NP-MRD: Showing NP-Card for ircinolin A (NP0036203)

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Record Information

Version

2.0

Created at

2021-06-20 19:26:19 UTC

Updated at

2021-06-30 00:07:44 UTC

NP-MRD ID

NP0036203

Secondary Accession Numbers

None

Natural Product Identification

Common Name

ircinolin A

Provided By

JEOL Database JEOL Logo

Description

Ircinolin A belongs to the class of organic compounds known as terpene lactones. These are prenol lipids containing a lactone ring. ircinolin A is found in Ircinia sp. ircinolin A was first documented in 2011 (PMID: 21902186). Based on a literature review very few articles have been published on Ircinolin A.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306202121263D          

 61 61  0  0  0  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1652306202121263D          

 61 61  0  0  0  0            999 V2000
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    2.4308   -1.6568    1.9079 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5260   -0.2881    0.4500 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7738   -1.2115   -4.2327 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4318   -0.4276   -5.2731 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2319   -0.5349   -5.8084 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3676    2.7585   -3.4248 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8792    1.7000   -4.7475 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1355    0.0911   -2.5747 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2994    2.5084   -3.0468 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9891    3.6536   -3.1822 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5496    4.1175   -1.3089 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1239    2.4988   -1.0275 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7485    3.3487    0.2498 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8397    1.5757   -1.0483 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0549    2.2219    1.4030 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7988    2.3172    1.3397 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9806   -0.1121    0.9485 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1231    0.2553    2.4322 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0327   -1.6016    1.2183 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8646   -0.6214   -0.2279 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0088    0.5106    3.3539 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4209   -1.1660    3.2207 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6418   -0.2932    2.7889 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8211    1.2682   -5.2020 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5620    2.2798   -3.8008 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3027    0.6027   -3.4632 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1677   -0.7152   -3.7378 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7337    1.3298   -1.4953 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2387   -0.0423   -0.8487 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1564    1.4638   -0.8308 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9811    0.0619   -0.1791 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8281    0.2401   -1.9340 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0795   -2.1756   -2.1864 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1866   -2.1617   -0.8201 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5630   -3.4433    0.1895 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2186   -2.6977   -0.7321 H   0  0  0  0  0  0  0  0  0  0  0  0
  9  7  2  0  0  0  0
  3  2  2  0  0  0  0
 27 25  1  0  0  0  0
 25 24  1  0  0  0  0
 24 23  1  0  0  0  0
 23 21  1  0  0  0  0
 25 26  2  0  0  0  0
  2 17  1  0  0  0  0
 19 20  1  0  0  0  0
  7  6  1  0  0  0  0
  2  1  1  0  0  0  0
 17 18  1  0  0  0  0
  4  5  1  0  0  0  0
 10  9  1  0  0  0  0
  7  8  1  0  0  0  0
 18 19  1  0  0  0  0
 11 12  1  0  0  0  0
  6  4  1  0  0  0  0
 12 13  1  0  0  0  0
 19 21  1  0  0  0  0
 13 15  1  0  0  0  0
 21 27  1  0  0  0  0
 13 14  2  0  0  0  0
 11 10  1  0  0  0  0
 15 16  1  0  0  0  0
  4  3  1  0  0  0  0
 21 22  1  1  0  0  0
 11 42  1  0  0  0  0
 11 43  1  0  0  0  0
 10 40  1  0  0  0  0
 10 41  1  0  0  0  0
  9 39  1  0  0  0  0
  6 34  1  0  0  0  0
  6 35  1  0  0  0  0
  4 32  1  6  0  0  0
  3 31  1  0  0  0  0
 17 49  1  0  0  0  0
 17 50  1  0  0  0  0
 18 51  1  0  0  0  0
 18 52  1  0  0  0  0
 19 53  1  1  0  0  0
 24 60  1  0  0  0  0
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 23 58  1  0  0  0  0
 23 59  1  0  0  0  0
 20 54  1  0  0  0  0
  1 28  1  0  0  0  0
  1 29  1  0  0  0  0
  1 30  1  0  0  0  0
  5 33  1  0  0  0  0
  8 36  1  0  0  0  0
  8 37  1  0  0  0  0
  8 38  1  0  0  0  0
 12 44  1  0  0  0  0
 12 45  1  0  0  0  0
 15 46  1  0  0  0  0
 15 47  1  0  0  0  0
 16 48  1  0  0  0  0
 22 55  1  0  0  0  0
 22 56  1  0  0  0  0
 22 57  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0036203

