NP-MRD: Showing NP-Card for (2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-{[(12-methyltetradecanoyl)oxy]methyl}oxan-2-yl (2e,4e,6e,8e,10e,12e,14e,16e,18e)-2,6,10,15,19,23-hexamethyltetracosa-2,4,6,8,10,12,14,16,18,22-decaenoate (NP0207326)

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Record Information

Version

2.0

Created at

2022-09-05 03:53:39 UTC

Updated at

2022-09-05 03:53:39 UTC

NP-MRD ID

NP0207326

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-{[(12-methyltetradecanoyl)oxy]methyl}oxan-2-yl (2e,4e,6e,8e,10e,12e,14e,16e,18e)-2,6,10,15,19,23-hexamethyltetracosa-2,4,6,8,10,12,14,16,18,22-decaenoate

Description

Staphyloxanthin belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units. (2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-{[(12-methyltetradecanoyl)oxy]methyl}oxan-2-yl (2e,4e,6e,8e,10e,12e,14e,16e,18e)-2,6,10,15,19,23-hexamethyltetracosa-2,4,6,8,10,12,14,16,18,22-decaenoate was first documented in 2005 (PMID: 16020541). Staphyloxanthin is an extremely weak basic (essentially neutral) compound (based on its pKa) (PMID: 16861688) (PMID: 18276850) (PMID: 19456099).

Structure

MOL 3D MOL SDF PDB SMILES InChI

 
  Mrv1533007211515372D          
 
 59 59  0  0  1  0            999 V2000
    3.1765   -7.7172    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8894   -7.3032    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5999   -7.7172    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3128   -7.3032    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0258   -7.7172    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7363   -7.3032    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4491   -7.7172    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1621   -7.3032    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8725   -7.7172    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5855   -7.3032    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2984   -7.7172    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0113   -7.3032    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7217   -7.7172    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4346   -7.3032    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1476   -7.7172    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3252  -10.7322    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.6241  -10.3264    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9106  -10.7383    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.9106  -11.5646    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.6070  -11.9679    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.3252  -11.5560    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1839  -11.9814    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1838  -10.3199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6071  -12.8020    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9052  -12.1385    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7422  -10.7381    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4579  -10.3237    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1714  -10.7381    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8873  -10.3237    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6031  -10.7381    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3166  -10.3237    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0324  -10.7381    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7458  -10.3237    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4616  -10.7381    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1775  -10.3237    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8884  -10.7381    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6067  -10.3237    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3177  -10.7381    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0336  -10.3237    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7494  -10.7381    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4629  -10.3237    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1787  -10.7381    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8920  -10.3237    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6078  -10.7381    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.3238  -10.3237    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.0371  -10.7381    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.7529  -10.3237    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.4665  -10.7381    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.1822  -10.3237    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4579   -9.5001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.4665  -11.5643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6078  -11.5643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7494  -11.5641    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3166   -9.5001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1775   -9.4999    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0285  -10.3236    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7422  -11.5640    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8821   -6.4801    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.7169   -8.5404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 14 15  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  4  5  1  0  0  0  0
  9 10  1  0  0  0  0
  2  3  1  0  0  0  0
 10 11  1  0  0  0  0
  5  6  1  0  0  0  0
 11 12  1  0  0  0  0
  1  2  1  0  0  0  0
 12 13  1  0  0  0  0
  6  7  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 16 21  1  0  0  0  0
 19 22  1  6  0  0  0
 18 23  1  1  0  0  0
 20 24  1  1  0  0  0
 21 25  1  6  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 30 31  1  0  0  0  0
 31 32  2  0  0  0  0
 32 33  1  0  0  0  0
 33 34  2  0  0  0  0
 34 35  1  0  0  0  0
 35 36  2  0  0  0  0
 36 37  1  0  0  0  0
 37 38  2  0  0  0  0
 38 39  1  0  0  0  0
 39 40  2  0  0  0  0
 40 41  1  0  0  0  0
 41 42  2  0  0  0  0
 42 43  1  0  0  0  0
 43 44  2  0  0  0  0
 44 45  1  0  0  0  0
 45 46  1  0  0  0  0
 46 47  1  0  0  0  0
 47 48  2  0  0  0  0
 48 49  1  0  0  0  0
 27 50  1  0  0  0  0
 48 51  1  0  0  0  0
 44 52  1  0  0  0  0
 40 53  1  0  0  0  0
 31 54  1  0  0  0  0
 35 55  1  0  0  0  0
 26 56  1  0  0  0  0
 26 57  2  0  0  0  0
 16 56  1  1  0  0  0
 23  1  1  0  0  0  0
 13 14  1  0  0  0  0
  2 58  2  0  0  0  0
  3  4  1  0  0  0  0
 13 59  1  0  0  0  0
M  END

