NP-MRD: Showing NP-Card for Undecaprenol diphosphate (NP0062859)

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Record Information

Version

2.0

Created at

2022-04-28 07:24:15 UTC

Updated at

2022-04-28 07:24:16 UTC

NP-MRD ID

NP0062859

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Undecaprenol diphosphate

Description

Undecaprenyl diphosphate, also known as undpp or bactoprenyl pyrophosphate, belongs to the class of organic compounds known as bactoprenol diphosphates. These are polyprenyl compounds consisting of a diphosphate group substituted by a bactoprenyl moiety. The all-trans-isomer of undecaprenyl diphosphate. Undecaprenyl diphosphate is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Undecaprenol diphosphate is found in Escherichia coli. Undecaprenyl diphosphate exists in all living species, ranging from bacteria to humans.

Structure

MOL 3D MOL SDF PDB SMILES InChI

  Mrv0541 02231219092D          

 64 63  0  0  0  0            999 V2000
   26.9267   -8.8792    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   27.7586   -8.8792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.9267   -8.0508    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.9336   -9.7077    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   28.5871   -8.8792    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   28.5871   -8.0508    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   29.4121   -8.8792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   28.5871   -9.7077    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.0500   -8.8667    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0830   -8.8083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3685   -8.3958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7975   -8.3958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5119   -8.8083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7975   -7.5708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6541   -8.8083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2251   -8.8083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5107   -8.3958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9396   -8.3958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9396   -7.5708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2038   -8.8083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6328   -8.8083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3472   -8.3958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9183   -8.3958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9183   -7.5708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0617   -8.8083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4906   -8.8083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2051   -8.3958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7762   -8.3958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7762   -7.5708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9196   -8.8083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3485   -8.8083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0630   -8.3958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6341   -8.3958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6341   -7.5708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7775   -8.8083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2064   -8.8083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9209   -8.3958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4919   -8.3958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4919   -7.5708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6354   -8.8083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0643   -8.8083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7788   -8.3958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3498   -8.3958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3498   -7.5708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4932   -8.8083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9222   -8.8083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6367   -8.3958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2077   -8.3958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2077   -7.5708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3511   -8.8083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7801   -8.8083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.4945   -8.3958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0656   -8.3958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0656   -7.5708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2090   -8.8083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.6379   -8.8083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.3524   -8.3958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.9235   -8.3958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.9235   -7.5708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.0669   -8.8083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.4958   -8.8083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.2103   -8.3958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.7814   -8.3958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.7814   -7.5708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 33 30  1  0  0  0  0
 16 18  2  0  0  0  0
 33 34  1  0  0  0  0
 18 15  1  0  0  0  0
 32 35  1  0  0  0  0
  9  1  1  0  0  0  0
 18 19  1  0  0  0  0
 36 37  1  0  0  0  0
  1  2  1  0  0  0  0
 36 38  2  0  0  0  0
 38 35  1  0  0  0  0
 17 20  1  0  0  0  0
 38 39  1  0  0  0  0
 10 11  1  0  0  0  0
 37 40  1  0  0  0  0
  1  3  1  0  0  0  0
 21 22  1  0  0  0  0
 41 42  1  0  0  0  0
 10 12  2  0  0  0  0
 41 43  2  0  0  0  0
 43 40  1  0  0  0  0
 21 23  2  0  0  0  0
 43 44  1  0  0  0  0
 23 20  1  0  0  0  0
 42 45  1  0  0  0  0
  1  4  2  0  0  0  0
 23 24  1  0  0  0  0
 46 47  1  0  0  0  0
 12 13  1  0  0  0  0
 46 48  2  0  0  0  0
 48 45  1  0  0  0  0
 22 25  1  0  0  0  0
 48 49  1  0  0  0  0
  2  5  1  0  0  0  0
 47 50  1  0  0  0  0
 12 14  1  0  0  0  0
 26 27  1  0  0  0  0
 51 52  1  0  0  0  0
  5  6  1  0  0  0  0
 51 53  2  0  0  0  0
 53 50  1  0  0  0  0
 26 28  2  0  0  0  0
 53 54  1  0  0  0  0
 28 25  1  0  0  0  0
 52 55  1  0  0  0  0
 11 15  1  0  0  0  0
 28 29  1  0  0  0  0
 56 57  1  0  0  0  0
  5  7  1  0  0  0  0
 56 58  2  0  0  0  0
 58 55  1  0  0  0  0
 27 30  1  0  0  0  0
 58 59  1  0  0  0  0
  5  8  2  0  0  0  0
 57 60  1  0  0  0  0
 16 17  1  0  0  0  0
 31 32  1  0  0  0  0
 61 62  1  0  0  0  0
 61 63  2  0  0  0  0
 63 60  1  0  0  0  0
 31 33  2  0  0  0  0
 63 64  1  0  0  0  0
 62  9  1  0  0  0  0
M  END

