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

Record Information
Version1.0
StatusDetected and Quantified
Creation Date2021-11-18 01:49:51 UTC
Update Date2022-08-31 18:24:52 UTC
Metabolite IDMMDBc0031801
Metabolite Identification
Common Name2,3-bis((3R)-3-hydroxymyristoyl)-beta-D-glucosaminyl 1-phosphate
Description2,3-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
MOLSDFPDBSMILESInChI

MOL for #<Metabolite:0x00007f925175ae00>

 
  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
Download

3D MOL for #<Metabolite:0x00007f925175ae00>

Download
3D SDF for #<Metabolite:0x00007f925175ae00>
 
  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

$$$$

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3D-SDF for #<Metabolite:0x00007f925175ae00>
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PDB for #<Metabolite:0x00007f925175ae00>
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

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3D PDB for #<Metabolite:0x00007f925175ae00>
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SMILES for #<Metabolite:0x00007f925175ae00>
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
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INCHI for #<Metabolite:0x00007f925175ae00>
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
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Synonyms
ValueSource
2,3-Bis(3-hydroxytetradecanoyl)-alpha-D-glucosaminyl 1-phosphateChEBI
2,3-Bis[(3R)-3-hydroxymyristoyl]-alpha-D-glucosaminyl 1-phosphateChEBI
2,3-Diacylglucosamine 1-phosphateKegg
2,3-Bis(3-hydroxytetradecanoyl)-a-D-glucosaminyl 1-phosphateGenerator
2,3-Bis(3-hydroxytetradecanoyl)-a-D-glucosaminyl 1-phosphoric acidGenerator
2,3-Bis(3-hydroxytetradecanoyl)-alpha-D-glucosaminyl 1-phosphoric acidGenerator
2,3-Bis(3-hydroxytetradecanoyl)-α-D-glucosaminyl 1-phosphateGenerator
2,3-Bis(3-hydroxytetradecanoyl)-α-D-glucosaminyl 1-phosphoric acidGenerator
2,3-Bis[(3R)-3-hydroxymyristoyl]-a-D-glucosaminyl 1-phosphateGenerator
2,3-Bis[(3R)-3-hydroxymyristoyl]-a-D-glucosaminyl 1-phosphoric acidGenerator
2,3-Bis[(3R)-3-hydroxymyristoyl]-alpha-D-glucosaminyl 1-phosphoric acidGenerator
2,3-Bis[(3R)-3-hydroxymyristoyl]-α-D-glucosaminyl 1-phosphateGenerator
2,3-Bis[(3R)-3-hydroxymyristoyl]-α-D-glucosaminyl 1-phosphoric acidGenerator
2,3-Diacylglucosamine 1-phosphoric acidGenerator
2,3-Bis((3R)-3-hydroxymyristoyl)-b-D-glucosaminyl 1-phosphateGenerator
2,3-Bis((3R)-3-hydroxymyristoyl)-b-D-glucosaminyl 1-phosphoric acidGenerator
2,3-Bis((3R)-3-hydroxymyristoyl)-beta-D-glucosaminyl 1-phosphoric acidGenerator
2,3-Bis((3R)-3-hydroxymyristoyl)-β-D-glucosaminyl 1-phosphateGenerator
2,3-Bis((3R)-3-hydroxymyristoyl)-β-D-glucosaminyl 1-phosphoric acidGenerator
Monosaccharide precursor, e coli lipid aMeSH
Molecular FormulaC34H66NO12P
Average Mass711.8611
Monoisotopic Mass711.432263093
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 Namelipid X
CAS Registry NumberNot 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 KeyHEHQDWUWJVPREQ-XQJZMFRCSA-N