     RDKit          3D

137137  0  0  0  0  0  0  0  0999 V2000
    2.0877   -5.6499   -0.6119 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2317   -4.7126   -1.8121 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7171   -5.4462   -3.0081 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2454   -5.7769   -2.7474 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9135   -4.7532   -4.3131 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2076   -3.3908   -4.3827 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4806   -2.8157   -5.7169 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8437   -1.6074   -6.1589 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9343   -0.2813   -5.5557 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4070   -0.1636   -4.1717 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4010    1.2861   -3.7500 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7021    1.9600   -3.7296 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6212    1.3150   -2.6977 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9387    2.0839   -2.6751 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8918    1.5642   -1.6752 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9515    0.9924   -2.0812 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6964    1.6569   -0.2913 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7316    1.1154    0.5225 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4474    1.1086    1.9817 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.2231    2.3299    2.5329 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7759    2.3651    3.8291 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4545    2.7779    3.8231 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8609    3.8613    4.4804 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.4469    3.9794    4.2488 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7602    2.9763    3.3090 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6199    4.8981    4.7829 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7498    4.8599    4.4378 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -6.6286    5.3857    3.5494 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2854    4.5258    2.6465 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3173    3.9876    1.4947 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5385    4.3024    2.2296 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6058    3.2351    1.3052 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6811    2.2969    0.4866 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6024    1.3905    0.2382 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4458    0.4271   -0.6312 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5272    0.1874   -1.5637 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2389   -0.3757   -0.4033 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7571   -1.3513   -1.1347 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5132   -2.0114   -0.6663 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8734   -2.9242   -1.3043 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4456   -3.3239   -2.6384 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6258   -3.5764   -0.7392 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3684   -3.0766    0.6487 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.2753   -4.3548   -1.9504 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6284   -3.8074   -1.6171 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2488   -6.4267   -3.0193 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1389   -5.0609   -2.0011 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1157   -6.8323   -2.4537 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3592   -5.6355   -3.6812 H   0  0  0  0  0  0  0  0  0  0  0  0
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    0.1513   -3.5497   -4.2065 H   0  0  0  0  0  0  0  0  0  0  0  0
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    6.5957    1.7367    0.3527 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0146    0.0770    0.1701 H   0  0  0  0  0  0  0  0  0  0  0  0
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    5.3591    3.1056    4.4196 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2940    3.4587    2.4634 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0784    2.4013    3.9809 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5045    2.2670    2.9599 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.0364    3.9793    3.8129 H   0  0  0  0  0  0  0  0  0  0  0  0
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 56134  1  6
 57135  1  0
 58136  1  1
 59137  1  0
M  END

 
  Mrv1533007211515372D          
 
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   11.7169   -8.5404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 14 15  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  4  5  1  0  0  0  0
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  2  3  1  0  0  0  0
 10 11  1  0  0  0  0
  5  6  1  0  0  0  0
 11 12  1  0  0  0  0
  1  2  1  0  0  0  0
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  6  7  1  0  0  0  0
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 16 21  1  0  0  0  0
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 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 28 29  1  0  0  0  0
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 30 31  1  0  0  0  0
 31 32  2  0  0  0  0
 32 33  1  0  0  0  0
 33 34  2  0  0  0  0
 34 35  1  0  0  0  0
 35 36  2  0  0  0  0
 36 37  1  0  0  0  0
 37 38  2  0  0  0  0
 38 39  1  0  0  0  0
 39 40  2  0  0  0  0
 40 41  1  0  0  0  0
 41 42  2  0  0  0  0
 42 43  1  0  0  0  0
 43 44  2  0  0  0  0
 44 45  1  0  0  0  0
 45 46  1  0  0  0  0
 46 47  1  0  0  0  0
 47 48  2  0  0  0  0
 48 49  1  0  0  0  0
 27 50  1  0  0  0  0
 48 51  1  0  0  0  0
 44 52  1  0  0  0  0
 40 53  1  0  0  0  0
 31 54  1  0  0  0  0
 35 55  1  0  0  0  0
 26 56  1  0  0  0  0
 26 57  2  0  0  0  0
 16 56  1  1  0  0  0
 23  1  1  0  0  0  0
 13 14  1  0  0  0  0
  2 58  2  0  0  0  0
  3  4  1  0  0  0  0
 13 59  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0207326

