MiMeDB: Showing metabocard for 2,3-bis((3R)-3-hydroxymyristoyl)-beta-D-glucosaminyl 1-phosphate (MMDBc0031801)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-18 01:49:51 UTC

Update Date

2022-08-31 18:24:52 UTC

Metabolite ID

MMDBc0031801

Metabolite Identification

Common Name

2,3-bis((3R)-3-hydroxymyristoyl)-beta-D-glucosaminyl 1-phosphate

Description

2,3-bis((3R)-3-hydroxymyristoyl)-beta-D-glucosaminyl 1-phosphate is an intermediate in Lipid IVA synthesis which is essesntial for the production of LPS. Lipopolysaccharide (LPS), a major outer membrane component, is composed of three domains: Lipid A, the core, which is an oligosaccharide consisting of an inner and outer region; and a distal repeating unit known as the O-antigen. Lipid A is linked to a beta-1,6-linked glucosamine disaccharide. Attached to this is the inner core containing at least two 3-deoxy-D-manno-octulosonate (KDO) units followed by two units of heptose. The outer core region and the O-antigen are attached to one of the heptose units. For some time it was thought that the minimum structure for cell viability in E. coli had the di-Kdo moiety, but viable mutants lacking Kdo and with the basic tetra-acyl form of lipid A, i.e. lacking the two secondary acyl groups (and termed 'lipid IVA'), have recently been produced. Indeed, lipid IVA may be the minimum structure required for the viability of E. coli.

Structure

MOL SDF PDB SMILES InChI

 
  Mrv0541 07191208532D          
 
 48 48  0  0  1  0            999 V2000
   13.0542   -9.3556    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   12.3296   -9.7768    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   13.0542   -8.5210    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   13.7637   -9.7692    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.6163   -9.3556    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   12.3485  -10.7026    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.3296   -8.1075    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.7676   -8.1075    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.7637  -10.5925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6163   -8.5210    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   10.8993   -9.7655    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.3747  -11.4272    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5909   -8.1037    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   14.4770  -11.0060    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0505  -11.0098    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.8993   -8.1075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6163  -11.8408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0880  -11.8445    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.4142   -8.1037    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.5871   -7.2803    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.5909   -8.9307    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.1903  -10.5925    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   10.9031  -11.4272    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   15.9073  -11.0060    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1903   -9.7692    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.1899  -11.8408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9031  -10.7279    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.6207  -10.5925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4727  -11.4272    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3339  -11.0060    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7595  -11.8408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0510  -10.5925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0424  -11.4272    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7642  -11.0060    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3292  -11.8408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.4812  -10.5850    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6083  -11.4235    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.4775   -9.7580    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6008  -10.5963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7642   -9.3480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3141  -10.1789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7604   -8.5248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3141   -9.3064    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0471   -8.1113    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0235   -8.8853    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0433   -7.2879    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0198   -8.0620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1898   -8.5173    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  1  0  0  0  0
  1  4  1  6  0  0  0
  2  5  1  0  0  0  0
  2  6  1  1  0  0  0
  3  7  1  0  0  0  0
  3  8  1  6  0  0  0
  4  9  1  0  0  0  0
  5 10  1  0  0  0  0
  5 11  1  6  0  0  0
  6 12  1  0  0  0  0
  8 13  1  0  0  0  0
  9 14  1  0  0  0  0
  9 15  2  0  0  0  0
 10 16  1  1  0  0  0
 12 17  1  0  0  0  0
 12 18  2  0  0  0  0
 13 19  1  0  0  0  0
 13 20  1  0  0  0  0
 13 21  2  0  0  0  0
 14 22  1  0  0  0  0
 17 23  1  0  0  0  0
 22 24  1  0  0  0  0
 22 25  1  6  0  0  0
 23 26  1  0  0  0  0
 23 27  1  1  0  0  0
 24 28  1  0  0  0  0
 26 29  1  0  0  0  0
 28 30  1  0  0  0  0
 29 31  1  0  0  0  0
 30 32  1  0  0  0  0
 31 33  1  0  0  0  0
 32 34  1  0  0  0  0
 33 35  1  0  0  0  0
 34 36  1  0  0  0  0
 35 37  1  0  0  0  0
 36 38  1  0  0  0  0
 37 39  1  0  0  0  0
 38 40  1  0  0  0  0
 39 41  1  0  0  0  0
 40 42  1  0  0  0  0
 41 43  1  0  0  0  0
 42 44  1  0  0  0  0
 43 45  1  0  0  0  0
 44 46  1  0  0  0  0
 45 47  1  0  0  0  0
  7 10  1  0  0  0  0
 16 48  1  0  0  0  0
M  END

