MiMeDB: Showing metabocard for UDP-3-O-(3-Hydroxymyristoyl)-N-acetylglucosamine (MMDBc0029812)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-17 23:42:45 UTC

Update Date

2022-08-31 17:18:43 UTC

Metabolite ID

MMDBc0029812

Metabolite Identification

Common Name

UDP-3-O-(3-Hydroxymyristoyl)-N-acetylglucosamine

Description

UDP-3-o-(3-hydroxymyristoyl)-n-acetylglucosamine is a member of the chemical class known as Pyrimidine Nucleotide Sugars. These are pyrimidine nucleotides bound to a saccharide derivative through the terminal phosphate group.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652303062018272D          

 55 57  0  0  1  0            999 V2000
   15.8981   -3.7906    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   16.6887   -3.5329    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.2554   -3.3198    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.6576   -4.5983    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   17.3073   -4.0827    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8605   -2.7251    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5852   -3.8113    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   14.8292   -4.5983    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   16.1422   -5.2616    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.0943   -3.8216    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.1423   -4.8871    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.6372   -2.4605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7982   -3.5569    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3412   -5.2580    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.2627   -3.0139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2140   -4.1309    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.0463   -2.7561    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.3924   -4.1309    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   11.5710   -4.1309    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.3891   -4.9523    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.3891   -3.3095    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.7496   -4.1276    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   10.7428   -4.9490    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.7428   -3.3026    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.9249   -4.1276    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.2104   -4.5400    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.4960   -4.1276    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7815   -4.5400    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.0670   -4.1276    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3525   -4.5400    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7815   -5.3650    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.0670   -5.7775    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.4960   -5.7775    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.4960   -6.6025    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0671   -6.6025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6382   -6.6025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9238   -7.0150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2092   -6.6025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4948   -7.0150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7803   -6.6025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0659   -7.0150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0658   -7.8400    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7803   -8.2525    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4948   -7.8400    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2092   -8.2525    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9237   -7.8399    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7816   -7.0150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7816   -7.8400    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3526   -7.0150    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.3526   -7.8400    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.2104   -5.3650    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    9.9248   -5.7774    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.9248   -6.6024    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6394   -7.0149    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2105   -7.0149    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  1  0  0  0
  1  3  1  0  0  0  0
  1  4  1  0  0  0  0
  2  5  1  0  0  0  0
  2  6  1  0  0  0  0
  3  7  1  0  0  0  0
  4  8  1  0  0  0  0
  4  9  1  6  0  0  0
  5 10  1  0  0  0  0
  5 11  2  0  0  0  0
  6 12  2  0  0  0  0
  7 13  1  1  0  0  0
  8 14  1  6  0  0  0
 10 15  1  0  0  0  0
 13 16  1  0  0  0  0
 15 17  2  0  0  0  0
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 20  1  0  0  0  0
 18 21  2  0  0  0  0
 19 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 25  1  0  0  0  0
 22 24  2  0  0  0  0
  7  8  1  0  0  0  0
 12 15  1  0  0  0  0
 26 25  1  6  0  0  0
 51 26  1  0  0  0  0
 27 26  1  0  0  0  0
 27 28  1  0  0  0  0
 28 31  1  0  0  0  0
 31 33  1  0  0  0  0
 33 51  1  0  0  0  0
 28 29  1  1  0  0  0
 29 30  1  0  0  0  0
 31 32  1  6  0  0  0
 33 34  1  1  0  0  0
 34 47  1  0  0  0  0
 47 35  1  0  0  0  0
 35 49  1  0  0  0  0
 49 36  1  0  0  0  0
 36 37  1  0  0  0  0
 37 38  1  0  0  0  0
 38 39  1  0  0  0  0
 39 40  1  0  0  0  0
 40 41  1  0  0  0  0
 41 42  1  0  0  0  0
 42 43  1  0  0  0  0
 43 44  1  0  0  0  0
 44 45  1  0  0  0  0
 45 46  1  0  0  0  0
 47 48  2  0  0  0  0
 49 50  1  6  0  0  0
 51 52  1  6  0  0  0
 52 53  1  0  0  0  0
 53 54  1  0  0  0  0
 53 55  2  0  0  0  0
M  END


