NAV

2'-deoxy-5-(hydroxymethyl)uridine 5'-(dihydrogen phosphate)

Identification

Generic Name
2'-deoxy-5-(hydroxymethyl)uridine 5'-(dihydrogen phosphate)
DrugBank Accession Number
DB03846
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 338.2079
Monoisotopic: 338.0515166
Chemical Formula
C10H15N2O9P
Synonyms
  • 5-hydroxymethyluridine-2'-deoxy-5'-monophosphate
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Pharmacology

Indication

Not Available

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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UThymidylate kinaseNot AvailableMycobacterium tuberculosis
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 pyrimidine 2'-deoxyribonucleoside monophosphates. These are pyrimidine nucleotides with a monophosphate group linked to the ribose moiety lacking a hydroxyl group at position 2.
Kingdom
Organic compounds
Super Class
Nucleosides, nucleotides, and analogues
Class
Pyrimidine nucleotides
Sub Class
Pyrimidine deoxyribonucleotides
Direct Parent
Pyrimidine 2'-deoxyribonucleoside monophosphates
Alternative Parents
Monoalkyl phosphates / Pyrimidones / Hydropyrimidines / Vinylogous amides / Heteroaromatic compounds / Tetrahydrofurans / Secondary alcohols / Ureas / Lactams / Oxacyclic compounds
show 7 more
Substituents
Alcohol / Alkyl phosphate / Aromatic alcohol / Aromatic heteromonocyclic compound / Azacycle / Heteroaromatic compound / Hydrocarbon derivative / Hydropyrimidine / Lactam / Monoalkyl phosphate
show 18 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
WEBVWKFGRVLCNS-XLPZGREQSA-N
InChI
InChI=1S/C10H15N2O9P/c13-3-5-2-12(10(16)11-9(5)15)8-1-6(14)7(21-8)4-20-22(17,18)19/h2,6-8,13-14H,1,3-4H2,(H,11,15,16)(H2,17,18,19)/t6-,7+,8+/m0/s1
IUPAC Name
{[(2R,3S,5R)-3-hydroxy-5-[5-(hydroxymethyl)-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl]oxolan-2-yl]methoxy}phosphonic acid
SMILES
[H]N1C(=O)N(C=C(CO)C1=O)[C@H]1C[C@H](O)[C@@H](COP(O)(O)=O)O1

References

General References
Not Available
PubChem Compound
447206
PubChem Substance
46505421
ChemSpider
394364
ChEMBL
CHEMBL1160818
ZINC
ZINC000013538464
PDBe Ligand
5HU
PDB Entries
1mrs / 1y6g / 1y8z / 4e9h / 4ea4 / 4ea5 / 4ew0 / 7jxf / 8qhq

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 Solubility8.39 mg/mLALOGPS
logP-1.6ALOGPS
logP-2.5Chemaxon
logS-1.6ALOGPS
pKa (Strongest Acidic)1.23Chemaxon
pKa (Strongest Basic)-2.8Chemaxon
Physiological Charge-2Chemaxon
Hydrogen Acceptor Count8Chemaxon
Hydrogen Donor Count5Chemaxon
Polar Surface Area165.86 Å2Chemaxon
Rotatable Bond Count5Chemaxon
Refractivity68.06 m3·mol-1Chemaxon
Polarizability28.74 Å3Chemaxon
Number of Rings2Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption-0.8916
Blood Brain Barrier+0.8241
Caco-2 permeable-0.6913
P-glycoprotein substrateNon-substrate0.644
P-glycoprotein inhibitor INon-inhibitor0.6845
P-glycoprotein inhibitor IINon-inhibitor0.9371
Renal organic cation transporterNon-inhibitor0.8849
CYP450 2C9 substrateNon-substrate0.7507
CYP450 2D6 substrateNon-substrate0.832
CYP450 3A4 substrateNon-substrate0.5077
CYP450 1A2 substrateNon-inhibitor0.8732
CYP450 2C9 inhibitorNon-inhibitor0.8685
CYP450 2D6 inhibitorNon-inhibitor0.8912
CYP450 2C19 inhibitorNon-inhibitor0.833
CYP450 3A4 inhibitorNon-inhibitor0.9513
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9371
Ames testAMES toxic0.5334
CarcinogenicityNon-carcinogens0.8324
BiodegradationNot ready biodegradable0.672
Rat acute toxicity2.4301 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9013
hERG inhibition (predictor II)Non-inhibitor0.7312
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-MSsplash10-01ow-9602000000-492364a8da16148e113b
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-004u-0924000000-1727877e416183779fb0
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-000i-2009000000-4feb3153474196dcb222
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-004r-9035000000-2e6ef88be84be6850562
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-004i-0900000000-8b2dd09f873d4260aa71
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-00ba-2971000000-080d8e00b9b3398ca82a
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-004i-9130000000-ba5e82529c7d9895a95b
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]-163.61583
predicted
DeepCCS 1.0 (2019)
[M+H]+166.0117
predicted
DeepCCS 1.0 (2019)
[M+Na]+172.34413
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. Thymidylate kinase
Kind
Protein
Organism
Mycobacterium tuberculosis
Pharmacological action
Unknown
General Function
Catalyzes the reversible phosphorylation of deoxythymidine monophosphate (dTMP) to deoxythymidine diphosphate (dTDP), using ATP as its preferred phosphoryl donor. Situated at the junction of both de novo and salvage pathways of deoxythymidine triphosphate (dTTP) synthesis, is essential for DNA synthesis and cellular growth. Has a broad specificity for nucleoside triphosphates, being highly active with ATP or dATP as phosphate donors, and less active with ITP, GTP, CTP and UTP.
Specific Function
Atp binding
Gene Name
tmk
Uniprot ID
P9WKE1
Uniprot Name
Thymidylate kinase
Molecular Weight
22634.285 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. [Article]
  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. [Article]

Drug created at June 13, 2005 13:24 / Updated at June 12, 2020 16:52