NP-MRD: Showing NP-Card for n-[(2r,3r,4s,5r)-3,4,5,6-tetrahydroxy-1-oxohexan-2-yl]ethanimidic acid (NP0227429)

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Record Information

Version

2.0

Created at

2022-09-06 06:45:09 UTC

Updated at

2022-09-06 06:45:09 UTC

NP-MRD ID

NP0227429

Secondary Accession Numbers

None

Natural Product Identification

Common Name

n-[(2r,3r,4s,5r)-3,4,5,6-tetrahydroxy-1-oxohexan-2-yl]ethanimidic acid

Description

Aldehydo-N-acetyl-D-glucosamine, also known as 2-acetamido-2-deoxy-D-glucose or D-glcnac, belongs to the class of organic compounds known as hexoses. These are monosaccharides in which the sugar unit is a is a six-carbon containing moeity. Aldehydo-N-acetyl-D-glucosamine is a drug which is used for the treatment and prevention of osteoarthritis, by itself or in combination with chondroitin sulfate. Aldehydo-N-acetyl-D-glucosamine is an extremely weak basic (essentially neutral) compound (based on its pKa). The open-chain form of N-acetyl-D-glucosamine.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 30 29  0  0  0  0  0  0  0  0999 V2000
   -2.7227    1.2255    1.6645 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0442   -0.0507    1.3246 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8787   -0.9525    2.1568 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5737   -0.2321   -0.0020 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9071   -1.4528   -0.3873 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.8413   -2.1681   -1.3371 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9012   -1.6968   -1.6270 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3622   -1.1711   -1.1150 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1242   -0.4253   -2.2853 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4517   -0.5479   -0.3038 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6595   -1.2758    0.8526 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2743    0.9161   -0.0243 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0567    1.6229   -1.2077 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5742    1.4593    0.5759 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6128    1.2558   -0.3252 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9213    1.9219    2.0164 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1945    1.6211    0.7492 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4997    1.0607    2.4391 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7014    0.5153   -0.7240 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7611   -2.1195    0.4924 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4913   -3.1154   -1.7276 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7915   -2.1558   -1.4836 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8422   -0.5298   -2.4778 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3990   -0.6816   -0.9258 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2317   -0.8006    1.6196 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4977    1.1191    0.7298 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8065    2.5598   -0.9891 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4003    2.5339    0.7735 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7307    0.9029    1.5128 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3077    0.6615    0.0355 H   0  0  0  0  0  0  0  0  0  0  0  0
  6  7  2  0
  6  5  1  0
  5  4  1  0
  4  2  1  0
  2  1  1  0
  2  3  2  0
  5  8  1  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 10 12  1  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
  6 21  1  0
  5 20  1  1
  4 19  1  0
  1 16  1  0
  1 17  1  0
  1 18  1  0
  8 22  1  6
  9 23  1  0
 10 24  1  6
 11 25  1  0
 12 26  1  1
 13 27  1  0
 14 28  1  0
 14 29  1  0
 15 30  1  0
M  END


  Mrv0541 04191212032D          

 16 15  0  0  1  0            999 V2000
   12.1995   -5.4501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4851   -5.8626    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   10.7706   -5.4501    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   10.0561   -5.8626    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    9.3417   -5.4501    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   12.1995   -4.6251    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.7706   -4.6251    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.0561   -6.6876    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.3417   -4.6251    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.9140   -5.8626    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.6271   -5.8626    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9127   -5.4501    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.4851   -6.6876    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.1995   -7.1001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9140   -6.6876    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.1995   -7.9251    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  6  1  2  0  0  0  0
  2  1  1  0  0  0  0
 10  1  1  0  0  0  0
  2 13  1  6  0  0  0
  3  2  1  0  0  0  0
  3  7  1  6  0  0  0
  4  3  1  0  0  0  0
  4  8  1  6  0  0  0
  5  4  1  0  0  0  0
  5  9  1  1  0  0  0
 11  5  1  0  0  0  0
 11 12  1  0  0  0  0
 15 14  2  0  0  0  0
 16 14  1  0  0  0  0
 13 14  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0227429

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]C(=O)[C@H](NC(C)=O)[C@@H](O)[C@H](O)[C@H](O)CO

> <INCHI_IDENTIFIER>
InChI=1S/C8H15NO6/c1-4(12)9-5(2-10)7(14)8(15)6(13)3-11/h2,5-8,11,13-15H,3H2,1H3,(H,9,12)/t5-,6+,7+,8+/m0/s1

> <INCHI_KEY>
MBLBDJOUHNCFQT-LXGUWJNJSA-N

> <FORMULA>
C8H15NO6

> <MOLECULAR_WEIGHT>
221.2078

> <EXACT_MASS>
221.089937217

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_AVERAGE_POLARIZABILITY>
20.489506839444218

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
N-[(2R,3R,4S,5R)-3,4,5,6-tetrahydroxy-1-oxohexan-2-yl]acetamide

> <ALOGPS_LOGP>
-2.10

> <JCHEM_LOGP>
-3.8563957566666667

> <ALOGPS_LOGS>
-0.18

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.800488730738557

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.564821144474056

> <JCHEM_PKA_STRONGEST_BASIC>
-1.1597845911248257

> <JCHEM_POLAR_SURFACE_AREA>
127.09

> <JCHEM_REFRACTIVITY>
48.4469

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.48e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
N acetylglucosamine