  Mrv1652303062018272D          

 55 57  0  0  1  0            999 V2000
   15.8981   -3.7906    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   16.6887   -3.5329    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.2554   -3.3198    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.6576   -4.5983    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   17.3073   -4.0827    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8605   -2.7251    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5852   -3.8113    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   14.8292   -4.5983    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   16.1422   -5.2616    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.0943   -3.8216    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.1423   -4.8871    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.6372   -2.4605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7982   -3.5569    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3412   -5.2580    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.2627   -3.0139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2140   -4.1309    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.0463   -2.7561    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.3924   -4.1309    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   11.5710   -4.1309    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.3891   -4.9523    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.3891   -3.3095    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.7496   -4.1276    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   10.7428   -4.9490    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.7428   -3.3026    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.9249   -4.1276    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.2104   -4.5400    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.4960   -4.1276    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7815   -4.5400    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.0670   -4.1276    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3525   -4.5400    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7815   -5.3650    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.0670   -5.7775    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.4960   -5.7775    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.4960   -6.6025    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0671   -6.6025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6382   -6.6025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9238   -7.0150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2092   -6.6025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4948   -7.0150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7803   -6.6025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0659   -7.0150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0658   -7.8400    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7803   -8.2525    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4948   -7.8400    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2092   -8.2525    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9237   -7.8399    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7816   -7.0150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7816   -7.8400    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3526   -7.0150    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.3526   -7.8400    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.2104   -5.3650    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    9.9248   -5.7774    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.9248   -6.6024    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6394   -7.0149    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2105   -7.0149    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  1  0  0  0
  1  3  1  0  0  0  0
  1  4  1  0  0  0  0
  2  5  1  0  0  0  0
  2  6  1  0  0  0  0
  3  7  1  0  0  0  0
  4  8  1  0  0  0  0
  4  9  1  6  0  0  0
  5 10  1  0  0  0  0
  5 11  2  0  0  0  0
  6 12  2  0  0  0  0
  7 13  1  1  0  0  0
  8 14  1  6  0  0  0
 10 15  1  0  0  0  0
 13 16  1  0  0  0  0
 15 17  2  0  0  0  0
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 20  1  0  0  0  0
 18 21  2  0  0  0  0
 19 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 25  1  0  0  0  0
 22 24  2  0  0  0  0
  7  8  1  0  0  0  0
 12 15  1  0  0  0  0
 26 25  1  6  0  0  0
 51 26  1  0  0  0  0
 27 26  1  0  0  0  0
 27 28  1  0  0  0  0
 28 31  1  0  0  0  0
 31 33  1  0  0  0  0
 33 51  1  0  0  0  0
 28 29  1  1  0  0  0
 29 30  1  0  0  0  0
 31 32  1  6  0  0  0
 33 34  1  1  0  0  0
 34 47  1  0  0  0  0
 47 35  1  0  0  0  0
 35 49  1  0  0  0  0
 49 36  1  0  0  0  0
 36 37  1  0  0  0  0
 37 38  1  0  0  0  0
 38 39  1  0  0  0  0
 39 40  1  0  0  0  0
 40 41  1  0  0  0  0
 41 42  1  0  0  0  0
 42 43  1  0  0  0  0
 43 44  1  0  0  0  0
 44 45  1  0  0  0  0
 45 46  1  0  0  0  0
 47 48  2  0  0  0  0
 49 50  1  6  0  0  0
 51 52  1  6  0  0  0
 52 53  1  0  0  0  0
 53 54  1  0  0  0  0
 53 55  2  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0029812

> <DATABASE_NAME>
MIME

> <SMILES>
CCCCCCCCCCC[C@@H](O)CC(=O)O[C@H]1[C@H](O)[C@@H](CO)O[C@H](OP(O)(=O)OP(O)(=O)OC[C@H]2O[C@H]([C@H](O)[C@@H]2O)N2C=CC(=O)NC2=O)[C@@H]1NC(C)=O

