NP-MRD: Showing NP-Card for Eryngiolide A (NP0010958)

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Record Information

Version

1.0

Created at

2021-01-05 20:44:57 UTC

Updated at

2021-07-15 17:07:34 UTC

NP-MRD ID

NP0010958

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Eryngiolide A

Provided By

NPAtlas

Description

Eryngiolide A belongs to the class of organic compounds known as macrolides and analogues. These are organic compounds containing a lactone ring of at least twelve members. Eryngiolide A is found in Pleurotus eryngii. It was first documented in 2012 (PMID: 22769974). Based on a literature review very few articles have been published on Eryngiolide A.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242107423D          

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M  END

     RDKit          3D

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M  END


  Mrv1652306242107423D          

 58 60  0  0  0  0            999 V2000
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    2.1489   -1.3245    1.6216 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8414   -0.4982    0.7579 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5322   -3.2032   -0.3522 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7798   -3.0965    1.2555 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1996   -4.0177   -1.4446 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1234   -4.2905    0.0487 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9134   -3.4299   -1.3619 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1114   -1.9160   -2.2416 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8515   -1.1694    1.5828 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6839   -3.1199    0.7265 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7933   -1.3952   -0.7848 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6622    2.1129    0.5928 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7696    2.4291   -1.3569 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1524    0.6499   -1.5351 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5947    1.3278   -2.0999 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0562    0.6895   -1.2174 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9361    2.2345    1.1559 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9177    0.8644    1.5790 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1354    1.2487   -1.0143 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8379    2.8368   -0.7024 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6635    3.4006    2.1671 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2479    2.3021    2.4639 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0127    3.9366    1.6389 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4549    3.2387   -1.2989 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9870    0.9814    1.4906 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2959    2.9412   -0.0379 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  6  0  0  0
 10 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 24 26  1  6  0  0  0
 24 27  1  0  0  0  0
 27 28  1  0  0  0  0
  7  2  1  0  0  0  0
 21 15  1  0  0  0  0
 27  6  1  0  0  0  0
  1 29  1  0  0  0  0
  1 30  1  0  0  0  0
  6 31  1  6  0  0  0
  7 32  1  6  0  0  0
  8 33  1  0  0  0  0
  8 34  1  0  0  0  0
  9 35  1  0  0  0  0
  9 36  1  0  0  0  0
 11 37  1  0  0  0  0
 11 38  1  0  0  0  0
 11 39  1  0  0  0  0
 12 40  1  0  0  0  0
 13 41  1  1  0  0  0
 14 42  1  0  0  0  0
 15 43  1  6  0  0  0
 19 44  1  1  0  0  0
 20 45  1  0  0  0  0
 20 46  1  0  0  0  0
 20 47  1  0  0  0  0
 21 48  1  6  0  0  0
 22 49  1  0  0  0  0
 22 50  1  0  0  0  0
 23 51  1  0  0  0  0
 23 52  1  0  0  0  0
 25 53  1  0  0  0  0
 25 54  1  0  0  0  0
 25 55  1  0  0  0  0
 26 56  1  0  0  0  0
 27 57  1  1  0  0  0
 28 58  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0010958

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]O[C@]1([H])[C@@]2([H])OC(=O)C(=C([H])[H])[C@@]2([H])C([H])([H])C([H])([H])[C@@](O[H])(C([H])([H])[H])[C@]([H])(O[H])[C@@]2([H])OC(=O)[C@]([H])(C([H])([H])[H])[C@@]2([H])C([H])([H])C([H])([H])[C@@]1(O[H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C20H30O8/c1-9-11-5-7-19(3,25)16(22)14-12(10(2)18(24)28-14)6-8-20(4,26)15(21)13(11)27-17(9)23/h10-16,21-22,25-26H,1,5-8H2,2-4H3/t10-,11-,12-,13+,14+,15-,16-,19+,20+/m1/s1

> <INCHI_KEY>
GHZVTIKGATYJRL-WZRMTEHQSA-N

> <FORMULA>
C20H30O8

> <MOLECULAR_WEIGHT>
398.452

> <EXACT_MASS>
398.194067926

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
58

> <JCHEM_AVERAGE_POLARIZABILITY>
40.51435370224608

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,4S,5R,6S,9R,10R,13S,14R,15S)-4,5,13,14-tetrahydroxy-4,9,13-trimethyl-18-methylidene-7,16-dioxatricyclo[13.3.0.0^{6,10}]octadecane-8,17-dione

