Showing metabocard for UDP-2-N,3-O-bis[(3R)-3-hydroxytetradecanoyl]-α-D-glucosamine (MMDBc0032137)

Record Information
Version1.0
StatusDetected and Quantified
Creation Date2021-11-18 02:03:54 UTC
Update Date2022-08-31 18:30:49 UTC
Metabolite IDMMDBc0032137
Metabolite Identification
Common NameUDP-2-N,3-O-bis[(3R)-3-hydroxytetradecanoyl]-α-D-glucosamine
DescriptionUDP-2-N,3-O-bis[(3R)-3-hydroxytetradecanoyl]-alpha-D-glucosamine is an intermediate in lipid IVA biosynthesis pathway in E.coli. It is a substrate for the enzyme UDP-2,3-diacylglucosamine hydrolase which catalyzes the reaction UDP-2-N,3-O-bis[(3R)-3-hydroxytetradecanoyl]-alpha-D-glucosamine + H2O -> 2,3-bis[(3R)-3-hydroxymyristoyl]-alpha-D-glucosaminyl 1-phosphate + UMP + 2 H+. It is also a product for enzyme UDP-3-O-(R-3-hydroxymyristoyl)-glucosamine N-acyltransferase which catalyzes reaction a (3R)-3-hydroxymyristoyl-[acp] + UDP-3-O-(3-hydroxymyristoyl)-α-D-glucosamine -> UDP-2-N,3-O-bis[(3R)-3-hydroxytetradecanoyl]-alpha-D-glucosamine + a holo-[acyl-carrier protein] + H+ (BioCyc compound: OH-MYRISTOYL).
Structure
MOLSDFPDBSMILESInChI

MOL for #<Metabolite:0x00007fdb44702ef8>


  Mrv1533005261511542D          

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M  END
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3D MOL for #<Metabolite:0x00007fdb44702ef8>

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3D SDF for #<Metabolite:0x00007fdb44702ef8>

  Mrv1533005261511542D          

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    8.6086    2.1112    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0437    3.0937    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2276    2.7749    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7582    1.8562    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  1  0  0  0  0
  4  2  1  0  0  0  0
  5  3  1  0  0  0  0
  6  4  1  0  0  0  0
  7  5  1  0  0  0  0
  8  6  1  0  0  0  0
  9  7  1  0  0  0  0
 10  8  1  0  0  0  0
 11  9  1  0  0  0  0
 12 10  1  0  0  0  0
 13 11  1  0  0  0  0
 14 12  1  0  0  0  0
 15 13  1  0  0  0  0
 16 14  1  0  0  0  0
 17 15  1  0  0  0  0
 18 16  1  0  0  0  0
 19 17  1  0  0  0  0
 20 18  1  0  0  0  0
 21 19  1  0  0  0  0
 22 20  1  0  0  0  0
 24 23  2  0  0  0  0
 29 21  1  0  0  0  0
 29 25  1  0  0  0  0
 30 22  1  0  0  0  0
 30 26  1  0  0  0  0
 31 27  1  1  0  0  0
 32 28  1  1  0  0  0
 33 23  1  0  0  0  0
 34 25  1  0  0  0  0
 35 26  1  0  0  0  0
 37 32  1  0  0  0  0
 38 31  1  0  0  0  0
 39 37  1  0  0  0  0
 40 36  1  0  0  0  0
 40 38  1  0  0  0  0
 41 39  1  0  0  0  0
 42 36  1  0  0  0  0
 44 34  2  0  0  0  0
 36 44  1  6  0  0  0
 45 33  2  0  0  0  0
 45 43  1  0  0  0  0
 46 24  1  0  0  0  0
 41 46  1  1  0  0  0
 46 43  1  0  0  0  0
 47 27  1  0  0  0  0
 48 29  1  0  0  0  0
 49 30  1  0  0  0  0
 50 33  1  0  0  0  0
 34 51  1  4  0  0  0
 52 35  2  0  0  0  0
 37 53  1  6  0  0  0
 38 54  1  6  0  0  0
 39 55  1  6  0  0  0
 56 43  2  0  0  0  0
 61 28  1  0  0  0  0
 62 32  1  0  0  0  0
 62 41  1  0  0  0  0
 63 31  1  0  0  0  0
 63 42  1  0  0  0  0
 64 35  1  0  0  0  0
 40 64  1  6  0  0  0
 65 42  1  0  0  0  0
 67 57  1  0  0  0  0
 67 58  2  0  0  0  0
 67 61  1  0  0  0  0
 67 66  1  0  0  0  0
 68 59  1  0  0  0  0
 68 60  2  0  0  0  0
 68 65  1  0  0  0  0
 68 66  1  0  0  0  0
 69 29  1  0  0  0  0
 70 30  1  0  0  0  0
 31 71  1  6  0  0  0
 32 72  1  6  0  0  0
 36 73  1  1  0  0  0
 37 74  1  1  0  0  0
 38 75  1  1  0  0  0
 39 76  1  1  0  0  0
 40 77  1  6  0  0  0
 41 78  1  6  0  0  0
 79 42  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0032137