> <INCHI_IDENTIFIER>
InChI=1S/C31H53N3O19P2/c1-3-4-5-6-7-8-9-10-11-12-19(37)15-23(39)51-28-24(32-18(2)36)30(50-20(16-35)26(28)41)52-55(46,47)53-54(44,45)48-17-21-25(40)27(42)29(49-21)34-14-13-22(38)33-31(34)43/h13-14,19-21,24-30,35,37,40-42H,3-12,15-17H2,1-2H3,(H,32,36)(H,44,45)(H,46,47)(H,33,38,43)/t19-,20-,21-,24-,25-,26-,27-,28-,29-,30-/m1/s1

> <INCHI_KEY>
TZSJGZGYQDNRRX-MPLCHSTDSA-N

> <FORMULA>
C31H53N3O19P2

> <MOLECULAR_WEIGHT>
833.7087

> <EXACT_MASS>
833.274849553

> <JCHEM_ACCEPTOR_COUNT>
17

> <JCHEM_ATOM_COUNT>
108

> <JCHEM_AVERAGE_POLARIZABILITY>
80.01643363555456

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
9

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
N-[(2R,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-{[(3R)-3-hydroxytetradecanoyl]oxy}oxan-3-yl]ethanimidic acid

> <ALOGPS_LOGP>
0.61

> <JCHEM_LOGP>
0.703567164333333

> <ALOGPS_LOGS>
-2.46

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
3.175931900478704

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.7345710055467292

> <JCHEM_PKA_STRONGEST_BASIC>
-3.6573575088071033

> <JCHEM_POLAR_SURFACE_AREA>
333.69000000000005

> <JCHEM_REFRACTIVITY>
184.30540000000005

> <JCHEM_ROTATABLE_BOND_COUNT>
24

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.89e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
N-[(2R,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-{[(3R)-3-hydroxytetradecanoyl]oxy}oxan-3-yl]ethanimidic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-MAR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAR-20         0                                  
HETATM    1  C   UNK     0      29.676  -7.076   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0      31.152  -6.595   0.000  0.00  0.00           N+0
HETATM    3  O   UNK     0      28.477  -6.197   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      29.227  -8.583   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      32.307  -7.621   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      31.473  -5.087   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      27.226  -7.114   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      27.681  -8.583   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      30.132  -9.822   0.000  0.00  0.00           O+0
HETATM   10  N   UNK     0      33.776  -7.134   0.000  0.00  0.00           N+0
HETATM   11  O   UNK     0      31.999  -9.123   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      32.923  -4.593   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      25.757  -6.639   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      26.770  -9.815   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      34.090  -5.626   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      24.666  -7.711   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0      35.553  -5.145   0.000  0.00  0.00           O+0
HETATM   18  P   UNK     0      23.132  -7.711   0.000  0.00  0.00           P+0
HETATM   19  O   UNK     0      21.599  -7.711   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      23.126  -9.244   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      23.126  -6.178   0.000  0.00  0.00           O+0
HETATM   22  P   UNK     0      20.066  -7.705   0.000  0.00  0.00           P+0
HETATM   23  O   UNK     0      20.053  -9.238   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0      20.053  -6.165   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0      18.527  -7.705   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      17.193  -8.475   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      15.859  -7.705   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      14.525  -8.475   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      13.192  -7.705   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      11.858  -8.475   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      14.525 -10.015   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      13.192 -10.785   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0      15.859 -10.785   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0      15.859 -12.325   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0      13.192 -12.325   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      10.525 -12.325   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       9.191 -13.095   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       7.857 -12.325   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       6.524 -13.095   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0       5.190 -12.325   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0       3.856 -13.095   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0       3.856 -14.635   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0       5.190 -15.405   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0       6.524 -14.635   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0       7.857 -15.405   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0       9.191 -14.634   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0      14.526 -13.095   0.000  0.00  0.00           C+0
HETATM   48  O   UNK     0      14.526 -14.635   0.000  0.00  0.00           O+0
HETATM   49  C   UNK     0      11.858 -13.095   0.000  0.00  0.00           C+0
HETATM   50  O   UNK     0      11.858 -14.635   0.000  0.00  0.00           O+0
HETATM   51  C   UNK     0      17.193 -10.015   0.000  0.00  0.00           C+0
HETATM   52  N   UNK     0      18.526 -10.784   0.000  0.00  0.00           N+0
HETATM   53  C   UNK     0      18.526 -12.324   0.000  0.00  0.00           C+0
HETATM   54  C   UNK     0      19.860 -13.094   0.000  0.00  0.00           C+0
HETATM   55  O   UNK     0      17.193 -13.094   0.000  0.00  0.00           O+0
CONECT    1    2    3    4                                                  
CONECT    2    1    5    6                                                  
CONECT    3    1    7                                                       
CONECT    4    1    8    9                                                  
CONECT    5    2   10   11                                                  
CONECT    6    2   12                                                       
CONECT    7    3   13    8                                                  
CONECT    8    4   14    7                                                  
CONECT    9    4                                                            
CONECT   10    5   15                                                       
CONECT   11    5                                                            
CONECT   12    6   15                                                       
CONECT   13    7   16                                                       
CONECT   14    8                                                            
CONECT   15   10   17   12                                                  
CONECT   16   13   18                                                       
CONECT   17   15                                                            
CONECT   18   16   19   20   21                                             
CONECT   19   18   22                                                       
CONECT   20   18                                                            
CONECT   21   18                                                            
CONECT   22   19   23   25   24                                             
CONECT   23   22                                                            
CONECT   24   22                                                            
CONECT   25   22   26                                                       
CONECT   26   25   51   27                                                  
CONECT   27   26   28                                                       
CONECT   28   27   31   29                                                  
CONECT   29   28   30                                                       
CONECT   30   29                                                            
CONECT   31   28   33   32                                                  
CONECT   32   31                                                            
CONECT   33   31   51   34                                                  
CONECT   34   33   47                                                       
CONECT   35   47   49                                                       
CONECT   36   49   37                                                       
CONECT   37   36   38                                                       
CONECT   38   37   39                                                       
CONECT   39   38   40                                                       
CONECT   40   39   41                                                       
CONECT   41   40   42                                                       
CONECT   42   41   43                                                       
CONECT   43   42   44                                                       
CONECT   44   43   45                                                       
CONECT   45   44   46                                                       
CONECT   46   45                                                            
CONECT   47   34   35   48                                                  
CONECT   48   47                                                            
CONECT   49   35   36   50                                                  
CONECT   50   49                                                            
CONECT   51   26   33   52                                                  
CONECT   52   51   53                                                       
CONECT   53   52   54   55                                                  
CONECT   54   53                                                            
CONECT   55   53                                                            
MASTER        0    0    0    0    0    0    0    0   55    0  114    0
END