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 19-APR-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-APR-12         0                                  
HETATM    1  C   UNK     0      22.772 -10.174   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      21.439 -10.944   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      20.105 -10.174   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      18.771 -10.944   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      17.438 -10.174   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      22.772  -8.634   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0      20.105  -8.634   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0      18.771 -12.484   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0      17.438  -8.634   0.000  0.00  0.00           O+0
HETATM   10  H   UNK     0      24.106 -10.944   0.000  0.00  0.00           H+0
HETATM   11  C   UNK     0      16.104 -10.944   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      14.770 -10.174   0.000  0.00  0.00           O+0
HETATM   13  N   UNK     0      21.439 -12.484   0.000  0.00  0.00           N+0
HETATM   14  C   UNK     0      22.772 -13.254   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      24.106 -12.484   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      22.772 -14.794   0.000  0.00  0.00           C+0
CONECT    1    6    2   10                                                  
CONECT    2    1   13    3                                                  
CONECT    3    2    7    4                                                  
CONECT    4    3    8    5                                                  
CONECT    5    4    9   11                                                  
CONECT    6    1                                                            
CONECT    7    3                                                            
CONECT    8    4                                                            
CONECT    9    5                                                            
CONECT   10    1                                                            
CONECT   11    5   12                                                       
CONECT   12   11                                                            
CONECT   13    2   14                                                       
CONECT   14   15   16   13                                                  
CONECT   15   14                                                            
CONECT   16   14                                                            
MASTER        0    0    0    0    0    0    0    0   16    0   30    0
END

View in JSmol

Synonyms

Value	Source
2-Acetamido-2-deoxy-D-glucose	ChEBI
D-GlcNAc	ChEBI
N-Acetyl-D-glucosamine	ChEBI
N-Acetylchitosamine	ChEBI
N Acetyl D glucosamine	HMDB
2 Acetamido 2 deoxy D glucose	HMDB
2 Acetamido 2 deoxyglucose	HMDB
2-Acetamido-2-deoxyglucose	HMDB
Acetylglucosamine	HMDB

Chemical Formula

C₈H₁₅NO₆

Average Mass

221.2078 Da

Monoisotopic Mass

221.08994 Da

IUPAC Name

N-[(2R,3R,4S,5R)-3,4,5,6-tetrahydroxy-1-oxohexan-2-yl]acetamide

Traditional Name

N acetylglucosamine

CAS Registry Number

Not Available

SMILES

[H]C(=O)[C@H](NC(C)=O)[C@@H](O)[C@H](O)[C@H](O)CO

InChI Identifier

InChI=1S/C8H15NO6/c1-4(12)9-5(2-10)7(14)8(15)6(13)3-11/h2,5-8,11,13-15H,3H2,1H3,(H,9,12)/t5-,6+,7+,8+/m0/s1

InChI Key

MBLBDJOUHNCFQT-LXGUWJNJSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as hexoses. These are monosaccharides in which the sugar unit is a is a six-carbon containing moeity.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

Hexoses

Alternative Parents

Substituents

Hexose monosaccharide
Amino saccharide
Beta-hydroxy aldehyde
Acetamide
Carboxamide group
Secondary alcohol
Secondary carboxylic acid amide
Carboxylic acid derivative
Polyol
Aldehyde
Organonitrogen compound
Organic oxide
Alcohol
Organopnictogen compound
Carbonyl group
Organic nitrogen compound
Primary alcohol
Hydrocarbon derivative
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

N-acetylglucosamine (CHEBI:17411 )

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	-2.1	ALOGPS
logP	-3.9	ChemAxon
logS	-0.18	ALOGPS
pKa (Strongest Acidic)	11.56	ChemAxon
pKa (Strongest Basic)	-1.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	127.09 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	48.45 m³·mol⁻¹	ChemAxon
Polarizability	20.49 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0062641

DrugBank ID

DB00141

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

1738118

PDB ID

Not Available

ChEBI ID

17411

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for n-[(2r,3r,4s,5r)-3,4,5,6-tetrahydroxy-1-oxohexan-2-yl]ethanimidic acid (NP0227429)

MOL for NP0227429 (n-[(2r,3r,4s,5r)-3,4,5,6-tetrahydroxy-1-oxohexan-2-yl]ethanimidic acid)

3D MOL for NP0227429 (n-[(2r,3r,4s,5r)-3,4,5,6-tetrahydroxy-1-oxohexan-2-yl]ethanimidic acid)

3D SDF for NP0227429 (n-[(2r,3r,4s,5r)-3,4,5,6-tetrahydroxy-1-oxohexan-2-yl]ethanimidic acid)

3D-SDF for NP0227429 (n-[(2r,3r,4s,5r)-3,4,5,6-tetrahydroxy-1-oxohexan-2-yl]ethanimidic acid)

PDB for NP0227429 (n-[(2r,3r,4s,5r)-3,4,5,6-tetrahydroxy-1-oxohexan-2-yl]ethanimidic acid)

3D PDB for NP0227429 (n-[(2r,3r,4s,5r)-3,4,5,6-tetrahydroxy-1-oxohexan-2-yl]ethanimidic acid)

SMILES for NP0227429 (n-[(2r,3r,4s,5r)-3,4,5,6-tetrahydroxy-1-oxohexan-2-yl]ethanimidic acid)

INCHI for NP0227429 (n-[(2r,3r,4s,5r)-3,4,5,6-tetrahydroxy-1-oxohexan-2-yl]ethanimidic acid)

Structure for NP0227429 (n-[(2r,3r,4s,5r)-3,4,5,6-tetrahydroxy-1-oxohexan-2-yl]ethanimidic acid)

3D Structure for NP0227429 (n-[(2r,3r,4s,5r)-3,4,5,6-tetrahydroxy-1-oxohexan-2-yl]ethanimidic acid)