> <DATABASE_NAME>
MIME

> <SMILES>
[H]C(O)(CCCCCCCCCCC)CC(=O)O[C@@]1([H])[C@]([H])(O)[C@@]([H])(CO)OC([H])(OP(O)(=O)OP(O)(=O)OC[C@@]2([H])O[C@@]([H])(N3C=CC(O)=NC3=O)[C@]([H])(O)[C@]2([H])O)[C@]1([H])N=C(O)CC([H])(O)CCCCCCCCCCC

> <INCHI_IDENTIFIER>
InChI=1S/C43H77N3O20P2/c1-3-5-7-9-11-13-15-17-19-21-29(48)25-34(51)44-36-40(64-35(52)26-30(49)22-20-18-16-14-12-10-8-6-4-2)38(54)31(27-47)63-42(36)65-68(59,60)66-67(57,58)61-28-32-37(53)39(55)41(62-32)46-24-23-33(50)45-43(46)56/h23-24,29-32,36-42,47-49,53-55H,3-22,25-28H2,1-2H3,(H,44,51)(H,57,58)(H,59,60)(H,45,50,56)/t29?,30?,31-,32-,36-,37-,38-,39-,40-,41-,42?/m1/s1

> <INCHI_KEY>
KOJCFMYSTWNMQW-LNGUGUEYSA-N

> <FORMULA>
C43H77N3O20P2

> <MOLECULAR_WEIGHT>
1018.038

> <EXACT_MASS>
1017.457565887

> <JCHEM_ACCEPTOR_COUNT>
18

> <JCHEM_ATOM_COUNT>
145

> <JCHEM_AVERAGE_POLARIZABILITY>
103.69958024240613

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
10

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
N-[(3R,4R,5S,6R)-2-({[({[(2R,3S,4R,5R)-3,4-dihydroxy-5-(4-hydroxy-2-oxo-1,2-dihydropyrimidin-1-yl)oxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)-5-hydroxy-6-(hydroxymethyl)-4-[(3-hydroxytetradecanoyl)oxy]oxan-3-yl]-3-hydroxytetradecanimidic acid

> <ALOGPS_LOGP>
2.93

> <JCHEM_LOGP>
5.063547259333331

> <ALOGPS_LOGS>
-3.70

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
3.1725005489435945

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.7344326381690132

> <JCHEM_PKA_STRONGEST_BASIC>
-3.6573576101780363

> <JCHEM_POLAR_SURFACE_AREA>
353.9200000000001

> <JCHEM_REFRACTIVITY>
241.0588000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
36

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.04e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
N-[(3R,4R,5S,6R)-2-[({[(2R,3S,4R,5R)-3,4-dihydroxy-5-(4-hydroxy-2-oxopyrimidin-1-yl)oxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy(hydroxy)phosphoryl)oxy]-5-hydroxy-6-(hydroxymethyl)-4-[(3-hydroxytetradecanoyl)oxy]oxan-3-yl]-3-hydroxytetradecanimidic acid