Synonyms

Value	Source
UDP-3-Hmaglc	ChEBI
UDP-3-O-(beta-Hydroxymyristoyl)-N-acetylglucosamine	Kegg
UDP-3-O-[(3R)-3-Hydroxymyristoyl]-N-acetylglucosamine	Kegg
UDP-3-O-(b-Hydroxymyristoyl)-N-acetylglucosamine	Generator
UDP-3-O-(Β-hydroxymyristoyl)-N-acetylglucosamine	Generator

Molecular Formula

C₃₁H₅₃N₃O₁₉P₂

Average Mass

833.7087

Monoisotopic Mass

833.274849553

IUPAC Name

N-[(2R,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-{[(3R)-3-hydroxytetradecanoyl]oxy}oxan-3-yl]ethanimidic acid

Traditional Name

N-[(2R,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-{[(3R)-3-hydroxytetradecanoyl]oxy}oxan-3-yl]ethanimidic acid

CAS Registry Number

108636-29-9

SMILES

CCCCCCCCCCC[C@@H](O)CC(=O)O[C@H]1[C@H](O)[C@@H](CO)O[C@H](OP(O)(=O)OP(O)(=O)OC[C@H]2O[C@H]([C@H](O)[C@@H]2O)N2C=CC(=O)NC2=O)[C@@H]1NC(C)=O

InChI Identifier

InChI=1S/C31H53N3O19P2/c1-3-4-5-6-7-8-9-10-11-12-19(37)15-23(39)51-28-24(32-18(2)36)30(50-20(16-35)26(28)41)52-55(46,47)53-54(44,45)48-17-21-25(40)27(42)29(49-21)34-14-13-22(38)33-31(34)43/h13-14,19-21,24-30,35,37,40-42H,3-12,15-17H2,1-2H3,(H,32,36)(H,44,45)(H,46,47)(H,33,38,43)/t19-,20-,21-,24-,25-,26-,27-,28-,29-,30-/m1/s1

InChI Key

TZSJGZGYQDNRRX-MPLCHSTDSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pyrimidine nucleotide sugars. These are pyrimidine nucleotides bound to a saccharide derivative through the terminal phosphate group.

