NP-MRD: Showing NP-Card for Milolide C (NP0025757)

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Record Information

Version

2.0

Created at

2021-06-19 17:47:45 UTC

Updated at

2021-06-29 23:50:54 UTC

NP-MRD ID

NP0025757

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Milolide C

Provided By

JEOL Database JEOL Logo

Description

Milolide C is found in Braiareum stechei and Briareum stechei. Milolide C was first documented in 2001 (Kwak, J. H., et al.). Based on a literature review very few articles have been published on Milolide C.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306192119473D          

 65 69  0  0  0  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1652306192119473D          

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    2.1534    1.2632   -3.1309 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8552    2.5445   -2.5898 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3080    1.5416   -1.6436 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.7075    1.8217   -1.1837 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1705    1.1585   -0.6703 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5129    0.9244    0.8429 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8673    0.5873    1.1102 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0075    2.0748    1.7805 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3297    2.4479    1.4163 O   0  0  0  0  0  0  0  0  0  0  0  0
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    1.9683    3.7682    3.1667 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.2764    1.2338    3.8528 C   0  0  1  0  0  0  0  0  0  0  0  0
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   -4.1248   -2.3998   -1.6895 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7652   -3.0483   -2.6702 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4401   -3.9979   -1.3297 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5599   -2.1142   -1.8386 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0679   -1.1989   -1.8158 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3314   -1.7076   -0.3059 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7944   -0.4708   -3.1064 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8337    3.8467   -3.5723 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2560    3.1665   -4.3874 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1267    3.0391   -2.6201 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6706    1.0219   -4.6089 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3547   -0.4752   -3.9959 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0334    1.1826   -3.7576 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7328    2.5402   -0.3662 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2166    0.8994   -0.8915 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3100    2.2598   -1.9892 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5119    2.0331   -0.6978 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9808    0.0365    1.1811 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0709   -0.2462    0.6480 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9529    3.0346    1.5110 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5085    4.8636    1.1407 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1964    5.2650    0.8508 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3841    4.1163   -0.2122 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7950    0.8399    3.3988 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0891    0.5449    4.6841 H   0  0  0  0  0  0  0  0  0  0  0  0
 17 18  1  0  0  0  0
 25 27  1  0  0  0  0
 27 29  1  0  0  0  0
 29 31  1  0  0  0  0
 25 23  1  0  0  0  0
 10 11  1  6  0  0  0
  5  4  1  0  0  0  0
 23 24  1  0  0  0  0
  4  3  1  0  0  0  0
  2  1  2  3  0  0  0
  3  2  1  0  0  0  0
 27 28  1  0  0  0  0
  2 33  1  0  0  0  0
 20 21  1  1  0  0  0
 33 32  1  0  0  0  0
 22 57  1  1  0  0  0
 18 20  1  0  0  0  0
 25 26  1  6  0  0  0
 18 19  1  0  0  0  0
 29 30  2  0  0  0  0
 20 19  1  0  0  0  0
 12 13  1  0  0  0  0
 22 23  1  0  0  0  0
  5  6  1  0  0  0  0
  5 10  1  0  0  0  0
  6  7  1  0  0  0  0
 17 12  1  0  0  0  0
  7  9  2  0  0  0  0
 32 25  1  0  0  0  0
  7  8  1  0  0  0  0
 20 22  1  0  0  0  0
 13 14  1  0  0  0  0
 10 12  1  0  0  0  0
 14 15  1  0  0  0  0
 10 22  1  0  0  0  0
 14 16  2  0  0  0  0
  3 26  1  0  0  0  0
 33 34  1  0  0  0  0
 32 31  1  0  0  0  0
 17 51  1  0  0  0  0
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 12 47  1  6  0  0  0
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  4 38  1  0  0  0  0
  4 39  1  0  0  0  0
  3 37  1  1  0  0  0
 33 65  1  1  0  0  0
 18 53  1  6  0  0  0
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  1 35  1  0  0  0  0
  1 36  1  0  0  0  0
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 15 48  1  0  0  0  0
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 15 50  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0025757

