Alpha-Methyl-N-Acetyl-D-Glucosamine
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Identification
- Generic Name
- Alpha-Methyl-N-Acetyl-D-Glucosamine
- DrugBank Accession Number
- DB04426
- Background
Not Available
- Type
- Small Molecule
- Groups
- Experimental
- Structure
- Weight
- Average: 235.2344
Monoisotopic: 235.105587281 - Chemical Formula
- C9H17NO6
- Synonyms
- Not Available
Pharmacology
- Indication
Not Available
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- Pharmacodynamics
Not Available
- Mechanism of action
Target Actions Organism AE-selectin inhibitorHumans AP-selectin inhibitorHumans UMannose-binding protein C Not Available Humans - 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 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
- O-glycosyl compounds / Oxanes / Monosaccharides / Acetamides / Secondary carboxylic acid amides / Secondary alcohols / Oxacyclic compounds / Acetals / Primary alcohols / Organopnictogen compounds show 4 more
- Substituents
- Acetal / Acetamide / Alcohol / Aliphatic heteromonocyclic compound / Carbonyl group / Carboxamide group / Carboxylic acid derivative / Glycosyl compound / Hydrocarbon derivative / Monosaccharide show 12 more
- Molecular Framework
- Aliphatic heteromonocyclic compounds
- External Descriptors
- Not Available
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- Not Available
- CAS number
- Not Available
- InChI Key
- ZEVOCXOZYFLVKN-JGKVKWKGSA-N
- InChI
- InChI=1S/C9H17NO6/c1-4(12)10-6-8(14)7(13)5(3-11)16-9(6)15-2/h5-9,11,13-14H,3H2,1-2H3,(H,10,12)/t5-,6-,7-,8-,9-/m1/s1
- IUPAC Name
- N-[(2R,3R,4R,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-2-methoxyoxan-3-yl]acetamide
- SMILES
- [H][C@]1(CO)O[C@@]([H])(OC)[C@]([H])(NC(C)=O)[C@@]([H])(O)[C@]1([H])O
References
- General References
- Not Available
- External Links
- PubChem Compound
- 445750
- PubChem Substance
- 46508169
- ChemSpider
- 393301
- ZINC
- ZINC000005234411
- PDBe Ligand
- MAG
- PDB Entries
- 1fwu / 1fwv / 1g1r / 1g1t / 1gsl / 1led / 1m7d / 1uz8 / 1zpl / 2kmb … show 11 more
Clinical Trials
- 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
Property Value Source Water Solubility 237.0 mg/mL ALOGPS logP -1.8 ALOGPS logP -2.6 Chemaxon logS 0 ALOGPS pKa (Strongest Acidic) 12.27 Chemaxon pKa (Strongest Basic) -1.6 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 6 Chemaxon Hydrogen Donor Count 4 Chemaxon Polar Surface Area 108.25 Å2 Chemaxon Rotatable Bond Count 3 Chemaxon Refractivity 51.78 m3·mol-1 Chemaxon Polarizability 22.48 Å3 Chemaxon Number of Rings 1 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption - 0.9132 Blood Brain Barrier - 0.9484 Caco-2 permeable - 0.7741 P-glycoprotein substrate Non-substrate 0.7054 P-glycoprotein inhibitor I Non-inhibitor 0.829 P-glycoprotein inhibitor II Non-inhibitor 0.8632 Renal organic cation transporter Non-inhibitor 0.947 CYP450 2C9 substrate Non-substrate 0.7715 CYP450 2D6 substrate Non-substrate 0.8486 CYP450 3A4 substrate Non-substrate 0.5 CYP450 1A2 substrate Non-inhibitor 0.9428 CYP450 2C9 inhibitor Non-inhibitor 0.9477 CYP450 2D6 inhibitor Non-inhibitor 0.9429 CYP450 2C19 inhibitor Non-inhibitor 0.9451 CYP450 3A4 inhibitor Non-inhibitor 0.9761 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9317 Ames test Non AMES toxic 0.671 Carcinogenicity Non-carcinogens 0.9768 Biodegradation Ready biodegradable 0.8067 Rat acute toxicity 1.7923 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9926 hERG inhibition (predictor II) Non-inhibitor 0.9423
