NAV

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

Identification

Generic Name
Uridine-5'-Diphosphate-N-Acetylmuramoyl-L-Alanine
DrugBank Accession Number
DB01673
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
Similar Structures
Weight
Average: 750.4943
Monoisotopic: 750.139812636
Chemical Formula
C23H36N4O20P2
Synonyms
Not Available

Pharmacology

Indication

Not Available

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Contraindications & Blackbox Warnings
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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UUDP-N-acetylmuramoylalanine--D-glutamate ligaseNot AvailableEscherichia coli (strain K12)
UUDP-N-acetylmuramate--L-alanine ligaseNot AvailableHaemophilus influenzae (strain ATCC 51907 / DSM 11121 / KW20 / Rd)
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 / N-acyl-L-alpha-amino acids / Alanine and derivatives / Glycosylamines / Monosaccharide phosphates / Organic pyrophosphates / Pyrimidones / Monoalkyl phosphates
show 21 more
Substituents
Acetamide / Alanine or derivatives / Alcohol / Alkyl phosphate / Alpha-amino acid or derivatives / Aromatic heteromonocyclic compound / Azacycle / Carbonyl group / Carboxamide group / Carboxylic acid
show 41 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
UDP-N-acetylmuramoyl-L-alanine (CHEBI:84726)
Affected organisms
Not Available

Chemical Identifiers

UNII
Not Available
CAS number
Not Available
InChI Key
NTMMCWJNQNKACG-KBKUWGQMSA-N
InChI
InChI=1S/C23H36N4O20P2/c1-8(21(35)36)24-19(34)9(2)43-18-14(25-10(3)29)22(45-11(6-28)16(18)32)46-49(40,41)47-48(38,39)42-7-12-15(31)17(33)20(44-12)27-5-4-13(30)26-23(27)37/h4-5,8-9,11-12,14-18,20,22,28,31-33H,6-7H2,1-3H3,(H,24,34)(H,25,29)(H,35,36)(H,38,39)(H,40,41)(H,26,30,37)/t8-,9+,11+,12+,14+,15+,16+,17+,18+,20+,22+/m0/s1
IUPAC Name
(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]propanoic 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)=O

References

General References
Not Available
KEGG Compound
C01212
PubChem Compound
5496796
PubChem Substance
46507193
ChemSpider
4593506
ChEBI
84726
ZINC
ZINC000085545647
PDBe Ligand
UMA
PDB Entries
1eeh / 1p3d / 1p4n / 1uag / 2jfg / 2jfn / 2uag / 3gkr / 3uag / 5a5f …
show 1 more

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 Solubility9.58 mg/mLALOGPS
logP-1.4ALOGPS
logP-5.1Chemaxon
logS-1.9ALOGPS
pKa (Strongest Acidic)1.73Chemaxon
pKa (Strongest Basic)-3.7Chemaxon
Physiological Charge-3Chemaxon
Hydrogen Acceptor Count17Chemaxon
Hydrogen Donor Count10Chemaxon
Polar Surface Area355.81 Å2Chemaxon
Rotatable Bond Count15Chemaxon
Refractivity150.18 m3·mol-1Chemaxon
Polarizability64.42 Å3Chemaxon
Number of Rings3Chemaxon
Bioavailability0Chemaxon
Rule of FiveNoChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleYesChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption-0.9598
Blood Brain Barrier-0.7833
Caco-2 permeable-0.8022
P-glycoprotein substrateNon-substrate0.6778
P-glycoprotein inhibitor INon-inhibitor0.7949
P-glycoprotein inhibitor IINon-inhibitor0.9441
Renal organic cation transporterNon-inhibitor0.956
CYP450 2C9 substrateNon-substrate0.6103
CYP450 2D6 substrateNon-substrate0.8476
CYP450 3A4 substrateSubstrate0.542
CYP450 1A2 substrateNon-inhibitor0.8479
CYP450 2C9 inhibitorNon-inhibitor0.8305
CYP450 2D6 inhibitorNon-inhibitor0.8506
CYP450 2C19 inhibitorNon-inhibitor0.7907
CYP450 3A4 inhibitorInhibitor0.6847
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.7215
Ames testNon AMES toxic0.7447
CarcinogenicityNon-carcinogens0.8445
BiodegradationNot ready biodegradable0.814
Rat acute toxicity2.4144 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9604
hERG inhibition (predictor II)Non-inhibitor0.5082
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/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

Targets

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Details1. 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]
Details2. UDP-N-acetylmuramate--L-alanine ligase
Kind
Protein
Organism
Haemophilus influenzae (strain ATCC 51907 / DSM 11121 / KW20 / Rd)
Pharmacological action
Unknown
General Function
Udp-n-acetylmuramate-l-alanine ligase activity
Specific Function
Cell wall formation.
Gene Name
murC
Uniprot ID
P45066
Uniprot Name
UDP-N-acetylmuramate--L-alanine ligase
Molecular Weight
51993.93 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 16:51