MiMeDB: Showing metabocard for N,N-diacetyllegionaminate (MMDBc0056157)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2022-06-17 20:18:21 UTC

Update Date

2022-08-12 20:09:36 UTC

Metabolite ID

MMDBc0056157

Metabolite Identification

Common Name

N,N-diacetyllegionaminate

Description

N,N-diacetyllegionaminate belongs to the class of organic compounds known as c-glucuronides. These are glucuronides in which the aglycone is linked to the carbohydrate unit through a C-glycosidic bond. Based on a literature review very few articles have been published on N,N-diacetyllegionaminate.

Structure

MOL SDF PDB SMILES InChI

  Mrv1652306172222182D          

 28 28  0  0  1  0            999 V2000
   -0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2414    0.1433    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4289    0.0000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -1.2375    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7717   -0.4887    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5236    0.9185    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7111   -0.7752    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000   -0.8250    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.6500    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -0.8250    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    0.4125    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    0.4125    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  5  1  1  0  0  0  0
  6  2  1  4  0  0  0
  7  3  1  4  0  0  0
  8  4  1  0  0  0  0
  9  5  1  0  0  0  0
 10  8  1  0  0  0  0
 11  9  1  1  0  0  0
 11 10  1  0  0  0  0
 13  4  1  0  0  0  0
 13 12  1  1  0  0  0
 14  6  2  0  0  0  0
  9 14  1  1  0  0  0
 15  7  2  0  0  0  0
 10 15  1  1  0  0  0
  5 16  1  6  0  0  0
 17  6  1  0  0  0  0
 18  7  1  0  0  0  0
  8 19  1  1  0  0  0
 20 12  2  0  0  0  0
 21 12  1  0  0  0  0
 13 22  1  6  0  0  0
 23 11  1  0  0  0  0
 23 13  1  0  0  0  0
  5 24  1  6  0  0  0
  8 25  1  6  0  0  0
  9 26  1  6  0  0  0
 10 27  1  1  0  0  0
 11 28  1  6  0  0  0
M  CHG  1  17  -1
M  END

  Mrv1652306172222182D          

 28 28  0  0  1  0            999 V2000
   -0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2414    0.1433    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4289    0.0000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -1.2375    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7717   -0.4887    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5236    0.9185    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7111   -0.7752    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000   -0.8250    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.6500    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -0.8250    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    0.4125    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    0.4125    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  5  1  1  0  0  0  0
  6  2  1  4  0  0  0
  7  3  1  4  0  0  0
  8  4  1  0  0  0  0
  9  5  1  0  0  0  0
 10  8  1  0  0  0  0
 11  9  1  1  0  0  0
 11 10  1  0  0  0  0
 13  4  1  0  0  0  0
 13 12  1  1  0  0  0
 14  6  2  0  0  0  0
  9 14  1  1  0  0  0
 15  7  2  0  0  0  0
 10 15  1  1  0  0  0
  5 16  1  6  0  0  0
 17  6  1  0  0  0  0
 18  7  1  0  0  0  0
  8 19  1  1  0  0  0
 20 12  2  0  0  0  0
 21 12  1  0  0  0  0
 13 22  1  6  0  0  0
 23 11  1  0  0  0  0
 23 13  1  0  0  0  0
  5 24  1  6  0  0  0
  8 25  1  6  0  0  0
  9 26  1  6  0  0  0
 10 27  1  1  0  0  0
 11 28  1  6  0  0  0
M  CHG  1  17  -1
M  END
> <DATABASE_ID>
MMDBc0056157

> <DATABASE_NAME>
MIME

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

> <INCHI_IDENTIFIER>
InChI=1S/C13H22N2O8/c1-5(16)9(14-6(2)17)11-10(15-7(3)18)8(19)4-13(22,23-11)12(20)21/h5,8-11,16,19,22H,4H2,1-3H3,(H,14,17)(H,15,18)(H,20,21)/p-1/t5-,8+,9-,10-,11+,13+/m1/s1

