(2S,5S)-2,5-diamino-6-[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]hexanoic acid

• ChemBase ID: 133647
• Molecular Formular: C15H23N7O5
• Molecular Mass: 381.38702
• Monoisotopic Mass: 381.17606687
• SMILES: c1nc(c2c(n1)n(cn2)[C@H]1[C@@H]([C@@H]([C@H](O1)C[C@H](CC[C@@H](C(=O)O)N)N)O)O)N
• Canonical SMILES: N[C@H](C[C@H]1O[C@H]([C@@H]([C@@H]1O)O)n1cnc2c1ncnc2N)CC[C@@H](C(=O)O)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
• InChIKey: LMXOHSDXUQEUSF-YECHIGJVSA-N

NAMES AND DATABASE IDS

Names

• 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
• IUPAC Traditional name: sinefungin
• Synonyms: 5′-Deoxy-5′-(1,4-diamino-4-carboxybutyl)adenosine; A-9145; Adenosylornithine; Antibiotic 32232RP; Sinefungin

Database IDs

• CAS Number: 58944-73-3
• PubChem SID: 24899800; 162227924
• PubChem CID: 65482

CALCULATED PROPERTIES

• Acid pKa: 1.9477124
• H Acceptors: 11
• H Donor: 6
• LogD (pH = 5.5): -7.964581
• LogD (pH = 7.4): -6.847281
• Log P: -5.1386905
• Molar Refractivity: 92.6784 cm^3
• Polarizability: 36.682793 Å^3
• Polar Surface Area: 208.65 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: H2O: soluble
• Apperance: white to yellow powder

Safety Information

• RTECS: HE3140000
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 22
• Safety Statements: 36
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: 2-8°C

Product Information

• Purity: 95% (HPLC)

DETAILS

Sigma Aldrich - S8559

Biochem/physiol Actions
Sinefungin blocks the methylation of bases in DNA and RNA, such as 5-methylcytosine or N6-methyladenosine, suggesting a role in gene expression. In addition, sinefugin is involved in physiological processes such as aging and carcinogenesis.
Sinefungin blocks the methylation of bases in DNA and RNA, such as 5-methylcytosine or N6-methyladenosine, suggesting a role in gene expression. In addition, sinefugin is involved in physiological processes such as aging and carcinogenesis.Methylation inhibition by sinefugin is often accompanied by an altered rate of cytosine deamination that is coupled to transition mutation in the DNA. Sinefugin inhibits Epstein-Barr viral activity and this inhibition is related to the change in DNA methylation and gene expression. It can cause a rate change in several restriction DNA endonuclease activities, including Mme I, which is not connected to the inhibition of the methytransferase activity.