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC([H])([H])C(=O)C([H])([H])C([H])([H])C([H])([H])C(\[H])=C(/C([H])([H])[H])C([H])([H])[C@]([H])(O[H])C(\[H])=C(/C([H])([H])[H])C([H])([H])C([H])([H])[C@@]([H])(O[H])[C@]1(OC(=O)C([H])([H])C1([H])[H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C21H34O6/c1-15(6-4-5-7-17(23)14-22)12-18(24)13-16(2)8-9-19(25)21(3)11-10-20(26)27-21/h6,13,18-19,22,24-25H,4-5,7-12,14H2,1-3H3/b15-6+,16-13+/t18-,19+,21-/m0/s1

> <INCHI_KEY>
YKUZFPGHZVFVLY-DZMSUEBXSA-N

> <FORMULA>
C21H34O6

> <MOLECULAR_WEIGHT>
382.497

> <EXACT_MASS>
382.235538815

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
61

> <JCHEM_AVERAGE_POLARIZABILITY>
41.49008319078849

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(5S)-5-methyl-5-[(1R,4E,6S,8E)-1,6,14-trihydroxy-4,8-dimethyl-13-oxotetradeca-4,8-dien-1-yl]oxolan-2-one

> <ALOGPS_LOGP>
1.75

> <JCHEM_LOGP>
1.9087809763333337

> <ALOGPS_LOGS>
-4.16

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.224883220624989

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.617721307157563

> <JCHEM_PKA_STRONGEST_BASIC>
-1.3869486379826097

> <JCHEM_POLAR_SURFACE_AREA>
104.06000000000002

> <JCHEM_REFRACTIVITY>
105.09299999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
12

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.66e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(5S)-5-methyl-5-[(1R,4E,6S,8E)-1,6,14-trihydroxy-4,8-dimethyl-13-oxotetradeca-4,8-dien-1-yl]oxolan-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 61 61  0  0  0  0  0  0  0  0999 V2000
    0.6036   -0.3812   -4.9242 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.0440    0.3055    1.3397 C   0  0  0  0  0  0  0  0  0  0  0  0
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    4.1823   -1.8591   -1.1452 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1725   -2.5138   -0.2322 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.4308   -1.6568    1.9079 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.4318   -0.4276   -5.2731 H   0  0  0  0  0  0  0  0  0  0  0  0
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    0.3676    2.7585   -3.4248 H   0  0  0  0  0  0  0  0  0  0  0  0
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    0.1239    2.4988   -1.0275 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.1231    0.2553    2.4322 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0327   -1.6016    1.2183 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8646   -0.6214   -0.2279 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0088    0.5106    3.3539 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4209   -1.1660    3.2207 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6418   -0.2932    2.7889 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8211    1.2682   -5.2020 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5620    2.2798   -3.8008 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3027    0.6027   -3.4632 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1677   -0.7152   -3.7378 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7337    1.3298   -1.4953 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2387   -0.0423   -0.8487 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1564    1.4638   -0.8308 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9811    0.0619   -0.1791 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8281    0.2401   -1.9340 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0795   -2.1756   -2.1864 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1866   -2.1617   -0.8201 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5630   -3.4433    0.1895 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2186   -2.6977   -0.7321 H   0  0  0  0  0  0  0  0  0  0  0  0
  9  7  2  0
  3  2  2  0
 27 25  1  0
 25 24  1  0
 24 23  1  0
 23 21  1  0
 25 26  2  0
  2 17  1  0
 19 20  1  0
  7  6  1  0
  2  1  1  0
 17 18  1  0
  4  5  1  0
 10  9  1  0
  7  8  1  0
 18 19  1  0
 11 12  1  0
  6  4  1  0
 12 13  1  0
 19 21  1  0
 13 15  1  0
 21 27  1  0
 13 14  2  0
 11 10  1  0
 15 16  1  0
  4  3  1  0
 21 22  1  1
 11 42  1  0
 11 43  1  0
 10 40  1  0
 10 41  1  0
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  6 34  1  0
  6 35  1  0
  4 32  1  6
  3 31  1  0
 17 49  1  0
 17 50  1  0
 18 51  1  0
 18 52  1  0
 19 53  1  1
 24 60  1  0
 24 61  1  0
 23 58  1  0
 23 59  1  0
 20 54  1  0
  1 28  1  0
  1 29  1  0
  1 30  1  0
  5 33  1  0
  8 36  1  0
  8 37  1  0
  8 38  1  0
 12 44  1  0
 12 45  1  0
 15 46  1  0
 15 47  1  0
 16 48  1  0
 22 55  1  0
 22 56  1  0
 22 57  1  0
M  END