 
  Mrv0541 07191208532D          
 
 48 48  0  0  1  0            999 V2000
   13.0542   -9.3556    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   12.3296   -9.7768    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   13.0542   -8.5210    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   13.7637   -9.7692    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.6163   -9.3556    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   12.3485  -10.7026    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.3296   -8.1075    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.7676   -8.1075    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.7637  -10.5925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6163   -8.5210    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   10.8993   -9.7655    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.3747  -11.4272    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5909   -8.1037    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   14.4770  -11.0060    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0505  -11.0098    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.8993   -8.1075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6163  -11.8408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0880  -11.8445    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.4142   -8.1037    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.5871   -7.2803    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.5909   -8.9307    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.1903  -10.5925    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   10.9031  -11.4272    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   15.9073  -11.0060    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1903   -9.7692    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.1899  -11.8408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9031  -10.7279    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.6207  -10.5925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4727  -11.4272    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3339  -11.0060    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7595  -11.8408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0510  -10.5925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0424  -11.4272    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7642  -11.0060    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3292  -11.8408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.4812  -10.5850    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6083  -11.4235    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.4775   -9.7580    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6008  -10.5963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7642   -9.3480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3141  -10.1789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7604   -8.5248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3141   -9.3064    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0471   -8.1113    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0235   -8.8853    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0433   -7.2879    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0198   -8.0620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1898   -8.5173    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  1  0  0  0  0
  1  4  1  6  0  0  0
  2  5  1  0  0  0  0
  2  6  1  1  0  0  0
  3  7  1  0  0  0  0
  3  8  1  6  0  0  0
  4  9  1  0  0  0  0
  5 10  1  0  0  0  0
  5 11  1  6  0  0  0
  6 12  1  0  0  0  0
  8 13  1  0  0  0  0
  9 14  1  0  0  0  0
  9 15  2  0  0  0  0
 10 16  1  1  0  0  0
 12 17  1  0  0  0  0
 12 18  2  0  0  0  0
 13 19  1  0  0  0  0
 13 20  1  0  0  0  0
 13 21  2  0  0  0  0
 14 22  1  0  0  0  0
 17 23  1  0  0  0  0
 22 24  1  0  0  0  0
 22 25  1  6  0  0  0
 23 26  1  0  0  0  0
 23 27  1  1  0  0  0
 24 28  1  0  0  0  0
 26 29  1  0  0  0  0
 28 30  1  0  0  0  0
 29 31  1  0  0  0  0
 30 32  1  0  0  0  0
 31 33  1  0  0  0  0
 32 34  1  0  0  0  0
 33 35  1  0  0  0  0
 34 36  1  0  0  0  0
 35 37  1  0  0  0  0
 36 38  1  0  0  0  0
 37 39  1  0  0  0  0
 38 40  1  0  0  0  0
 39 41  1  0  0  0  0
 40 42  1  0  0  0  0
 41 43  1  0  0  0  0
 42 44  1  0  0  0  0
 43 45  1  0  0  0  0
 44 46  1  0  0  0  0
 45 47  1  0  0  0  0
  7 10  1  0  0  0  0
 16 48  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0031801

> <DATABASE_NAME>
MIME

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

> <INCHI_IDENTIFIER>
InChI=1S/C34H66NO12P/c1-3-5-7-9-11-13-15-17-19-21-26(37)23-29(39)35-31-33(32(41)28(25-36)45-34(31)47-48(42,43)44)46-30(40)24-27(38)22-20-18-16-14-12-10-8-6-4-2/h26-28,31-34,36-38,41H,3-25H2,1-2H3,(H,35,39)(H2,42,43,44)/t26-,27-,28-,31-,32-,33-,34-/m1/s1

