NAV

N-acetyl-beta-D-glucosaminyl-(1->4)-N-acetyl-beta-D-glucosamine

Identification

Generic Name
N-acetyl-beta-D-glucosaminyl-(1->4)-N-acetyl-beta-D-glucosamine
DrugBank Accession Number
DB03013
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 424.4003
Monoisotopic: 424.169309748
Chemical Formula
C16H28N2O11
Synonyms
  • Chitodextrin
  • β-D-GlcNAc-(1→4)-β-D-GlcNAc
  • β-D-GlcpNAc-(1→4)-β-D-GlcpNAc
  • βGlcNAc(1→4)βGlcNAc

Pharmacology

Indication

Not Available

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Contraindications & Blackbox Warnings
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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UChitobiaseNot AvailableSerratia marcescens
ULysozyme CNot AvailableHumans
UBeta-1,4-galactosyltransferase 1Not 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 acylaminosugars. These are organic compounds containing a sugar linked to a chain through N-acyl group.
Kingdom
Organic compounds
Super Class
Organic oxygen compounds
Class
Organooxygen compounds
Sub Class
Carbohydrates and carbohydrate conjugates
Direct Parent
Acylaminosugars
Alternative Parents
N-acyl-alpha-hexosamines / Disaccharides / O-glycosyl compounds / Oxanes / Acetamides / Secondary carboxylic acid amides / Secondary alcohols / Hemiacetals / Oxacyclic compounds / Acetals
show 6 more
Substituents
Acetal / Acetamide / Acylaminosugar / Alcohol / Aliphatic heteromonocyclic compound / Carbonyl group / Carboxamide group / Carboxylic acid derivative / Disaccharide / Glycosyl compound
show 14 more
Molecular Framework
Aliphatic heteromonocyclic compounds
External Descriptors
N,N'-diacetylchitobiose (CHEBI:50670)
Affected organisms
Not Available

Chemical Identifiers

UNII
Not Available
CAS number
35061-50-8
InChI Key
CDOJPCSDOXYJJF-KSKNGZLJSA-N
InChI
InChI=1S/C16H28N2O11/c1-5(21)17-9-13(25)14(8(4-20)27-15(9)26)29-16-10(18-6(2)22)12(24)11(23)7(3-19)28-16/h7-16,19-20,23-26H,3-4H2,1-2H3,(H,17,21)(H,18,22)/t7-,8-,9-,10-,11-,12-,13-,14-,15-,16+/m1/s1
IUPAC Name
N-[(2S,3R,4R,5S,6R)-2-{[(2R,3S,4R,5R,6R)-5-acetamido-4,6-dihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide
SMILES
CC(=O)N[C@H]1[C@H](O)O[C@H](CO)[C@@H](O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2NC(C)=O)[C@@H]1O

References

General References
Not Available
PubChem Compound
439326
PubChem Substance
46505382
ChemSpider
388457
ChEBI
50670
ChEMBL
CHEMBL467754
ZINC
ZINC000004095478
PDBe Ligand
CBS
PDB Entries
1qbb / 1tw5 / 1zu0 / 2bs7 / 2hrg / 2hrh / 3qdu / 3qdx / 3qdy / 3qnq

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 Solubility111.0 mg/mLALOGPS
logP-2.6ALOGPS
logP-5.3Chemaxon
logS-0.58ALOGPS
pKa (Strongest Acidic)11.5Chemaxon
pKa (Strongest Basic)-3Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count11Chemaxon
Hydrogen Donor Count8Chemaxon
Polar Surface Area207.27 Å2Chemaxon
Rotatable Bond Count6Chemaxon
Refractivity90.54 m3·mol-1Chemaxon
Polarizability40.86 Å3Chemaxon
Number of Rings2Chemaxon
Bioavailability0Chemaxon
Rule of FiveNoChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption-0.9707
Blood Brain Barrier-0.9721
Caco-2 permeable-0.818
P-glycoprotein substrateNon-substrate0.5653
P-glycoprotein inhibitor INon-inhibitor0.6413
P-glycoprotein inhibitor IINon-inhibitor0.8605
Renal organic cation transporterNon-inhibitor0.9414
CYP450 2C9 substrateNon-substrate0.7545
CYP450 2D6 substrateNon-substrate0.8713
CYP450 3A4 substrateNon-substrate0.5509
CYP450 1A2 substrateNon-inhibitor0.9606
CYP450 2C9 inhibitorNon-inhibitor0.9241
CYP450 2D6 inhibitorNon-inhibitor0.9411
CYP450 2C19 inhibitorNon-inhibitor0.9247
CYP450 3A4 inhibitorNon-inhibitor0.9183
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8784
Ames testNon AMES toxic0.7959
CarcinogenicityNon-carcinogens0.9466
BiodegradationNot ready biodegradable0.8241
Rat acute toxicity1.7961 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9928
hERG inhibition (predictor II)Non-inhibitor0.8337
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. Chitobiase
Kind
Protein
Organism
Serratia marcescens
Pharmacological action
Unknown
General Function
Polysaccharide binding
Specific Function
Digests the beta-1,4-glycosidic bonds in N-acetylglucosamine (GlcNAc) oligomers (mainly dimers).
Gene Name
chb
Uniprot ID
Q54468
Uniprot Name
Chitobiase
Molecular Weight
98547.55 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. [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. Lysozyme C
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Lysozyme activity
Specific Function
Lysozymes have primarily a bacteriolytic function; those in tissues and body fluids are associated with the monocyte-macrophage system and enhance the activity of immunoagents.
Gene Name
LYZ
Uniprot ID
P61626
Uniprot Name
Lysozyme C
Molecular Weight
16536.885 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]
  3. 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]
Details3. Beta-1,4-galactosyltransferase 1
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Udp-galactosyltransferase activity
Specific Function
The Golgi complex form catalyzes the production of lactose in the lactating mammary gland and could also be responsible for the synthesis of complex-type N-linked oligosaccharides in many glycoprot...
Gene Name
B4GALT1
Uniprot ID
P15291
Uniprot Name
Beta-1,4-galactosyltransferase 1
Molecular Weight
43919.895 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]
  3. 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 June 13, 2005 13:24 / Updated at June 12, 2020 16:52