> <JCHEM_VEBER_RULE>
0

$$$$

Download
3D-SDF for #<Metabolite:0x00007fdb44702ef8>
Download
PDB for #<Metabolite:0x00007fdb44702ef8>
HEADER    PROTEIN                                 26-MAY-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   26-MAY-15         0                                  
HETATM    1  C   UNK     0      15.818  -8.855   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0     -17.524   4.235   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      14.484  -9.625   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0     -16.190   5.005   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      13.151  -8.855   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0     -14.856   4.235   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      13.151  -7.315   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0     -13.523   5.005   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      11.817  -6.545   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0     -12.189   4.235   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      11.817  -5.005   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0     -10.855   5.005   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      10.483  -4.235   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -9.522   4.235   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      10.483  -2.695   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -8.188   5.005   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       9.150  -1.925   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -6.854   4.235   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       9.150  -0.385   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -5.521   5.005   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       7.816   0.385   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -4.187   4.235   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      14.808   8.043   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      14.182   6.636   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       6.482   2.695   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -1.520   4.235   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       3.815   8.855   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      11.460   1.361   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       7.816   1.925   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -2.853   5.005   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       3.815   7.315   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      12.793   2.131   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      16.340   8.204   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       5.149   1.925   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      -0.186   5.005   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       3.815   4.235   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      14.200   1.505   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       2.481   6.545   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      15.231   2.649   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0       2.481   5.005   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0      14.461   3.983   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0       5.149   5.005   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0      16.619   5.551   0.000  0.00  0.00           C+0
HETATM   44  N   UNK     0       3.815   2.695   0.000  0.00  0.00           N+0
HETATM   45  N   UNK     0      17.245   6.958   0.000  0.00  0.00           N+0
HETATM   46  N   UNK     0      15.087   5.390   0.000  0.00  0.00           N+0
HETATM   47  O   UNK     0       5.149   9.625   0.000  0.00  0.00           O+0
HETATM   48  O   UNK     0       9.150   2.695   0.000  0.00  0.00           O+0
HETATM   49  O   UNK     0      -2.853   6.545   0.000  0.00  0.00           O+0
HETATM   50  O   UNK     0      16.966   9.610   0.000  0.00  0.00           O+0
HETATM   51  O   UNK     0       5.149   0.385   0.000  0.00  0.00           O+0
HETATM   52  O   UNK     0      -0.186   6.545   0.000  0.00  0.00           O+0
HETATM   53  O   UNK     0      14.520  -0.001   0.000  0.00  0.00           O+0
HETATM   54  O   UNK     0       1.148   7.315   0.000  0.00  0.00           O+0
HETATM   55  O   UNK     0      16.762   2.488   0.000  0.00  0.00           O+0
HETATM   56  O   UNK     0      17.524   4.305   0.000  0.00  0.00           O+0
HETATM   57  O   UNK     0      11.666   3.671   0.000  0.00  0.00           O+0
HETATM   58  O   UNK     0      10.126   5.211   0.000  0.00  0.00           O+0
HETATM   59  O   UNK     0       9.150   5.775   0.000  0.00  0.00           O+0
HETATM   60  O   UNK     0       7.046   6.339   0.000  0.00  0.00           O+0
HETATM   61  O   UNK     0      10.126   2.131   0.000  0.00  0.00           O+0
HETATM   62  O   UNK     0      12.954   3.663   0.000  0.00  0.00           O+0
HETATM   63  O   UNK     0       5.149   6.545   0.000  0.00  0.00           O+0
HETATM   64  O   UNK     0       1.148   4.235   0.000  0.00  0.00           O+0
HETATM   65  O   UNK     0       6.482   4.235   0.000  0.00  0.00           O+0
HETATM   66  O   UNK     0       8.586   3.671   0.000  0.00  0.00           O+0
HETATM   67  P   UNK     0      10.126   3.671   0.000  0.00  0.00           P+0
HETATM   68  P   UNK     0       7.816   5.005   0.000  0.00  0.00           P+0
HETATM   69  H   UNK     0       6.482   1.155   0.000  0.00  0.00           H+0
HETATM   70  H   UNK     0      -2.853   3.465   0.000  0.00  0.00           H+0
HETATM   71  H   UNK     0       2.481   8.085   0.000  0.00  0.00           H+0
HETATM   72  H   UNK     0      12.874   0.593   0.000  0.00  0.00           H+0
HETATM   73  H   UNK     0       2.481   3.465   0.000  0.00  0.00           H+0
HETATM   74  H   UNK     0      15.688   1.106   0.000  0.00  0.00           H+0
HETATM   75  H   UNK     0       1.148   5.775   0.000  0.00  0.00           H+0
HETATM   76  H   UNK     0      16.069   3.941   0.000  0.00  0.00           H+0
HETATM   77  H   UNK     0       3.815   5.775   0.000  0.00  0.00           H+0
