Zidovudine diphosphate

Identification

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Name
Zidovudine diphosphate
Accession Number
DB04542  (EXPT00601)
Type
Small Molecule
Groups
Experimental
Description
Not Available
Structure
Thumb
Synonyms
  • 3'-Azido-3'-deoxythymidine 5'-diphosphate
  • AZTDP
Categories
UNII
K7ZG448V5M
CAS number
106060-89-3
Weight
Average: 427.2011
Monoisotopic: 427.029414749
Chemical Formula
C10H15N5O10P2
InChI Key
QOYVAFWJURKBJG-XLPZGREQSA-N
InChI
InChI=1S/C10H15N5O10P2/c1-5-3-15(10(17)12-9(5)16)8-2-6(13-14-11)7(24-8)4-23-27(21,22)25-26(18,19)20/h3,6-8H,2,4H2,1H3,(H,21,22)(H,12,16,17)(H2,18,19,20)/t6-,7+,8+/m0/s1
IUPAC Name
[({[(2S,3S,5R)-3-azido-5-(5-methyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)oxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy]phosphonic acid
SMILES
CC1=CN([C@H]2C[C@H](N=[N+]=[N-])[C@@H](COP(O)(=O)OP(O)(O)=O)O2)C(=O)NC1=O

Pharmacology

Indication
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UNucleoside diphosphate kinase ANot AvailableHumans
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
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Not Available
Food Interactions
Not Available

References

General References
Not Available
External Links
PubChem Compound
455742
PubChem Substance
46506772
ChemSpider
401306
ZINC
ZINC000012504398
HET
AZD
PDB Entries
1lwx

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 Solubility6.79 mg/mLALOGPS
logP0.55ALOGPS
logP-0.84ChemAxon
logS-1.8ALOGPS
pKa (Strongest Acidic)1.77ChemAxon
pKa (Strongest Basic)-4.2ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count10ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area201.36 Å2ChemAxon
Rotatable Bond Count7ChemAxon
Refractivity83.45 m3·mol-1ChemAxon
Polarizability33.43 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption-0.8888
Blood Brain Barrier+0.5
Caco-2 permeable-0.7566
P-glycoprotein substrateNon-substrate0.6357
P-glycoprotein inhibitor INon-inhibitor0.8068
P-glycoprotein inhibitor IINon-inhibitor0.9249
Renal organic cation transporterNon-inhibitor0.9015
CYP450 2C9 substrateNon-substrate0.6082
CYP450 2D6 substrateNon-substrate0.8547
CYP450 3A4 substrateSubstrate0.5578
CYP450 1A2 substrateNon-inhibitor0.8492
CYP450 2C9 inhibitorNon-inhibitor0.8505
CYP450 2D6 inhibitorNon-inhibitor0.9061
CYP450 2C19 inhibitorNon-inhibitor0.8351
CYP450 3A4 inhibitorNon-inhibitor0.8619
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9177
Ames testAMES toxic0.5823
CarcinogenicityNon-carcinogens0.8174
BiodegradationReady biodegradable0.7941
Rat acute toxicity2.4595 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.8655
hERG inhibition (predictor II)Non-inhibitor0.7497
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 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 organic pyrophosphates. These are organic compounds containing the pyrophosphate oxoanion, with the structure OP([O-])(=O)OP(O)([O-])=O.
Kingdom
Organic compounds
Super Class
Organic oxygen compounds
Class
Organic oxoanionic compounds
Sub Class
Organic pyrophosphates
Direct Parent
Organic pyrophosphates
Alternative Parents
Pyrimidones / Monoalkyl phosphates / Hydropyrimidines / Vinylogous amides / Oxolanes / Heteroaromatic compounds / Ureas / Azo compounds / Azo imides / Lactams
show 7 more
Substituents
Organic pyrophosphate / Pyrimidone / Monoalkyl phosphate / Hydropyrimidine / Organic phosphoric acid derivative / Phosphoric acid ester / Pyrimidine / Alkyl phosphate / Heteroaromatic compound / Oxolane
show 16 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
Not Available

Targets

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Ribosomal small subunit binding
Specific Function
Major role in the synthesis of nucleoside triphosphates other than ATP. The ATP gamma phosphate is transferred to the NDP beta phosphate via a ping-pong mechanism, using a phosphorylated active-sit...
Gene Name
NME1
Uniprot ID
P15531
Uniprot Name
Nucleoside diphosphate kinase A
Molecular Weight
17148.635 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]
  3. 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 June 13, 2005 07:24 / Updated on February 06, 2020 12:01