Tubercidin

• CAS: 69-33-0
• Catalog Number: ACM69330
• Category: Inhibitors
• Molecular Weight: 266.25
• Molecular Formula: C₁₁H₁₄N₄O₄
• Description: Tubercidin (7-Deazaadenosine) is an antibiotic obtained from Streptomyces tubercidicus. Tubercidin inhibits the growth of Streptococcus faecalis (8043) with an IC50 of 0.02 μM. Tubercidin inhibits polymerases by incorporating DNA or RNA, thereby inhibiting DNA replication, RNA and protein synthesis. Tubercidin is a weak inhibitor of adenosine phosphorylase, and interferes with the phosphorylation of adenosine and AMP. Tubercidin has antiviral activity.
• Synonyms: TUBERCIDIN;TUBERCIDINE;3-d)pyrimidin-4-amine,7-beta-d-ribofuranosyl-7h-pyrrolo(;3-d)pyrimidine,4-amino-7-beta-d-ribofuranosyl-7h-pyrrolo(;4-amino-7-(beta-d-ribofuranosyl)-pyrrolo(2,3-d)pyrimidine;4-amino-7-beta-d-ribofuranosyl-7h-pyrrolo(2,3-d)pyrimidine;7-beta-d-ribofuranosyl-7h-pyrrolo(2,3-d)pyrimidine-4-amine;7-deaza-adenosin
• Canonical SMILES: O[C@H]1[C@@H](O)[C@H](N2C=CC3=C2N=CN=C3N)O[C@@H]1CO
• Appearance: Solid
• Storage: Powder-20°C, 3 years; 4°C, 2 years; In solvent-80°C, 6 months; -20°C, 1 month.
• Hazard Statements: T+
• Safety Description: 36/37/39-45
• Shipping: Can be shipped at room temperature, where not in use may vary.
• Source: Streptomyces tubercidicus
• Supplemental Hazard Statements: H300
• Symbol: GHS06

Custom Q&A

What is the PubChem CID of Tubercidin?

The PubChem CID of Tubercidin is 6245.

What is the molecular formula of Tubercidin?

The molecular formula of Tubercidin is C11H14N4O4.

What is the molecular weight of Tubercidin?

The molecular weight of Tubercidin is 266.25 g/mol.

What is the IUPAC name of Tubercidin?

The IUPAC name of Tubercidin is (2R,3R,4S,5R)-2-(4-aminopyrrolo[2,3-d]pyrimidin-7-yl)-5-(hydroxymethyl)oxolane-3,4-diol.

What is the InChI of Tubercidin?

The InChI of Tubercidin is InChI=1S/C11H14N4O4/c12-9-5-1-2-15(10(5)14-4-13-9)11-8(18)7(17)6(3-16)19-11/h1-2,4,6-8,11,16-18H,3H2,(H2,12,13,14)/t6-,7-,8-,11-/m1/s1.

What is the InChIKey of Tubercidin?

The InChIKey of Tubercidin is HDZZVAMISRMYHH-KCGFPETGSA-N.

What is the Canonical SMILES of Tubercidin?

The Canonical SMILES of Tubercidin is C1=CN(C2=NC=NC(=C21)N)C3C(C(C(O3)CO)O)O.

What is the CAS number of Tubercidin?

The CAS number of Tubercidin is 69-33-0.

What is the XLogP3-AA value of Tubercidin?

The XLogP3-AA value of Tubercidin is -1.3.

How many hydrogen bond donor counts does Tubercidin have?

Tubercidin has 4 hydrogen bond donor counts.

Synthetic Use

Upstream Synthesis Route 1

• 16754-80-6

• 69-33-0

Reference: [1] Helvetica Chimica Acta, 1988, vol. 71, # 6, p. 1573 - 1585
[2] Tetrahedron Letters, 1987, vol. 28, # 43, p. 5107 - 5110
[3] Journal of Heterocyclic Chemistry, 1988, vol. 25, # 6, p. 1893 - 1898
[4] Patent: WO2018/133854, 2018, A1, . Location in patent: Paragraph 0191; 0198; 0199
[5] Patent: WO2018/156625, 2018, A1, . Location in patent: Paragraph 0278

Upstream Synthesis Route 2

• 24386-93-4

• 69-33-0

Reference: [1] Journal of Organic Chemistry, 2018, vol. 83, # 15, p. 8589 - 8595
[2] Bioorganic and Medicinal Chemistry, 2017, vol. 25, # 20, p. 5433 - 5440

Upstream Synthesis Route 3

• 120401-34-5

• 69-33-0

Reference: [1] Helvetica Chimica Acta, 1988, vol. 71, # 6, p. 1573 - 1585

Downstream Synthesis Route 1

• 69-33-0
• 870-63-3

• 23589-13-1

Reference: [1]Liebigs Annalen der Chemie,1984,p. 1972 - 1980

Downstream Synthesis Route 2

• 69304-37-6
• 69-33-0

• 85335-76-8

Reference: [1]Journal of the American Chemical Society,1983,vol. 105,p. 4059 - 4065

Downstream Synthesis Route 3

• 40635-67-4
• 69-33-0

• 115899-25-7

Reference: [1]Journal of Heterocyclic Chemistry,1990,vol. 27,p. 31 - 46

* For details of the synthesis route, please refer to the original source to ensure accuracy.