NP-MRD: Showing NP-Card for (3s,3ar,4s,6as,10s,13r,14s,17ar)-4-ethyl-1,13,14-trihydroxy-3-[(1r)-1-(1h-indol-3-yl)ethyl]-5,10,12-trimethyl-3h,3ah,4h,6ah,9h,10h,13h,14h-cyclotrideca[d]isoindol-17-one (NP0302662)

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Record Information

Version

2.0

Created at

2022-09-10 16:23:42 UTC

Updated at

2024-09-12 20:35:34 UTC

NP-MRD ID

NP0302662

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(3s,3ar,4s,6as,10s,13r,14s,17ar)-4-ethyl-1,13,14-trihydroxy-3-[(1r)-1-(1h-indol-3-yl)ethyl]-5,10,12-trimethyl-3h,3ah,4h,6ah,9h,10h,13h,14h-cyclotrideca[d]isoindol-17-one

Description

Chaetoglobolsin-542 belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. (3s,3ar,4s,6as,10s,13r,14s,17ar)-4-ethyl-1,13,14-trihydroxy-3-[(1r)-1-(1h-indol-3-yl)ethyl]-5,10,12-trimethyl-3h,3ah,4h,6ah,9h,10h,13h,14h-cyclotrideca[d]isoindol-17-one is found in Phomopsis asparagi. Based on a literature review very few articles have been published on Chaetoglobolsin-542.

Structure

MOL SDF PDB SMILES InChI

NP0006114
  Mrv2104 05272322263D          

 82 86  0  0  0  0            999 V2000
    4.2595    1.1268   -2.1231 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4822    2.1097   -1.2578 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9519    1.9044   -1.3397 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1071    3.0976   -0.9063 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7453    4.3605   -0.4116 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

NP0006114
  Mrv2104 05272322263D          

 82 86  0  0  0  0            999 V2000
    4.2595    1.1268   -2.1231 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4822    2.1097   -1.2578 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9519    1.9044   -1.3397 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1071    3.0976   -0.9063 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7453    4.3605   -0.4116 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2295    2.9915   -1.0398 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.3521    1.6740   -1.5195 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2112    2.2640   -0.6710 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -6.5801   -1.8055   -1.3649 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3224   -3.0683    1.2808 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4544   -2.7467   -1.3398 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3105   -2.0820    2.2533 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2157   -4.4151    0.7144 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1189   -2.0784    1.1691 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8185   -1.3012   -1.2836 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8304    0.7836    2.5141 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7791    0.7629    0.9889 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2324   -1.8568    0.5663 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2580   -1.4955    2.9368 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9734   -1.0640    2.9386 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4711   -2.7208    2.5703 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4019   -3.2819   -1.2914 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7640   -3.6977   -1.9973 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3619   -2.8583   -1.3653 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5878   -1.3303    0.1670 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3624    0.0421    1.8140 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9017   -0.0756    1.9703 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7704   -0.2245   -1.4316 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 24 22  1  6  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 25 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 29 31  1  0  0  0  0
 31 32  2  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  2  0  0  0  0
 35 36  1  0  0  0  0
 36 37  2  0  0  0  0
 37 38  1  0  0  0  0
 38 39  2  0  0  0  0
 28 40  1  0  0  0  0
 40  3  1  0  0  0  0
 24  7  1  0  0  0  0
 39 31  1  0  0  0  0
 40 24  1  0  0  0  0
 39 34  1  0  0  0  0
  1 41  1  0  0  0  0
  1 42  1  0  0  0  0
  1 43  1  0  0  0  0
  2 44  1  0  0  0  0
  2 45  1  0  0  0  0
  3 46  1  6  0  0  0
  5 47  1  0  0  0  0
  5 48  1  0  0  0  0
  5 49  1  0  0  0  0
  6 50  1  0  0  0  0
  7 51  1  6  0  0  0
  8 52  1  0  0  0  0
  9 53  1  0  0  0  0
 10 54  1  0  0  0  0
 10 55  1  0  0  0  0
 11 56  1  6  0  0  0
 12 57  1  0  0  0  0
 12 58  1  0  0  0  0
 12 59  1  0  0  0  0
 13 60  1  0  0  0  0
 15 61  1  0  0  0  0
 15 62  1  0  0  0  0
 15 63  1  0  0  0  0
 16 64  1  1  0  0  0
 17 65  1  0  0  0  0
 18 66  1  1  0  0  0
 19 67  1  0  0  0  0
 20 68  1  0  0  0  0
 21 69  1  0  0  0  0
 27 70  1  0  0  0  0
 28 71  1  1  0  0  0
 29 72  1  6  0  0  0
 30 73  1  0  0  0  0
 30 74  1  0  0  0  0
 30 75  1  0  0  0  0
 32 76  1  0  0  0  0
 33 77  1  0  0  0  0
 35 78  1  0  0  0  0
 36 79  1  0  0  0  0
 37 80  1  0  0  0  0
 38 81  1  0  0  0  0
 40 82  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0302662

