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2-ACETAMIDO-2-DEOXY-BETA-D-GLUCOPYRANOSE(BETA1-4)-2-ACETAMIDO-1,6-ANHYDRO-3-O-[(R)-1-CARBOXYETHYL]-2-DEOXY-BETA-D-GLUCOPYRANOSE-L-ALANYL-GAMMA-D-GLUTAMYL-MESO-DIAMINOPIMELYL-D-ALANINE

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Identification

Generic Name
2-ACETAMIDO-2-DEOXY-BETA-D-GLUCOPYRANOSE(BETA1-4)-2-ACETAMIDO-1,6-ANHYDRO-3-O-[(R)-1-CARBOXYETHYL]-2-DEOXY-BETA-D-GLUCOPYRANOSE-L-ALANYL-GAMMA-D-GLUTAMYL-MESO-DIAMINOPIMELYL-D-ALANINE
DrugBank Accession Number
DB04736
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
Similar Structures
Weight
Average: 921.8993
Monoisotopic: 921.381487363
Chemical Formula
C37H59N7O20
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
UPeptidoglycan recognition protein 3Not AvailableHumans
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 oligopeptides. These are organic compounds containing a sequence of between three and ten alpha-amino acids joined by peptide bonds.
Kingdom
Organic compounds
Super Class
Organic acids and derivatives
Class
Carboxylic acids and derivatives
Sub Class
Amino acids, peptides, and analogues
Direct Parent
Oligopeptides
Alternative Parents
Gamma-glutamyl peptides / Glutamine and derivatives / N-acyl-alpha-hexosamines / N-acyl-alpha amino acids / Alpha amino acid amides / Disaccharides / Alanine and derivatives / O-glycosyl compounds / D-alpha-amino acids / Tricarboxylic acids and derivatives
show 18 more
Substituents
Acetal / Acetamide / Alanine or derivatives / Alcohol / Aliphatic heteropolycyclic compound / Alpha-amino acid / Alpha-amino acid amide / Alpha-amino acid or derivatives / Alpha-oligopeptide / Amine
show 38 more
Molecular Framework
Aliphatic heteropolycyclic compounds
External Descriptors
N-acetyl-beta-D-glycosaminyl glycopeptide (CHEBI:46763)
Affected organisms
Not Available

Chemical Identifiers

UNII
Not Available
CAS number
Not Available
InChI Key
UPFMKPIBAIPLHT-RSJSDIDPSA-N
InChI
InChI=1S/C37H59N7O20/c1-13(30(51)44-20(35(58)59)9-10-23(48)43-19(8-6-7-18(38)34(56)57)32(53)40-14(2)33(54)55)39-31(52)15(3)61-29-25(42-17(5)47)36-60-12-22(63-36)28(29)64-37-24(41-16(4)46)27(50)26(49)21(11-45)62-37/h13-15,18-22,24-29,36-37,45,49-50H,6-12,38H2,1-5H3,(H,39,52)(H,40,53)(H,41,46)(H,42,47)(H,43,48)(H,44,51)(H,54,55)(H,56,57)(H,58,59)/t13-,14+,15+,18+,19-,20+,21+,22+,24+,25+,26+,27+,28+,29+,36+,37-/m0/s1
IUPAC Name
(2R,6S)-2-amino-6-[(4R)-4-carboxy-4-[(2S)-2-[(2R)-2-{[(1R,2S,3R,4R,5R)-4-acetamido-2-{[(2S,3R,4R,5S,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-6,8-dioxabicyclo[3.2.1]octan-3-yl]oxy}propanamido]propanamido]butanamido]-6-{[(1R)-1-carboxyethyl]carbamoyl}hexanoic acid
SMILES
C[C@@H](NC(=O)[C@H](CCC[C@@H](N)C(O)=O)NC(=O)CC[C@@H](NC(=O)[C@H](C)NC(=O)[C@@H](C)O[C@@H]1[C@@H](NC(C)=O)[C@@H]2OC[C@@H](O2)[C@H]1O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1NC(C)=O)C(O)=O)C(O)=O