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]O[C@]1([H])[C@@]2([H])[C@@]3(O[C@]3([H])C([H])([H])[C@]([H])(OC(=O)C([H])([H])[H])[C@]2(C([H])([H])[H])[C@]([H])(OC(=O)C([H])([H])[H])C([H])([H])[C@]2([H])O[C@]11[C@]([H])(C(=O)O[C@@]1([H])[C@@]([H])(Cl)C2=C([H])[H])C([H])([H])[H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C24H31ClO9/c1-9-13-7-14(30-11(3)26)22(5)15(31-12(4)27)8-16-23(6,34-16)18(22)19(28)24(33-13)10(2)21(29)32-20(24)17(9)25/h10,13-20,28H,1,7-8H2,2-6H3/t10-,13-,14+,15-,16+,17-,18+,19+,20-,22-,23+,24+/m0/s1

> <INCHI_KEY>
VMMRHHZYJGRXOJ-XWJMZCPYSA-N

> <FORMULA>
C24H31ClO9

> <MOLECULAR_WEIGHT>
498.95

> <EXACT_MASS>
498.1656603

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
65

> <JCHEM_AVERAGE_POLARIZABILITY>
48.5739034236383

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,2R,3S,4S,6R,8S,9S,10R,12S,14S,15R,18R)-10-(acetyloxy)-14-chloro-2-hydroxy-4,9,18-trimethyl-13-methylidene-17-oxo-5,16,19-trioxapentacyclo[10.6.1.0^{1,15}.0^{3,9}.0^{4,6}]nonadecan-8-yl acetate

> <ALOGPS_LOGP>
2.25

> <JCHEM_LOGP>
0.7359505483333331

> <ALOGPS_LOGS>
-3.24

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.550058893995487

> <JCHEM_PKA_STRONGEST_BASIC>
-3.4330042397663743

> <JCHEM_POLAR_SURFACE_AREA>
120.89

> <JCHEM_REFRACTIVITY>
114.95059999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.86e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2R,3S,4S,6R,8S,9S,10R,12S,14S,15R,18R)-10-(acetyloxy)-14-chloro-2-hydroxy-4,9,18-trimethyl-13-methylidene-17-oxo-5,16,19-trioxapentacyclo[10.6.1.0^{1,15}.0^{3,9}.0^{4,6}]nonadecan-8-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 65 69  0  0  0  0  0  0  0  0999 V2000
   -1.6756   -0.6239    2.9682 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1499    0.6020    2.7955 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3813    1.4882    1.5880 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.8088    0.8612    0.2377 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9868   -0.3127   -0.3417 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.9258   -1.0988   -1.1360 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2228   -2.3611   -0.7262 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2028   -2.9862   -1.6707 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7606   -2.9149    0.2602 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2789   -0.0096   -1.2519 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1074   -1.3272   -1.3082 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1724    0.3445   -2.7157 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9576    1.5553   -2.6965 O   0  0  0  0  0  0  0  0  0  0  0  0
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    2.1534    1.2632   -3.1309 C   0  0  1  0  0  0  0  0  0  0  0  0
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    1.1705    1.1585   -0.6703 C   0  0  2  0  0  0  0  0  0  0  0  0
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    2.8673    0.5873    1.1102 O   0  0  0  0  0  0  0  0  0  0  0  0
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    1.4705    4.4444    0.8260 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.2061    2.5853    4.6010 Cl  0  0  0  0  0  0  0  0  0  0  0  0
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   -4.1248   -2.3998   -1.6895 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7652   -3.0483   -2.6702 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4401   -3.9979   -1.3297 H   0  0  0  0  0  0  0  0  0  0  0  0
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    2.9529    3.0346    1.5110 H   0  0  0  0  0  0  0  0  0  0  0  0
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    1.7950    0.8399    3.3988 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0891    0.5449    4.6841 H   0  0  0  0  0  0  0  0  0  0  0  0
 17 18  1  0
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 29 31  1  0
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 23 24  1  0
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  2  1  2  3
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 22 23  1  0
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 32 25  1  0
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 15 50  1  0
M  END

