NP-MRD: Showing NP-Card for Methyl N-acetyl-alpha-D-glucosaminide (NP0002649)

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Record Information

Version

2.0

Created at

2020-11-23 18:26:03 UTC

Updated at

2021-08-12 19:51:45 UTC

NP-MRD ID

NP0002649

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Methyl N-acetyl-alpha-D-glucosaminide

Provided By

BMRB

Description

N-[(2S,3R,4R,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-2-methoxyoxan-3-yl]ethanimidic acid 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. Based on a literature review very few articles have been published on N-[(2S,3R,4R,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-2-methoxyoxan-3-yl]ethanimidic acid.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI


     RDKit          2D

 33 33  0  0  0  0  0  0  0  0999 V2000
   -0.5804   -3.3627    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6494   -2.5038    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5205   -1.0094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9289   -1.3958    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9882   -0.3339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3469    0.3017    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7056    0.9373    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5982    1.1146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7271    2.6090    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1489    1.5010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0809    2.3599    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9105    0.4390    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2692   -0.1965    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.4990    0.6623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8576    0.0267    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3701    2.1568    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2785   -4.5925    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7113   -2.3773    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8102   -4.2215    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9873   -1.3231    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8501   -1.5615    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0997    1.0596    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9825   -1.0570    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9354    0.0785    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3778    1.2813    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0858    3.2446    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7811    2.8612    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9520    3.8543    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7724    1.6667    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5793   -1.6641    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4932    1.3854    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2220   -1.3320    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2163   -0.6089    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  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
 13 14  1  0
 14 15  1  0
 14 16  2  0
 12  3  1  0
  1 17  1  1
  1 18  1  0
  1 19  1  0
  3 20  1  6
  5 21  1  1
  6 22  1  6
  6 23  1  0
  7 24  1  0
  8 25  1  6
  9 26  1  0
 10 27  1  1
 11 28  1  0
 12 29  1  6
 13 30  1  0
 15 31  1  1
 15 32  1  0
 15 33  1  0
M  END

NP0002649
     RDKit          3D

 33 33  0  0  0  0  0  0  0  0999 V2000
    0.4202    2.8219   -0.1275 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1859    1.5867   -0.3415 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3324    0.5932    0.4812 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7566    0.1226    1.2499 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8840   -0.0683    0.4369 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.0398   -0.3522    1.3674 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1629    0.7755    2.1979 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5685   -1.2458   -0.4612 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.6418   -1.6994   -1.1778 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4351   -0.7608   -1.3732 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1463   -1.6536   -2.3701 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7405   -0.5560   -0.4109 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9650   -0.3402   -1.1075 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1096   -0.3537   -0.5342 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2447   -0.5981    0.9143 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2603   -0.1295   -1.3115 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5127    2.7862   -0.3208 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0197    3.5262   -0.8624 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1806    3.1570    0.8831 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1142    0.9505    1.1430 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0691    0.8612   -0.1340 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8026   -1.2320    1.9867 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0032   -0.4536    0.8474 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9006    1.3739    1.8949 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1135   -2.0331    0.2051 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5131   -1.6018   -0.7652 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7358    0.2446   -1.7357 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5441   -1.3861   -3.2148 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7606   -1.4867    0.2069 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1410   -1.2566    1.0860 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3887   -1.1002    1.3660 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4294    0.3820    1.4098 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9228   -0.8739   -1.4283 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  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
 13 14  2  3
 14 15  1  0
 14 16  1  0
 12  3  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  3 20  1  1
  5 21  1  6
  6 22  1  0
  6 23  1  0
  7 24  1  0
  8 25  1  1
  9 26  1  0
 10 27  1  6
 11 28  1  0
 12 29  1  1
 15 30  1  0
 15 31  1  0
 15 32  1  0
 16 33  1  0
M  END


     RDKit          2D

 33 33  0  0  0  0  0  0  0  0999 V2000
   -0.5804   -3.3627    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6494   -2.5038    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5205   -1.0094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9289   -1.3958    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9882   -0.3339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3469    0.3017    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7056    0.9373    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5982    1.1146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7271    2.6090    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1489    1.5010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0809    2.3599    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9105    0.4390    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2692   -0.1965    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.4990    0.6623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8576    0.0267    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3701    2.1568    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2785   -4.5925    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7113   -2.3773    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8102   -4.2215    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9873   -1.3231    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8501   -1.5615    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0997    1.0596    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9825   -1.0570    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9354    0.0785    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3778    1.2813    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0858    3.2446    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7811    2.8612    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9520    3.8543    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7724    1.6667    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5793   -1.6641    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4932    1.3854    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2220   -1.3320    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2163   -0.6089    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  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
 13 14  1  0
 14 15  1  0
 14 16  2  0
 12  3  1  0
  1 17  1  1
  1 18  1  0
  1 19  1  0
  3 20  1  6
  5 21  1  1
  6 22  1  6
  6 23  1  0
  7 24  1  0
  8 25  1  6
  9 26  1  0
 10 27  1  1
 11 28  1  0
 12 29  1  6
 13 30  1  0
 15 31  1  1
 15 32  1  0
 15 33  1  0
M  END
> <DATABASE_ID>
NP0002649