References

General References
Not Available
PubChem Compound
163626
PubChem Substance
46508748
ChemSpider
143523
ChEBI
46763
ZINC
ZINC000096006131
PDBe Ligand
MLD
PDB Entries
2cb3 / 2f2l / 4qr7 / 4qrb / 4qtf / 6top / 7nt0

Clinical Trials

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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 Solubility4.18 mg/mLALOGPS
logP-2.4ALOGPS
logP-8.8Chemaxon
logS-2.3ALOGPS
pKa (Strongest Acidic)1.92Chemaxon
pKa (Strongest Basic)9.52Chemaxon
Physiological Charge-2Chemaxon
Hydrogen Acceptor Count21Chemaxon
Hydrogen Donor Count13Chemaxon
Polar Surface Area419.36 Å2Chemaxon
Rotatable Bond Count24Chemaxon
Refractivity205.48 m3·mol-1Chemaxon
Polarizability87.71 Å3Chemaxon
Number of Rings3Chemaxon
Bioavailability0Chemaxon
Rule of FiveNoChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleYesChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption-0.9679
Blood Brain Barrier-0.993
Caco-2 permeable-0.7989
P-glycoprotein substrateSubstrate0.6429
P-glycoprotein inhibitor INon-inhibitor0.7312
P-glycoprotein inhibitor IINon-inhibitor0.9193
Renal organic cation transporterNon-inhibitor0.8873
CYP450 2C9 substrateNon-substrate0.8045
CYP450 2D6 substrateNon-substrate0.8336
CYP450 3A4 substrateSubstrate0.5745
CYP450 1A2 substrateNon-inhibitor0.9441
CYP450 2C9 inhibitorNon-inhibitor0.9383
CYP450 2D6 inhibitorNon-inhibitor0.9301
CYP450 2C19 inhibitorNon-inhibitor0.9121
CYP450 3A4 inhibitorNon-inhibitor0.8948
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9227
Ames testNon AMES toxic0.6606
CarcinogenicityNon-carcinogens0.9431
BiodegradationNot ready biodegradable0.9042
Rat acute toxicity2.4244 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.987
hERG inhibition (predictor II)Non-inhibitor0.5684
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/MSsplash10-0w39-0131230095-c8c2d9abd8d18583648a
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0kk9-1000110095-bad6738b4389dedea309
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-00dl-9583220263-d8085030469857925431
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-002r-2001111391-f900f8f122b9bbbd5220
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-00bc-5954010041-f69474e0499ba27def56
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-06yo-5333312792-7a7279c1a140e2bc179e
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-310.0406478
predicted
DarkChem Lite v0.1.0
[M-H]-270.57126
predicted
DeepCCS 1.0 (2019)
[M+H]+309.4153478
predicted
DarkChem Lite v0.1.0
[M+H]+272.22446
predicted
DeepCCS 1.0 (2019)
[M+Na]+308.6062478
predicted
DarkChem Lite v0.1.0
[M+Na]+278.3813
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. Peptidoglycan recognition protein 3
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Pattern receptor that binds to murein peptidoglycans (PGN) of Gram-positive bacteria. Has bactericidal activity towards Gram-positive bacteria. May kill Gram-positive bacteria by interfering with peptidoglycan biosynthesis. Binds also to Gram-negative bacteria, and has bacteriostatic activity towards Gram-negative bacteria. Plays a role in innate immunity
Specific Function
N-acetylmuramoyl-L-alanine amidase activity
Gene Name
PGLYRP3
Uniprot ID
Q96LB9
Uniprot Name
Peptidoglycan recognition protein 3
Molecular Weight
37610.98 Da
References
  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [Article]

Drug created at September 11, 2007 17:49 / Updated at June 12, 2020 16:52