> <INCHI_KEY>
ZJOSXOOPEBJBMC-DAJNMGJPSA-M

> <FORMULA>
C13H21N2O8

> <MOLECULAR_WEIGHT>
333.318

> <EXACT_MASS>
333.130339224

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
44

> <JCHEM_AVERAGE_POLARIZABILITY>
31.377341192821635

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
-1

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
N-[(1R,2R)-1-[(2S,3R,4S,6S)-6-carboxy-4,6-dihydroxy-3-[(1-hydroxyethylidene)amino]oxan-2-yl]-2-hydroxypropyl]ethanecarboximidate

> <JCHEM_LOGP>
-1.5692528171211038

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
5.486717707391844

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.208846575428846

> <JCHEM_PKA_STRONGEST_BASIC>
2.523396399848139

> <JCHEM_POLAR_SURFACE_AREA>
175.23

> <JCHEM_REFRACTIVITY>
84.93270000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
N-[(1R,2R)-1-[(2S,3R,4S,6S)-6-carboxy-4,6-dihydroxy-3-[(1-hydroxyethylidene)amino]oxan-2-yl]-2-hydroxypropyl]ethanecarboximidate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 17-JUN-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-JUN-22         0                                  
HETATM    1  C   UNK     0      -0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -5.335   0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.667   4.620   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.334   3.850   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.184   0.267   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM   14  N   UNK     0      -2.667   0.000   0.000  0.00  0.00           N+0
HETATM   15  N   UNK     0      -1.334   2.310   0.000  0.00  0.00           N+0
HETATM   16  O   UNK     0      -2.667  -3.080   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0      -4.001  -2.310   0.000  0.00  0.00           O-1
HETATM   18  O   UNK     0       0.000   4.620   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       1.334   3.850   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       5.174  -0.912   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       4.711   1.715   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       3.194  -1.447   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       1.334  -0.770   0.000  0.00  0.00           O+0
HETATM   24  H   UNK     0      -0.000  -1.540   0.000  0.00  0.00           H+0
HETATM   25  H   UNK     0       0.000   3.080   0.000  0.00  0.00           H+0
HETATM   26  H   UNK     0      -2.667  -1.540   0.000  0.00  0.00           H+0
HETATM   27  H   UNK     0       1.334   0.770   0.000  0.00  0.00           H+0
HETATM   28  H   UNK     0      -1.334   0.770   0.000  0.00  0.00           H+0
CONECT    1    5                                                            
CONECT    2    6                                                            
CONECT    3    7                                                            
CONECT    4    8   13                                                       
CONECT    5    1    9   16   24                                             
CONECT    6    2   14   17                                                  
CONECT    7    3   15   18                                                  
CONECT    8    4   10   19   25                                             
CONECT    9    5   11   14   26                                             
CONECT   10    8   11   15   27                                             
CONECT   11    9   10   23   28                                             
CONECT   12   13   20   21                                                  
CONECT   13    4   12   22   23                                             
CONECT   14    6    9                                                       
CONECT   15    7   10                                                       
CONECT   16    5                                                            
CONECT   17    6                                                            
CONECT   18    7                                                            
CONECT   19    8                                                            
CONECT   20   12                                                            
CONECT   21   12                                                            
CONECT   22   13                                                            
CONECT   23   11   13                                                       
CONECT   24    5                                                            
CONECT   25    8                                                            
CONECT   26    9                                                            
CONECT   27   10                                                            
CONECT   28   11                                                            
MASTER        0    0    0    0    0    0    0    0   28    0   56    0
END