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@]1(CO)O[C@]([H])(OC)[C@]([H])(N=C(C)O)[C@@]([H])(O)[C@]1([H])O

> <INCHI_IDENTIFIER>
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

> <INCHI_KEY>
ZEVOCXOZYFLVKN-OKNNCHMLSA-N

> <FORMULA>
C9H17NO6

> <MOLECULAR_WEIGHT>
235.2344

> <EXACT_MASS>
235.105587281

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_AVERAGE_POLARIZABILITY>
22.50338789573907

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
N-[(2S,3R,4R,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-2-methoxyoxan-3-yl]ethanimidic acid

> <ALOGPS_LOGP>
-1.73

> <JCHEM_LOGP>
-1.7578437810000003

> <ALOGPS_LOGS>
-0.71

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
12.902601461323563

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.459207258920225

> <JCHEM_PKA_STRONGEST_BASIC>
1.5482046709746549

> <JCHEM_POLAR_SURFACE_AREA>
111.74000000000002

> <JCHEM_REFRACTIVITY>
52.29760000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.63e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
N-[(2S,3R,4R,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-2-methoxyoxan-3-yl]ethanimidic acid

> <JCHEM_VEBER_RULE>
0

$$$$

NP0002649
     RDKit          3D

 33 33  0  0  0  0  0  0  0  0999 V2000
    0.4202    2.8219   -0.1275 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1859    1.5867   -0.3415 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3324    0.5932    0.4812 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7566    0.1226    1.2499 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8840   -0.0683    0.4369 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.0398   -0.3522    1.3674 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1629    0.7755    2.1979 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5685   -1.2458   -0.4612 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.6418   -1.6994   -1.1778 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4351   -0.7608   -1.3732 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1463   -1.6536   -2.3701 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7405   -0.5560   -0.4109 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9650   -0.3402   -1.1075 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1096   -0.3537   -0.5342 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2447   -0.5981    0.9143 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2603   -0.1295   -1.3115 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5127    2.7862   -0.3208 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0197    3.5262   -0.8624 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1806    3.1570    0.8831 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1142    0.9505    1.1430 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0691    0.8612   -0.1340 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8026   -1.2320    1.9867 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0032   -0.4536    0.8474 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9006    1.3739    1.8949 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1135   -2.0331    0.2051 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5131   -1.6018   -0.7652 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7358    0.2446   -1.7357 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5441   -1.3861   -3.2148 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7606   -1.4867    0.2069 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1410   -1.2566    1.0860 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3887   -1.1002    1.3660 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4294    0.3820    1.4098 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9228   -0.8739   -1.4283 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  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
 13 14  2  3
 14 15  1  0
 14 16  1  0
 12  3  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  3 20  1  1
  5 21  1  6
  6 22  1  0
  6 23  1  0
  7 24  1  0
  8 25  1  1
  9 26  1  0
 10 27  1  6
 11 28  1  0
 12 29  1  1
 15 30  1  0
 15 31  1  0
 15 32  1  0
 16 33  1  0
M  END

HEADER    PROTEIN                                 03-MAY-14   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-MAY-14         0                                  
HETATM    1  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   10  N   UNK     0       0.000   0.000   0.000  0.00  0.00           N+0
HETATM   11  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   17  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
HETATM   18  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
HETATM   19  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
HETATM   20  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
HETATM   21  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
CONECT    1    4                                                            
CONECT    2   15                                                            
CONECT    3    5   11                                                       
CONECT    4    1   10   12                                                  
CONECT    5    3    7   16   17                                             
CONECT    6    8    9   10   18                                             
CONECT    7    5    8   13   19                                             
CONECT    8    6    7   14   20                                             
CONECT    9    6   15   16   21                                             
CONECT   10    4    6                                                       
CONECT   11    3                                                            
CONECT   12    4                                                            
CONECT   13    7                                                            
CONECT   14    8                                                            
CONECT   15    2    9                                                       
CONECT   16    5    9                                                       
CONECT   17    5                                                            
CONECT   18    6                                                            
CONECT   19    7                                                            
CONECT   20    8                                                            
CONECT   21    9                                                            
MASTER        0    0    0    0    0    0    0    0   21    0   42    0
END