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]O[C@@]1([H])\C([H])=C([H])\C(=O)[C@@]23C(=O)N([H])[C@@]([H])([C@@]([H])(C4=C([H])N([H])C5=C([H])C([H])=C([H])C([H])=C45)C([H])([H])[H])[C@]2([H])[C@@]([H])(C(=C([H])[C@]3([H])\C([H])=C([H])\C([H])([H])[C@@]([H])(\C([H])=C(C([H])([H])[H])\[C@@]1([H])O[H])C([H])([H])[H])C([H])([H])[H])C([H])([H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1/C34H42N2O4/c1-6-24-20(3)17-23-11-9-10-19(2)16-21(4)32(39)28(37)14-15-29(38)34(23)30(24)31(36-33(34)40)22(5)26-18-35-27-13-8-7-12-25(26)27/h7-9,11-19,22-24,28,30-32,35,37,39H,6,10H2,1-5H3,(H,36,40)/b11-9+,15-14+,21-16+/t19-,22+,23-,24+,28-,30-,31-,32+,34+/s2

> <INCHI_KEY>
HLDZSBBZXQCNRA-INCCLJDCNA-N

> <FORMULA>
C34H42N2O4

> <MOLECULAR_WEIGHT>
542.72

> <EXACT_MASS>
542.31445784

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
82

> <JCHEM_AVERAGE_POLARIZABILITY>
61.12363212783353

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(3S,3aR,4S,6aS,10S,13R,14S,17aS)-4-ethyl-13,14-dihydroxy-3-[(1R)-1-(1H-indol-3-yl)ethyl]-5,10,12-trimethyl-1H,2H,3H,3aH,4H,6aH,9H,10H,13H,14H,17H-cyclotrideca[d]isoindole-1,17-dione

