Tubercidin

Synonyms :
7-deazaadenosine, 7-Deazadenosine, Sparsomycin A, TBN, Toyocamycin, Tubercidine

Status : experimental

Category

Antibiotics, Antineoplastic

Description

An antibiotic purine ribonucleoside that readily substitutes for adenosine in the biological system, but its incorporation into DNA and RNA has an inhibitory effect on the metabolism of these nucleic acids. [PubChem]

Chemical Classification

This compound belongs to the class of organic compounds known as pyrrolopyrimidine nucleosides and nucleotides. These are nucleoside derivatives containing a ribose derivative which is n-glycosylated to a pyrrolopyrimidine. Also called deazapurine nucleosides, they are analogs of purine nucleosides with the N atom of the purine being replaced by a C atom at position 7.

Pyrrolopyrimidine nucleosides and nucleotides

Organic compounds

Nucleosides, nucleotides, and analogues

Pyrrolopyrimidine nucleosides and nucleotides

Chemical Name

7-deazaadenosine

Calculated Property

kind Value Source
logP -0.83 ALOGPS
logS -1.2 ALOGPS
Water Solubility 1.66e+01 g/l ALOGPS
logP -1.3 ChemAxon
IUPAC Name (2R,3R,4R,5S)-2-{4-amino-7H-pyrrolo[2,3-d]pyrimidin-7-yl}-5-(hydroxymethyl)oxolane-3,4-diol ChemAxon
Traditional IUPAC Name toyocamycin ChemAxon
Molecular Weight 266.2533 ChemAxon
Monoisotopic Weight 266.101504956 ChemAxon
SMILES NC1=NC=NC2=C1C=CN2[C@@H]1O[C@@H](CO)[C@H](O)[C@H]1O ChemAxon
Molecular Formula C11H14N4O4 ChemAxon
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+/m0/s1 ChemAxon
InChIKey InChIKey=HDZZVAMISRMYHH-LITAXDCLSA-N ChemAxon
Polar Surface Area (PSA) 126.65 ChemAxon
Refractivity 65.37 ChemAxon
Polarizability 25.6 ChemAxon
Rotatable Bond Count 2 ChemAxon
H Bond Acceptor Count 7 ChemAxon
H Bond Donor Count 4 ChemAxon
pKa (strongest acidic) 12.46 ChemAxon
pKa (strongest basic) 7.2 ChemAxon
Physiological Charge 1 ChemAxon
Number of Rings 3 ChemAxon
Bioavailability 1 ChemAxon
Rule of Five 1 ChemAxon
Ghose Filter 0 ChemAxon
MDDR-Like Rule 0 ChemAxon

Target within organism

  • Purine nucleoside phosphorylase DeoD-type : in Escherichia coli (strain K12)