COMPND    NP0002649
HETATM    1  C1  UNL     1       0.420   2.822  -0.128  1.00  0.00           C  
HETATM    2  O1  UNL     1      -0.186   1.587  -0.341  1.00  0.00           O  
HETATM    3  C2  UNL     1       0.332   0.593   0.481  1.00  0.00           C  
HETATM    4  O2  UNL     1      -0.757   0.123   1.250  1.00  0.00           O  
HETATM    5  C3  UNL     1      -1.884  -0.068   0.437  1.00  0.00           C  
HETATM    6  C4  UNL     1      -3.040  -0.352   1.367  1.00  0.00           C  
HETATM    7  O3  UNL     1      -3.163   0.776   2.198  1.00  0.00           O  
HETATM    8  C5  UNL     1      -1.569  -1.246  -0.461  1.00  0.00           C  
HETATM    9  O4  UNL     1      -2.642  -1.699  -1.178  1.00  0.00           O  
HETATM   10  C6  UNL     1      -0.435  -0.761  -1.373  1.00  0.00           C  
HETATM   11  O5  UNL     1      -0.146  -1.654  -2.370  1.00  0.00           O  
HETATM   12  C7  UNL     1       0.741  -0.556  -0.411  1.00  0.00           C  
HETATM   13  N1  UNL     1       1.965  -0.340  -1.108  1.00  0.00           N  
HETATM   14  C8  UNL     1       3.110  -0.354  -0.534  1.00  0.00           C  
HETATM   15  C9  UNL     1       3.245  -0.598   0.914  1.00  0.00           C  
HETATM   16  O6  UNL     1       4.260  -0.129  -1.311  1.00  0.00           O  
HETATM   17  H1  UNL     1       1.513   2.786  -0.321  1.00  0.00           H  
HETATM   18  H2  UNL     1      -0.020   3.526  -0.862  1.00  0.00           H  
HETATM   19  H3  UNL     1       0.181   3.157   0.883  1.00  0.00           H  
HETATM   20  H4  UNL     1       1.114   0.950   1.143  1.00  0.00           H  
HETATM   21  H5  UNL     1      -2.069   0.861  -0.134  1.00  0.00           H  
HETATM   22  H6  UNL     1      -2.803  -1.232   1.987  1.00  0.00           H  
HETATM   23  H7  UNL     1      -4.003  -0.454   0.847  1.00  0.00           H  
HETATM   24  H8  UNL     1      -3.901   1.374   1.895  1.00  0.00           H  
HETATM   25  H9  UNL     1      -1.113  -2.033   0.205  1.00  0.00           H  
HETATM   26  H10 UNL     1      -3.513  -1.602  -0.765  1.00  0.00           H  
HETATM   27  H11 UNL     1      -0.736   0.245  -1.736  1.00  0.00           H  
HETATM   28  H12 UNL     1      -0.544  -1.386  -3.215  1.00  0.00           H  
HETATM   29  H13 UNL     1       0.761  -1.487   0.207  1.00  0.00           H  
HETATM   30  H14 UNL     1       4.141  -1.257   1.086  1.00  0.00           H  
HETATM   31  H15 UNL     1       2.389  -1.100   1.366  1.00  0.00           H  
HETATM   32  H16 UNL     1       3.429   0.382   1.410  1.00  0.00           H  
HETATM   33  H17 UNL     1       4.923  -0.874  -1.428  1.00  0.00           H  
CONECT    1    2   17   18   19
CONECT    2    3
CONECT    3    4   12   20
CONECT    4    5
CONECT    5    6    8   21
CONECT    6    7   22   23
CONECT    7   24
CONECT    8    9   10   25
CONECT    9   26
CONECT   10   11   12   27
CONECT   11   28
CONECT   12   13   29
CONECT   13   14   14
CONECT   14   15   16
CONECT   15   30   31   32
CONECT   16   33
END