> <ALOGPS_LOGP>
0.09

> <JCHEM_LOGP>
0.35809479766666696

> <ALOGPS_LOGS>
-1.75

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.279278406150862

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.689405324201275

> <JCHEM_PKA_STRONGEST_BASIC>
-3.2445560071579242

> <JCHEM_POLAR_SURFACE_AREA>
133.52

> <JCHEM_REFRACTIVITY>
96.71740000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.03e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,4S,5R,6S,9R,10R,13S,14R,15S)-4,5,13,14-tetrahydroxy-4,9,13-trimethyl-18-methylidene-7,16-dioxatricyclo[13.3.0.0^{6,10}]octadecane-8,17-dione

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 58 60  0  0  0  0  0  0  0  0999 V2000
    4.4595   -2.0049    0.5738 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9397   -0.9411    0.0010 C   0  0  0  0  0  0  0  0  0  0  0  0
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    5.7832    0.6014    0.0763 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7589    1.0152   -1.1418 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4366    0.7245   -0.6546 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5442   -0.7598   -0.4379 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6292   -1.2664    0.6406 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9241   -2.5549    0.2931 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4323   -2.2466   -0.2989 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9774   -3.5943   -0.7873 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3548   -1.4431   -1.4141 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3625   -1.6514    0.7394 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.9729   -2.7909    1.3386 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4656   -0.8634    0.1581 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.6023   -0.9434    1.0151 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4025    0.1723    0.8743 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5322    0.3185    1.3868 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7075    1.1448    0.0300 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.3633    1.3836   -1.2899 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2892    0.5616   -0.1171 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3664    1.3673    0.7059 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3204    1.9606   -0.2015 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9156    2.4479    0.4031 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6699    3.0536    1.7931 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3754    3.5509   -0.3626 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0791    1.5333    0.5336 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.1898    2.3896    0.7854 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5080   -2.0199    0.8537 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8868   -2.8804    0.7839 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7833    0.9638   -1.5370 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4122   -1.2611   -1.4114 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1489   -1.3245    1.6216 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8414   -0.4982    0.7579 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5322   -3.2032   -0.3522 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7798   -3.0965    1.2555 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1996   -4.0177   -1.4446 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1234   -4.2905    0.0487 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9134   -3.4299   -1.3619 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1114   -1.9160   -2.2416 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8515   -1.1694    1.5828 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6839   -3.1199    0.7265 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7933   -1.3952   -0.7848 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6622    2.1129    0.5928 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7696    2.4291   -1.3569 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1524    0.6499   -1.5351 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5947    1.3278   -2.0999 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0562    0.6895   -1.2174 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9361    2.2345    1.1559 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9177    0.8644    1.5790 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1354    1.2487   -1.0143 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8379    2.8368   -0.7024 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6635    3.4006    2.1671 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2479    2.3021    2.4639 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0127    3.9366    1.6389 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4549    3.2387   -1.2989 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9870    0.9814    1.4906 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2959    2.9412   -0.0379 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 10 12  1  6
 10 13  1  0
 13 14  1  0
 13 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 17 19  1  0
 19 20  1  0
 19 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 24 26  1  6
 24 27  1  0
 27 28  1  0
  7  2  1  0
 21 15  1  0
 27  6  1  0
  1 29  1  0
  1 30  1  0
  6 31  1  6
  7 32  1  6
  8 33  1  0
  8 34  1  0
  9 35  1  0
  9 36  1  0
 11 37  1  0
 11 38  1  0
 11 39  1  0
 12 40  1  0
 13 41  1  1
 14 42  1  0
 15 43  1  6
 19 44  1  1
 20 45  1  0
 20 46  1  0
 20 47  1  0
 21 48  1  6
 22 49  1  0
 22 50  1  0
 23 51  1  0
 23 52  1  0
 25 53  1  0
 25 54  1  0
 25 55  1  0
 26 56  1  0
 27 57  1  1
 28 58  1  0
M  END

