2-amino-9-[3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-8-sulfanyl-6,9-dihydro-3H-purin-6-one

• ChemBase ID: 131968
• Molecular Formular: C10H13N5O5S
• Molecular Mass: 315.30572
• Monoisotopic Mass: 315.06373954
• SMILES: C(C1C(C(C(O1)n1c2c(c(=O)nc([nH]2)N)nc1S)O)O)O
• Canonical SMILES: OCC1OC(C(C1O)O)n1c(S)nc2c1[nH]c(N)nc2=O
• InChI: InChI=1S/C10H13N5O5S/c11-9-13-6-3(7(19)14-9)12-10(21)15(6)8-5(18)4(17)2(1-16)20-8/h2,4-5,8,16-18H,1H2,(H,12,21)(H3,11,13,14,19)
• InChIKey: KZELNMSPWPFAEB-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-amino-9-[3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-8-sulfanyl-6,9-dihydro-3H-purin-6-one
• IUPAC Traditional name: 2-amino-9-[3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-8-sulfanyl-3H-purin-6-one
• Synonyms: 8-Thioguanosine; 8-Mercaptoguanosine

Database IDs

• CAS Number: 26001-38-7
• EC Number: 247-402-4
• MDL Number: MFCD00057038
• PubChem SID: 162226245; 24897181
• PubChem CID: 3770994

CALCULATED PROPERTIES

• Acid pKa: 7.377908
• H Acceptors: 9
• H Donor: 6
• LogD (pH = 5.5): -1.4166627
• LogD (pH = 7.4): -1.7050726
• Log P: -1.4111502
• Molar Refractivity: 71.6708 cm^3
• Polarizability: 27.566757 Å^3
• Polar Surface Area: 155.22 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Apperance: light yellow crystalline

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: 2-8°C

DETAILS

Sigma Aldrich - M7772

Biochem/physiol Actions
8-Mercaptoguanosine is used to stimulate gene activation; in CD38-activated B cells it induces activation-induced cytidine deaminase (AID) expression. 8-Mercaptoguanosine is also used as an inhibitor of enzymes such as GTP cyclohydrolase I.