2-amino-7H-pyrrolo[2,3-d]pyrimidin-4-ol

• ChemBase ID: 61449
• Molecular Formular: C6H6N4O
• Molecular Mass: 150.13804
• Monoisotopic Mass: 150.05416083
• SMILES: n1c2c(c(nc1N)O)cc[nH]2
• Canonical SMILES: Nc1nc(O)c2c(n1)[nH]cc2
• InChI: InChI=1S/C6H6N4O/c7-6-9-4-3(1-2-8-4)5(11)10-6/h1-2H,(H4,7,8,9,10,11)
• InChIKey: OLAFFPNXVJANFR-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-amino-7H-pyrrolo[2,3-d]pyrimidin-4-ol
• IUPAC Traditional name: 2-amino-7H-pyrrolo[2,3-d]pyrimidin-4-ol
• Synonyms: 2-Amino-7H-pyrrolo[2,3-d]pyrimidin-4-ol; 2-Amino-4-hydroxy-pyrrolo-[2,3-d]-pyrimidine; 7-Deazaguanine

Database IDs

• CAS Number: 41687-92-7; 7355-55-7
• MDL Number: MFCD00079103
• PubChem SID: 24893330; 162027190
• PubChem CID: 96253

CALCULATED PROPERTIES

• Acid pKa: 12.429268
• H Acceptors: 4
• H Donor: 3
• LogD (pH = 5.5): 0.65670586
• LogD (pH = 7.4): 0.65670776
• Log P: 0.65671176
• Molar Refractivity: 40.7022 cm^3
• Polarizability: 14.854075 Å^3
• Polar Surface Area: 87.82 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Apperance: tan crystalline

Safety Information

• Storage Warning: IRRITANT
• German water hazard class: 3
• TSCA Listed: false
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Product Information

• Purity: ~95%
• Empirical Formula (Hill Notation): C6H6N4O

DETAILS

Sigma Aldrich - D1035

Application
Ethidium bromide efficiently intercalates into synthetic duplex DNAs with 7-deazaguanine in place of guanine, but shows none of the fluorescence enhancement usually observed upon intercalation. 7-Deazaadenine-duplexes show about 70% of the expected fluorescence enhancement.1