HETATM   78  H   UNK     0      13.492   5.180   0.000  0.00  0.00           H+0
HETATM   79  H   UNK     0       5.149   3.465   0.000  0.00  0.00           H+0
CONECT    1    3                                                            
CONECT    2    4                                                            
CONECT    3    1    5                                                       
CONECT    4    2    6                                                       
CONECT    5    3    7                                                       
CONECT    6    4    8                                                       
CONECT    7    5    9                                                       
CONECT    8    6   10                                                       
CONECT    9    7   11                                                       
CONECT   10    8   12                                                       
CONECT   11    9   13                                                       
CONECT   12   10   14                                                       
CONECT   13   11   15                                                       
CONECT   14   12   16                                                       
CONECT   15   13   17                                                       
CONECT   16   14   18                                                       
CONECT   17   15   19                                                       
CONECT   18   16   20                                                       
CONECT   19   17   21                                                       
CONECT   20   18   22                                                       
CONECT   21   19   29                                                       
CONECT   22   20   30                                                       
CONECT   23   24   33                                                       
CONECT   24   23   46                                                       
CONECT   25   29   34                                                       
CONECT   26   30   35                                                       
CONECT   27   31   47                                                       
CONECT   28   32   61                                                       
CONECT   29   21   25   48   69                                             
CONECT   30   22   26   49   70                                             
CONECT   31   27   38   63   71                                             
CONECT   32   28   37   62   72                                             
CONECT   33   23   45   50                                                  
CONECT   34   25   44   51                                                  
CONECT   35   26   52   64                                                  
CONECT   36   40   42   44   73                                             
CONECT   37   32   39   53   74                                             
CONECT   38   31   40   54   75                                             
CONECT   39   37   41   55   76                                             
CONECT   40   36   38   64   77                                             
CONECT   41   39   46   62   78                                             
CONECT   42   36   63   65   79                                             
CONECT   43   45   46   56                                                  
CONECT   44   34   36                                                       
CONECT   45   33   43                                                       
CONECT   46   24   41   43                                                  
CONECT   47   27                                                            
CONECT   48   29                                                            
CONECT   49   30                                                            
CONECT   50   33                                                            
CONECT   51   34                                                            
CONECT   52   35                                                            
CONECT   53   37                                                            
CONECT   54   38                                                            
CONECT   55   39                                                            
CONECT   56   43                                                            
CONECT   57   67                                                            
CONECT   58   67                                                            
CONECT   59   68                                                            
CONECT   60   68                                                            
CONECT   61   28   67                                                       
CONECT   62   32   41                                                       
CONECT   63   31   42                                                       
CONECT   64   35   40                                                       
CONECT   65   42   68                                                       
CONECT   66   67   68                                                       
CONECT   67   57   58   61   66                                             
CONECT   68   59   60   65   66                                             
CONECT   69   29                                                            
CONECT   70   30                                                            
CONECT   71   31                                                            
CONECT   72   32                                                            
CONECT   73   36                                                            
CONECT   74   37                                                            
CONECT   75   38                                                            
CONECT   76   39                                                            
CONECT   77   40                                                            
CONECT   78   41                                                            
CONECT   79   42                                                            
MASTER        0    0    0    0    0    0    0    0   79    0  162    0
END