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCC(C)CCCCCCCCCCC(=O)OC[C@H]1O[C@@H](OC(=O)C(\C)=C\C=C\C(\C)=C\C=C\C(\C)=C\C=C\C=C(/C)\C=C\C=C(/C)CCC=C(C)C)[C@H](O)[C@@H](O)[C@@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C51H78O8/c1-10-39(4)26-17-15-13-11-12-14-16-18-36-46(52)57-37-45-47(53)48(54)49(55)51(58-45)59-50(56)44(9)35-24-34-43(8)33-23-31-41(6)28-20-19-27-40(5)30-22-32-42(7)29-21-25-38(2)3/h19-20,22-25,27-28,30-35,39,45,47-49,51,53-55H,10-18,21,26,29,36-37H2,1-9H3/b20-19+,30-22+,31-23+,34-24+,40-27+,41-28+,42-32+,43-33+,44-35+/t39?,45-,47-,48+,49-,51+/m1/s1

> <INCHI_KEY>
PDOUICUKTQRPHO-MENSNCDRSA-N

> <FORMULA>
C51H78O8

> <MOLECULAR_WEIGHT>
819.177

> <EXACT_MASS>
818.569669472

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
137

> <JCHEM_AVERAGE_POLARIZABILITY>
102.59433783599422

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-{[(12-methyltetradecanoyl)oxy]methyl}oxan-2-yl (2E,4E,6E,8E,10E,12E,14E,16E,18E)-2,6,10,15,19,23-hexamethyltetracosa-2,4,6,8,10,12,14,16,18,22-decaenoate

> <ALOGPS_LOGP>
9.16

> <JCHEM_LOGP>
12.450218433666667

> <ALOGPS_LOGS>
-6.24

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.2090019832632

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.197274382977161

> <JCHEM_PKA_STRONGEST_BASIC>
-3.6491055724468664

> <JCHEM_POLAR_SURFACE_AREA>
122.52000000000001

> <JCHEM_REFRACTIVITY>
252.1706000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
29