HEADER    PROTEIN                                 20-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-JUN-21         0                                  
HETATM    1  C   UNK     0       0.604  -0.381  -4.924  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.939   0.934  -4.271  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.015   1.802  -3.806  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.479   1.605  -3.731  0.00  0.00           C+0
HETATM    5  O   UNK     0      -1.787   0.289  -3.273  0.00  0.00           O+0
HETATM    6  C   UNK     0      -2.225   2.635  -2.849  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.002   2.538  -1.340  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.729   3.152  -0.824  0.00  0.00           C+0
HETATM    9  C   UNK     0      -2.946   1.968  -0.561  0.00  0.00           C+0
HETATM   10  C   UNK     0      -2.935   1.780   0.930  0.00  0.00           C+0
HETATM   11  C   UNK     0      -3.044   0.306   1.340  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.888  -0.574   0.867  0.00  0.00           C+0
HETATM   13  C   UNK     0      -0.528  -0.109   1.353  0.00  0.00           C+0
HETATM   14  O   UNK     0       0.340   0.238   0.546  0.00  0.00           O+0
HETATM   15  C   UNK     0      -0.283  -0.142   2.863  0.00  0.00           C+0
HETATM   16  O   UNK     0       1.005   0.299   3.248  0.00  0.00           O+0
HETATM   17  C   UNK     0       2.414   1.261  -4.182  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.260   0.298  -3.329  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.898   0.298  -1.831  0.00  0.00           C+0
HETATM   20  O   UNK     0       1.653  -0.392  -1.673  0.00  0.00           O+0
HETATM   21  C   UNK     0       3.978  -0.364  -0.920  0.00  0.00           C+0
HETATM   22  C   UNK     0       5.310   0.390  -0.982  0.00  0.00           C+0
HETATM   23  C   UNK     0       4.182  -1.859  -1.145  0.00  0.00           C+0
HETATM   24  C   UNK     0       3.172  -2.514  -0.232  0.00  0.00           C+0
HETATM   25  C   UNK     0       2.991  -1.482   0.835  0.00  0.00           C+0
HETATM   26  O   UNK     0       2.431  -1.657   1.908  0.00  0.00           O+0
HETATM   27  O   UNK     0       3.526  -0.288   0.450  0.00  0.00           O+0
HETATM   28  H   UNK     0       0.774  -1.212  -4.233  0.00  0.00           H+0
HETATM   29  H   UNK     0      -0.432  -0.428  -5.273  0.00  0.00           H+0
HETATM   30  H   UNK     0       1.232  -0.535  -5.808  0.00  0.00           H+0
HETATM   31  H   UNK     0       0.368   2.759  -3.425  0.00  0.00           H+0
HETATM   32  H   UNK     0      -1.879   1.700  -4.747  0.00  0.00           H+0
HETATM   33  H   UNK     0      -1.135   0.091  -2.575  0.00  0.00           H+0
HETATM   34  H   UNK     0      -3.299   2.508  -3.047  0.00  0.00           H+0
HETATM   35  H   UNK     0      -1.989   3.654  -3.182  0.00  0.00           H+0
HETATM   36  H   UNK     0      -0.550   4.117  -1.309  0.00  0.00           H+0
HETATM   37  H   UNK     0       0.124   2.499  -1.028  0.00  0.00           H+0
HETATM   38  H   UNK     0      -0.749   3.349   0.250  0.00  0.00           H+0
HETATM   39  H   UNK     0      -3.840   1.576  -1.048  0.00  0.00           H+0
HETATM   40  H   UNK     0      -2.055   2.222   1.403  0.00  0.00           H+0
HETATM   41  H   UNK     0      -3.799   2.317   1.340  0.00  0.00           H+0
HETATM   42  H   UNK     0      -3.981  -0.112   0.949  0.00  0.00           H+0
HETATM   43  H   UNK     0      -3.123   0.255   2.432  0.00  0.00           H+0
HETATM   44  H   UNK     0      -2.033  -1.602   1.218  0.00  0.00           H+0
HETATM   45  H   UNK     0      -1.865  -0.621  -0.228  0.00  0.00           H+0
HETATM   46  H   UNK     0      -1.009   0.511   3.354  0.00  0.00           H+0
HETATM   47  H   UNK     0      -0.421  -1.166   3.221  0.00  0.00           H+0
HETATM   48  H   UNK     0       1.642  -0.293   2.789  0.00  0.00           H+0
HETATM   49  H   UNK     0       2.821   1.268  -5.202  0.00  0.00           H+0
HETATM   50  H   UNK     0       2.562   2.280  -3.801  0.00  0.00           H+0
HETATM   51  H   UNK     0       4.303   0.603  -3.463  0.00  0.00           H+0
HETATM   52  H   UNK     0       3.168  -0.715  -3.738  0.00  0.00           H+0
HETATM   53  H   UNK     0       2.734   1.330  -1.495  0.00  0.00           H+0
HETATM   54  H   UNK     0       1.239  -0.042  -0.849  0.00  0.00           H+0
HETATM   55  H   UNK     0       5.156   1.464  -0.831  0.00  0.00           H+0
HETATM   56  H   UNK     0       5.981   0.062  -0.179  0.00  0.00           H+0
HETATM   57  H   UNK     0       5.828   0.240  -1.934  0.00  0.00           H+0
HETATM   58  H   UNK     0       4.080  -2.176  -2.186  0.00  0.00           H+0
HETATM   59  H   UNK     0       5.187  -2.162  -0.820  0.00  0.00           H+0