> <INCHI_KEY>
HEHQDWUWJVPREQ-XQJZMFRCSA-N

> <FORMULA>
C34H66NO12P

> <MOLECULAR_WEIGHT>
711.8611

> <EXACT_MASS>
711.432263093

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_AVERAGE_POLARIZABILITY>
80.09939236277873

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
{[(2R,3R,4R,5S,6R)-5-hydroxy-6-(hydroxymethyl)-3-[(3R)-3-hydroxytetradecanamido]-4-{[(3R)-3-hydroxytetradecanoyl]oxy}oxan-2-yl]oxy}phosphonic acid

> <ALOGPS_LOGP>
4.38

> <JCHEM_LOGP>
5.816945157333333

> <ALOGPS_LOGS>
-5.05

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
6.2356884281702385

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.1754259072473596

> <JCHEM_PKA_STRONGEST_BASIC>
-1.2769127001503402

> <JCHEM_POLAR_SURFACE_AREA>
212.30999999999997

> <JCHEM_REFRACTIVITY>
180.5559

> <JCHEM_ROTATABLE_BOND_COUNT>
30

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
6.33e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
lipid X

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 19-JUL-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE:                                                   
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-JUL-12         0                                  
HETATM    1  C   UNK     0      24.368 -17.464   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      23.015 -18.250   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      24.368 -15.906   0.000  0.00  0.00           C+0
HETATM    4  N   UNK     0      25.692 -18.236   0.000  0.00  0.00           N+0
HETATM    5  C   UNK     0      21.684 -17.464   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      23.051 -19.978   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0      23.015 -15.134   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0      25.700 -15.134   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      25.692 -19.773   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      21.684 -15.906   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      20.345 -18.229   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      23.099 -21.331   0.000  0.00  0.00           C+0
HETATM   13  P   UNK     0      27.236 -15.127   0.000  0.00  0.00           P+0
HETATM   14  C   UNK     0      27.024 -20.545   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      24.361 -20.552   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      20.345 -15.134   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      21.684 -22.103   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      24.431 -22.110   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0      28.773 -15.127   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      27.229 -13.590   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      27.236 -16.671   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      28.355 -19.773   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      20.352 -21.331   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      29.694 -20.545   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      28.355 -18.236   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      19.021 -22.103   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      20.352 -20.025   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      31.025 -19.773   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      17.682 -21.331   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      32.357 -20.545   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      16.351 -22.103   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      33.695 -19.773   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      15.013 -21.331   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      35.026 -20.545   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      13.681 -22.103   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      36.365 -19.759   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      12.335 -21.324   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      36.358 -18.215   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      12.321 -19.780   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      35.026 -17.450   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0      13.653 -19.001   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0      35.019 -15.913   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0      13.653 -17.372   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0      33.688 -15.141   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0      14.977 -16.586   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0      33.681 -13.604   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0      14.970 -15.049   0.000  0.00  0.00           C+0
HETATM   48  O   UNK     0      19.021 -15.899   0.000  0.00  0.00           O+0
CONECT    1    2    3    4                                                  
CONECT    2    1    5    6                                                  
CONECT    3    1    7    8                                                  
CONECT    4    1    9                                                       
CONECT    5    2   10   11                                                  
CONECT    6    2   12                                                       
CONECT    7    3   10                                                       
CONECT    8    3   13                                                       
CONECT    9    4   14   15                                                  
CONECT   10    5   16    7                                                  
CONECT   11    5                                                            
CONECT   12    6   17   18                                                  
CONECT   13    8   19   20   21                                             
CONECT   14    9   22                                                       
CONECT   15    9                                                            
CONECT   16   10   48                                                       
CONECT   17   12   23                                                       
CONECT   18   12                                                            
CONECT   19   13                                                            
CONECT   20   13                                                            
CONECT   21   13                                                            
CONECT   22   14   24   25                                                  
CONECT   23   17   26   27                                                  
CONECT   24   22   28                                                       
CONECT   25   22                                                            
CONECT   26   23   29                                                       
CONECT   27   23                                                            
CONECT   28   24   30                                                       
CONECT   29   26   31                                                       
CONECT   30   28   32                                                       
CONECT   31   29   33                                                       
CONECT   32   30   34                                                       
CONECT   33   31   35                                                       
CONECT   34   32   36                                                       
CONECT   35   33   37                                                       
CONECT   36   34   38                                                       
CONECT   37   35   39                                                       
CONECT   38   36   40                                                       
CONECT   39   37   41                                                       
CONECT   40   38   42                                                       
CONECT   41   39   43                                                       
CONECT   42   40   44                                                       
CONECT   43   41   45                                                       
CONECT   44   42   46                                                       
CONECT   45   43   47                                                       
CONECT   46   44                                                            
CONECT   47   45                                                            
CONECT   48   16                                                            
MASTER        0    0    0    0    0    0    0    0   48    0   96    0
END