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.71e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-{[(12-methyltetradecanoyl)oxy]methyl}oxan-2-yl (2E,4E,6E,8E,10E,12E,14E,16E,18E)-2,6,10,15,19,23-hexamethyltetracosa-2,4,6,8,10,12,14,16,18,22-decaenoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 21-JUL-15   NONE
TITLE     NULL                                                        
COMPND    MOLECULE:                                                   
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   21-JUL-15         0                                  
HETATM    1  O   UNK     0       5.930 -14.405   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       7.260 -13.633   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.586 -14.405   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       9.917 -13.633   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      11.248 -14.405   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      12.574 -13.633   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      13.905 -14.405   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      15.236 -13.633   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      16.562 -14.405   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      17.893 -13.633   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      19.224 -14.405   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      20.554 -13.633   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      21.881 -14.405   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      23.211 -13.633   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      24.542 -14.405   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       9.940 -20.033   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       8.632 -19.276   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       7.300 -20.045   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       7.300 -21.587   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       8.600 -22.340   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       9.940 -21.571   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       5.943 -22.365   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       5.943 -19.264   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       8.600 -23.897   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0      11.023 -22.659   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      12.585 -20.044   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      13.921 -19.271   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      15.253 -20.044   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      16.590 -19.271   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      17.926 -20.044   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      19.258 -19.271   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      20.594 -20.044   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      21.925 -19.271   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      23.262 -20.044   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      24.598 -19.271   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      25.925 -20.044   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      27.266 -19.271   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      28.593 -20.044   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      29.929 -19.271   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      31.266 -20.044   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0      32.597 -19.271   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0      33.934 -20.044   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0      35.265 -19.271   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0      36.601 -20.044   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0      37.938 -19.271   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0      39.269 -20.044   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0      40.605 -19.271   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0      41.937 -20.044   0.000  0.00  0.00           C+0
HETATM   49  C   UNK     0      43.273 -19.271   0.000  0.00  0.00           C+0
HETATM   50  C   UNK     0      13.921 -17.733   0.000  0.00  0.00           C+0
HETATM   51  C   UNK     0      41.937 -21.587   0.000  0.00  0.00           C+0
HETATM   52  C   UNK     0      36.601 -21.587   0.000  0.00  0.00           C+0
HETATM   53  C   UNK     0      31.266 -21.586   0.000  0.00  0.00           C+0
HETATM   54  C   UNK     0      19.258 -17.734   0.000  0.00  0.00           C+0
HETATM   55  C   UNK     0      24.598 -17.733   0.000  0.00  0.00           C+0
HETATM   56  O   UNK     0      11.253 -19.271   0.000  0.00  0.00           O+0
HETATM   57  O   UNK     0      12.585 -21.586   0.000  0.00  0.00           O+0
HETATM   58  O   UNK     0       7.247 -12.096   0.000  0.00  0.00           O+0
HETATM   59  C   UNK     0      21.871 -15.942   0.000  0.00  0.00           C+0
CONECT    1    2   23                                                       
CONECT    2    3    1   58                                                  
CONECT    3    2    4                                                       
CONECT    4    5    3                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    8    6                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   59                                                  
CONECT   14   15   13                                                       
CONECT   15   14                                                            
CONECT   16   17   21   56                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19   23                                                  
CONECT   19   18   20   22                                                  
CONECT   20   19   21   24                                                  
CONECT   21   20   16   25                                                  
CONECT   22   19                                                            
CONECT   23   18    1                                                       
CONECT   24   20                                                            
CONECT   25   21                                                            
CONECT   26   27   56   57                                                  
CONECT   27   26   28   50                                                  
CONECT   28   27   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   32   54                                                  
CONECT   32   31   33                                                       
CONECT   33   32   34                                                       
CONECT   34   33   35                                                       
CONECT   35   34   36   55                                                  
CONECT   36   35   37                                                       
CONECT   37   36   38                                                       
CONECT   38   37   39                                                       
CONECT   39   38   40                                                       
CONECT   40   39   41   53                                                  
CONECT   41   40   42                                                       
CONECT   42   41   43                                                       
CONECT   43   42   44                                                       
CONECT   44   43   45   52                                                  
CONECT   45   44   46                                                       
CONECT   46   45   47                                                       
CONECT   47   46   48                                                       
CONECT   48   47   49   51                                                  
CONECT   49   48                                                            
CONECT   50   27                                                            
CONECT   51   48                                                            
CONECT   52   44                                                            
CONECT   53   40                                                            
CONECT   54   31                                                            
CONECT   55   35                                                            
CONECT   56   26   16                                                       
CONECT   57   26                                                            
CONECT   58    2                                                            
CONECT   59   13                                                            
MASTER        0    0    0    0    0    0    0    0   59    0  118    0
END

View in JSmol

Synonyms

Value	Source
8'-Apo-psi,psi-carotenoic acid, 6-O-(12-methyl-1-oxotetradecyl)-alpha-D-glucopyranosyl ester	ChEBI
beta-D-Glucopyranosyl 1-O-(4,4'-diaponeurosporen-4-Oate)-6-O-(12-methyltetradecanoate)	ChEBI
8'-Apo-psi,psi-carotenoate, 6-O-(12-methyl-1-oxotetradecyl)-a-D-glucopyranosyl ester	Generator
8'-Apo-psi,psi-carotenoate, 6-O-(12-methyl-1-oxotetradecyl)-alpha-D-glucopyranosyl ester	Generator
8'-Apo-psi,psi-carotenoate, 6-O-(12-methyl-1-oxotetradecyl)-α-D-glucopyranosyl ester	Generator
8'-Apo-psi,psi-carotenoic acid, 6-O-(12-methyl-1-oxotetradecyl)-a-D-glucopyranosyl ester	Generator
8'-Apo-psi,psi-carotenoic acid, 6-O-(12-methyl-1-oxotetradecyl)-α-D-glucopyranosyl ester	Generator
b-D-Glucopyranosyl 1-O-(4,4'-diaponeurosporen-4-Oate)-6-O-(12-methyltetradecanoate)	Generator
b-D-Glucopyranosyl 1-O-(4,4'-diaponeurosporen-4-Oic acid)-6-O-(12-methyltetradecanoic acid)	Generator
beta-D-Glucopyranosyl 1-O-(4,4'-diaponeurosporen-4-Oic acid)-6-O-(12-methyltetradecanoic acid)	Generator
Β-D-glucopyranosyl 1-O-(4,4'-diaponeurosporen-4-Oate)-6-O-(12-methyltetradecanoate)	Generator
Β-D-glucopyranosyl 1-O-(4,4'-diaponeurosporen-4-Oic acid)-6-O-(12-methyltetradecanoic acid)	Generator
Alapha-D-glucopyranosyl 1-O-(4,4'-diaponeurosporen-4-Oate) 6-O-(12-methyltetradecanoate)	MeSH