     RDKit          3D

156155  0  0  0  0  0  0  0  0999 V2000
  -19.5632    1.5007   -3.0588 C   0  0  0  0  0  0  0  0  0  0  0  0
  -18.1431    1.2294   -3.3805 C   0  0  0  0  0  0  0  0  0  0  0  0
  -17.7838    0.8813   -4.7800 C   0  0  0  0  0  0  0  0  0  0  0  0
  -17.2018    1.2955   -2.4295 C   0  0  0  0  0  0  0  0  0  0  0  0
  -17.5973    1.6457   -1.0495 C   0  0  0  0  0  0  0  0  0  0  0  0
  -17.3315    0.6015   -0.0361 C   0  0  0  0  0  0  0  0  0  0  0  0
  -15.9685    0.2152    0.2625 C   0  0  0  0  0  0  0  0  0  0  0  0
  -15.7973   -0.9058    1.2679 C   0  0  0  0  0  0  0  0  0  0  0  0
  -14.8329    0.7084   -0.2052 C   0  0  0  0  0  0  0  0  0  0  0  0
  -13.5000    0.1419    0.2469 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.8250    1.1772    1.0871 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.5279    0.7871    1.6553 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.8421    1.7586    2.5611 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.9000   -0.3632    1.4405 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.5731   -0.6104    2.1095 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -7.7596   -3.3188    3.3312 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -5.2801   -3.8505    3.2349 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8092   -2.5464    2.7418 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5175   -1.4784    3.7620 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.6428   -0.8964    0.6607 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.7208    2.3957    0.8259 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.0162    2.3178   -1.2908 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5847    1.6154   -2.4562 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1024    1.6996   -2.5091 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7688    1.1032   -1.3272 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5303    1.6077    0.0337 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6361    0.0850   -1.4717 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2645   -0.4745   -0.2710 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7339   -0.3118   -0.2332 C   0  0  0  0  0  0  0  0  0  0  0  0
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    9.8091   -0.7945   -3.3977 C   0  0  0  0  0  0  0  0  0  0  0  0
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   19.3298    0.0531    1.9970 P   0  0  1  0  0  5  0  0  0  0  0  0
   20.4933    0.9292    2.4257 O   0  0  0  0  0  0  0  0  0  0  0  0
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   18.8599   -2.5551    3.2138 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -9.3025    0.2045    2.7814 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.9311   -2.7259    2.0958 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.5999   -1.8097    3.5063 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7529   -1.8337    5.6167 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9844   -0.7280    5.0025 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3735   -0.5847    4.2966 H   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

  Mrv0541 02231219092D          

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M  END
> <DATABASE_ID>
NP0062859

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)=CCC\C(C)=C\CC\C(C)=C\CC\C(C)=C\CC\C(C)=C\CC\C(C)=C\CC\C(C)=C\CC\C(C)=C\CC\C(C)=C\CC\C(C)=C\CC\C(C)=C\COP(O)(=O)OP(O)(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C55H92O7P2/c1-45(2)23-13-24-46(3)25-14-26-47(4)27-15-28-48(5)29-16-30-49(6)31-17-32-50(7)33-18-34-51(8)35-19-36-52(9)37-20-38-53(10)39-21-40-54(11)41-22-42-55(12)43-44-61-64(59,60)62-63(56,57)58/h23,25,27,29,31,33,35,37,39,41,43H,13-22,24,26,28,30,32,34,36,38,40,42,44H2,1-12H3,(H,59,60)(H2,56,57,58)/b46-25+,47-27+,48-29+,49-31+,50-33+,51-35+,52-37+,53-39+,54-41+,55-43+