HEADER    PROTEIN                                 24-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-JUN-21         0                                  
HETATM    1  C   UNK     0       4.460  -2.005   0.574  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.940  -0.941   0.001  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.628   0.299  -0.329  0.00  0.00           C+0
HETATM    4  O   UNK     0       5.783   0.601   0.076  0.00  0.00           O+0
HETATM    5  O   UNK     0       3.759   1.015  -1.142  0.00  0.00           O+0
HETATM    6  C   UNK     0       2.437   0.725  -0.655  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.544  -0.760  -0.438  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.629  -1.266   0.641  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.924  -2.555   0.293  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.432  -2.247  -0.299  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.977  -3.594  -0.787  0.00  0.00           C+0
HETATM   12  O   UNK     0      -0.355  -1.443  -1.414  0.00  0.00           O+0
HETATM   13  C   UNK     0      -1.363  -1.651   0.739  0.00  0.00           C+0
HETATM   14  O   UNK     0      -1.973  -2.791   1.339  0.00  0.00           O+0
HETATM   15  C   UNK     0      -2.466  -0.863   0.158  0.00  0.00           C+0
HETATM   16  O   UNK     0      -3.602  -0.943   1.015  0.00  0.00           O+0
HETATM   17  C   UNK     0      -4.402   0.172   0.874  0.00  0.00           C+0
HETATM   18  O   UNK     0      -5.532   0.319   1.387  0.00  0.00           O+0
HETATM   19  C   UNK     0      -3.708   1.145   0.030  0.00  0.00           C+0
HETATM   20  C   UNK     0      -4.363   1.384  -1.290  0.00  0.00           C+0
HETATM   21  C   UNK     0      -2.289   0.562  -0.117  0.00  0.00           C+0
HETATM   22  C   UNK     0      -1.366   1.367   0.706  0.00  0.00           C+0
HETATM   23  C   UNK     0      -0.320   1.961  -0.202  0.00  0.00           C+0
HETATM   24  C   UNK     0       0.916   2.448   0.403  0.00  0.00           C+0
HETATM   25  C   UNK     0       0.670   3.054   1.793  0.00  0.00           C+0
HETATM   26  O   UNK     0       1.375   3.551  -0.363  0.00  0.00           O+0
HETATM   27  C   UNK     0       2.079   1.533   0.534  0.00  0.00           C+0
HETATM   28  O   UNK     0       3.190   2.390   0.785  0.00  0.00           O+0
HETATM   29  H   UNK     0       5.508  -2.020   0.854  0.00  0.00           H+0
HETATM   30  H   UNK     0       3.887  -2.880   0.784  0.00  0.00           H+0
HETATM   31  H   UNK     0       1.783   0.964  -1.537  0.00  0.00           H+0
HETATM   32  H   UNK     0       2.412  -1.261  -1.411  0.00  0.00           H+0
HETATM   33  H   UNK     0       2.149  -1.325   1.622  0.00  0.00           H+0
HETATM   34  H   UNK     0       0.841  -0.498   0.758  0.00  0.00           H+0
HETATM   35  H   UNK     0       1.532  -3.203  -0.352  0.00  0.00           H+0
HETATM   36  H   UNK     0       0.780  -3.096   1.256  0.00  0.00           H+0
HETATM   37  H   UNK     0      -0.200  -4.018  -1.445  0.00  0.00           H+0
HETATM   38  H   UNK     0      -1.123  -4.290   0.049  0.00  0.00           H+0
HETATM   39  H   UNK     0      -1.913  -3.430  -1.362  0.00  0.00           H+0
HETATM   40  H   UNK     0      -0.111  -1.916  -2.242  0.00  0.00           H+0
HETATM   41  H   UNK     0      -0.852  -1.169   1.583  0.00  0.00           H+0
HETATM   42  H   UNK     0      -2.684  -3.120   0.727  0.00  0.00           H+0
HETATM   43  H   UNK     0      -2.793  -1.395  -0.785  0.00  0.00           H+0
HETATM   44  H   UNK     0      -3.662   2.113   0.593  0.00  0.00           H+0
HETATM   45  H   UNK     0      -4.770   2.429  -1.357  0.00  0.00           H+0
HETATM   46  H   UNK     0      -5.152   0.650  -1.535  0.00  0.00           H+0
HETATM   47  H   UNK     0      -3.595   1.328  -2.100  0.00  0.00           H+0
HETATM   48  H   UNK     0      -2.056   0.690  -1.217  0.00  0.00           H+0
HETATM   49  H   UNK     0      -1.936   2.235   1.156  0.00  0.00           H+0
HETATM   50  H   UNK     0      -0.918   0.864   1.579  0.00  0.00           H+0
HETATM   51  H   UNK     0      -0.135   1.249  -1.014  0.00  0.00           H+0
HETATM   52  H   UNK     0      -0.838   2.837  -0.702  0.00  0.00           H+0
HETATM   53  H   UNK     0       1.664   3.401   2.167  0.00  0.00           H+0
HETATM   54  H   UNK     0       0.248   2.302   2.464  0.00  0.00           H+0
HETATM   55  H   UNK     0       0.013   3.937   1.639  0.00  0.00           H+0
HETATM   56  H   UNK     0       1.455   3.239  -1.299  0.00  0.00           H+0
HETATM   57  H   UNK     0       1.987   0.981   1.491  0.00  0.00           H+0
HETATM   58  H   UNK     0       3.296   2.941  -0.038  0.00  0.00           H+0
CONECT    1    2   29   30                                                  
CONECT    2    1    3    7                                                  
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6    5    7   27   31                                             
CONECT    7    6    8    2   32                                             
CONECT    8    7    9   33   34                                             
CONECT    9    8   10   35   36                                             
CONECT   10    9   11   12   13                                             
CONECT   11   10   37   38   39                                             
CONECT   12   10   40                                                       
CONECT   13   10   14   15   41                                             
CONECT   14   13   42                                                       
CONECT   15   13   16   21   43                                             
CONECT   16   15   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20   21   44                                             
CONECT   20   19   45   46   47                                             
CONECT   21   19   22   15   48                                             
CONECT   22   21   23   49   50                                             
CONECT   23   22   24   51   52                                             
CONECT   24   23   25   26   27                                             
CONECT   25   24   53   54   55                                             
CONECT   26   24   56                                                       
CONECT   27   24   28    6   57                                             
CONECT   28   27   58                                                       
CONECT   29    1                                                            
CONECT   30    1                                                            
CONECT   31    6                                                            
CONECT   32    7                                                            
CONECT   33    8                                                            
CONECT   34    8                                                            
CONECT   35    9                                                            
CONECT   36    9                                                            
CONECT   37   11                                                            
CONECT   38   11                                                            
CONECT   39   11                                                            
CONECT   40   12                                                            
CONECT   41   13                                                            
CONECT   42   14                                                            
CONECT   43   15                                                            
CONECT   44   19                                                            
CONECT   45   20                                                            
CONECT   46   20                                                            
CONECT   47   20                                                            
CONECT   48   21                                                            
CONECT   49   22                                                            
CONECT   50   22                                                            
CONECT   51   23                                                            
CONECT   52   23                                                            
CONECT   53   25                                                            
CONECT   54   25                                                            
CONECT   55   25                                                            
CONECT   56   26                                                            
CONECT   57   27                                                            
CONECT   58   28                                                            
MASTER        0    0    0    0    0    0    0    0   58    0  120    0
END