> <JCHEM_LOGP>
5.271120271333331

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.315446334524502

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.304285815295268

> <JCHEM_PKA_STRONGEST_BASIC>
-2.33336915167258

> <JCHEM_POLAR_SURFACE_AREA>
102.41999999999999

> <JCHEM_REFRACTIVITY>
162.07759999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(3S,3aR,4S,6aS,10S,13R,14S,17aS)-4-ethyl-13,14-dihydroxy-3-[(1R)-1-(1H-indol-3-yl)ethyl]-5,10,12-trimethyl-2H,3H,3aH,4H,6aH,9H,10H,13H,14H-cyclotrideca[d]isoindole-1,17-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 27-MAY-23   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: NP0006114                                         
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-23         0                                  
HETATM    1  C   UNK     0       4.260   1.127  -2.123  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.482   2.110  -1.258  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.952   1.904  -1.340  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.107   3.098  -0.906  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.745   4.361  -0.412  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.230   2.991  -1.040  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.834   1.670  -1.467  0.00  0.00           C+0
HETATM    8  C   UNK     0      -2.352   1.674  -1.520  0.00  0.00           C+0
HETATM    9  C   UNK     0      -3.211   2.264  -0.671  0.00  0.00           C+0
HETATM   10  C   UNK     0      -4.710   2.127  -0.777  0.00  0.00           C+0
HETATM   11  C   UNK     0      -5.393   1.400   0.408  0.00  0.00           C+0
HETATM   12  C   UNK     0      -5.297   2.209   1.708  0.00  0.00           C+0
HETATM   13  C   UNK     0      -4.826   0.009   0.627  0.00  0.00           C+0
HETATM   14  C   UNK     0      -5.347  -1.192   0.292  0.00  0.00           C+0
HETATM   15  C   UNK     0      -6.694  -1.356  -0.373  0.00  0.00           C+0
HETATM   16  C   UNK     0      -4.655  -2.522   0.601  0.00  0.00           C+0
HETATM   17  O   UNK     0      -4.605  -3.339  -0.584  0.00  0.00           O+0
HETATM   18  C   UNK     0      -3.239  -2.563   1.270  0.00  0.00           C+0
HETATM   19  O   UNK     0      -2.903  -3.940   1.511  0.00  0.00           O+0
HETATM   20  C   UNK     0      -2.027  -1.995   0.575  0.00  0.00           C+0
HETATM   21  C   UNK     0      -1.968  -1.396  -0.623  0.00  0.00           C+0
HETATM   22  C   UNK     0      -0.705  -0.826  -1.161  0.00  0.00           C+0
HETATM   23  O   UNK     0      -0.198  -1.402  -2.127  0.00  0.00           O+0
HETATM   24  C   UNK     0      -0.179   0.515  -0.643  0.00  0.00           C+0
HETATM   25  C   UNK     0      -0.398   0.742   0.850  0.00  0.00           C+0
HETATM   26  O   UNK     0      -1.448   0.913   1.448  0.00  0.00           O+0
HETATM   27  N   UNK     0       0.808   0.705   1.504  0.00  0.00           N+0
HETATM   28  C   UNK     0       1.887   0.211   0.692  0.00  0.00           C+0
HETATM   29  C   UNK     0       2.114  -1.316   0.934  0.00  0.00           C+0
HETATM   30  C   UNK     0       2.214  -1.665   2.429  0.00  0.00           C+0
HETATM   31  C   UNK     0       3.311  -1.857   0.189  0.00  0.00           C+0
HETATM   32  C   UNK     0       3.249  -2.789  -0.831  0.00  0.00           C+0
HETATM   33  N   UNK     0       4.521  -3.054  -1.258  0.00  0.00           N+0
HETATM   34  C   UNK     0       5.427  -2.310  -0.540  0.00  0.00           C+0
HETATM   35  C   UNK     0       6.822  -2.256  -0.642  0.00  0.00           C+0
HETATM   36  C   UNK     0       7.503  -1.395   0.222  0.00  0.00           C+0
HETATM   37  C   UNK     0       6.814  -0.621   1.150  0.00  0.00           C+0
HETATM   38  C   UNK     0       5.418  -0.690   1.240  0.00  0.00           C+0
HETATM   39  C   UNK     0       4.702  -1.549   0.380  0.00  0.00           C+0
HETATM   40  C   UNK     0       1.413   0.551  -0.746  0.00  0.00           C+0
HETATM   41  H   UNK     0       4.030   0.092  -1.875  0.00  0.00           H+0
HETATM   42  H   UNK     0       4.025   1.276  -3.182  0.00  0.00           H+0
HETATM   43  H   UNK     0       5.336   1.279  -1.994  0.00  0.00           H+0
HETATM   44  H   UNK     0       3.745   3.110  -1.622  0.00  0.00           H+0
HETATM   45  H   UNK     0       3.840   2.064  -0.226  0.00  0.00           H+0
HETATM   46  H   UNK     0       1.761   1.836  -2.424  0.00  0.00           H+0
HETATM   47  H   UNK     0       2.336   4.834  -1.202  0.00  0.00           H+0
HETATM   48  H   UNK     0       2.395   4.151   0.444  0.00  0.00           H+0
HETATM   49  H   UNK     0       0.999   5.091  -0.081  0.00  0.00           H+0
HETATM   50  H   UNK     0      -0.878   3.831  -0.807  0.00  0.00           H+0
HETATM   51  H   UNK     0      -0.547   1.537  -2.522  0.00  0.00           H+0
HETATM   52  H   UNK     0      -2.770   1.092  -2.342  0.00  0.00           H+0
HETATM   53  H   UNK     0      -2.835   2.838   0.174  0.00  0.00           H+0
HETATM   54  H   UNK     0      -5.135   3.134  -0.875  0.00  0.00           H+0
HETATM   55  H   UNK     0      -4.971   1.599  -1.704  0.00  0.00           H+0
HETATM   56  H   UNK     0      -6.460   1.344   0.170  0.00  0.00           H+0
HETATM   57  H   UNK     0      -5.713   3.213   1.570  0.00  0.00           H+0
HETATM   58  H   UNK     0      -5.865   1.722   2.509  0.00  0.00           H+0
HETATM   59  H   UNK     0      -4.264   2.316   2.054  0.00  0.00           H+0
HETATM   60  H   UNK     0      -3.862   0.037   1.135  0.00  0.00           H+0
HETATM   61  H   UNK     0      -7.333  -2.009   0.231  0.00  0.00           H+0
HETATM   62  H   UNK     0      -7.236  -0.419  -0.512  0.00  0.00           H+0
HETATM   63  H   UNK     0      -6.580  -1.806  -1.365  0.00  0.00           H+0
HETATM   64  H   UNK     0      -5.322  -3.068   1.281  0.00  0.00           H+0
HETATM   65  H   UNK     0      -4.454  -2.747  -1.340  0.00  0.00           H+0
HETATM   66  H   UNK     0      -3.311  -2.082   2.253  0.00  0.00           H+0
HETATM   67  H   UNK     0      -3.216  -4.415   0.714  0.00  0.00           H+0
HETATM   68  H   UNK     0      -1.119  -2.078   1.169  0.00  0.00           H+0
HETATM   69  H   UNK     0      -2.818  -1.301  -1.284  0.00  0.00           H+0
HETATM   70  H   UNK     0       0.830   0.784   2.514  0.00  0.00           H+0
HETATM   71  H   UNK     0       2.779   0.763   0.989  0.00  0.00           H+0
HETATM   72  H   UNK     0       1.232  -1.857   0.566  0.00  0.00           H+0
HETATM   73  H   UNK     0       1.258  -1.496   2.937  0.00  0.00           H+0
HETATM   74  H   UNK     0       2.973  -1.064   2.939  0.00  0.00           H+0
HETATM   75  H   UNK     0       2.471  -2.721   2.570  0.00  0.00           H+0
