3'-1-carboxy-1-phosphonooxy-ethoxy-uridine-diphosphate-N-acetylglucosamine
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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
- Weight
- Average: 775.3957
Monoisotopic: 775.063943881 - Chemical Formula
- C20H32N3O23P3
- Synonyms
- Not Available
Pharmacology
- Indication
Not Available
Reduce drug development failure ratesBuild, train, & validate machine-learning modelswith evidence-based and structured datasets.Build, train, & validate predictive machine-learning models with structured datasets.- Contraindications & Blackbox Warnings
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- Pharmacodynamics
Not Available
- Mechanism of action
Target Actions Organism UUDP-N-acetylglucosamine 1-carboxyvinyltransferase Not Available Enterobacter 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
- Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.
- 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
- External Links
- PubChem Compound
- 448003
- PubChem Substance
- 46509124
- ChemSpider
- 394940
- ChEMBL
- CHEMBL1236544
- ZINC
- ZINC000095543621
- PDBe Ligand
- UDA
- PDB Entries
- 1q3g
Clinical Trials
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
Property Value Source Water Solubility 13.6 mg/mL ALOGPS logP -0.8 ALOGPS logP -5.1 Chemaxon logS -1.8 ALOGPS pKa (Strongest Acidic) 0.8 Chemaxon pKa (Strongest Basic) -3.8 Chemaxon Physiological Charge -5 Chemaxon Hydrogen Acceptor Count 19 Chemaxon Hydrogen Donor Count 11 Chemaxon Polar Surface Area 393.47 Å2 Chemaxon Rotatable Bond Count 15 Chemaxon Refractivity 145.47 m3·mol-1 Chemaxon Polarizability 62.08 Å3 Chemaxon Number of Rings 3 Chemaxon Bioavailability 0 Chemaxon Rule of Five No Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule Yes Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption - 0.9767 Blood Brain Barrier - 0.7109 Caco-2 permeable - 0.7939 P-glycoprotein substrate Non-substrate 0.6422 P-glycoprotein inhibitor I Non-inhibitor 0.8452 P-glycoprotein inhibitor II Non-inhibitor 0.977 Renal organic cation transporter Non-inhibitor 0.9477 CYP450 2C9 substrate Non-substrate 0.5602 CYP450 2D6 substrate Non-substrate 0.849 CYP450 3A4 substrate Non-substrate 0.5 CYP450 1A2 substrate Non-inhibitor 0.8351 CYP450 2C9 inhibitor Non-inhibitor 0.851 CYP450 2D6 inhibitor Non-inhibitor 0.8533 CYP450 2C19 inhibitor Non-inhibitor 0.7896 CYP450 3A4 inhibitor Inhibitor 0.5239 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.7748 Ames test Non AMES toxic 0.7776 Carcinogenicity Non-carcinogens 0.8551 Biodegradation Not ready biodegradable 0.7382 Rat acute toxicity 2.4553 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9735 hERG inhibition (predictor II) Non-inhibitor 0.532
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 198.06537 predictedDeepCCS 1.0 (2019) [M+H]+ 199.78818 predictedDeepCCS 1.0 (2019) [M+Na]+ 206.11938 predictedDeepCCS 1.0 (2019)
Targets
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- 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
Drug created at June 13, 2005 13:24 / Updated at June 12, 2020 16:52