HEADER    PROTEIN                                 19-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-JUN-21         0                                  
HETATM    1  C   UNK     0      -1.676  -0.624   2.968  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.150   0.602   2.796  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.381   1.488   1.588  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.809   0.861   0.238  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.987  -0.313  -0.342  0.00  0.00           C+0
HETATM    6  O   UNK     0      -1.926  -1.099  -1.136  0.00  0.00           O+0
HETATM    7  C   UNK     0      -2.223  -2.361  -0.726  0.00  0.00           C+0
HETATM    8  C   UNK     0      -3.203  -2.986  -1.671  0.00  0.00           C+0
HETATM    9  O   UNK     0      -1.761  -2.915   0.260  0.00  0.00           O+0
HETATM   10  C   UNK     0       0.279  -0.010  -1.252  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.107  -1.327  -1.308  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.172   0.345  -2.716  0.00  0.00           C+0
HETATM   13  O   UNK     0      -0.958   1.555  -2.696  0.00  0.00           O+0
HETATM   14  C   UNK     0      -1.854   1.719  -3.707  0.00  0.00           C+0
HETATM   15  C   UNK     0      -2.560   3.030  -3.555  0.00  0.00           C+0
HETATM   16  O   UNK     0      -2.064   0.918  -4.607  0.00  0.00           O+0
HETATM   17  C   UNK     0       0.997   0.516  -3.693  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.153   1.263  -3.131  0.00  0.00           C+0
HETATM   19  O   UNK     0       1.855   2.545  -2.590  0.00  0.00           O+0
HETATM   20  C   UNK     0       2.308   1.542  -1.644  0.00  0.00           C+0
HETATM   21  C   UNK     0       3.708   1.822  -1.184  0.00  0.00           C+0
HETATM   22  C   UNK     0       1.171   1.159  -0.670  0.00  0.00           C+0
HETATM   23  C   UNK     0       1.513   0.924   0.843  0.00  0.00           C+0
HETATM   24  O   UNK     0       2.867   0.587   1.110  0.00  0.00           O+0
HETATM   25  C   UNK     0       1.008   2.075   1.781  0.00  0.00           C+0
HETATM   26  O   UNK     0      -0.330   2.448   1.416  0.00  0.00           O+0
HETATM   27  C   UNK     0       1.920   3.311   1.738  0.00  0.00           C+0
HETATM   28  C   UNK     0       1.470   4.444   0.826  0.00  0.00           C+0
HETATM   29  C   UNK     0       1.968   3.768   3.167  0.00  0.00           C+0
HETATM   30  O   UNK     0       2.353   4.861   3.552  0.00  0.00           O+0
HETATM   31  O   UNK     0       1.617   2.764   4.007  0.00  0.00           O+0
HETATM   32  C   UNK     0       1.082   1.663   3.265  0.00  0.00           C+0
HETATM   33  C   UNK     0      -0.276   1.234   3.853  0.00  0.00           C+0
HETATM   34 Cl   UNK     0      -1.206   2.585   4.601  0.00  0.00          Cl+0
HETATM   35  H   UNK     0      -2.337  -1.086   2.241  0.00  0.00           H+0
HETATM   36  H   UNK     0      -1.487  -1.205   3.868  0.00  0.00           H+0
HETATM   37  H   UNK     0      -2.239   2.119   1.861  0.00  0.00           H+0
HETATM   38  H   UNK     0      -1.886   1.662  -0.503  0.00  0.00           H+0
HETATM   39  H   UNK     0      -2.841   0.505   0.372  0.00  0.00           H+0
HETATM   40  H   UNK     0      -0.658  -0.931   0.494  0.00  0.00           H+0
HETATM   41  H   UNK     0      -4.125  -2.400  -1.690  0.00  0.00           H+0
HETATM   42  H   UNK     0      -2.765  -3.048  -2.670  0.00  0.00           H+0
HETATM   43  H   UNK     0      -3.440  -3.998  -1.330  0.00  0.00           H+0
HETATM   44  H   UNK     0       0.560  -2.114  -1.839  0.00  0.00           H+0
HETATM   45  H   UNK     0       2.068  -1.199  -1.816  0.00  0.00           H+0
HETATM   46  H   UNK     0       1.331  -1.708  -0.306  0.00  0.00           H+0
HETATM   47  H   UNK     0      -0.794  -0.471  -3.106  0.00  0.00           H+0
HETATM   48  H   UNK     0      -1.834   3.847  -3.572  0.00  0.00           H+0
HETATM   49  H   UNK     0      -3.256   3.167  -4.387  0.00  0.00           H+0
HETATM   50  H   UNK     0      -3.127   3.039  -2.620  0.00  0.00           H+0
HETATM   51  H   UNK     0       0.671   1.022  -4.609  0.00  0.00           H+0
HETATM   52  H   UNK     0       1.355  -0.475  -3.996  0.00  0.00           H+0
HETATM   53  H   UNK     0       3.033   1.183  -3.758  0.00  0.00           H+0
HETATM   54  H   UNK     0       3.733   2.540  -0.366  0.00  0.00           H+0
HETATM   55  H   UNK     0       4.217   0.899  -0.892  0.00  0.00           H+0
HETATM   56  H   UNK     0       4.310   2.260  -1.989  0.00  0.00           H+0
HETATM   57  H   UNK     0       0.512   2.033  -0.698  0.00  0.00           H+0
HETATM   58  H   UNK     0       0.981   0.037   1.181  0.00  0.00           H+0
HETATM   59  H   UNK     0       3.071  -0.246   0.648  0.00  0.00           H+0
HETATM   60  H   UNK     0       2.953   3.035   1.511  0.00  0.00           H+0
HETATM   61  H   UNK     0       0.508   4.864   1.141  0.00  0.00           H+0
HETATM   62  H   UNK     0       2.196   5.265   0.851  0.00  0.00           H+0
HETATM   63  H   UNK     0       1.384   4.116  -0.212  0.00  0.00           H+0