HETATM   76  H   UNK     0       2.402  -3.282  -1.291  0.00  0.00           H+0
HETATM   77  H   UNK     0       4.764  -3.698  -1.997  0.00  0.00           H+0
HETATM   78  H   UNK     0       7.362  -2.858  -1.365  0.00  0.00           H+0
HETATM   79  H   UNK     0       8.588  -1.330   0.167  0.00  0.00           H+0
HETATM   80  H   UNK     0       7.362   0.042   1.814  0.00  0.00           H+0
HETATM   81  H   UNK     0       4.902  -0.076   1.970  0.00  0.00           H+0
HETATM   82  H   UNK     0       1.770  -0.225  -1.432  0.00  0.00           H+0
CONECT    1    2   41   42   43                                             
CONECT    2    1    3   44   45                                             
CONECT    3    2    4   40   46                                             
CONECT    4    3    5    6                                                  
CONECT    5    4   47   48   49                                             
CONECT    6    4    7   50                                                  
CONECT    7    6    8   24   51                                             
CONECT    8    7    9   52                                                  
CONECT    9    8   10   53                                                  
CONECT   10    9   11   54   55                                             
CONECT   11   10   12   13   56                                             
CONECT   12   11   57   58   59                                             
CONECT   13   11   14   60                                                  
CONECT   14   13   15   16                                                  
CONECT   15   14   61   62   63                                             
CONECT   16   14   17   18   64                                             
CONECT   17   16   65                                                       
CONECT   18   16   19   20   66                                             
CONECT   19   18   67                                                       
CONECT   20   18   21   68                                                  
CONECT   21   20   22   69                                                  
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25    7   40                                             
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   28   70                                                  
CONECT   28   27   29   40   71                                             
CONECT   29   28   30   31   72                                             
CONECT   30   29   73   74   75                                             
CONECT   31   29   32   39                                                  
CONECT   32   31   33   76                                                  
CONECT   33   32   34   77                                                  
CONECT   34   33   35   39                                                  
CONECT   35   34   36   78                                                  
CONECT   36   35   37   79                                                  
CONECT   37   36   38   80                                                  
CONECT   38   37   39   81                                                  
CONECT   39   38   31   34                                                  
CONECT   40   28    3   24   82                                             
CONECT   41    1                                                            
CONECT   42    1                                                            
CONECT   43    1                                                            
CONECT   44    2                                                            
CONECT   45    2                                                            
CONECT   46    3                                                            
CONECT   47    5                                                            
CONECT   48    5                                                            
CONECT   49    5                                                            
CONECT   50    6                                                            
CONECT   51    7                                                            
CONECT   52    8                                                            
CONECT   53    9                                                            
CONECT   54   10                                                            
CONECT   55   10                                                            
CONECT   56   11                                                            
CONECT   57   12                                                            
CONECT   58   12                                                            
CONECT   59   12                                                            
CONECT   60   13                                                            
CONECT   61   15                                                            
CONECT   62   15                                                            
CONECT   63   15                                                            
CONECT   64   16                                                            
CONECT   65   17                                                            
CONECT   66   18                                                            
CONECT   67   19                                                            
CONECT   68   20                                                            
CONECT   69   21                                                            
CONECT   70   27                                                            
CONECT   71   28                                                            
CONECT   72   29                                                            
CONECT   73   30                                                            
CONECT   74   30                                                            
CONECT   75   30                                                            
CONECT   76   32                                                            
CONECT   77   33                                                            
CONECT   78   35                                                            
CONECT   79   36                                                            
CONECT   80   37                                                            
CONECT   81   38                                                            
CONECT   82   40                                                            
MASTER        0    0    0    0    0    0    0    0   82    0  172    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₄H₄₂N₂O₄