RDKit          3D

58 60  0  0  0  0  0  0  0  0999 V2000
    4.4595   -2.0049    0.5738 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9397   -0.9411    0.0010 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6282    0.2994   -0.3288 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7832    0.6014    0.0763 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7589    1.0152   -1.1418 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4366    0.7245   -0.6546 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5442   -0.7598   -0.4379 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6292   -1.2664    0.6406 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9241   -2.5549    0.2931 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4323   -2.2466   -0.2989 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9774   -3.5943   -0.7873 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3548   -1.4431   -1.4141 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3625   -1.6514    0.7394 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.9729   -2.7909    1.3386 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4656   -0.8634    0.1581 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.6023   -0.9434    1.0151 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4025    0.1723    0.8743 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5322    0.3185    1.3868 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7075    1.1448    0.0300 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.3633    1.3836   -1.2899 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2892    0.5616   -0.1171 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3664    1.3673    0.7059 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3204    1.9606   -0.2015 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9156    2.4479    0.4031 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6699    3.0536    1.7931 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3754    3.5509   -0.3626 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0791    1.5333    0.5336 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.1898    2.3896    0.7854 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5080   -2.0199    0.8537 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8868   -2.8804    0.7839 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7833    0.9638   -1.5370 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4122   -1.2611   -1.4114 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1489   -1.3245    1.6216 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8414   -0.4982    0.7579 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5322   -3.2032   -0.3522 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7798   -3.0965    1.2555 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1996   -4.0177   -1.4446 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1234   -4.2905    0.0487 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9134   -3.4299   -1.3619 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1114   -1.9160   -2.2416 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8515   -1.1694    1.5828 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6839   -3.1199    0.7265 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7933   -1.3952   -0.7848 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6622    2.1129    0.5928 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7696    2.4291   -1.3569 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1524    0.6499   -1.5351 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5947    1.3278   -2.0999 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0562    0.6895   -1.2174 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9361    2.2345    1.1559 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9177    0.8644    1.5790 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1354    1.2487   -1.0143 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8379    2.8368   -0.7024 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6635    3.4006    2.1671 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2479    2.3021    2.4639 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0127    3.9366    1.6389 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4549    3.2387   -1.2989 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9870    0.9814    1.4906 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2959    2.9412   -0.0379 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 10 12  1  6
 10 13  1  0
 13 14  1  0
 13 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 17 19  1  0
 19 20  1  0
 19 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 24 26  1  6
 24 27  1  0
 27 28  1  0
  7  2  1  0
 21 15  1  0
 27  6  1  0
  1 29  1  0
  1 30  1  0
  6 31  1  6
  7 32  1  6
  8 33  1  0
  8 34  1  0
  9 35  1  0
  9 36  1  0
 11 37  1  0
 11 38  1  0
 11 39  1  0
 12 40  1  0
 13 41  1  1
 14 42  1  0
 15 43  1  6
 19 44  1  1
 20 45  1  0
 20 46  1  0
 20 47  1  0
 21 48  1  6
 22 49  1  0
 22 50  1  0
 23 51  1  0
 23 52  1  0
 25 53  1  0
 25 54  1  0
 25 55  1  0
 26 56  1  0
 27 57  1  1
 28 58  1  0
M  END