HETATM   64  H   UNK     0       1.795   0.840   3.399  0.00  0.00           H+0
HETATM   65  H   UNK     0      -0.089   0.545   4.684  0.00  0.00           H+0
CONECT    1    2   35   36                                                  
CONECT    2    1    3   33                                                  
CONECT    3    4    2   26   37                                             
CONECT    4    5    3   38   39                                             
CONECT    5    4    6   10   40                                             
CONECT    6    5    7                                                       
CONECT    7    6    9    8                                                  
CONECT    8    7   41   42   43                                             
CONECT    9    7                                                            
CONECT   10   11    5   12   22                                             
CONECT   11   10   44   45   46                                             
CONECT   12   13   17   10   47                                             
CONECT   13   12   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14   48   49   50                                             
CONECT   16   14                                                            
CONECT   17   18   12   51   52                                             
CONECT   18   17   20   19   53                                             
CONECT   19   18   20                                                       
CONECT   20   21   18   19   22                                             
CONECT   21   20   54   55   56                                             
CONECT   22   57   23   20   10                                             
CONECT   23   25   24   22   58                                             
CONECT   24   23   59                                                       
CONECT   25   27   23   26   32                                             
CONECT   26   25    3                                                       
CONECT   27   25   29   28   60                                             
CONECT   28   27   61   62   63                                             
CONECT   29   27   31   30                                                  
CONECT   30   29                                                            
CONECT   31   29   32                                                       
CONECT   32   33   25   31   64                                             
CONECT   33    2   32   34   65                                             
CONECT   34   33                                                            
CONECT   35    1                                                            
CONECT   36    1                                                            
CONECT   37    3                                                            
CONECT   38    4                                                            
CONECT   39    4                                                            
CONECT   40    5                                                            
CONECT   41    8                                                            
CONECT   42    8                                                            
CONECT   43    8                                                            
CONECT   44   11                                                            
CONECT   45   11                                                            
CONECT   46   11                                                            
CONECT   47   12                                                            
CONECT   48   15                                                            
CONECT   49   15                                                            
CONECT   50   15                                                            
CONECT   51   17                                                            
CONECT   52   17                                                            
CONECT   53   18                                                            
CONECT   54   21                                                            
CONECT   55   21                                                            
CONECT   56   21                                                            
CONECT   57   22                                                            
CONECT   58   23                                                            
CONECT   59   24                                                            
CONECT   60   27                                                            
CONECT   61   28                                                            
CONECT   62   28                                                            
CONECT   63   28                                                            
CONECT   64   32                                                            
CONECT   65   33                                                            
MASTER        0    0    0    0    0    0    0    0   65    0  138    0
END

