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Tubercidin

CAT: 0013-GTR19161742-04Size: 5 mgDry Ice: NoHazardous: No
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CAT#:0013-GTR19161742-04Size:5 mg
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Description
An antibiotic and adenosine analog isolated from the bacterium Streptomyces tubercidicus with potential antineoplastic activity; incorporates into DNA and inhibits polymerases, thereby inhibiting DNA replication and RNA and protein synthesis; also exhibits antifungal and antiviral activities. (In Vitro) :Tubercidin (7-Deazaadenosine) (0-10 nM; 14 days) has a dose-dependent inhibitory effect on myeloid and erythroid human bone marrow progenitor cells, and the IC50s of tubercidin were 3.4 nM and 3.7 nM for CFU-GM and BFU-E, respectively. (In Vivo) :Tubercidin (7-Deazaadenosine) (intraperitoneal injection; 5 mg/kg; 10 days) in cooperation with NBMPR-P protects the mice from the lethality of tubercidin and allowed the repetition of the regimen for a second time with 100% survival.
CAS Number
69-33-0
Product Name Alternative
Sparsomycin A | 7-Deazaadenosine | NSC-56408
Purity
>98% (HPLC)
Solubility
DMSO: ≥ 30 mg/mL
Smiles
NC1=NC=NC2=C1C=CN2[C@H]3[C@H] (O) [C@H] (O) [C@@H] (CO) O3
Molecular Formula
C11H14N4O4
Molecular Weight
266.2533
Storage Conditions
Storage temperature: -20°C. Stability: ≥ 2 years
Notes
For research use only.
Other Product Names
7H-Pyrrolo[2,3-d]pyrimidin-4-amine, 7-β-D-ribofuranosyl-

Chemical Information

Tubercidin

Tubercidin is an N-glycosylpyrrolopyrimidine that is adenosine in which the in the 5-membered ring that is not attached to the ribose moiety is replaced by a carbon. Tubercidin is produced in the culture broth of Streptomyces tubericidus. It has a role as an antimetabolite, an antineoplastic agent and a bacterial metabolite. It is a ribonucleoside, a N-glycosylpyrrolopyrimidine and an antibiotic antifungal agent.

CAS Number69-33-0
PubChem CID6245
IUPAC Name(2R,3R,4S,5R)-2-(4-aminopyrrolo[2,3-d]pyrimidin-7-yl)-5-(hydroxymethyl)oxolane-3,4-diol
Molecular FormulaC11H14N4O4
Molecular Weight266.25
XLogP-1.3
Topological Polar Surface Area127
Hydrogen Bond Donor Count4
Hydrogen Bond Acceptor Count7
Rotatable Bond Count2
Heavy Atom Count19
Formal Charge0
Complexity334
SMILES
C1=CN(C2=NC=NC(=C21)N)[C@H]3[C@@H]([C@@H]([C@H](O3)CO)O)O
InChI
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
InChIKey
HDZZVAMISRMYHH-KCGFPETGSA-N
Chemical Structure
2D Structure
2D structure of Tubercidin
CAS: 69-33-0
CID: 6245
Formula: C11H14N4O4
MW: 266.25
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight266.25
XLogP3-1.3
Hydrogen Bond Donor Count4
Hydrogen Bond Acceptor Count7
Rotatable Bond Count2
Exact Mass266.10150494
Monoisotopic Mass266.10150494
Topological Polar Surface Area127 Ų
Heavy Atom Count19
Formal Charge0
Complexity334
Isotope Atom Count0
Defined Atom Stereocenter Count4
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count1
Compound Is CanonicalizedYes

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