Synonyms

Value	Source
2,3-Bis(3-hydroxytetradecanoyl)-alpha-D-glucosaminyl 1-phosphate	ChEBI
2,3-Bis[(3R)-3-hydroxymyristoyl]-alpha-D-glucosaminyl 1-phosphate	ChEBI
2,3-Diacylglucosamine 1-phosphate	Kegg
2,3-Bis(3-hydroxytetradecanoyl)-a-D-glucosaminyl 1-phosphate	Generator
2,3-Bis(3-hydroxytetradecanoyl)-a-D-glucosaminyl 1-phosphoric acid	Generator
2,3-Bis(3-hydroxytetradecanoyl)-alpha-D-glucosaminyl 1-phosphoric acid	Generator
2,3-Bis(3-hydroxytetradecanoyl)-α-D-glucosaminyl 1-phosphate	Generator
2,3-Bis(3-hydroxytetradecanoyl)-α-D-glucosaminyl 1-phosphoric acid	Generator
2,3-Bis[(3R)-3-hydroxymyristoyl]-a-D-glucosaminyl 1-phosphate	Generator
2,3-Bis[(3R)-3-hydroxymyristoyl]-a-D-glucosaminyl 1-phosphoric acid	Generator
2,3-Bis[(3R)-3-hydroxymyristoyl]-alpha-D-glucosaminyl 1-phosphoric acid	Generator
2,3-Bis[(3R)-3-hydroxymyristoyl]-α-D-glucosaminyl 1-phosphate	Generator
2,3-Bis[(3R)-3-hydroxymyristoyl]-α-D-glucosaminyl 1-phosphoric acid	Generator
2,3-Diacylglucosamine 1-phosphoric acid	Generator
2,3-Bis((3R)-3-hydroxymyristoyl)-b-D-glucosaminyl 1-phosphate	Generator
2,3-Bis((3R)-3-hydroxymyristoyl)-b-D-glucosaminyl 1-phosphoric acid	Generator
2,3-Bis((3R)-3-hydroxymyristoyl)-beta-D-glucosaminyl 1-phosphoric acid	Generator
2,3-Bis((3R)-3-hydroxymyristoyl)-β-D-glucosaminyl 1-phosphate	Generator
2,3-Bis((3R)-3-hydroxymyristoyl)-β-D-glucosaminyl 1-phosphoric acid	Generator
Monosaccharide precursor, e coli lipid a	MeSH

Molecular Formula

C₃₄H₆₆NO₁₂P

Average Mass

711.8611

Monoisotopic Mass

711.432263093

IUPAC Name

{[(2R,3R,4R,5S,6R)-5-hydroxy-6-(hydroxymethyl)-3-[(3R)-3-hydroxytetradecanamido]-4-{[(3R)-3-hydroxytetradecanoyl]oxy}oxan-2-yl]oxy}phosphonic acid

