NAV

Uridine-5'-Diphosphate-N-Acetylmuramoyl-L-Alanine-D-Glutamate

Identification

Generic Name
Uridine-5'-Diphosphate-N-Acetylmuramoyl-L-Alanine-D-Glutamate
DrugBank Accession Number
DB02314
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
Similar Structures
Weight
Average: 879.6082
Monoisotopic: 879.182405731
Chemical Formula
C28H43N5O23P2
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-acetylmuramoyl-L-alanyl-D-glutamate--2,6-diaminopimelate ligaseNot AvailableEscherichia coli (strain K12)
UUDP-N-acetylmuramoylalanine--D-glutamate ligaseNot AvailableEscherichia coli (strain K12)
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 / Dipeptides / Pentose phosphates / Glutamic acid and derivatives / N-acyl-alpha-hexosamines / N-acyl-alpha amino acids / Alpha amino acid amides / Alanine and derivatives / Glycosylamines / Monosaccharide phosphates
show 24 more
Substituents
Acetamide / Alanine or derivatives / Alcohol / Alkyl phosphate / Alpha peptide / Alpha-amino acid amide / Alpha-amino acid or derivatives / Alpha-dipeptide / Aromatic heteromonocyclic compound / Azacycle
show 45 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
UDP-N-acetylmuramoyl-L-alanyl-D-glutamic acid (CHEBI:46143)
Affected organisms
Not Available

Chemical Identifiers

UNII
Not Available
CAS number
Not Available
InChI Key
OJZCATPXPWFLHF-HPUCEMLMSA-N
InChI
InChI=1S/C28H43N5O23P2/c1-10(23(42)31-13(26(44)45)4-5-17(37)38)29-24(43)11(2)52-22-18(30-12(3)35)27(54-14(8-34)20(22)40)55-58(49,50)56-57(47,48)51-9-15-19(39)21(41)25(53-15)33-7-6-16(36)32-28(33)46/h6-7,10-11,13-15,18-22,25,27,34,39-41H,4-5,8-9H2,1-3H3,(H,29,43)(H,30,35)(H,31,42)(H,37,38)(H,44,45)(H,47,48)(H,49,50)(H,32,36,46)/t10-,11+,13+,14+,15+,18+,19+,20+,21+,22+,25+,27+/m0/s1
IUPAC Name
(2R)-2-[(2S)-2-[(2R)-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}propanamido]propanamido]pentanedioic acid
SMILES
C[C@H](NC(=O)[C@@H](C)O[C@H]1[C@H](O)[C@@H](CO)O[C@H](OP(O)(=O)OP(O)(=O)OC[C@H]2O[C@H]([C@H](O)[C@@H]2O)N2C=CC(=O)NC2=O)[C@@H]1NC(C)=O)C(=O)N[C@H](CCC(O)=O)C(O)=O

References

General References
Not Available
KEGG Compound
C00692
PubChem Compound
449538
PubChem Substance
46505208
ChemSpider
396037
ChEBI
46143
ZINC
ZINC000096068408
PDBe Ligand
UAG
PDB Entries
1e8c / 2wtz / 2xja / 4uag

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 Solubility9.13 mg/mLALOGPS
logP-1.2ALOGPS
logP-6Chemaxon
logS-2ALOGPS
pKa (Strongest Acidic)1.73Chemaxon
Physiological Charge-4Chemaxon
Hydrogen Acceptor Count20Chemaxon
Hydrogen Donor Count12Chemaxon
Polar Surface Area422.21 Å2Chemaxon
Rotatable Bond Count20Chemaxon
Refractivity178.27 m3·mol-1Chemaxon
Polarizability76.18 Å3Chemaxon
Number of Rings3Chemaxon
Bioavailability0Chemaxon
Rule of FiveNoChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleYesChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption-0.9703
Blood Brain Barrier-0.9542
Caco-2 permeable-0.7293
P-glycoprotein substrateSubstrate0.5477
P-glycoprotein inhibitor INon-inhibitor0.7555
P-glycoprotein inhibitor IINon-inhibitor0.9649
Renal organic cation transporterNon-inhibitor0.9418
CYP450 2C9 substrateNon-substrate0.6307
CYP450 2D6 substrateNon-substrate0.8465
CYP450 3A4 substrateSubstrate0.5912
CYP450 1A2 substrateNon-inhibitor0.8387
CYP450 2C9 inhibitorNon-inhibitor0.8211
CYP450 2D6 inhibitorNon-inhibitor0.8157
CYP450 2C19 inhibitorNon-inhibitor0.8054
CYP450 3A4 inhibitorInhibitor0.727
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.7428
Ames testNon AMES toxic0.6822
CarcinogenicityNon-carcinogens0.8557
BiodegradationNot ready biodegradable0.8116
Rat acute toxicity2.3272 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9082
hERG inhibition (predictor II)Inhibitor0.6099
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/MSsplash10-03e9-0301115690-967be9548c2cd35f56ab
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-02dl-0000000190-c33e893ead5b8d6afee9
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0udj-1900001230-2188b6c7410cb14ef5d8
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-116u-2910063040-c4a63d667899c54f7c28
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0ugi-2704900440-50bd23ef3bd3925b1b13
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-005i-5602016590-3e4f86e1f6d74b88cce4
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-235.89775
predicted
DeepCCS 1.0 (2019)
[M+H]+237.62154
predicted
DeepCCS 1.0 (2019)
[M+Na]+243.78293
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. UDP-N-acetylmuramoyl-L-alanyl-D-glutamate--2,6-diaminopimelate ligase
Kind
Protein
Organism
Escherichia coli (strain K12)
Pharmacological action
Unknown
General Function
Udp-n-acetylmuramoylalanyl-d-glutamate-2,6-diaminopimelate ligase activity
Specific Function
Catalyzes the addition of meso-diaminopimelic acid to the nucleotide precursor UDP-N-acetylmuramoyl-L-alanyl-D-glutamate (UMAG) in the biosynthesis of bacterial cell-wall peptidoglycan. Is also abl...
Gene Name
murE
Uniprot ID
P22188
Uniprot Name
UDP-N-acetylmuramoyl-L-alanyl-D-glutamate--2,6-diaminopimelate ligase
Molecular Weight
53343.13 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]
Details2. UDP-N-acetylmuramoylalanine--D-glutamate ligase
Kind
Protein
Organism
Escherichia coli (strain K12)
Pharmacological action
Unknown
General Function
Udp-n-acetylmuramoylalanine-d-glutamate ligase activity
Specific Function
Cell wall formation. Catalyzes the addition of glutamate to the nucleotide precursor UDP-N-acetylmuramoyl-L-alanine (UMA).
Gene Name
murD
Uniprot ID
P14900
Uniprot Name
UDP-N-acetylmuramoylalanine--D-glutamate ligase
Molecular Weight
46973.185 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 July 02, 2020 13:14