RDKit          3D

65 69  0  0  0  0  0  0  0  0999 V2000
   -1.6756   -0.6239    2.9682 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1499    0.6020    2.7955 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3813    1.4882    1.5880 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.8088    0.8612    0.2377 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9868   -0.3127   -0.3417 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.9258   -1.0988   -1.1360 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2228   -2.3611   -0.7262 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2028   -2.9862   -1.6707 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7606   -2.9149    0.2602 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2789   -0.0096   -1.2519 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1074   -1.3272   -1.3082 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1724    0.3445   -2.7157 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9576    1.5553   -2.6965 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8539    1.7187   -3.7073 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5602    3.0304   -3.5546 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0637    0.9182   -4.6073 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9969    0.5163   -3.6932 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1534    1.2632   -3.1309 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8552    2.5445   -2.5898 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3080    1.5416   -1.6436 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.7075    1.8217   -1.1837 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1705    1.1585   -0.6703 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5129    0.9244    0.8429 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8673    0.5873    1.1102 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0075    2.0748    1.7805 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3297    2.4479    1.4163 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9196    3.3106    1.7380 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4705    4.4444    0.8260 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9683    3.7682    3.1667 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3532    4.8611    3.5520 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6169    2.7639    4.0068 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0820    1.6629    3.2652 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2764    1.2338    3.8528 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.2061    2.5853    4.6010 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -2.3368   -1.0863    2.2413 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4866   -1.2054    3.8675 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2394    2.1188    1.8612 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8859    1.6618   -0.5033 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8405    0.5046    0.3717 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6575   -0.9314    0.4944 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1248   -2.3998   -1.6895 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7652   -3.0483   -2.6702 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4401   -3.9979   -1.3297 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5599   -2.1142   -1.8386 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0679   -1.1989   -1.8158 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3314   -1.7076   -0.3059 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7944   -0.4708   -3.1064 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8337    3.8467   -3.5723 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2560    3.1665   -4.3874 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1267    3.0391   -2.6201 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6706    1.0219   -4.6089 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3547   -0.4752   -3.9959 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0334    1.1826   -3.7576 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7328    2.5402   -0.3662 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2166    0.8994   -0.8915 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3100    2.2598   -1.9892 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5119    2.0331   -0.6978 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9808    0.0365    1.1811 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0709   -0.2462    0.6480 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9529    3.0346    1.5110 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5085    4.8636    1.1407 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1964    5.2650    0.8508 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3841    4.1163   -0.2122 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7950    0.8399    3.3988 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0891    0.5449    4.6841 H   0  0  0  0  0  0  0  0  0  0  0  0
 17 18  1  0
 25 27  1  0
 27 29  1  0
 29 31  1  0
 25 23  1  0
 10 11  1  6
  5  4  1  0
 23 24  1  0
  4  3  1  0
  2  1  2  3
  3  2  1  0
 27 28  1  0
  2 33  1  0
 20 21  1  1
 33 32  1  0
 22 57  1  1
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 25 26  1  6
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 29 30  2  0
 20 19  1  0
 12 13  1  0
 22 23  1  0
  5  6  1  0
  5 10  1  0
  6  7  1  0
 17 12  1  0
  7  9  2  0
 32 25  1  0
  7  8  1  0
 20 22  1  0
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 10 12  1  0
 14 15  1  0
 10 22  1  0
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  3 26  1  0
 33 34  1  0
 32 31  1  0
 17 51  1  0
 17 52  1  0
 12 47  1  6
 23 58  1  1
  5 40  1  1
  4 38  1  0
  4 39  1  0
  3 37  1  1
 33 65  1  1
 18 53  1  6
 32 64  1  6
 27 60  1  6
 11 44  1  0
 11 45  1  0
 11 46  1  0
 24 59  1  0
  1 35  1  0
  1 36  1  0
 28 61  1  0
 28 62  1  0
 28 63  1  0
 21 54  1  0
 21 55  1  0
 21 56  1  0
  8 41  1  0
  8 42  1  0
  8 43  1  0
 15 48  1  0
 15 49  1  0
 15 50  1  0
M  END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₄H₃₁ClO₉