Kingdom

Organic compounds

Super Class

Nucleosides, nucleotides, and analogues

Class

Pyrimidine nucleotides

Sub Class

Pyrimidine nucleotide sugars

Direct Parent

Pyrimidine nucleotide sugars

Alternative Parents

Substituents

Pyrimidine nucleotide sugar
Pyrimidine ribonucleoside diphosphate
Saccharolipid
Pentose-5-phosphate
Pentose phosphate
N-acyl-alpha-hexosamine
Glycosyl compound
N-glycosyl compound
Organic pyrophosphate
Monosaccharide phosphate
Beta-hydroxy acid
Monoalkyl phosphate
Pyrimidone
Fatty acid ester
Fatty acyl
Organic phosphoric acid derivative
Alkyl phosphate
Oxane
Hydroxy acid
Hydropyrimidine
Phosphoric acid ester
Pyrimidine
Monosaccharide
Heteroaromatic compound
Acetamide
Vinylogous amide
Tetrahydrofuran
Urea
Secondary alcohol
Secondary carboxylic acid amide
Carboxamide group
Lactam
Carboxylic acid ester
Organoheterocyclic compound
Carboxylic acid derivative
Azacycle
Oxacycle
Monocarboxylic acid or derivatives
Primary alcohol
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic oxygen compound
Alcohol
Organic nitrogen compound
Carbonyl group
Organonitrogen compound
Organooxygen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

UDP-amino sugar (CHEBI:61537 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	2.89 g/L	ALOGPS
logP	0.61	ALOGPS
logP	0.7	ChemAxon
logS	-2.5	ALOGPS
pKa (Strongest Acidic)	1.73	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	17	ChemAxon
Hydrogen Donor Count	9	ChemAxon
Polar Surface Area	333.69 Å²	ChemAxon
Rotatable Bond Count	24	ChemAxon
Refractivity	184.31 m³·mol⁻¹	ChemAxon
Polarizability	80.02 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03di-0910000020-fedcabb1e352348e4b41	2015-09-14	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03di-2910010000-9c7cdad9942cd448b2e2	2015-09-14	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-03di-3910000000-1906defd57b0d60b4180	2015-09-14	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0ik9-7912501340-ee6a700cf210afdb6a69	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-03dl-8915131020-7c28b07f154e3dacae45	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-052f-5922000000-e1498ccc14935f8be289	2015-09-15	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-20	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria	Proteobacteria	1	Human ; Human feces; Human feces; pleural fluid plaque; bal; Human stool	Unknown

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

C04738

BioCyc ID

UDP-OHMYR-ACETYLGLUCOSAMINE

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

194791

PDB ID

Not Available

ChEBI ID

61537

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Wishart DS, Li C, Marcu A, Badran H, Pon A, Budinski Z, Patron J, Lipton D, Cao X, Oler E, Li K, Paccoud M, Hong C, Guo AC, Chan C, Wei W, Ramirez-Gaona M: PathBank: a comprehensive pathway database for model organisms. Nucleic Acids Res. 2020 Jan 8;48(D1):D470-D478. doi: 10.1093/nar/gkz861. [PubMed:31602464 ]

Showing metabocard for UDP-3-O-(3-Hydroxymyristoyl)-N-acetylglucosamine (MMDBc0029812)

MOL for #<Metabolite:0x00007fecdbf12410>

3D MOL for #<Metabolite:0x00007fecdbf12410>

3D SDF for #<Metabolite:0x00007fecdbf12410>

3D-SDF for #<Metabolite:0x00007fecdbf12410>

PDB for #<Metabolite:0x00007fecdbf12410>

3D PDB for #<Metabolite:0x00007fecdbf12410>

SMILES for #<Metabolite:0x00007fecdbf12410>

INCHI for #<Metabolite:0x00007fecdbf12410>

Structure for #<Metabolite:0x00007fecdbf12410>

3D Structure for #<Metabolite:0x00007fecdbf12410>