Average Mass

542.7200 Da

Monoisotopic Mass

542.31446 Da

IUPAC Name

(3S,3aR,4S,6aS,10S,13R,14S,17aS)-4-ethyl-13,14-dihydroxy-3-[(1R)-1-(1H-indol-3-yl)ethyl]-5,10,12-trimethyl-1H,2H,3H,3aH,4H,6aH,9H,10H,13H,14H,17H-cyclotrideca[d]isoindole-1,17-dione

Traditional Name

(3S,3aR,4S,6aS,10S,13R,14S,17aS)-4-ethyl-13,14-dihydroxy-3-[(1R)-1-(1H-indol-3-yl)ethyl]-5,10,12-trimethyl-2H,3H,3aH,4H,6aH,9H,10H,13H,14H-cyclotrideca[d]isoindole-1,17-dione

CAS Registry Number

Not Available

SMILES

[H]O[C@@]1([H])\C([H])=C([H])\C(=O)[C@@]23C(=O)N([H])[C@@]([H])([C@@]([H])(C4=C([H])N([H])C5=C([H])C([H])=C([H])C([H])=C45)C([H])([H])[H])[C@]2([H])[C@@]([H])(C(=C([H])[C@]3([H])\C([H])=C([H])\C([H])([H])[C@@]([H])(\C([H])=C(C([H])([H])[H])\[C@@]1([H])O[H])C([H])([H])[H])C([H])([H])[H])C([H])([H])C([H])([H])[H]

InChI Identifier

InChI=1/C34H42N2O4/c1-6-24-20(3)17-23-11-9-10-19(2)16-21(4)32(39)28(37)14-15-29(38)34(23)30(24)31(36-33(34)40)22(5)26-18-35-27-13-8-7-12-25(26)27/h7-9,11-19,22-24,28,30-32,35,37,39H,6,10H2,1-5H3,(H,36,40)/b11-9+,15-14+,21-16+/t19-,22+,23-,24+,28-,30-,31-,32+,34+/s2

InChI Key

HLDZSBBZXQCNRA-INCCLJDCNA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Phomopsis asparagi	LOTUS Database	35616633

Chemical Taxonomy

Description

This compound belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Sesquiterpenoids

Alternative Parents

Substituents

Farsesane sesquiterpenoid
Sesquiterpenoid
Isoindolone
Isoindole or derivatives
Isoindoline
Indole or derivatives
Indole
Fatty acyl
Benzenoid
2-pyrrolidone
Pyrrolidone
N-acyl-amine
Fatty amide
Heteroaromatic compound
Alpha,beta-unsaturated ketone
Pyrrolidine
Pyrrole
Enone
Acryloyl-group
Secondary alcohol
Lactam
Ketone
Carboxamide group
Azacycle
Organoheterocyclic compound
Carboxylic acid derivative
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Alcohol
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