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS splash10-0v4i-6940000000-a9969711f6e636e296a0 Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-000i-0090000000-7fa233edd22133907390 Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-001l-0590000000-29a03d2099d030d99c12 Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-0fl9-4940000000-04f3523d7be6f675bb06 Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-000x-5950000000-0417d19c1f9f0d3e750c Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-00di-9400000000-45c1d11483f2ec74e97d Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-0a4l-9300000000-a65b468145ca56d8d56f Predicted 1H NMR Spectrum 1D NMR Not Applicable Predicted 13C NMR Spectrum 1D NMR Not Applicable - Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 152.06067 predictedDeepCCS 1.0 (2019) [M+H]+ 154.45622 predictedDeepCCS 1.0 (2019) [M+Na]+ 161.98601 predictedDeepCCS 1.0 (2019)
Targets
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1. DetailsE-selectin
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Cell-surface glycoprotein having a role in immunoadhesion. Mediates in the adhesion of blood neutrophils in cytokine-activated endothelium through interaction with SELPLG/PSGL1. May have a role in capillary morphogenesis
- Specific Function
- metal ion binding
- Gene Name
- SELE
- Uniprot ID
- P16581
- Uniprot Name
- E-selectin
- Molecular Weight
- 66654.575 Da
References
- Zhou Y, Zhang Y, Zhao D, Yu X, Shen X, Zhou Y, Wang S, Qiu Y, Chen Y, Zhu F: TTD: Therapeutic Target Database describing target druggability information. Nucleic Acids Res. 2024 Jan 5;52(D1):D1465-D1477. doi: 10.1093/nar/gkad751. [Article]
2. DetailsP-selectin
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Ca(2+)-dependent receptor for myeloid cells that binds to carbohydrates on neutrophils and monocytes. Mediates the interaction of activated endothelial cells or platelets with leukocytes. The ligand recognized is sialyl-Lewis X. Mediates rapid rolling of leukocyte rolling over vascular surfaces during the initial steps in inflammation through interaction with SELPLG. Mediates cell-cell interactions and cell adhesion via the interaction with integrin alpha-IIb/beta3 (ITGA2B:ITGB3) and integrin alpha-V/beta-3 (ITGAV:ITGB3) (PubMed:37184585)
- Specific Function
- calcium ion binding
- Gene Name
- SELP
- Uniprot ID
- P16109
- Uniprot Name
- P-selectin
- Molecular Weight
- 90819.085 Da
References
- Zhou Y, Zhang Y, Zhao D, Yu X, Shen X, Zhou Y, Wang S, Qiu Y, Chen Y, Zhu F: TTD: Therapeutic Target Database describing target druggability information. Nucleic Acids Res. 2024 Jan 5;52(D1):D1465-D1477. doi: 10.1093/nar/gkad751. [Article]
3. DetailsMannose-binding protein C
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Calcium-dependent lectin involved in innate immune defense (PubMed:35102342). Binds mannose, fucose and N-acetylglucosamine on different microorganisms and activates the lectin complement pathway. Binds to late apoptotic cells, as well as to apoptotic blebs and to necrotic cells, but not to early apoptotic cells, facilitating their uptake by macrophages. May bind DNA. Upon SARS coronavirus-2/SARS-CoV-2 infection, activates the complement lectin pathway which leads to the inhibition SARS-CoV-2 infection and a reduction of the induced inflammatory response (PubMed:35102342)
- Specific Function
- calcium-dependent protein binding
- Gene Name
- MBL2
- Uniprot ID
- P11226
- Uniprot Name
- Mannose-binding protein C
- Molecular Weight
- 26143.345 Da
References
- Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
- 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]
- 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 August 26, 2024 19:22