5-iodotubercidin

Identification

Name
5-iodotubercidin
Accession Number
DB04604
Type
Small Molecule
Groups
Experimental
Description
Not Available
Structure
Thumb
Synonyms
Not Available
Categories
UNII
Not Available
CAS number
24386-93-4
Weight
Average: 392.1498
Monoisotopic: 391.998148344
Chemical Formula
C11H13IN4O4
InChI Key
WHSIXKUPQCKWBY-IOSLPCCCSA-N
InChI
InChI=1S/C11H13IN4O4/c12-4-1-16(10-6(4)9(13)14-3-15-10)11-8(19)7(18)5(2-17)20-11/h1,3,5,7-8,11,17-19H,2H2,(H2,13,14,15)/t5-,7-,8-,11-/m1/s1
IUPAC Name
(2R,3R,4S,5R)-2-{4-amino-5-iodo-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=C(I)C3=C(N)N=CN=C23)[[email protected]]([H])(O)[[email protected]]1([H])O

Pharmacology

Indication
Not Available
Structured Indications
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UCasein kinase I isoform gamma-2Not AvailableHuman
USerine/threonine-protein kinase haspinNot AvailableHuman
UMitogen-activated protein kinase 3Not AvailableHuman
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
Not Available
Food Interactions
Not Available

References

General References
Not Available
External Links
PubChem Compound
97297
PubChem Substance
46506259
ChemSpider
87822
BindingDB
50375654
ChEBI
40167
ChEMBL
CHEMBL99203
HET
5ID
PDB Entries
2c47 / 2vuw / 2zoq / 3iq7 / 3uwp / 4ouc / 5ax3

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
Not Available
Predicted Properties
PropertyValueSource
Water Solubility3.61 mg/mLALOGPS
logP-0.38ALOGPS
logP-0.35ChemAxon
logS-2ALOGPS
pKa (Strongest Acidic)12.46ChemAxon
pKa (Strongest Basic)6.56ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area126.65 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity78.73 m3·mol-1ChemAxon
Polarizability31.07 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.7807
Blood Brain Barrier+0.9299
Caco-2 permeable-0.8193
P-glycoprotein substrateNon-substrate0.7747
P-glycoprotein inhibitor INon-inhibitor0.9572
P-glycoprotein inhibitor IINon-inhibitor0.8596
Renal organic cation transporterNon-inhibitor0.9413
CYP450 2C9 substrateNon-substrate0.8591
CYP450 2D6 substrateNon-substrate0.8284
CYP450 3A4 substrateNon-substrate0.5622
CYP450 1A2 substrateNon-inhibitor0.9205
CYP450 2C9 inhibitorNon-inhibitor0.9235
CYP450 2D6 inhibitorNon-inhibitor0.9365
CYP450 2C19 inhibitorNon-inhibitor0.9123
CYP450 3A4 inhibitorNon-inhibitor0.9282
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9296
Ames testNon AMES toxic0.8441
CarcinogenicityNon-carcinogens0.8951
BiodegradationNot ready biodegradable1.0
Rat acute toxicity2.5829 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9893
hERG inhibition (predictor II)Non-inhibitor0.8477
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

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 / Aryl iodides / Imidolactams / Tetrahydrofurans / Heteroaromatic compounds / Secondary alcohols
show 7 more
Substituents
Pyrrolopyrimidine ribonucleoside / Glycosyl compound / N-glycosyl compound / Pentose monosaccharide / Pyrrolo[2,3-d]pyrimidine / Pyrrolopyrimidine / Aminopyrimidine / Aryl halide / Aryl iodide / Monosaccharide
show 23 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
organoiodine compound (CHEBI:40167)

Targets

Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Protein serine/threonine kinase activity
Specific Function
Serine/threonine-protein kinase. Casein kinases are operationally defined by their preferential utilization of acidic proteins such as caseins as substrates. It can phosphorylate a large number of ...
Gene Name
CSNK1G2
Uniprot ID
P78368
Uniprot Name
Casein kinase I isoform gamma-2
Molecular Weight
47456.89 Da
References
  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Protein kinase activity
Specific Function
Serine/threonine-protein kinase that phosphorylates histone H3 at 'Ser-3' (H3T3ph) during mitosis. This positions and activates AURKB and other components of the chromosomal passenger complex (CPC)...
Gene Name
GSG2
Uniprot ID
Q8TF76
Uniprot Name
Serine/threonine-protein kinase haspin
Molecular Weight
88494.565 Da
References
  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Phosphatase binding
Specific Function
Serine/threonine kinase which acts as an essential component of the MAP kinase signal transduction pathway. MAPK1/ERK2 and MAPK3/ERK1 are the 2 MAPKs which play an important role in the MAPK/ERK ca...
Gene Name
MAPK3
Uniprot ID
P27361
Uniprot Name
Mitogen-activated protein kinase 3
Molecular Weight
43135.16 Da
References
  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235]

Drug created on September 11, 2007 11:48 / Updated on December 01, 2017 15:30