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	5.27	ChemAxon
pKa (Strongest Acidic)	13.3	ChemAxon
pKa (Strongest Basic)	-2.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	102.42 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	162.08 m³·mol⁻¹	ChemAxon
Polarizability	61.12 Å³	ChemAxon
Number of Rings	5	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

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (3s,3ar,4s,6as,10s,13r,14s,17ar)-4-ethyl-1,13,14-trihydroxy-3-[(1r)-1-(1h-indol-3-yl)ethyl]-5,10,12-trimethyl-3h,3ah,4h,6ah,9h,10h,13h,14h-cyclotrideca[d]isoindol-17-one (NP0302662)

MOL for NP0302662 ((3s,3ar,4s,6as,10s,13r,14s,17ar)-4-ethyl-1,13,14-trihydroxy-3-[(1r)-1-(1h-indol-3-yl)ethyl]-5,10,12-trimethyl-3h,3ah,4h,6ah,9h,10h,13h,14h-cyclotrideca[d]isoindol-17-one)

3D MOL for NP0302662 ((3s,3ar,4s,6as,10s,13r,14s,17ar)-4-ethyl-1,13,14-trihydroxy-3-[(1r)-1-(1h-indol-3-yl)ethyl]-5,10,12-trimethyl-3h,3ah,4h,6ah,9h,10h,13h,14h-cyclotrideca[d]isoindol-17-one)

3D SDF for NP0302662 ((3s,3ar,4s,6as,10s,13r,14s,17ar)-4-ethyl-1,13,14-trihydroxy-3-[(1r)-1-(1h-indol-3-yl)ethyl]-5,10,12-trimethyl-3h,3ah,4h,6ah,9h,10h,13h,14h-cyclotrideca[d]isoindol-17-one)

3D-SDF for NP0302662 ((3s,3ar,4s,6as,10s,13r,14s,17ar)-4-ethyl-1,13,14-trihydroxy-3-[(1r)-1-(1h-indol-3-yl)ethyl]-5,10,12-trimethyl-3h,3ah,4h,6ah,9h,10h,13h,14h-cyclotrideca[d]isoindol-17-one)

PDB for NP0302662 ((3s,3ar,4s,6as,10s,13r,14s,17ar)-4-ethyl-1,13,14-trihydroxy-3-[(1r)-1-(1h-indol-3-yl)ethyl]-5,10,12-trimethyl-3h,3ah,4h,6ah,9h,10h,13h,14h-cyclotrideca[d]isoindol-17-one)

3D PDB for NP0302662 ((3s,3ar,4s,6as,10s,13r,14s,17ar)-4-ethyl-1,13,14-trihydroxy-3-[(1r)-1-(1h-indol-3-yl)ethyl]-5,10,12-trimethyl-3h,3ah,4h,6ah,9h,10h,13h,14h-cyclotrideca[d]isoindol-17-one)

SMILES for NP0302662 ((3s,3ar,4s,6as,10s,13r,14s,17ar)-4-ethyl-1,13,14-trihydroxy-3-[(1r)-1-(1h-indol-3-yl)ethyl]-5,10,12-trimethyl-3h,3ah,4h,6ah,9h,10h,13h,14h-cyclotrideca[d]isoindol-17-one)

INCHI for NP0302662 ((3s,3ar,4s,6as,10s,13r,14s,17ar)-4-ethyl-1,13,14-trihydroxy-3-[(1r)-1-(1h-indol-3-yl)ethyl]-5,10,12-trimethyl-3h,3ah,4h,6ah,9h,10h,13h,14h-cyclotrideca[d]isoindol-17-one)

Structure for NP0302662 ((3s,3ar,4s,6as,10s,13r,14s,17ar)-4-ethyl-1,13,14-trihydroxy-3-[(1r)-1-(1h-indol-3-yl)ethyl]-5,10,12-trimethyl-3h,3ah,4h,6ah,9h,10h,13h,14h-cyclotrideca[d]isoindol-17-one)

3D Structure for NP0302662 ((3s,3ar,4s,6as,10s,13r,14s,17ar)-4-ethyl-1,13,14-trihydroxy-3-[(1r)-1-(1h-indol-3-yl)ethyl]-5,10,12-trimethyl-3h,3ah,4h,6ah,9h,10h,13h,14h-cyclotrideca[d]isoindol-17-one)