefungin. - Food Interactions
- Not Available
Categories
- Drug Categories
- Chemical TaxonomyProvided by Classyfire
- 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
- 1,2-diol / 5'-deoxyribonucleoside / 6-aminopurine / Alcohol / Alpha-amino acid / Alpha-amino acid or derivatives / Amine / Amino acid / Amino acid or derivatives / Amino fatty acid show 38 more
- Molecular Framework
- Aromatic heteropolycyclic compounds
- External Descriptors
- adenosines, non-proteinogenic alpha-amino acid (CHEBI:45453)
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- W2U467CIIL
- CAS number
- 58944-73-3
- 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
References
- General References
- Not Available
- External Links
- KEGG Drug
- D05846
- PubChem Compound
- 65482
- PubChem Substance
- 46508037
- ChemSpider
- 58931
- BindingDB
- 50378739
- ChEBI
- 45453
- ChEMBL
- CHEMBL1214186
- ZINC
- ZINC000004217451
- PDBe Ligand
- SFG
- PDB Entries
- 1aqj / 1nw6 / 1qaq / 1xdu / 1yfl / 2h2j / 2hv9 / 2xva / 2xyr / 2y1w … show 111 more
Clinical Trials
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
Property Value Source Water Solubility 4.63 mg/mL ALOGPS logP -3 ALOGPS logP -5.1 Chemaxon logS -1.9 ALOGPS pKa (Strongest Acidic) 1.94 Chemaxon pKa (Strongest Basic) 10.18 Chemaxon Physiological Charge 1 Chemaxon Hydrogen Acceptor Count 11 Chemaxon Hydrogen Donor Count 6 Chemaxon Polar Surface Area 208.65 Å2 Chemaxon Rotatable Bond Count 7 Chemaxon Refractivity 92.68 m3·mol-1 Chemaxon Polarizability 37.68 Å3 Chemaxon Number of Rings 3 Chemaxon Bioavailability 0 Chemaxon Rule of Five No Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule Yes Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.8761 Blood Brain Barrier + 0.5494 Caco-2 permeable - 0.8305 P-glycoprotein substrate Substrate 0.5 P-glycoprotein inhibitor I Non-inhibitor 0.9415 P-glycoprotein inhibitor II Non-inhibitor 0.9378 Renal organic cation transporter Non-inhibitor 0.9402 CYP450 2C9 substrate Non-substrate 0.866 CYP450 2D6 substrate Non-substrate 0.8329 CYP450 3A4 substrate Non-substrate 0.5259 CYP450 1A2 substrate Non-inhibitor 0.8975 CYP450 2C9 inhibitor Non-inhibitor 0.93 CYP450 2D6 inhibitor Non-inhibitor 0.9419 CYP450 2C19 inhibitor Non-inhibitor 0.9085 CYP450 3A4 inhibitor Non-inhibitor 0.8717 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9296 Ames test Non AMES toxic 0.7312 Carcinogenicity Non-carcinogens 0.9336 Biodegradation Not ready biodegradable 0.9707 Rat acute toxicity 2.3802 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9855 hERG inhibition (predictor II) Non-inhibitor 0.9144
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-001i-0009000000-d98f3c74c4b684745e5e Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-001i-0209000000-0ad4a089521b38d74115 Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-00kr-1529000000-4266fb0273414ce45869 Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-001i-1926000000-85a4a65ca1f8f233c70f Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-000i-2901000000-6c32f44104d06f10322a Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-001i-0902000000-fe3bf9169f46e1aa986e Predicted 1H NMR Spectrum 1D NMR Not Applicable Predicted 13C NMR Spectrum 1D NMR Not Applicable - Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 209.5227165 predictedDarkChem Lite v0.1.0 [M-H]- 176.58144 predictedDeepCCS 1.0 (2019) [M+H]+ 208.0217165 predictedDarkChem Lite v0.1.0 [M+H]+ 178.54453 predictedDeepCCS 1.0 (2019) [M+Na]+ 207.9592165 predictedDarkChem Lite v0.1.0 [M+Na]+ 184.28493 predictedDeepCCS 1.0 (2019)
Targets
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1. DetailsModification methylase RsrI
- 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
2. DetailsRdmB
- 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
3. DetailsrRNA adenine N-6-methyltransferase
- 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
4. DetailsModification methylase TaqI
- 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
Drug created at June 13, 2005 13:24 / Updated at February 21, 2021 18:51