NAV

3'-1-carboxy-1-phosphonooxy-ethoxy-uridine-diphosphate-N-acetylglucosamine

Identification

Generic Name
3'-1-carboxy-1-phosphonooxy-ethoxy-uridine-diphosphate-N-acetylglucosamine
DrugBank Accession Number
DB04174
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
Similar Structures
Weight
Average: 775.3957
Monoisotopic: 775.063943881
Chemical Formula
C20H32N3O23P3
Synonyms
Not Available
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Pharmacology

Indication

Not Available

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Contraindications & Blackbox Warnings
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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UUDP-N-acetylglucosamine 1-carboxyvinyltransferaseNot AvailableEnterobacter cloacae subsp. cloacae (strain ATCC 13047 / DSM 30054 / NBRC 13535 / NCDC 279-56)
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 nucleotide sugars. These are pyrimidine nucleotides bound to a saccharide derivative through the terminal phosphate group.
Kingdom
Organic compounds
Super Class
Nucleosides, nucleotides, and analogues
Class
Pyrimidine nucleotides
Sub Class
Pyrimidine nucleotide sugars
Direct Parent
Pyrimidine nucleotide sugars
Alternative Parents
Pyrimidine ribonucleoside diphosphates / Pentose phosphates / N-acyl-alpha-hexosamines / Glycosylamines / Monosaccharide phosphates / Organic pyrophosphates / Pyrimidones / Sugar acids and derivatives / Monoalkyl phosphates / Hydropyrimidines
show 18 more
Substituents
Acetamide / Alcohol / Alkyl phosphate / Aromatic heteromonocyclic compound / Azacycle / Carbonyl group / Carboxamide group / Carboxylic acid / Carboxylic acid derivative / Glycosyl compound
show 34 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
NLBIPGBVVPCESQ-BVDGEXFOSA-N
InChI
InChI=1S/C20H32N3O23P3/c1-7(25)21-11-15(43-20(2,18(30)31)45-47(33,34)35)13(28)8(5-24)42-17(11)44-49(38,39)46-48(36,37)40-6-9-12(27)14(29)16(41-9)23-4-3-10(26)22-19(23)32/h3-4,8-9,11-17,24,27-29H,5-6H2,1-2H3,(H,21,25)(H,30,31)(H,36,37)(H,38,39)(H,22,26,32)(H2,33,34,35)/t8-,9-,11-,12-,13-,14-,15-,16-,17-,20+/m1/s1
IUPAC Name
2-{[(2R,3R,4R,5S,6R)-2-({[({[(2R,3S,4R,5R)-5-(2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)-3-acetamido-5-hydroxy-6-(hydroxymethyl)oxan-4-yl]oxy}-2-(phosphonooxy)propanoic acid
SMILES
[H]N([C@H]1[C@@H](OP(O)(=O)OP(O)(=O)OC[C@H]2O[C@H]([C@H](O)[C@@H]2O)N2C=CC(=O)N([H])C2=O)O[C@H](CO)[C@@H](O)[C@@H]1OC(C)(OP(O)(O)=O)C(O)=O)C(C)=O

References

General References
Not Available
PubChem Compound
448003
PubChem Substance
46509124
ChemSpider
394940
ChEMBL
CHEMBL1236544
ZINC
ZINC000095543621
PDBe Ligand
UDA
PDB Entries
1q3g

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 Solubility13.6 mg/mLALOGPS
logP-0.8ALOGPS
logP-5.1Chemaxon
logS-1.8ALOGPS
pKa (Strongest Acidic)0.8Chemaxon
pKa (Strongest Basic)-3.8Chemaxon
Physiological Charge-5Chemaxon
Hydrogen Acceptor Count19Chemaxon
Hydrogen Donor Count11Chemaxon
Polar Surface Area393.47 Å2Chemaxon
Rotatable Bond Count15Chemaxon
Refractivity145.47 m3·mol-1Chemaxon
Polarizability62.08 Å3Chemaxon
Number of Rings3Chemaxon
Bioavailability0Chemaxon
Rule of FiveNoChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleYesChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption-0.9767
Blood Brain Barrier-0.7109
Caco-2 permeable-0.7939
P-glycoprotein substrateNon-substrate0.6422
P-glycoprotein inhibitor INon-inhibitor0.8452
P-glycoprotein inhibitor IINon-inhibitor0.977
Renal organic cation transporterNon-inhibitor0.9477
CYP450 2C9 substrateNon-substrate0.5602
CYP450 2D6 substrateNon-substrate0.849
CYP450 3A4 substrateNon-substrate0.5
CYP450 1A2 substrateNon-inhibitor0.8351
CYP450 2C9 inhibitorNon-inhibitor0.851
CYP450 2D6 inhibitorNon-inhibitor0.8533
CYP450 2C19 inhibitorNon-inhibitor0.7896
CYP450 3A4 inhibitorInhibitor0.5239
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.7748
Ames testNon AMES toxic0.7776
CarcinogenicityNon-carcinogens0.8551
BiodegradationNot ready biodegradable0.7382
Rat acute toxicity2.4553 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9735
hERG inhibition (predictor II)Non-inhibitor0.532
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/MSsplash10-06vi-0020039300-7f2dcf49b6f6aabd5a1e
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-00e9-1000000900-72dda006bdc10fe703b9
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-004i-9200000300-d35f745b06e2f01f2f4d
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-052f-0101398600-e51aaaf09e37a18163f3
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-057i-8403133900-276e5c9191db14805dd8
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0udi-1229123100-f333725ec6d9ddbb981c
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-198.06537
predicted
DeepCCS 1.0 (2019)
[M+H]+199.78818
predicted
DeepCCS 1.0 (2019)
[M+Na]+206.11938
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. UDP-N-acetylglucosamine 1-carboxyvinyltransferase
Kind
Protein
Organism
Enterobacter cloacae subsp. cloacae (strain ATCC 13047 / DSM 30054 / NBRC 13535 / NCDC 279-56)
Pharmacological action
Unknown
General Function
Udp-n-acetylglucosamine 1-carboxyvinyltransferase activity
Specific Function
Cell wall formation. Adds enolpyruvyl to UDP-N-acetylglucosamine. Target for the antibiotic fosfomycin.
Gene Name
murA
Uniprot ID
P33038
Uniprot Name
UDP-N-acetylglucosamine 1-carboxyvinyltransferase
Molecular Weight
44776.16 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