(2S,5R)-3-Amino-6-hydroxymethyl-tetrahydro-pyran-2,4,5-triol

ID: ALA493287

Cas Number: 3416-24-8

PubChem CID: 439213

Product Number: G413437, Order Now?

Max Phase: Approved

Molecular Formula: C6H13NO5

Molecular Weight: 179.17

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Chitosamine | Glucosamine | Mediflex | 2-Amino-2-Deoxy-D-Glucopyranose|2-Amino-2-Deoxy-D-Glucopyranoside|2-Amino-2-Deoxy-D-Glucose|2-Amino-2-Deoxy-Glucopyranose|2-Amino-2-Deoxy-Glucopyranoside|2-Amino-2-Deoxy-Glucose|2-Deoxy-2-Amino-D-Glucopyranose|2-Deoxy-2-Amino-D-Glucopyranoside|2-Deoxy-2-Amino-D-Glucose|2-Deoxy-2-Amino-Glucopyranose|2-Deoxy-2-Amino-Glucopyranoside|2-Deoxy-2-Amino-Glucose|D-GlcN|D-Glucosamine|GlcN|Glucosamine|chitosamine|Glucosamine free base|CHEBI:47977|(3R,4R,5S,6R)-3-aminoShow More⌵

Synonyms from Alternative Forms(33): Glucosamine hydrochloride | Chitosamine hydrochloride | Cosamin | D-glucosamine hydrochloride | Glucosamine (as hydrochloride) | Glucosamine hcl | NSC-234443 | NSC-758 | Alateris | Ardern | Bio-health | Br pharm | Cozachew fizz | Cozachew fizz combi | Cozachew meltdown 1500 | Cozachew meltdown combi | Flexi-melt | Fosachew | Fosaveg | Glucosamine hcl meltdown | Gosachew | Gosaveg | Joint-flex daily | Pro coxam | Glucosamine sulfate potassium chloride | Glucosamine sulfate sodium chloride | Glucosamine sulf | Glucosamine sulfate salt | Faximin | Glucosamine sulfate | Tiocondramina | Dolenio | Glusartel

Canonical SMILES:  N[C@H]1C(O)O[C@H](CO)[C@@H](O)[C@@H]1O

Standard InChI:  InChI=1S/C6H13NO5/c7-3-5(10)4(9)2(1-8)12-6(3)11/h2-6,8-11H,1,7H2/t2-,3-,4-,5-,6?/m1/s1

Standard InChI Key:  MSWZFWKMSRAUBD-IVMDWMLBSA-N

Molfile:  

     RDKit          2D

 12 12  0  0  0  0  0  0  0  0999 V2000
    0.8949   -0.5095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6094   -0.9220    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1804   -0.9220    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1804   -1.7470    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5340   -0.5095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2485   -0.9220    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5340    0.3155    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2485    0.7280    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1804    0.7280    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8949    0.3155    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1804    1.5530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5340    1.9655    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  1  3  1  0
  1 10  1  0
  3  4  1  6
  3  5  1  0
  5  6  1  1
  5  7  1  0
  7  8  1  6
  7  9  1  0
  9 10  1  0
  9 11  1  1
 11 12  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA493287

   Glucosamine

2. Alternative Forms:

   

   ALA493287

   (3R,4R,5S,6R)-3-amino-6-(hydroxymethyl)tetrahydro-2H-pyran-2,4,5-triol hydrochloride
3. 

   ALA493287

   GLUCOSAMINE SULFATE POTASSIUM CHLORIDE
4. 

   ALA493287

   GLUCOSAMINE SULFATE SODIUM CHLORIDE
5. 

   ALA493287

   GLUCOSAMINE SULFATE

Molecule Features

Natural Product: Yes

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: Yes

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 179.17

Molecular Weight (Monoisotopic): 179.0794

AlogP: -3.25

#Rotatable Bonds: 1

Polar Surface Area: 116.17

Molecular Species: NEUTRAL

HBA: 6

HBD: 5

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 11.73

CX Basic pKa: 8.23

CX LogP: -3.04

CX LogD: -3.93

Aromatic Rings: ┄

Heavy Atoms: 12

QED Weighted: 0.29

Np Likeness Score: 2.14

References

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11. Lowe R, Glen RC, Mitchell JB..  (2010)  Predicting phospholipidosis using machine learning.,  7  (5): [PMID:20799726] [10.1021/mp100103e]

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13. Greene N, Fisk L, Naven RT, Note RR, Patel ML, Pelletier DJ..  (2010)  Developing structure-activity relationships for the prediction of hepatotoxicity.,  23  (7): [PMID:20553011] [10.1021/tx1000865]

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Source

Source(6):

• Scientific Literature
• Clinical Candidates
• USP Dictionary of USAN and International Drug Names
• Patent Bioactivity Data
• WHO Anatomical Therapeutic Chemical Classification
• SARS-CoV-2 Screening Data 2020-21