HETATM   60  H   UNK     0       3.563  -3.443   0.190  0.00  0.00           H+0
HETATM   61  H   UNK     0       2.219  -2.698  -0.732  0.00  0.00           H+0
CONECT    1    2   28   29   30                                             
CONECT    2    3   17    1                                                  
CONECT    3    2    4   31                                                  
CONECT    4    5    6    3   32                                             
CONECT    5    4   33                                                       
CONECT    6    7    4   34   35                                             
CONECT    7    9    6    8                                                  
CONECT    8    7   36   37   38                                             
CONECT    9    7   10   39                                                  
CONECT   10    9   11   40   41                                             
CONECT   11   12   10   42   43                                             
CONECT   12   11   13   44   45                                             
CONECT   13   12   15   14                                                  
CONECT   14   13                                                            
CONECT   15   13   16   46   47                                             
CONECT   16   15   48                                                       
CONECT   17    2   18   49   50                                             
CONECT   18   17   19   51   52                                             
CONECT   19   20   18   21   53                                             
CONECT   20   19   54                                                       
CONECT   21   23   19   27   22                                             
CONECT   22   21   55   56   57                                             
CONECT   23   24   21   58   59                                             
CONECT   24   25   23   60   61                                             
CONECT   25   27   24   26                                                  
CONECT   26   25                                                            
CONECT   27   25   21                                                       
CONECT   28    1                                                            
CONECT   29    1                                                            
CONECT   30    1                                                            
CONECT   31    3                                                            
CONECT   32    4                                                            
CONECT   33    5                                                            
CONECT   34    6                                                            
CONECT   35    6                                                            
CONECT   36    8                                                            
CONECT   37    8                                                            
CONECT   38    8                                                            
CONECT   39    9                                                            
CONECT   40   10                                                            
CONECT   41   10                                                            
CONECT   42   11                                                            
CONECT   43   11                                                            
CONECT   44   12                                                            
CONECT   45   12                                                            
CONECT   46   15                                                            
CONECT   47   15                                                            
CONECT   48   16                                                            
CONECT   49   17                                                            
CONECT   50   17                                                            
CONECT   51   18                                                            
CONECT   52   18                                                            
CONECT   53   19                                                            
CONECT   54   20                                                            
CONECT   55   22                                                            
CONECT   56   22                                                            
CONECT   57   22                                                            
CONECT   58   23                                                            
CONECT   59   23                                                            
CONECT   60   24                                                            
CONECT   61   24                                                            
MASTER        0    0    0    0    0    0    0    0   61    0  122    0
END