Chemical Formula

C₅₁H₇₈O₈

Average Mass

819.1770 Da

Monoisotopic Mass

818.56967 Da

IUPAC Name

(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-{[(12-methyltetradecanoyl)oxy]methyl}oxan-2-yl (2E,4E,6E,8E,10E,12E,14E,16E,18E)-2,6,10,15,19,23-hexamethyltetracosa-2,4,6,8,10,12,14,16,18,22-decaenoate

Traditional Name

(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-{[(12-methyltetradecanoyl)oxy]methyl}oxan-2-yl (2E,4E,6E,8E,10E,12E,14E,16E,18E)-2,6,10,15,19,23-hexamethyltetracosa-2,4,6,8,10,12,14,16,18,22-decaenoate

CAS Registry Number

Not Available

SMILES

CCC(C)CCCCCCCCCCC(=O)OC[C@H]1O[C@@H](OC(=O)C(\C)=C\C=C\C(\C)=C\C=C\C(\C)=C\C=C\C=C(/C)\C=C\C=C(/C)CCC=C(C)C)[C@H](O)[C@@H](O)[C@@H]1O

InChI Identifier

InChI=1S/C51H78O8/c1-10-39(4)26-17-15-13-11-12-14-16-18-36-46(52)57-37-45-47(53)48(54)49(55)51(58-45)59-50(56)44(9)35-24-34-43(8)33-23-31-41(6)28-20-19-27-40(5)30-22-32-42(7)29-21-25-38(2)3/h19-20,22-25,27-28,30-35,39,45,47-49,51,53-55H,10-18,21,26,29,36-37H2,1-9H3/b20-19+,30-22+,31-23+,34-24+,40-27+,41-28+,42-32+,43-33+,44-35+/t39?,45-,47-,48+,49-,51+/m1/s1

InChI Key

PDOUICUKTQRPHO-MENSNCDRSA-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, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Triterpenoids

Direct Parent

Triterpenoids

Alternative Parents

Substituents

Triterpenoid
Saccharolipid
Fatty acid ester
Dicarboxylic acid or derivatives
Monosaccharide
Fatty acyl
Oxane
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Carboxylic acid ester
Secondary alcohol
Acetal
Carboxylic acid derivative
Oxacycle
Organoheterocyclic compound
Polyol
Organic oxide
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

fatty acid ester (CHEBI:71690 )
triol (CHEBI:71690 )
apo carotenoid triterpenoid (CHEBI:71690 )
xanthophyll (CHEBI:71690 )
D-aldohexose derivative (CHEBI:71690 )

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	9.16	ALOGPS
logP	12.45	ChemAxon
logS	-6.2	ALOGPS
pKa (Strongest Acidic)	12.2	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	122.52 Å²	ChemAxon
Rotatable Bond Count	29	ChemAxon
Refractivity	252.17 m³·mol⁻¹	ChemAxon
Polarizability	102.59 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

