(2R,3R,4S,5S)-2-(6-amino-9H-purin-9-yl)-5-{[(3-aminopropyl)sulfanyl]methyl}oxolane-3,4-diol

• ChemBase ID: 154395
• Molecular Formular: C13H20N6O3S
• Molecular Mass: 340.4013
• Monoisotopic Mass: 340.13175953
• SMILES: c1nc(c2c(n1)n(cn2)[C@H]1[C@@H]([C@@H]([C@H](O1)CSCCCN)O)O)N
• Canonical SMILES: NCCCSC[C@H]1O[C@H]([C@@H]([C@@H]1O)O)n1cnc2c1ncnc2N
• InChI: InChI=1S/C13H20N6O3S/c14-2-1-3-23-4-7-9(20)10(21)13(22-7)19-6-18-8-11(15)16-5-17-12(8)19/h5-7,9-10,13,20-21H,1-4,14H2,(H2,15,16,17)/t7-,9-,10-,13-/m1/s1
• InChIKey: FUSRAALGPJJIRO-QYVSTXNMSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3R,4S,5S)-2-(6-amino-9H-purin-9-yl)-5-{[(3-aminopropyl)sulfanyl]methyl}oxolane-3,4-diol
• IUPAC Traditional name: (2S,3S,4R,5R)-2-{[(3-aminopropyl)sulfanyl]methyl}-5-(6-aminopurin-9-yl)oxolane-3,4-diol
• Synonyms: 5′-[(3-Aminopropyl)thio]-5′-deoxyadenosine; S-Adenosyl-3-thiopropylamine; dc-SAH; dcAdoHcy; decarboxylated S-Adenosyl-L-homocysteine; S-(5′-Adenosyl)-3-thiopropylamine

Database IDs

• CAS Number: 53186-57-5
• MDL Number: MFCD17215932
• PubChem SID: 162248534
• PubChem CID: 171251

CALCULATED PROPERTIES

• Acid pKa: 12.473982
• H Acceptors: 8
• H Donor: 4
• LogD (pH = 5.5): -4.5879173
• LogD (pH = 7.4): -4.039746
• Log P: -1.4492948
• Molar Refractivity: 86.8936 cm^3
• Polarizability: 33.93544 Å^3
• Polar Surface Area: 145.33 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Safety Information

• European Hazard Symbols: Highly toxic (T+)
• German water hazard class: 3
• Risk Statements: 28
• Safety Statements: 28-36/37-45
• GHS Pictograms: GHS06
• GHS Signal Word: Danger
• GHS Hazard statements: H300
• GHS Precautionary statements: P264-P301 + P310
• Personal Protective Equipment: Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98.0% (HPLC)
• Empirical Formula (Hill Notation): C13H20N6O3S

DETAILS

Sigma Aldrich - 43713

Other Notes
This decarboxylated S-Adenosyl-L-methionine is an important metabolite in polyamine biosynthesis, acting as aminopropyl group donor for propylamine transferases such as spermine synthase and spermidine synthase.