(2R,3S,5S)-2-(Hydroxymethyl)-5-[(2-sulfoethyl)carbamoyl]-3-pyrrolidiniumyl 2-acetamido-2-deoxy-4-O-sulfo-beta-D-glucopyranoside

Identification

Generic Name
(2R,3S,5S)-2-(Hydroxymethyl)-5-[(2-sulfoethyl)carbamoyl]-3-pyrrolidiniumyl 2-acetamido-2-deoxy-4-O-sulfo-beta-D-glucopyranoside
DrugBank Accession Number
DB02595
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
Thumb
Weight
Average: 552.551
Monoisotopic: 552.116919063
Chemical Formula
C16H30N3O14S2
Synonyms
Not Available

Pharmacology

Indication

Not Available

Pharmacology
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Contraindications & Blackbox Warnings
Contraindications
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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
USoluble lytic murein transglycosylaseNot AvailableEscherichia coli (strain K12)
UMembrane-bound lytic murein transglycosylase BNot 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
Medicalerrors
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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 n-acyl-alpha-hexosamines. These are carbohydrate derivatives containing a hexose moiety in which the oxygen atom is replaced by an n-acyl group.
Kingdom
Organic compounds
Super Class
Organic oxygen compounds
Class
Organooxygen compounds
Sub Class
Carbohydrates and carbohydrate conjugates
Direct Parent
N-acyl-alpha-hexosamines
Alternative Parents
Proline and derivatives / Alpha amino acid amides / Hexoses / O-glycosyl compounds / Monosaccharide sulfates / Pyrrolidinecarboxamides / Oxanes / Alkyl sulfates / Sulfuric acid monoesters / Organosulfonic acids
show 16 more
Substituents
1,2-aminoalcohol / Acetal / Acetamide / Alcohol / Aliphatic heteromonocyclic compound / Alkanesulfonic acid / Alkyl sulfate / Alpha-amino acid amide / Alpha-amino acid or derivatives / Amine
show 38 more
Molecular Framework
Aliphatic heteromonocyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
Not Available
CAS number
92953-54-3
InChI Key
RPNZWZDLNYCCIG-HMMVDTEZSA-O
InChI
InChI=1S/C16H29N3O14S2/c1-7(22)18-12-13(23)14(33-35(28,29)30)11(6-21)32-16(12)31-10-4-8(19-9(10)5-20)15(24)17-2-3-34(25,26)27/h8-14,16,19-21,23H,2-6H2,1H3,(H,17,24)(H,18,22)(H,25,26,27)(H,28,29,30)/p+1/t8-,9+,10-,11+,12+,13+,14+,16+/m0/s1
IUPAC Name
(2R,3S,5S)-3-{[(2R,3R,4R,5S,6R)-3-acetamido-4-hydroxy-6-(hydroxymethyl)-5-(sulfooxy)oxan-2-yl]oxy}-2-(hydroxymethyl)-5-[(2-sulfoethyl)carbamoyl]pyrrolidin-1-ium
SMILES
[H]N(CCS(O)(=O)=O)C(=O)[C@@H]1C[C@H](O[C@@H]2O[C@H](CO)[C@@H](OS(O)(=O)=O)[C@H](O)[C@H]2N([H])C(C)=O)[C@@H](CO)[N+]1([H])[H]

References

General References
Not Available
PubChem Compound
101059193
PubChem Substance
46507352
ChemSpider
4450095
PDBe Ligand
BLG
PDB Entries
1d0l / 1d0m / 1sly / 4hjv / 4p0g / 5mpq / 6cfc

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 Solubility5.61 mg/mLALOGPS
logP-1.3ALOGPS
logP-7.7ChemAxon
logS-2ALOGPS
pKa (Strongest Acidic)-1.9ChemAxon
pKa (Strongest Basic)8.56ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count13ChemAxon
Hydrogen Donor Count8ChemAxon
Polar Surface Area271.93 Å2ChemAxon
Rotatable Bond Count11ChemAxon
Refractivity121.67 m3·mol-1ChemAxon
Polarizability50.88 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption-0.9924
Blood Brain Barrier-0.877
Caco-2 permeable-0.6667
P-glycoprotein substrateSubstrate0.5
P-glycoprotein inhibitor INon-inhibitor0.7943
P-glycoprotein inhibitor IINon-inhibitor0.9958
Renal organic cation transporterNon-inhibitor0.9334
CYP450 2C9 substrateNon-substrate0.8789
CYP450 2D6 substrateNon-substrate0.803
CYP450 3A4 substrateNon-substrate0.5253
CYP450 1A2 substrateNon-inhibitor0.8513
CYP450 2C9 inhibitorNon-inhibitor0.809
CYP450 2D6 inhibitorNon-inhibitor0.8905
CYP450 2C19 inhibitorNon-inhibitor0.7711
CYP450 3A4 inhibitorNon-inhibitor0.9892
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9769
Ames testNon AMES toxic0.5793
CarcinogenicityNon-carcinogens0.7157
BiodegradationNot ready biodegradable0.5426
Rat acute toxicity2.4563 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.8237
hERG inhibition (predictor II)Non-inhibitor0.6686
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

Drugtargets
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Kind
Protein
Organism
Escherichia coli (strain K12)
Pharmacological action
Unknown
General Function
Lytic transglycosylase activity
Specific Function
Murein-degrading enzyme. Catalyzes the cleavage of the glycosidic bonds between N-acetylmuramic acid and N-acetylglucosamine residues in peptidoglycan. May play a role in recycling of muropeptides ...
Gene Name
slt
Uniprot ID
P0AGC3
Uniprot Name
Soluble lytic murein transglycosylase
Molecular Weight
73352.56 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. [PubMed:17139284]
  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. [PubMed:17016423]
Kind
Protein
Organism
Escherichia coli (strain K12)
Pharmacological action
Unknown
General Function
Lytic transglycosylase activity
Specific Function
Murein-degrading enzyme. Catalyzes the cleavage of the glycosidic bonds between N-acetylmuramic acid and N-acetylglucosamine residues in peptidoglycan. May play a role in recycling of muropeptides ...
Gene Name
mltB
Uniprot ID
P41052
Uniprot Name
Membrane-bound lytic murein transglycosylase B
Molecular Weight
40255.55 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. [PubMed:17139284]
  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. [PubMed:17016423]

Drug created on June 13, 2005 13:24 / Updated on August 01, 2020 13:44