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

C16148

BioCyc ID

CPD-9916

BiGG ID

Not Available

Wikipedia Link

Staphyloxanthin

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

71690

Good Scents ID

Not Available

References

General References

Pelz A, Wieland KP, Putzbach K, Hentschel P, Albert K, Gotz F: Structure and biosynthesis of staphyloxanthin from Staphylococcus aureus. J Biol Chem. 2005 Sep 16;280(37):32493-8. doi: 10.1074/jbc.M505070200. Epub 2005 Jul 14. [PubMed:16020541 ]
Clauditz A, Resch A, Wieland KP, Peschel A, Gotz F: Staphyloxanthin plays a role in the fitness of Staphylococcus aureus and its ability to cope with oxidative stress. Infect Immun. 2006 Aug;74(8):4950-3. doi: 10.1128/IAI.00204-06. [PubMed:16861688 ]
Liu CI, Liu GY, Song Y, Yin F, Hensler ME, Jeng WY, Nizet V, Wang AH, Oldfield E: A cholesterol biosynthesis inhibitor blocks Staphylococcus aureus virulence. Science. 2008 Mar 7;319(5868):1391-4. doi: 10.1126/science.1153018. Epub 2008 Feb 14. [PubMed:18276850 ]
Song Y, Liu CI, Lin FY, No JH, Hensler M, Liu YL, Jeng WY, Low J, Liu GY, Nizet V, Wang AH, Oldfield E: Inhibition of staphyloxanthin virulence factor biosynthesis in Staphylococcus aureus: in vitro, in vivo, and crystallographic results. J Med Chem. 2009 Jul 9;52(13):3869-80. doi: 10.1021/jm9001764. [PubMed:19456099 ]
LOTUS database [Link]

Showing NP-Card for (2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-{[(12-methyltetradecanoyl)oxy]methyl}oxan-2-yl (2e,4e,6e,8e,10e,12e,14e,16e,18e)-2,6,10,15,19,23-hexamethyltetracosa-2,4,6,8,10,12,14,16,18,22-decaenoate (NP0207326)

MOL for NP0207326 ((2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-{[(12-methyltetradecanoyl)oxy]methyl}oxan-2-yl (2e,4e,6e,8e,10e,12e,14e,16e,18e)-2,6,10,15,19,23-hexamethyltetracosa-2,4,6,8,10,12,14,16,18,22-decaenoate)

3D MOL for NP0207326 ((2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-{[(12-methyltetradecanoyl)oxy]methyl}oxan-2-yl (2e,4e,6e,8e,10e,12e,14e,16e,18e)-2,6,10,15,19,23-hexamethyltetracosa-2,4,6,8,10,12,14,16,18,22-decaenoate)

3D SDF for NP0207326 ((2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-{[(12-methyltetradecanoyl)oxy]methyl}oxan-2-yl (2e,4e,6e,8e,10e,12e,14e,16e,18e)-2,6,10,15,19,23-hexamethyltetracosa-2,4,6,8,10,12,14,16,18,22-decaenoate)

3D-SDF for NP0207326 ((2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-{[(12-methyltetradecanoyl)oxy]methyl}oxan-2-yl (2e,4e,6e,8e,10e,12e,14e,16e,18e)-2,6,10,15,19,23-hexamethyltetracosa-2,4,6,8,10,12,14,16,18,22-decaenoate)

PDB for NP0207326 ((2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-{[(12-methyltetradecanoyl)oxy]methyl}oxan-2-yl (2e,4e,6e,8e,10e,12e,14e,16e,18e)-2,6,10,15,19,23-hexamethyltetracosa-2,4,6,8,10,12,14,16,18,22-decaenoate)

3D PDB for NP0207326 ((2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-{[(12-methyltetradecanoyl)oxy]methyl}oxan-2-yl (2e,4e,6e,8e,10e,12e,14e,16e,18e)-2,6,10,15,19,23-hexamethyltetracosa-2,4,6,8,10,12,14,16,18,22-decaenoate)

SMILES for NP0207326 ((2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-{[(12-methyltetradecanoyl)oxy]methyl}oxan-2-yl (2e,4e,6e,8e,10e,12e,14e,16e,18e)-2,6,10,15,19,23-hexamethyltetracosa-2,4,6,8,10,12,14,16,18,22-decaenoate)

INCHI for NP0207326 ((2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-{[(12-methyltetradecanoyl)oxy]methyl}oxan-2-yl (2e,4e,6e,8e,10e,12e,14e,16e,18e)-2,6,10,15,19,23-hexamethyltetracosa-2,4,6,8,10,12,14,16,18,22-decaenoate)

Structure for NP0207326 ((2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-{[(12-methyltetradecanoyl)oxy]methyl}oxan-2-yl (2e,4e,6e,8e,10e,12e,14e,16e,18e)-2,6,10,15,19,23-hexamethyltetracosa-2,4,6,8,10,12,14,16,18,22-decaenoate)

3D Structure for NP0207326 ((2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-{[(12-methyltetradecanoyl)oxy]methyl}oxan-2-yl (2e,4e,6e,8e,10e,12e,14e,16e,18e)-2,6,10,15,19,23-hexamethyltetracosa-2,4,6,8,10,12,14,16,18,22-decaenoate)