Tubercidin

Identification

Name
Tubercidin
Accession Number
DB03172  (EXPT03017)
Type
Small Molecule
Groups
Experimental
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.

Structure
Thumb
Synonyms
  • 7-deazaadenosine
  • Sparsomycin A
  • Tubercidine
External IDs
Antibiotic 155B2T / Antibiotic XK 101-1 / U-10071
Categories
UNII
M351LCX45Y
CAS number
69-33-0
Weight
Average: 266.2533
Monoisotopic: 266.101504956
Chemical Formula
C11H14N4O4
InChI Key
HDZZVAMISRMYHH-KCGFPETGSA-N
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
IUPAC Name
(2R,3R,4S,5R)-2-{4-amino-7H-pyrrolo[2,3-d]pyrimidin-7-yl}-5-(hydroxymethyl)oxolane-3,4-diol
SMILES

Pharmacology

Indication
Not Available
Structured Indications
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UPurine nucleoside phosphorylase DeoD-typeNot AvailableEscherichia coli (strain K12)
Absorption
Not Available
Volume of distribution
Not Available
Protein binding
Not Available
Metabolism
Not Available
Route of elimination
Not Available
Half life
Not Available
Clearance
Not Available
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteractionDrug group
AcetyldigitoxinAcetyldigitoxin may decrease the cardiotoxic activities of Tubercidin.Approved
AcetyldigoxinAcetyldigoxin may decrease the cardiotoxic activities of Tubercidin.Experimental
BevacizumabBevacizumab may increase the cardiotoxic activities of Tubercidin.Approved, Investigational
CabazitaxelThe risk or severity of adverse effects can be increased when Cabazitaxel is combined with Tubercidin.Approved
CyclophosphamideCyclophosphamide may increase the cardiotoxic activities of Tubercidin.Approved, Investigational
CymarinCymarin may decrease the cardiotoxic activities of Tubercidin.Experimental
DeslanosideDeslanoside may decrease the cardiotoxic activities of Tubercidin.Approved
DigitoxinDigitoxin may decrease the cardiotoxic activities of Tubercidin.Approved, Investigational
DigoxinDigoxin may decrease the cardiotoxic activities of Tubercidin.Approved
Digoxin Immune Fab (Ovine)Digoxin Immune Fab (Ovine) may decrease the cardiotoxic activities of Tubercidin.Approved
DocetaxelThe risk or severity of adverse effects can be increased when Docetaxel is combined with Tubercidin.Approved, Investigational
GitoformateGitoformate may decrease the cardiotoxic activities of Tubercidin.Experimental
Lanatoside CLanatoside C may decrease the cardiotoxic activities of Tubercidin.Experimental
MetildigoxinMetildigoxin may decrease the cardiotoxic activities of Tubercidin.Experimental
OleandrinOleandrin may decrease the cardiotoxic activities of Tubercidin.Experimental, Investigational
OuabainOuabain may decrease the cardiotoxic activities of Tubercidin.Approved
PaclitaxelThe risk or severity of adverse effects can be increased when Paclitaxel is combined with Tubercidin.Approved, Vet Approved
PeruvosidePeruvoside may decrease the cardiotoxic activities of Tubercidin.Experimental
ProscillaridinProscillaridin may decrease the cardiotoxic activities of Tubercidin.Experimental
TrastuzumabTrastuzumab may increase the cardiotoxic activities of Tubercidin.Approved, Investigational
Food Interactions
Not Available

References

Synthesis Reference

Charles G. Smith, "Tubercidin preparation." U.S. Patent US4065556, issued December 27, 1977.

US4065556
General References
  1. Zimmerman TP, Wolberg G, Duncan GS: Metabolism of tubercidin and formycin to their 3':5'-cyclic nucleotides in mammalian cells. J Biol Chem. 1978 Dec 25;253(24):8792-7. [PubMed:721814]
External Links
PubChem Compound
6245
PubChem Substance
46505938
ChemSpider
6009
BindingDB
50000298
ChEBI
48267
ChEMBL
CHEMBL267099
Therapeutic Targets Database
DNC001412
PharmGKB
PA152530738
HET
TBN
PDB Entries
1pr5 / 3uq9 / 4dar / 4l5a / 5f7x / 5tbv

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
water solubility3000 mg/LMERCK INDEX (1996)
logP-0.80HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
Water Solubility16.6 mg/mLALOGPS
logP-0.83ALOGPS
logP-1.3ChemAxon
logS-1.2ALOGPS
pKa (Strongest Acidic)12.46ChemAxon
pKa (Strongest Basic)6.51ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area126.65 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity65.37 m3·mol-1ChemAxon
Polarizability25.65 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9411
Blood Brain Barrier+0.9544
Caco-2 permeable-0.8848
P-glycoprotein substrateNon-substrate0.7783
P-glycoprotein inhibitor INon-inhibitor0.9643
P-glycoprotein inhibitor IINon-inhibitor0.9007
Renal organic cation transporterNon-inhibitor0.9438
CYP450 2C9 substrateNon-substrate0.8419
CYP450 2D6 substrateNon-substrate0.8362
CYP450 3A4 substrateNon-substrate0.5788
CYP450 1A2 substrateNon-inhibitor0.9688
CYP450 2C9 inhibitorNon-inhibitor0.9479
CYP450 2D6 inhibitorNon-inhibitor0.9743
CYP450 2C19 inhibitorNon-inhibitor0.9397
CYP450 3A4 inhibitorNon-inhibitor0.9559
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9623
Ames testNon AMES toxic0.8976
CarcinogenicityNon-carcinogens0.9253
BiodegradationNot ready biodegradable0.9382
Rat acute toxicity2.6214 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9907
hERG inhibition (predictor II)Non-inhibitor0.9027
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSNot Available
MS/MS Spectrum - , positiveLC-MS/MSsplash10-000i-0900000000-36d410d303827e6de6d9

Taxonomy

Description
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.
Kingdom
Organic compounds
Super Class
Nucleosides, nucleotides, and analogues
Class
Pyrrolopyrimidine nucleosides and nucleotides
Sub Class
Not Available
Direct Parent
Pyrrolopyrimidine nucleosides and nucleotides
Alternative Parents
Glycosylamines / Pentoses / Pyrrolo[2,3-d]pyrimidines / Aminopyrimidines and derivatives / Substituted pyrroles / Imidolactams / Tetrahydrofurans / Heteroaromatic compounds / Secondary alcohols / Oxacyclic compounds
show 5 more
Substituents
Pyrrolopyrimidine ribonucleoside / Glycosyl compound / N-glycosyl compound / Pentose monosaccharide / Pyrrolo[2,3-d]pyrimidine / Pyrrolopyrimidine / Aminopyrimidine / Monosaccharide / Pyrimidine / Imidolactam
show 19 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
N-glycosylpyrrolopyrimidine (CHEBI:45836)

Targets

Kind
Protein
Organism
Escherichia coli (strain K12)
Pharmacological action
Unknown
General Function
Purine-nucleoside phosphorylase activity
Specific Function
Cleavage of guanosine or inosine to respective bases and sugar-1-phosphate molecules.
Gene Name
deoD
Uniprot ID
P0ABP8
Uniprot Name
Purine nucleoside phosphorylase DeoD-type
Molecular Weight
25949.68 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423]

Drug created on June 13, 2005 07:24 / Updated on November 09, 2017 03:24