RDKit          3D

61 61  0  0  0  0  0  0  0  0999 V2000
    0.6036   -0.3812   -4.9242 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9387    0.9341   -4.2707 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.2255    2.6347   -2.8489 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0021    2.5375   -1.3401 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7289    3.1518   -0.8241 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.0440    0.3055    1.3397 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8880   -0.5736    0.8667 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5281   -0.1085    1.3527 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3400    0.2375    0.5457 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2825   -0.1415    2.8631 C   0  0  0  0  0  0  0  0  0  0  0  0
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    5.3104    0.3895   -0.9824 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1823   -1.8591   -1.1452 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1725   -2.5138   -0.2322 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9915   -1.4818    0.8354 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4308   -1.6568    1.9079 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5260   -0.2881    0.4500 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7738   -1.2115   -4.2327 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4318   -0.4276   -5.2731 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2319   -0.5349   -5.8084 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3676    2.7585   -3.4248 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8792    1.7000   -4.7475 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1355    0.0911   -2.5747 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2994    2.5084   -3.0468 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9891    3.6536   -3.1822 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5496    4.1175   -1.3089 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1239    2.4988   -1.0275 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7485    3.3487    0.2498 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8397    1.5757   -1.0483 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0549    2.2219    1.4030 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7988    2.3172    1.3397 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9806   -0.1121    0.9485 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1231    0.2553    2.4322 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0327   -1.6016    1.2183 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8646   -0.6214   -0.2279 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0088    0.5106    3.3539 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4209   -1.1660    3.2207 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6418   -0.2932    2.7889 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8211    1.2682   -5.2020 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5620    2.2798   -3.8008 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3027    0.6027   -3.4632 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1677   -0.7152   -3.7378 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7337    1.3298   -1.4953 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2387   -0.0423   -0.8487 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1564    1.4638   -0.8308 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9811    0.0619   -0.1791 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8281    0.2401   -1.9340 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0795   -2.1756   -2.1864 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1866   -2.1617   -0.8201 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5630   -3.4433    0.1895 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2186   -2.6977   -0.7321 H   0  0  0  0  0  0  0  0  0  0  0  0
  9  7  2  0
  3  2  2  0
 27 25  1  0
 25 24  1  0
 24 23  1  0
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 25 26  2  0
  2 17  1  0
 19 20  1  0
  7  6  1  0
  2  1  1  0
 17 18  1  0
  4  5  1  0
 10  9  1  0
  7  8  1  0
 18 19  1  0
 11 12  1  0
  6  4  1  0
 12 13  1  0
 19 21  1  0
 13 15  1  0
 21 27  1  0
 13 14  2  0
 11 10  1  0
 15 16  1  0
  4  3  1  0
 21 22  1  1
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 10 40  1  0
 10 41  1  0
  9 39  1  0
  6 34  1  0
  6 35  1  0
  4 32  1  6
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  1 28  1  0
  1 29  1  0
  1 30  1  0
  5 33  1  0
  8 36  1  0
  8 37  1  0
  8 38  1  0
 12 44  1  0
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 15 46  1  0
 15 47  1  0
 16 48  1  0
 22 55  1  0
 22 56  1  0
 22 57  1  0
M  END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₁H₃₄O₆