Average Mass

498.9500 Da

Monoisotopic Mass

498.16566 Da

IUPAC Name

(1R,2R,3S,4S,6R,8S,9S,10R,12S,14S,15R,18R)-10-(acetyloxy)-14-chloro-2-hydroxy-4,9,18-trimethyl-13-methylidene-17-oxo-5,16,19-trioxapentacyclo[10.6.1.0^{1,15}.0^{3,9}.0^{4,6}]nonadecan-8-yl acetate

Traditional Name

(1R,2R,3S,4S,6R,8S,9S,10R,12S,14S,15R,18R)-10-(acetyloxy)-14-chloro-2-hydroxy-4,9,18-trimethyl-13-methylidene-17-oxo-5,16,19-trioxapentacyclo[10.6.1.0^{1,15}.0^{3,9}.0^{4,6}]nonadecan-8-yl acetate

CAS Registry Number

Not Available

SMILES

[H]O[C@]1([H])[C@@]2([H])[C@@]3(O[C@]3([H])C([H])([H])[C@]([H])(OC(=O)C([H])([H])[H])[C@]2(C([H])([H])[H])[C@]([H])(OC(=O)C([H])([H])[H])C([H])([H])[C@]2([H])O[C@]11[C@]([H])(C(=O)O[C@@]1([H])[C@@]([H])(Cl)C2=C([H])[H])C([H])([H])[H])C([H])([H])[H]

InChI Identifier

InChI=1S/C24H31ClO9/c1-9-13-7-14(30-11(3)26)22(5)15(31-12(4)27)8-16-23(6,34-16)18(22)19(28)24(33-13)10(2)21(29)32-20(24)17(9)25/h10,13-20,28H,1,7-8H2,2-6H3/t10-,13-,14+,15-,16+,17-,18+,19+,20-,22-,23+,24+/m0/s1

InChI Key

VMMRHHZYJGRXOJ-XWJMZCPYSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Braiareum stechei	-	KNApSAcK
Briareum stechei	JEOL database	Kwak, J. H., et al, J. Nat. Prod. 64, 754 (2001)

Chemical Taxonomy

Classification

Not classified

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	2.25	ALOGPS
logP	0.74	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Acidic)	13.55	ChemAxon
pKa (Strongest Basic)	-3.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	120.89 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	114.95 m³·mol⁻¹	ChemAxon
Polarizability	48.57 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	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

10478598

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

21776116

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Kwak, J. H., et al. (2001). Kwak, J. H., et al, J. Nat. Prod. 64, 754 (2001). J. Nat. Prod..

Showing NP-Card for Milolide C (NP0025757)

MOL for NP0025757 (Milolide C)

3D MOL for NP0025757 (Milolide C)

3D SDF for NP0025757 (Milolide C)

3D-SDF for NP0025757 (Milolide C)

PDB for NP0025757 (Milolide C)

3D PDB for NP0025757 (Milolide C)

SMILES for NP0025757 (Milolide C)

INCHI for NP0025757 (Milolide C)

Structure for NP0025757 (Milolide C)

3D Structure for NP0025757 (Milolide C)