NAV

3'-THIO-THYMIDINE-5'-PHOSPHATE

Identification

Generic Name
3'-THIO-THYMIDINE-5'-PHOSPHATE
DrugBank Accession Number
DB08651
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 338.274
Monoisotopic: 338.033758046
Chemical Formula
C10H15N2O7PS
Synonyms
Not Available
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Pharmacology

Indication

Not Available

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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UType-2 restriction enzyme EcoRVNot AvailableEscherichia coli
UDNA topoisomerase 2-betaNot 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

Adverse Effects
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Toxicity

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

Categories

Drug Categories
Not Available
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as 2',3'-dideoxy-3'-thionucleoside monophosphates. These are 2',3'-deoxyribonucleoside derivatives, where the ribose unit is thio-substituted at the 3'-position, and at the 5'-position by a monophosphate group. The nucleobases here are limited to purine, pyrimidine, and pyridine derivatives.
Kingdom
Organic compounds
Super Class
Nucleosides, nucleotides, and analogues
Class
2',3'-dideoxy-3'-thionucleoside monophosphates
Sub Class
Not Available
Direct Parent
2',3'-dideoxy-3'-thionucleoside monophosphates
Alternative Parents
2',3'-dideoxy-3'-thionucleosides / Pyrimidones / Monoalkyl phosphates / Hydropyrimidines / Vinylogous amides / Tetrahydrofurans / Heteroaromatic compounds / Ureas / Lactams / Oxacyclic compounds
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Substituents
2',3'-dideoxy-3'-thionucleoside / 2',3'-dideoxy-3'-thionucleoside monophosphate / Alkyl phosphate / Alkylthiol / Aromatic heteromonocyclic compound / Azacycle / Heteroaromatic compound / Hydrocarbon derivative / Hydropyrimidine / Lactam
show 17 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
Not Available
CAS number
Not Available
InChI Key
BORVFKJZAOEGOO-GJMOJQLCSA-N
InChI
InChI=1S/C10H15N2O7PS/c1-5-3-12(10(14)11-9(5)13)8-2-7(21)6(19-8)4-18-20(15,16)17/h3,6-8,21H,2,4H2,1H3,(H,11,13,14)(H2,15,16,17)/t6-,7+,8-/m1/s1
IUPAC Name
{[(2R,3S,5R)-5-(5-methyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)-3-sulfanyloxolan-2-yl]methoxy}phosphonic acid
SMILES
[H][C@]1(S)C[C@@]([H])(O[C@]1([H])COP(O)(O)=O)N1C=C(C)C(=O)NC1=O

References

General References
Not Available
PubChem Compound
46937170
PubChem Substance
99445122
ChemSpider
25058112
ZINC
ZINC000033516765
PDBe Ligand
TSP
PDB Entries
1ac3 / 1eo3 / 1eo4 / 1eon / 3l4j / 3l4k / 4gfh

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

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 Solubility1.25 mg/mLALOGPS
logP-0.66ALOGPS
logP-0.17Chemaxon
logS-2.4ALOGPS
pKa (Strongest Acidic)1.28Chemaxon
pKa (Strongest Basic)-4.2Chemaxon
Physiological Charge-2Chemaxon
Hydrogen Acceptor Count6Chemaxon
Hydrogen Donor Count4Chemaxon
Polar Surface Area125.4 Å2Chemaxon
Rotatable Bond Count4Chemaxon
Refractivity72.44 m3·mol-1Chemaxon
Polarizability29.53 Å3Chemaxon
Number of Rings2Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption-0.7857
Blood Brain Barrier+0.6322
Caco-2 permeable-0.7478
P-glycoprotein substrateNon-substrate0.6744
P-glycoprotein inhibitor INon-inhibitor0.7745
P-glycoprotein inhibitor IINon-inhibitor0.9749
Renal organic cation transporterNon-inhibitor0.9051
CYP450 2C9 substrateNon-substrate0.5834
CYP450 2D6 substrateNon-substrate0.8364
CYP450 3A4 substrateSubstrate0.5171
CYP450 1A2 substrateNon-inhibitor0.8531
CYP450 2C9 inhibitorNon-inhibitor0.8051
CYP450 2D6 inhibitorNon-inhibitor0.8901
CYP450 2C19 inhibitorNon-inhibitor0.7984
CYP450 3A4 inhibitorNon-inhibitor0.6434
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8517
Ames testNon AMES toxic0.6061
CarcinogenicityNon-carcinogens0.7596
BiodegradationNot ready biodegradable0.8144
Rat acute toxicity2.4116 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9762
hERG inhibition (predictor II)Non-inhibitor0.7641
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-MSsplash10-002b-9511000000-6fdb62647fad92a3f82a
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-00n3-0966000000-065be2ca3a443cc0ca3b
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-000i-2019000000-84ff62883252caa09e93
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-017i-4900000000-1ae0112bc690868fe9f3
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-004i-9000000000-17ac54c1c09a70562840
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0kdi-3920000000-38003584814b4c0f75de
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-004i-9030000000-11e793472be4d8f4cb21
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-165.22673
predicted
DeepCCS 1.0 (2019)
[M+H]+167.62254
predicted
DeepCCS 1.0 (2019)
[M+Na]+173.81595
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. Type-2 restriction enzyme EcoRV
Kind
Protein
Organism
Escherichia coli
Pharmacological action
Unknown
General Function
Type ii site-specific deoxyribonuclease activity
Specific Function
Recognizes the double-stranded sequence GATATC and cleaves after T-3.
Gene Name
ecoRVR
Uniprot ID
P04390
Uniprot Name
Type-2 restriction enzyme EcoRV
Molecular Weight
28650.14 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. [Article]
Details2. DNA topoisomerase 2-beta
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Protein kinase c binding
Specific Function
Control of topological states of DNA by transient breakage and subsequent rejoining of DNA strands. Topoisomerase II makes double-strand breaks.
Gene Name
TOP2B
Uniprot ID
Q02880
Uniprot Name
DNA topoisomerase 2-beta
Molecular Weight
183265.825 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. [Article]

Drug created at September 15, 2010 21:33 / Updated at June 12, 2020 16:52