Synonyms

Value	Source
(6S)-5-Acetamido-6-[(1R,2R)-1-acetamido-2-hydroxypropyl]-3,5-dideoxy-alpha-L-threo-hex-2-ulopyranosonate	ChEBI
5,7-Diacetamido-3,5,7,9-tetradeoxy-D-glycero-D-galacto-non-2-ulosonate	ChEBI
N,N-Diacetyllegionaminate anion	ChEBI
N,N-Diacetyllegionaminate(1-)	ChEBI
(6S)-5-Acetamido-6-[(1R,2R)-1-acetamido-2-hydroxypropyl]-3,5-dideoxy-a-L-threo-hex-2-ulopyranosonate	Generator
(6S)-5-Acetamido-6-[(1R,2R)-1-acetamido-2-hydroxypropyl]-3,5-dideoxy-a-L-threo-hex-2-ulopyranosonic acid	Generator
(6S)-5-Acetamido-6-[(1R,2R)-1-acetamido-2-hydroxypropyl]-3,5-dideoxy-alpha-L-threo-hex-2-ulopyranosonic acid	Generator
(6S)-5-Acetamido-6-[(1R,2R)-1-acetamido-2-hydroxypropyl]-3,5-dideoxy-α-L-threo-hex-2-ulopyranosonate	Generator
(6S)-5-Acetamido-6-[(1R,2R)-1-acetamido-2-hydroxypropyl]-3,5-dideoxy-α-L-threo-hex-2-ulopyranosonic acid	Generator
5,7-Diacetamido-3,5,7,9-tetradeoxy-D-glycero-D-galacto-non-2-ulosonic acid	Generator
N,N-Diacetyllegionaminic acid anion	Generator
N,N-Diacetyllegionaminic acid(1-)	Generator
N,N-Diacetyllegionaminic acid	Generator

Molecular Formula

C₁₃H₂₁N₂O₈

Average Mass

333.318

Monoisotopic Mass

333.130339224

IUPAC Name

N-[(1R,2R)-1-[(2S,3R,4S,6S)-6-carboxy-4,6-dihydroxy-3-[(1-hydroxyethylidene)amino]oxan-2-yl]-2-hydroxypropyl]ethanecarboximidate

Traditional Name

N-[(1R,2R)-1-[(2S,3R,4S,6S)-6-carboxy-4,6-dihydroxy-3-[(1-hydroxyethylidene)amino]oxan-2-yl]-2-hydroxypropyl]ethanecarboximidate

CAS Registry Number

Not Available

SMILES

[H][C@](C)(O)[C@@]([H])(N=C(C)[O-])[C@]1([H])O[C@@](O)(C[C@]([H])(O)[C@@]1([H])N=C(C)O)C(O)=O

InChI Identifier

InChI=1S/C13H22N2O8/c1-5(16)9(14-6(2)17)11-10(15-7(3)18)8(19)4-13(22,23-11)12(20)21/h5,8-11,16,19,22H,4H2,1-3H3,(H,14,17)(H,15,18)(H,20,21)/p-1/t5-,8+,9-,10-,11+,13+/m1/s1

InChI Key

ZJOSXOOPEBJBMC-DAJNMGJPSA-M

Chemical Taxonomy

Functional Ontology

Physical Properties

Spectra

Biological Properties

Human Proteins and Enzymes

Human Pathways

Metabolic Reactions

Health Effects and Bioactivity

Microbial Sources

Exposure Sources

Host Biospecimen and Location

External Links

References

Showing metabocard for N,N-diacetyllegionaminate (MMDBc0056157)

MOL for #<Metabolite:0x00007fd58e4e4448>

3D MOL for #<Metabolite:0x00007fd58e4e4448>

3D SDF for #<Metabolite:0x00007fd58e4e4448>

3D-SDF for #<Metabolite:0x00007fd58e4e4448>

PDB for #<Metabolite:0x00007fd58e4e4448>

3D PDB for #<Metabolite:0x00007fd58e4e4448>

SMILES for #<Metabolite:0x00007fd58e4e4448>

INCHI for #<Metabolite:0x00007fd58e4e4448>

Structure for #<Metabolite:0x00007fd58e4e4448>

3D Structure for #<Metabolite:0x00007fd58e4e4448>