Download
3D PDB for #<Metabolite:0x00007fdb44702ef8>
Download
SMILES for #<Metabolite:0x00007fdb44702ef8>
[H]C(O)(CCCCCCCCCCC)CC(=O)O[C@@]1([H])[C@]([H])(O)[C@@]([H])(CO)OC([H])(OP(O)(=O)OP(O)(=O)OC[C@@]2([H])O[C@@]([H])(N3C=CC(O)=NC3=O)[C@]([H])(O)[C@]2([H])O)[C@]1([H])N=C(O)CC([H])(O)CCCCCCCCCCC
Download
INCHI for #<Metabolite:0x00007fdb44702ef8>
InChI=1S/C43H77N3O20P2/c1-3-5-7-9-11-13-15-17-19-21-29(48)25-34(51)44-36-40(64-35(52)26-30(49)22-20-18-16-14-12-10-8-6-4-2)38(54)31(27-47)63-42(36)65-68(59,60)66-67(57,58)61-28-32-37(53)39(55)41(62-32)46-24-23-33(50)45-43(46)56/h23-24,29-32,36-42,47-49,53-55H,3-22,25-28H2,1-2H3,(H,44,51)(H,57,58)(H,59,60)(H,45,50,56)/t29?,30?,31-,32-,36-,37-,38-,39-,40-,41-,42?/m1/s1
Download
Synonyms
ValueSource
UDP-2,3-Bis(3-hydroxytetradecanoyl)glucosamineChEBI
UDP-2,3-Bis(beta-hydroxymyristoyl)-D-glucosamineChEBI
UDP-2,3-Bis(b-hydroxymyristoyl)-D-glucosamineGenerator
UDP-2,3-Bis(β-hydroxymyristoyl)-D-glucosamineGenerator
Molecular FormulaC43H77N3O20P2
Average Mass1018.038
Monoisotopic Mass1017.457565887
IUPAC NameN-[(3R,4R,5S,6R)-2-({[({[(2R,3S,4R,5R)-3,4-dihydroxy-5-(4-hydroxy-2-oxo-1,2-dihydropyrimidin-1-yl)oxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)-5-hydroxy-6-(hydroxymethyl)-4-[(3-hydroxytetradecanoyl)oxy]oxan-3-yl]-3-hydroxytetradecanimidic acid
Traditional NameN-[(3R,4R,5S,6R)-2-[({[(2R,3S,4R,5R)-3,4-dihydroxy-5-(4-hydroxy-2-oxopyrimidin-1-yl)oxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy(hydroxy)phosphoryl)oxy]-5-hydroxy-6-(hydroxymethyl)-4-[(3-hydroxytetradecanoyl)oxy]oxan-3-yl]-3-hydroxytetradecanimidic acid
CAS Registry NumberNot Available
SMILES
[H]C(O)(CCCCCCCCCCC)CC(=O)O[C@@]1([H])[C@]([H])(O)[C@@]([H])(CO)OC([H])(OP(O)(=O)OP(O)(=O)OC[C@@]2([H])O[C@@]([H])(N3C=CC(O)=NC3=O)[C@]([H])(O)[C@]2([H])O)[C@]1([H])N=C(O)CC([H])(O)CCCCCCCCCCC
InChI Identifier
InChI=1S/C43H77N3O20P2/c1-3-5-7-9-11-13-15-17-19-21-29(48)25-34(51)44-36-40(64-35(52)26-30(49)22-20-18-16-14-12-10-8-6-4-2)38(54)31(27-47)63-42(36)65-68(59,60)66-67(57,58)61-28-32-37(53)39(55)41(62-32)46-24-23-33(50)45-43(46)56/h23-24,29-32,36-42,47-49,53-55H,3-22,25-28H2,1-2H3,(H,44,51)(H,57,58)(H,59,60)(H,45,50,56)/t29?,30?,31-,32-,36-,37-,38-,39-,40-,41-,42?/m1/s1
InChI KeyKOJCFMYSTWNMQW-LNGUGUEYSA-N