Average Mass

382.4970 Da

Monoisotopic Mass

382.23554 Da

IUPAC Name

(5S)-5-methyl-5-[(1R,4E,6S,8E)-1,6,14-trihydroxy-4,8-dimethyl-13-oxotetradeca-4,8-dien-1-yl]oxolan-2-one

Traditional Name

(5S)-5-methyl-5-[(1R,4E,6S,8E)-1,6,14-trihydroxy-4,8-dimethyl-13-oxotetradeca-4,8-dien-1-yl]oxolan-2-one

CAS Registry Number

Not Available

SMILES

[H]OC([H])([H])C(=O)C([H])([H])C([H])([H])C([H])([H])C(\[H])=C(/C([H])([H])[H])C([H])([H])[C@]([H])(O[H])C(\[H])=C(/C([H])([H])[H])C([H])([H])C([H])([H])[C@@]([H])(O[H])[C@]1(OC(=O)C([H])([H])C1([H])[H])C([H])([H])[H]

InChI Identifier

InChI=1S/C21H34O6/c1-15(6-4-5-7-17(23)14-22)12-18(24)13-16(2)8-9-19(25)21(3)11-10-20(26)27-21/h6,13,18-19,22,24-25H,4-5,7-12,14H2,1-3H3/b15-6+,16-13+/t18-,19+,21-/m0/s1

InChI Key

YKUZFPGHZVFVLY-DZMSUEBXSA-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
Ircinia sp.	JEOL database	Su, J. -H., et al, J. Nat. Prod. 74, 2005 (2011)

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as terpene lactones. These are prenol lipids containing a lactone ring.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Terpene lactones

Alternative Parents

Substituents

Terpene lactone
Sesquiterpenoid
Long chain fatty alcohol
Fatty alcohol
Gamma butyrolactone
Monosaccharide
Fatty acyl
Alpha-hydroxy ketone
Tetrahydrofuran
Secondary alcohol
Carboxylic acid ester
Ketone
Lactone
Organoheterocyclic compound
Carboxylic acid derivative
Polyol
Monocarboxylic acid or derivatives
Oxacycle
Organic oxide
Organic oxygen compound
Primary alcohol
Alcohol
Organooxygen compound
Hydrocarbon derivative
Carbonyl group
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

terpene lactone (CHEBI:69461 )

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	1.75	ALOGPS
logP	1.91	ChemAxon
logS	-4.2	ALOGPS
pKa (Strongest Acidic)	13.62	ChemAxon
pKa (Strongest Basic)	-1.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	104.06 Å²	ChemAxon
Rotatable Bond Count	12	ChemAxon
Refractivity	105.09 m³·mol⁻¹	ChemAxon
Polarizability	41.49 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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

26618407

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

54672087

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Su JH, Tseng SW, Lu MC, Liu LL, Chou Y, Sung PJ: Cytotoxic C21 and C22 terpenoid-derived metabolites from the sponge Ircinia sp. J Nat Prod. 2011 Sep 23;74(9):2005-9. doi: 10.1021/np2004209. Epub 2011 Sep 8. [PubMed:21902186 ]
Su, J. -H., et al. (2011). Su, J. -H., et al, J. Nat. Prod. 74, 2005 (2011). J. Nat. Prod..

Showing NP-Card for ircinolin A (NP0036203)

MOL for NP0036203 (ircinolin A)

3D MOL for NP0036203 (ircinolin A)

3D SDF for NP0036203 (ircinolin A)

3D-SDF for NP0036203 (ircinolin A)

PDB for NP0036203 (ircinolin A)

3D PDB for NP0036203 (ircinolin A)

SMILES for NP0036203 (ircinolin A)

INCHI for NP0036203 (ircinolin A)

Structure for NP0036203 (ircinolin A)

3D Structure for NP0036203 (ircinolin A)