NP0002649
     RDKit          3D

33 33  0  0  0  0  0  0  0  0999 V2000
    0.4202    2.8219   -0.1275 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1859    1.5867   -0.3415 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3324    0.5932    0.4812 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7566    0.1226    1.2499 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8840   -0.0683    0.4369 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.0398   -0.3522    1.3674 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1629    0.7755    2.1979 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5685   -1.2458   -0.4612 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.6418   -1.6994   -1.1778 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4351   -0.7608   -1.3732 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1463   -1.6536   -2.3701 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7405   -0.5560   -0.4109 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9650   -0.3402   -1.1075 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1096   -0.3537   -0.5342 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2447   -0.5981    0.9143 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2603   -0.1295   -1.3115 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5127    2.7862   -0.3208 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0197    3.5262   -0.8624 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1806    3.1570    0.8831 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1142    0.9505    1.1430 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0691    0.8612   -0.1340 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8026   -1.2320    1.9867 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0032   -0.4536    0.8474 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9006    1.3739    1.8949 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1135   -2.0331    0.2051 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5131   -1.6018   -0.7652 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7358    0.2446   -1.7357 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5441   -1.3861   -3.2148 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7606   -1.4867    0.2069 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1410   -1.2566    1.0860 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3887   -1.1002    1.3660 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4294    0.3820    1.4098 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9228   -0.8739   -1.4283 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  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
 13 14  2  3
 14 15  1  0
 14 16  1  0
 12  3  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  3 20  1  1
  5 21  1  6
  6 22  1  0
  6 23  1  0
  7 24  1  0
  8 25  1  1
  9 26  1  0
 10 27  1  6
 11 28  1  0
 12 29  1  1
 15 30  1  0
 15 31  1  0
 15 32  1  0
 16 33  1  0
M  END

View in JSmol

Synonyms

Value	Source
N-[(2S,3R,4R,5S,6R)-4,5-Dihydroxy-6-(hydroxymethyl)-2-methoxyoxan-3-yl]ethanimidate	Generator
Methyl-2-acetamido-2-deoxy-D-glucopyranoside, (beta-D)-isomer	MeSH
Methyl-N-acetylglucosamine	MeSH
Methyl-2-acetamido-2-deoxy-D-glucopyranoside	MeSH
Methyl 2-acetamido-2-deoxy-a-D-glucopyranoside	Generator
Methyl 2-acetamido-2-deoxy-α-D-glucopyranoside	Generator

Chemical Formula

C₉H₁₇NO₆

Average Mass

235.2344 Da

Monoisotopic Mass

235.10559 Da

IUPAC Name

N-[(2S,3R,4R,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-2-methoxyoxan-3-yl]ethanimidic acid

Traditional Name

N-[(2S,3R,4R,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-2-methoxyoxan-3-yl]ethanimidic acid

CAS Registry Number

Not Available

SMILES

[H][C@]1(CO)O[C@]([H])(OC)[C@]([H])(N=C(C)O)[C@@]([H])(O)[C@]1([H])O

InChI Identifier

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

InChI Key

ZEVOCXOZYFLVKN-OKNNCHMLSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, experimental)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

Chemical Taxonomy

Description

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

Substituents

N-acyl-alpha-hexosamine
O-glycosyl compound
Glycosyl compound
Oxane
Monosaccharide
Acetamide
Secondary carboxylic acid amide
Secondary alcohol
Carboxamide group
Oxacycle
Organoheterocyclic compound
Carboxylic acid derivative
Acetal
Organic nitrogen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Primary alcohol
Organonitrogen compound
Carbonyl group
Alcohol
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

N-acyl-hexosamine (CHEBI:86902 )

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	-1.7	ALOGPS
logP	-1.8	ChemAxon
logS	-0.71	ALOGPS
pKa (Strongest Acidic)	7.46	ChemAxon
pKa (Strongest Basic)	1.55	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	111.74 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	52.3 m³·mol⁻¹	ChemAxon
Polarizability	22.5 Å³	ChemAxon
Number of Rings	1	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

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

87139

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for Methyl N-acetyl-alpha-D-glucosaminide (NP0002649)

MOL for NP0002649 (Methyl N-acetyl-alpha-D-glucosaminide)

3D MOL for NP0002649 (Methyl N-acetyl-alpha-D-glucosaminide)

3D SDF for NP0002649 (Methyl N-acetyl-alpha-D-glucosaminide)

3D-SDF for NP0002649 (Methyl N-acetyl-alpha-D-glucosaminide)

PDB for NP0002649 (Methyl N-acetyl-alpha-D-glucosaminide)

3D PDB for NP0002649 (Methyl N-acetyl-alpha-D-glucosaminide)

SMILES for NP0002649 (Methyl N-acetyl-alpha-D-glucosaminide)

INCHI for NP0002649 (Methyl N-acetyl-alpha-D-glucosaminide)

Structure for NP0002649 (Methyl N-acetyl-alpha-D-glucosaminide)

3D Structure for NP0002649 (Methyl N-acetyl-alpha-D-glucosaminide)