Identification
NameTubercidin
Accession NumberDB03172  (EXPT03017)
TypeSmall Molecule
GroupsExperimental
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]

Structure
Thumb
Synonyms
7-deazaadenosine
7-Deazadenosine
Sparsomycin A
TBN
Toyocamycin
Tubercidine
External IDs Antibiotic 155B2T / Antibiotic XK 101-1 / U-10071
Product Ingredients Not Available
Approved Prescription ProductsNot Available
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International BrandsNot Available
Brand mixturesNot Available
Categories
UNIIL7995C4D7F
CAS number69-33-0
WeightAverage: 266.2533
Monoisotopic: 266.101504956
Chemical FormulaC11H14N4O4
InChI KeyHDZZVAMISRMYHH-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
[H][[email protected]]1(CO)O[[email protected]@]([H])(N2C=CC3=C(N)N=CN=C23)[[email protected]]([H])(O)[[email protected]]1([H])O
Pharmacology
IndicationNot Available
Structured Indications Not Available
PharmacodynamicsNot Available
Mechanism of action
TargetKindPharmacological actionActionsOrganismUniProt ID
Purine nucleoside phosphorylase DeoD-typeProteinunknownNot AvailableEscherichia coli (strain K12)P0ABP8 details
Related Articles
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
MetabolismNot Available
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organismsNot Available
PathwaysNot Available
Pharmacogenomic Effects/ADRs Not Available
Interactions
Drug Interactions
DrugInteractionDrug group
AcetyldigitoxinAcetyldigitoxin may decrease the cardiotoxic activities of Tubercidin.Approved
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
DeslanosideDeslanoside may decrease the cardiotoxic activities of Tubercidin.Approved
DigitoxinDigitoxin may decrease the cardiotoxic activities of Tubercidin.Approved
DigoxinDigoxin 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
OleandrinAnvirzel may decrease the cardiotoxic activities of Tubercidin.Experimental
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
TrastuzumabTrastuzumab may increase the cardiotoxic activities of Tubercidin.Approved, Investigational
Food InteractionsNot 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
ATC CodesNot Available
AHFS CodesNot Available
PDB Entries
FDA labelNot Available
MSDSNot Available
Clinical Trials
Clinical Trials Not Available
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
StateSolid
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)7.2ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area126.65 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity65.37 m3·mol-1ChemAxon
Polarizability25.62 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
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MSNot Available
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , PositiveNot Available
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-000i-0900000000-36d410d303827e6de6d9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
Taxonomy
DescriptionThis compound belongs to the class of chemical entities 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.
KingdomChemical entities
Super ClassOrganic compounds
ClassNucleosides, nucleotides, and analogues
Sub ClassPyrrolopyrimidine nucleosides and nucleotides
Direct ParentPyrrolopyrimidine nucleosides and nucleotides
Alternative ParentsGlycosylamines / Pentoses / Pyrrolo[2,3-d]pyrimidines / Aminopyrimidines and derivatives / Substituted pyrroles / Primary aromatic amines / Imidolactams / Oxolanes / Heteroaromatic compounds / Secondary alcohols
SubstituentsPyrrolopyrimidine ribonucleoside / Glycosyl compound / N-glycosyl compound / Pentose monosaccharide / Pyrrolo[2,3-d]pyrimidine / Pyrrolopyrimidine / Aminopyrimidine / Monosaccharide / Primary aromatic amine / Imidolactam
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsN-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 September 01, 2017 11:01