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Record Information
Version3.6
Creation Date2013-07-04 18:54:25 UTC
Update Date2016-02-11 08:11:28 UTC
HMDB IDHMDB60713
Secondary Accession NumbersNone
Metabolite Identification
Common Name2-Chloro-2'-deoxyadenosine-5'-triphosphate
Description2-Chloro-2'-deoxyadenosine-5'-triphosphate is a metabolite of cladribine. Cladribine (trade names Litak and Movectro) is a drug used to treat hairy cell leukemia (HCL, leukemic reticuloendotheliosis) and multiple sclerosis. Its chemical name is 2-chlorodeoxyadenosine (2CDA). As a purine analog, it is a synthetic anti-cancer agent that also suppresses the immune system. Chemically, it mimics the nucleoside adenosine and thus inhibits the enzyme adenosine deaminase, which interferes with the cell's ability to process DNA. (Wikipedia)
Structure
Thumb
SynonymsNot Available
Chemical FormulaC10H15ClN5O12P3
Average Molecular Weight525.627
Monoisotopic Molecular Weight524.961858212
IUPAC Name({[({[(2R,3S,5R)-5-(6-amino-2-chloro-9H-purin-9-yl)-3-hydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)phosphonic acid
Traditional Name({[(2R,3S,5R)-5-(6-amino-2-chloropurin-9-yl)-3-hydroxyoxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy(hydroxy)phosphoryl)oxyphosphonic acid
CAS Registry NumberNot Available
SMILES
NC1=C2N=CN([C@H]3C[C@H](O)[C@@H](COP(O)(=O)OP(O)(=O)OP(O)(O)=O)O3)C2=NC(Cl)=N1
InChI Identifier
InChI=1/C10H15ClN5O12P3/c11-10-14-8(12)7-9(15-10)16(3-13-7)6-1-4(17)5(26-6)2-25-30(21,22)28-31(23,24)27-29(18,19)20/h3-6,17H,1-2H2,(H,21,22)(H,23,24)(H2,12,14,15)(H2,18,19,20)/t4-,5+,6+/s2
InChI KeyInChIKey=PZCJNHCKXRBBNN-DWFKHXNSNA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as purine 2'-deoxyribonucleoside triphosphates. These are purine nucleotides with triphosphate group linked to the ribose moiety lacking a hydroxyl group at position 2.
KingdomOrganic compounds
Super ClassNucleosides, nucleotides, and analogues
ClassPurine nucleotides
Sub ClassPurine deoxyribonucleotides
Direct ParentPurine 2'-deoxyribonucleoside triphosphates
Alternative Parents
Substituents
  • Purine 2'-deoxyribonucleoside triphosphate
  • Organic pyrophosphate
  • 6-aminopurine
  • Purine
  • Imidazopyrimidine
  • Monoalkyl phosphate
  • Halopyrimidine
  • Aminopyrimidine
  • Imidolactam
  • Alkyl phosphate
  • Pyrimidine
  • Primary aromatic amine
  • Phosphoric acid ester
  • Organic phosphoric acid derivative
  • Organic phosphate
  • N-substituted imidazole
  • Saccharide
  • Aryl halide
  • Aryl chloride
  • Heteroaromatic compound
  • Oxolane
  • Imidazole
  • Azole
  • Secondary alcohol
  • Oxacycle
  • Azacycle
  • Organoheterocyclic compound
  • Hydrocarbon derivative
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Organochloride
  • Organohalogen compound
  • Amine
  • Alcohol
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
StatusExpected but not Quantified
Origin
  • Drug metabolite
Biofunction
  • Waste products
ApplicationNot Available
Cellular locations
  • Cytoplasm
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility3.46 mg/mLALOGPS
logP-0.01ALOGPS
logP-1.8ChemAxon
logS-2.2ALOGPS
pKa (Strongest Acidic)1.14ChemAxon
pKa (Strongest Basic)0.54ChemAxon
Physiological Charge-3ChemAxon
Hydrogen Acceptor Count13ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area258.9 Å2ChemAxon
Rotatable Bond Count8ChemAxon
Refractivity99.8 m3·mol-1ChemAxon
Polarizability40.02 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Cytoplasm
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Kidney
  • Liver
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableNormal
  • Not Applicable
details
UrineExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableNormal
  • Not Applicable
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDDBMET00677
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB60713
Metagene LinkHMDB60713
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available