View in JSmol View NMR Assignments

Synonyms

Not Available

Chemical Formula

C₂₀H₃₀O₈

Average Mass

398.4520 Da

Monoisotopic Mass

398.19407 Da

IUPAC Name

(1R,4S,5R,6S,9R,10R,13S,14R,15S)-4,5,13,14-tetrahydroxy-4,9,13-trimethyl-18-methylidene-7,16-dioxatricyclo[13.3.0.0^{6,10}]octadecane-8,17-dione

Traditional Name

(1R,4S,5R,6S,9R,10R,13S,14R,15S)-4,5,13,14-tetrahydroxy-4,9,13-trimethyl-18-methylidene-7,16-dioxatricyclo[13.3.0.0^{6,10}]octadecane-8,17-dione

CAS Registry Number

Not Available

SMILES

C[C@@H]1[C@H]2CC[C@](C)(O)[C@H](O)[C@H]3OC(=O)C(=C)[C@H]3CC[C@](C)(O)[C@H](O)[C@H]2OC1=O

InChI Identifier

InChI=1S/C20H30O8/c1-9-11-5-7-19(3,25)16(22)14-12(10(2)18(24)28-14)6-8-20(4,26)15(21)13(11)27-17(9)23/h10-16,21-22,25-26H,1,5-8H2,2-4H3/t10-,11-,12-,13+,14+,15-,16-,19+,20+/m1/s1

InChI Key

GHZVTIKGATYJRL-WZRMTEHQSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 150 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 250 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 175 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 225 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 125 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

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

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Pleurotus eryngii	NPAtlas	22769974

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as macrolides and analogues. These are organic compounds containing a lactone ring of at least twelve members.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Macrolides and analogues

Sub Class

Not Available

Direct Parent

Macrolides and analogues

Alternative Parents

Substituents

Macrolide
Dicarboxylic acid or derivatives
Gamma butyrolactone
Tertiary alcohol
Tetrahydrofuran
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Secondary alcohol
Lactone
Carboxylic acid ester
Polyol
Carboxylic acid derivative
Organoheterocyclic compound
Oxacycle
Alcohol
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Carbonyl group
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic 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	0.09	ALOGPS
logP	0.36	ChemAxon
logS	-1.8	ALOGPS
pKa (Strongest Acidic)	12.69	ChemAxon
pKa (Strongest Basic)	-3.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	133.52 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	96.72 m³·mol⁻¹	ChemAxon
Polarizability	40.51 Å³	ChemAxon
Number of Rings	3	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

NPAtlas ID

NPA008879

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

78441057

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

60200847

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Wang SJ, Li YX, Bao L, Han JJ, Yang XL, Li HR, Wang YQ, Li SJ, Liu HW: Eryngiolide A, a cytotoxic macrocyclic diterpenoid with an unusual cyclododecane core skeleton produced by the edible mushroom Pleurotus eryngii. Org Lett. 2012 Jul 20;14(14):3672-5. doi: 10.1021/ol301519m. Epub 2012 Jul 6. [PubMed:22769974 ]

Showing NP-Card for Eryngiolide A (NP0010958)

MOL for NP0010958 (Eryngiolide A)

3D MOL for NP0010958 (Eryngiolide A)

3D SDF for NP0010958 (Eryngiolide A)

3D-SDF for NP0010958 (Eryngiolide A)

PDB for NP0010958 (Eryngiolide A)

3D PDB for NP0010958 (Eryngiolide A)

SMILES for NP0010958 (Eryngiolide A)

INCHI for NP0010958 (Eryngiolide A)

Structure for NP0010958 (Eryngiolide A)

3D Structure for NP0010958 (Eryngiolide A)