Traditional Name

lipid X

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C34H66NO12P/c1-3-5-7-9-11-13-15-17-19-21-26(37)23-29(39)35-31-33(32(41)28(25-36)45-34(31)47-48(42,43)44)46-30(40)24-27(38)22-20-18-16-14-12-10-8-6-4-2/h26-28,31-34,36-38,41H,3-25H2,1-2H3,(H,35,39)(H2,42,43,44)/t26-,27-,28-,31-,32-,33-,34-/m1/s1

InChI Key

HEHQDWUWJVPREQ-XQJZMFRCSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as saccharolipids. Saccharolipids are compounds in which fatty acids are linked directly to a sugar backbone, forming structures that are compatible with membrane bilayers. In the saccharolipids, a sugar substitutes for the glycerol backbone that is present in glycerolipids and glycerophospholipids. The most familiar saccharolipids contain an acylated glucosamine. In contrast to others glycolipids, the fatty acid is not glycosidically linked to the sugar moiety.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Saccharolipids

Sub Class

Not Available

Direct Parent

Saccharolipids

Alternative Parents

Substituents

Saccharolipid
N-acyl-alpha-hexosamine
Hexose monosaccharide
Monosaccharide phosphate
Beta-hydroxy acid
Fatty acid ester
Monoalkyl phosphate
Hydroxy acid
Fatty acyl
Monosaccharide
Organic phosphoric acid derivative
Alkyl phosphate
Oxane
Phosphoric acid ester
Carboxylic acid ester
Secondary alcohol
Carboximidic acid
Carboximidic acid derivative
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Oxacycle
Organoheterocyclic compound
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Carbonyl group
Alcohol
Organic nitrogen compound
Organic oxygen compound
Organonitrogen compound
Organooxygen compound
Primary alcohol
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

N-acyl-D-glucosamine 1-phosphate (CHEBI:16942 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	0.0063 g/L	ALOGPS
logP	4.38	ALOGPS
logP	5.82	ChemAxon
logS	-5	ALOGPS
pKa (Strongest Acidic)	1.18	ChemAxon
pKa (Strongest Basic)	-1.3	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	212.31 Å²	ChemAxon
Rotatable Bond Count	30	ChemAxon
Refractivity	180.56 m³·mol⁻¹	ChemAxon
Polarizability	80.1 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_5) - 70eV, Positive	Not Available	2022-08-08	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-002b-9011121100-e8bdff78108540e8031e	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-9010111000-c7f37736fa4eb93cbeaa	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9000000000-32488362320385f7b7a3	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-01r6-0010409200-dc9e868ae4b7c3f9d21c	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-016v-5251928000-f7e47fd0819ffd3e4060	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0693-2491325000-ce7b99b0dafa1b81f642	2015-09-15	View Spectrum
MS	Mass Spectrum (Electron Ionization)	Not Available	2022-08-06	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

Not Available

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

C04824

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

123907

PDB ID

Not Available

ChEBI ID

16942

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Sajed T, Marcu A, Ramirez M, Pon A, Guo AC, Knox C, Wilson M, Grant JR, Djoumbou Y, Wishart DS: ECMDB 2.0: A richer resource for understanding the biochemistry of E. coli. Nucleic Acids Res. 2016 Jan 4;44(D1):D495-501. doi: 10.1093/nar/gkv1060. Epub 2015 Oct 19. [PubMed:26481353 ]

Showing metabocard for 2,3-bis((3R)-3-hydroxymyristoyl)-beta-D-glucosaminyl 1-phosphate (MMDBc0031801)

MOL for #<Metabolite:0x00005634c2c11ce8>

3D MOL for #<Metabolite:0x00005634c2c11ce8>

3D SDF for #<Metabolite:0x00005634c2c11ce8>

3D-SDF for #<Metabolite:0x00005634c2c11ce8>

PDB for #<Metabolite:0x00005634c2c11ce8>

3D PDB for #<Metabolite:0x00005634c2c11ce8>

SMILES for #<Metabolite:0x00005634c2c11ce8>

INCHI for #<Metabolite:0x00005634c2c11ce8>

Structure for #<Metabolite:0x00005634c2c11ce8>

3D Structure for #<Metabolite:0x00005634c2c11ce8>