> <INCHI_KEY>
NTXGVHCCXVHYCL-RDQGWRCRSA-N

> <FORMULA>
C55H92O7P2

> <MOLECULAR_WEIGHT>
927.2623

> <EXACT_MASS>
926.631828322

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
114.76665829676878

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
{[hydroxy({[(2E,6E,10E,14E,18E,22E,26E,30E,34E,38E)-3,7,11,15,19,23,27,31,35,39,43-undecamethyltetratetraconta-2,6,10,14,18,22,26,30,34,38,42-undecaen-1-yl]oxy})phosphoryl]oxy}phosphonic acid

> <ALOGPS_LOGP>
9.29

> <JCHEM_LOGP>
16.894447260666666

> <ALOGPS_LOGS>
-6.40

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
3.1843406094078315

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.7672186885241006

> <JCHEM_POLAR_SURFACE_AREA>
113.29

> <JCHEM_REFRACTIVITY>
287.15130000000005

> <JCHEM_ROTATABLE_BOND_COUNT>
35

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.67e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
undecaprenyl pyrophosphate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  P   UNK     0      50.263 -16.575   0.000  0.00  0.00           P+0
HETATM    2  O   UNK     0      51.816 -16.575   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      50.263 -15.028   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      50.276 -18.121   0.000  0.00  0.00           O+0
HETATM    5  P   UNK     0      53.363 -16.575   0.000  0.00  0.00           P+0
HETATM    6  O   UNK     0      53.363 -15.028   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0      54.903 -16.575   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0      53.363 -18.121   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0      48.627 -16.551   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      -7.622 -16.442   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -6.288 -15.672   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -8.955 -15.672   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0     -10.289 -16.442   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -8.955 -14.132   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -4.954 -16.442   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -2.287 -16.442   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -0.953 -15.672   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -3.621 -15.672   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -3.621 -14.132   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       0.380 -16.442   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       3.048 -16.442   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       4.381 -15.672   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       1.714 -15.672   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       1.714 -14.132   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       5.715 -16.442   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       8.382 -16.442   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       9.716 -15.672   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       7.049 -15.672   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       7.049 -14.132   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      11.050 -16.442   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      13.717 -16.442   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      15.051 -15.672   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      12.384 -15.672   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      12.384 -14.132   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      16.385 -16.442   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      19.052 -16.442   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      20.386 -15.672   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      17.718 -15.672   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      17.718 -14.132   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      21.719 -16.442   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0      24.387 -16.442   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0      25.720 -15.672   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0      23.053 -15.672   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0      23.053 -14.132   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0      27.054 -16.442   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0      29.721 -16.442   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0      31.055 -15.672   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0      28.388 -15.672   0.000  0.00  0.00           C+0
HETATM   49  C   UNK     0      28.388 -14.132   0.000  0.00  0.00           C+0
HETATM   50  C   UNK     0      32.389 -16.442   0.000  0.00  0.00           C+0
HETATM   51  C   UNK     0      35.056 -16.442   0.000  0.00  0.00           C+0
HETATM   52  C   UNK     0      36.390 -15.672   0.000  0.00  0.00           C+0
HETATM   53  C   UNK     0      33.722 -15.672   0.000  0.00  0.00           C+0
HETATM   54  C   UNK     0      33.722 -14.132   0.000  0.00  0.00           C+0
HETATM   55  C   UNK     0      37.723 -16.442   0.000  0.00  0.00           C+0
HETATM   56  C   UNK     0      40.391 -16.442   0.000  0.00  0.00           C+0
HETATM   57  C   UNK     0      41.724 -15.672   0.000  0.00  0.00           C+0
HETATM   58  C   UNK     0      39.057 -15.672   0.000  0.00  0.00           C+0
HETATM   59  C   UNK     0      39.057 -14.132   0.000  0.00  0.00           C+0
HETATM   60  C   UNK     0      43.058 -16.442   0.000  0.00  0.00           C+0
HETATM   61  C   UNK     0      45.725 -16.442   0.000  0.00  0.00           C+0
HETATM   62  C   UNK     0      47.059 -15.672   0.000  0.00  0.00           C+0
