2',3'-Dehydro-2',3'-Deoxy-Thymidine 5'-Diphosphate

Identification

Name
2',3'-Dehydro-2',3'-Deoxy-Thymidine 5'-Diphosphate
Accession Number
DB02569  (EXPT01096)
Type
Small Molecule
Groups
Experimental
Description
Not Available
Structure
Thumb
Synonyms
Not Available
Categories
Not Available
UNII
Not Available
CAS number
Not Available
Weight
Average: 384.1731
Monoisotopic: 384.012367702
Chemical Formula
C10H14N2O10P2
InChI Key
LXCAIISEDMYORY-JGVFFNPUSA-N
InChI
InChI=1S/C10H14N2O10P2/c1-6-4-12(10(14)11-9(6)13)8-3-2-7(21-8)5-20-24(18,19)22-23(15,16)17/h2-4,7-8H,5H2,1H3,(H,18,19)(H,11,13,14)(H2,15,16,17)/t7-,8+/m0/s1
IUPAC Name
{[hydroxy({[(2S,5R)-5-(5-methyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)-2,5-dihydrofuran-2-yl]methoxy})phosphoryl]oxy}phosphonic acid
SMILES
CC1=CN([[email protected]@H]2O[[email protected]](CO[[email protected]@](O)(=O)OP(O)(O)=O)C=C2)C(=O)NC1=O

Pharmacology

Indication
Not Available
Structured Indications
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UNucleoside diphosphate kinase ANot 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
461279
PubChem Substance
46508621
ChemSpider
405849
ChEMBL
CHEMBL405730
HET
D4D
PDB Entries
1f3f

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 Solubility4.53 mg/mLALOGPS
logP-0.2ALOGPS
logP-0.78ChemAxon
logS-1.9ALOGPS
pKa (Strongest Acidic)1.77ChemAxon
pKa (Strongest Basic)-4.2ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area171.93 Å2ChemAxon
Rotatable Bond Count6ChemAxon
Refractivity77.06 m3·mol-1ChemAxon
Polarizability30.35 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption-0.6359
Blood Brain Barrier+0.8914
Caco-2 permeable-0.8076
P-glycoprotein substrateNon-substrate0.746
P-glycoprotein inhibitor INon-inhibitor0.8053
P-glycoprotein inhibitor IINon-inhibitor0.9457
Renal organic cation transporterNon-inhibitor0.941
CYP450 2C9 substrateNon-substrate0.5957
CYP450 2D6 substrateNon-substrate0.8525
CYP450 3A4 substrateNon-substrate0.5464
CYP450 1A2 substrateNon-inhibitor0.8476
CYP450 2C9 inhibitorNon-inhibitor0.851
CYP450 2D6 inhibitorNon-inhibitor0.8863
CYP450 2C19 inhibitorNon-inhibitor0.819
CYP450 3A4 inhibitorNon-inhibitor0.8965
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8829
Ames testNon AMES toxic0.7753
CarcinogenicityNon-carcinogens0.8556
BiodegradationNot ready biodegradable0.6711
Rat acute toxicity2.3691 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9597
hERG inhibition (predictor II)Non-inhibitor0.8247
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 pyrimidine 2',3'-dideoxyribonucleoside diphosphates. These are pyrimidine nucleotides with diphosphate group linked to the ribose moiety lacking a hydroxyl group at positions 2 and 3.
Kingdom
Organic compounds
Super Class
Nucleosides, nucleotides, and analogues
Class
Pyrimidine nucleotides
Sub Class
Pyrimidine deoxyribonucleotides
Direct Parent
Pyrimidine 2',3'-dideoxyribonucleoside diphosphates
Alternative Parents
Nucleoside and nucleotide analogues / Organic pyrophosphates / Pyrimidones / Monoalkyl phosphates / Hydropyrimidines / Vinylogous amides / Dihydrofurans / Heteroaromatic compounds / Ureas / Lactams
show 7 more
Substituents
Pyrimidine 2',3'-dideoxyribonucleoside diphosphate / Organic pyrophosphate / Monoalkyl phosphate / Pyrimidone / Hydropyrimidine / Organic phosphoric acid derivative / Phosphoric acid ester / Pyrimidine / Alkyl phosphate / Dihydrofuran
show 15 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
Not Available

Targets

Kind
Protein
Organism
Human
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 December 01, 2017 14:59