HETATM   63  C   UNK     0      44.392 -15.672   0.000  0.00  0.00           C+0
HETATM   64  C   UNK     0      44.392 -14.132   0.000  0.00  0.00           C+0
CONECT    1    9    2    3    4                                             
CONECT    2    1    5                                                       
CONECT    3    1                                                            
CONECT    4    1                                                            
CONECT    5    2    6    7    8                                             
CONECT    6    5                                                            
CONECT    7    5                                                            
CONECT    8    5                                                            
CONECT    9    1   62                                                       
CONECT   10   11   12                                                       
CONECT   11   10   15                                                       
CONECT   12   10   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12                                                            
CONECT   15   18   11                                                       
CONECT   16   18   17                                                       
CONECT   17   20   16                                                       
CONECT   18   16   15   19                                                  
CONECT   19   18                                                            
CONECT   20   17   23                                                       
CONECT   21   22   23                                                       
CONECT   22   21   25                                                       
CONECT   23   21   20   24                                                  
CONECT   24   23                                                            
CONECT   25   22   28                                                       
CONECT   26   27   28                                                       
CONECT   27   26   30                                                       
CONECT   28   26   25   29                                                  
CONECT   29   28                                                            
CONECT   30   33   27                                                       
CONECT   31   32   33                                                       
CONECT   32   35   31                                                       
CONECT   33   30   34   31                                                  
CONECT   34   33                                                            
CONECT   35   32   38                                                       
CONECT   36   37   38                                                       
CONECT   37   36   40                                                       
CONECT   38   36   35   39                                                  
CONECT   39   38                                                            
CONECT   40   37   43                                                       
CONECT   41   42   43                                                       
CONECT   42   41   45                                                       
CONECT   43   41   40   44                                                  
CONECT   44   43                                                            
CONECT   45   42   48                                                       
CONECT   46   47   48                                                       
CONECT   47   46   50                                                       
CONECT   48   46   45   49                                                  
CONECT   49   48                                                            
CONECT   50   47   53                                                       
CONECT   51   52   53                                                       
CONECT   52   51   55                                                       
CONECT   53   51   50   54                                                  
CONECT   54   53                                                            
CONECT   55   52   58                                                       
CONECT   56   57   58                                                       
CONECT   57   56   60                                                       
CONECT   58   56   55   59                                                  
CONECT   59   58                                                            
CONECT   60   57   63                                                       
CONECT   61   62   63                                                       
CONECT   62   61    9                                                       
CONECT   63   61   60   64                                                  
CONECT   64   63                                                            
MASTER        0    0    0    0    0    0    0    0   64    0  126    0
END

View in JSmol

Synonyms

Value	Source
Diphosphoric acid, mono(3,7,11,15,19,23,27,31,35,39,43-undecamethyl-2,6,10,14,18,22,26,30,34,38,42-tetratetracontaundecaenyl) ester	ChEBI
Undecaprenyl pyrophosphate	ChEBI
UndPP	ChEBI
Diphosphate, mono(3,7,11,15,19,23,27,31,35,39,43-undecamethyl-2,6,10,14,18,22,26,30,34,38,42-tetratetracontaundecaenyl) ester	Generator
Undecaprenyl pyrophosphoric acid	Generator
Undecaprenyl diphosphoric acid	Generator
Bactoprenyl pyrophosphate	HMDB
Diphosphoric acid mono(3,7,11,15,19,23,27,31,35,39,43-undecamethyl-2,6,10,14,18,22,26,30,34,38,42-tetratetracontaundecaenyl) ester	HMDB
Undecaprenyl-PP	HMDB
UPP	HMDB

Chemical Formula

C₅₅H₉₂O₇P₂

Average Mass

927.2623 Da

Monoisotopic Mass

926.63183 Da

IUPAC Name

{[hydroxy({[(2E,6E,10E,14E,18E,22E,26E,30E,34E,38E)-3,7,11,15,19,23,27,31,35,39,43-undecamethyltetratetraconta-2,6,10,14,18,22,26,30,34,38,42-undecaen-1-yl]oxy})phosphoryl]oxy}phosphonic acid

Traditional Name

undecaprenyl pyrophosphate

CAS Registry Number

Not Available

SMILES

CC(C)=CCC\C(C)=C\CC\C(C)=C\CC\C(C)=C\CC\C(C)=C\CC\C(C)=C\CC\C(C)=C\CC\C(C)=C\CC\C(C)=C\CC\C(C)=C\CC\C(C)=C\COP(O)(=O)OP(O)(O)=O

InChI Identifier

InChI=1S/C55H92O7P2/c1-45(2)23-13-24-46(3)25-14-26-47(4)27-15-28-48(5)29-16-30-49(6)31-17-32-50(7)33-18-34-51(8)35-19-36-52(9)37-20-38-53(10)39-21-40-54(11)41-22-42-55(12)43-44-61-64(59,60)62-63(56,57)58/h23,25,27,29,31,33,35,37,39,41,43H,13-22,24,26,28,30,32,34,36,38,40,42,44H2,1-12H3,(H,59,60)(H2,56,57,58)/b46-25+,47-27+,48-29+,49-31+,50-33+,51-35+,52-37+,53-39+,54-41+,55-43+

InChI Key

NTXGVHCCXVHYCL-RDQGWRCRSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Anas platyrhynchos	FooDB	FooDB
Anatidae	FooDB	FooDB
Anser anser	FooDB	FooDB
Bison bison	FooDB	FooDB
Bos taurus	FooDB	FooDB
Bos taurus X Bison bison	FooDB	FooDB
Bubalus bubalis	FooDB	FooDB
Capra aegagrus hircus	FooDB	FooDB
Cervidae	FooDB	FooDB
Cervus canadensis	FooDB	FooDB
Columba	FooDB	FooDB
Columbidae	FooDB	FooDB
Dromaius novaehollandiae	FooDB	FooDB
Equus caballus	FooDB	FooDB
Escherichia coli	Bacteria	KNApSAcK
Gallus gallus	FooDB	FooDB
Lagopus muta	FooDB	FooDB
Leporidae	FooDB	FooDB
Lepus timidus	FooDB	FooDB
Melanitta fusca	FooDB	FooDB
Meleagris gallopavo	FooDB	FooDB
Numida meleagris	FooDB	FooDB
Odocoileus	FooDB	FooDB
Oryctolagus	FooDB	FooDB
Ovis aries	FooDB	FooDB
Phasianidae	FooDB	FooDB
Phasianus colchicus	FooDB	FooDB
Struthio camelus	FooDB	FooDB
Sus scrofa	FooDB	FooDB
Sus scrofa domestica	FooDB	FooDB

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as bactoprenol diphosphates. These are polyprenyl compounds consisting of a diphosphate group substituted by a bactoprenyl moiety.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Polyprenols

Direct Parent

Bactoprenol diphosphates

Alternative Parents

Substituents

Polyterpenoid
Bactoprenol diphosphate
Polyprenyl diphosphate
Polyprenyl monophosphate
Organic pyrophosphate
Isoprenoid phosphate
Monoalkyl phosphate
Alkyl phosphate
Phosphoric acid ester
Organic phosphoric acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

undecaprenyl phosphate (CHEBI:17047 )
undecaprenyl diphosphate (CHEBI:17047 )
all-trans-polyprenyl diphosphate (CHEBI:17047 )
Bactoprenol diphosphates (LMPR03030004 )

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	9.29	ALOGPS
logP	16.89	ChemAxon
logS	-6.4	ALOGPS
pKa (Strongest Acidic)	1.77	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	113.29 Å²	ChemAxon
Rotatable Bond Count	35	ChemAxon
Refractivity	287.15 m³·mol⁻¹	ChemAxon
Polarizability	114.77 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon