NP-MRD: Showing NP-Card for Chenopodolin (NP0011862)

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Record Information

Version

2.0

Created at

2021-01-05 21:25:22 UTC

Updated at

2021-07-15 17:10:10 UTC

NP-MRD ID

NP0011862

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Chenopodolin

Provided By

NPAtlas

Description

Chenopodolin is found in Didymella chenopodii and Phoma. Chenopodolin was first documented in 2013 (PMID: 23786488). Based on a literature review very few articles have been published on (1S,2S,7S,8S,10R,11S,12S,13S,16S)-8-(acetyloxy)-7-ethenyl-16-hydroxy-1,7,11-trimethyl-3,15-dioxo-14-oxatetracyclo[11.2.1.0²,¹¹.0⁵,¹⁰]Hexadec-4-en-12-yl acetate.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242116593D          

 62 65  0  0  0  0            999 V2000
    4.3396   -0.4403   -1.6293 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2590   -0.8130   -0.9837 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9973   -0.2962    0.3843 C   0  0  2  0  0  0  0  0  0  0  0  0
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  1  2  2  3  0  0  0
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M  END

     RDKit          3D

 62 65  0  0  0  0  0  0  0  0999 V2000
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M  END


  Mrv1652306242116593D          

 62 65  0  0  0  0            999 V2000
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   -1.6033    3.2571   -0.0684 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2158   -0.5326   -0.6067 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0551   -0.6686   -2.1014 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0790   -0.2854    0.1032 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9627    0.6933   -0.6276 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1452    0.9915    0.3113 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.9027    2.0851   -0.1339 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0888    3.2192    0.6322 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8902    4.3823    0.1673 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5568    3.2684    1.7717 O   0  0  0  0  0  0  0  0  0  0  0  0
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    4.1279    0.1756    2.1552 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5858    1.0818    0.6419 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0665   -0.6908    0.8706 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8866   -0.7502    2.1420 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6711   -2.2226    1.3633 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1633   -3.5622    0.4941 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7331   -1.7545    1.0269 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0769   -3.9881    0.6597 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4791   -4.1143   -1.1310 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6798   -3.5189    0.0412 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2570    1.0089   -0.1413 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5554   -1.0321    1.4020 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7149   -1.6951    1.1057 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.4144    3.3584    2.5383 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8829    4.3056    2.2035 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0719    2.7645    3.0773 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0450   -1.7550   -2.4130 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8699   -0.1870   -2.6789 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1316   -0.2606   -2.5152 H   0  0  0  0  0  0  0  0  0  0  0  0
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    0.4643    1.6336   -0.8307 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4922    0.2368   -1.5099 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7267    1.1382    1.3170 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4831    4.7542    1.0247 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2442    5.2057   -0.1743 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6354    4.0771   -0.6105 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3  0  0  0
  3  2  1  6  0  0  0
  3  4  1  0  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  1  0  0  0
 11 13  1  0  0  0  0
 13 14  2  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  1  0  0  0  0
 16 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  2  0  0  0  0
 19 24  1  0  0  0  0
 24 25  1  6  0  0  0
 24 26  1  0  0  0  0
 26 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
 30 31  1  0  0  0  0
 30 32  2  0  0  0  0
 28  3  1  0  0  0  0
 26  6  1  0  0  0  0
 24 10  1  0  0  0  0
 17 11  1  0  0  0  0
  1 33  1  0  0  0  0
  1 34  1  0  0  0  0
  2 35  1  0  0  0  0
  4 36  1  0  0  0  0
  4 37  1  0  0  0  0
  4 38  1  0  0  0  0
  5 39  1  0  0  0  0
  5 40  1  0  0  0  0
  7 41  1  0  0  0  0
 10 42  1  1  0  0  0
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 16 46  1  1  0  0  0
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 18 48  1  0  0  0  0
 19 49  1  6  0  0  0
 22 50  1  0  0  0  0
 22 51  1  0  0  0  0
 22 52  1  0  0  0  0
 25 53  1  0  0  0  0
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 27 57  1  0  0  0  0
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 28 59  1  1  0  0  0
 31 60  1  0  0  0  0
 31 61  1  0  0  0  0
 31 62  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0011862

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]O[C@]1([H])[C@]2([H])OC(=O)[C@@]1(C([H])([H])[H])[C@@]1([H])C(=O)C([H])=C3C([H])([H])[C@](C([H])=C([H])[H])(C([H])([H])[H])[C@@]([H])(OC(=O)C([H])([H])[H])C([H])([H])[C@@]3([H])[C@]1(C([H])([H])[H])[C@]2([H])OC(=O)C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C24H30O8/c1-7-22(4)10-13-8-15(27)18-23(5,14(13)9-16(22)30-11(2)25)20(31-12(3)26)17-19(28)24(18,6)21(29)32-17/h7-8,14,16-20,28H,1,9-10H2,2-6H3/t14-,16+,17+,18+,19-,20-,22-,23+,24+/m1/s1

> <INCHI_KEY>
LIOQTLKMMDOYDZ-RHMXXYPNSA-N

> <FORMULA>
C24H30O8

> <MOLECULAR_WEIGHT>
446.496

> <EXACT_MASS>
446.194067926

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
62

> <JCHEM_AVERAGE_POLARIZABILITY>
45.66693070257137

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,2S,7S,8S,10R,11S,12S,13S,16S)-8-(acetyloxy)-7-ethenyl-16-hydroxy-1,7,11-trimethyl-3,15-dioxo-14-oxatetracyclo[11.2.1.0^{2,11}.0^{5,10}]hexadec-4-en-12-yl acetate

> <ALOGPS_LOGP>
1.36

> <JCHEM_LOGP>
1.5948792393333338

> <ALOGPS_LOGS>
-3.86

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.119813084765063

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.33097910861591

> <JCHEM_PKA_STRONGEST_BASIC>
-3.508449693205212

> <JCHEM_POLAR_SURFACE_AREA>
116.20000000000002

> <JCHEM_REFRACTIVITY>
111.38960000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.22e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2S,7S,8S,10R,11S,12S,13S,16S)-8-(acetyloxy)-7-ethenyl-16-hydroxy-1,7,11-trimethyl-3,15-dioxo-14-oxatetracyclo[11.2.1.0^{2,11}.0^{5,10}]hexadec-4-en-12-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 62 65  0  0  0  0  0  0  0  0999 V2000
    4.3396   -0.4403   -1.6293 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2590   -0.8130   -0.9837 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.5042   -2.7451    0.2130 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7748   -2.9015   -0.4641 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9557   -3.8454   -1.2520 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7527   -1.8551   -0.1057 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.1649   -2.1126   -0.4641 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.5903   -3.5024   -0.1905 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5932   -1.6924   -1.8033 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.6412    0.1581   -0.4384 C   0  0  1  0  0  0  0  0  0  0  0  0
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   -5.2932   -1.3554    0.2853 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1971    0.5825   -0.3420 C   0  0  1  0  0  0  0  0  0  0  0  0
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   -1.6968    2.5721    0.9812 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4761    3.2759    2.2705 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6033    3.2571   -0.0684 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2158   -0.5326   -0.6067 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0551   -0.6686   -2.1014 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0790   -0.2854    0.1032 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9627    0.6933   -0.6276 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1452    0.9915    0.3113 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.9027    2.0851   -0.1339 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0888    3.2192    0.6322 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8902    4.3823    0.1673 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5568    3.2684    1.7717 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5486   -0.8018   -2.6197 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0338    0.2381   -1.1679 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5750   -1.4965   -1.4687 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1279    0.1756    2.1552 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5858    1.0818    0.6419 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0665   -0.6908    0.8706 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8866   -0.7502    2.1420 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6711   -2.2226    1.3633 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.7331   -1.7545    1.0269 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0769   -3.9881    0.6597 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4791   -4.1143   -1.1310 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6798   -3.5189    0.0412 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2570    1.0089   -0.1413 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5554   -1.0321    1.4020 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7149   -1.6951    1.1057 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0599    1.3393   -1.1424 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4144    3.3584    2.5383 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8829    4.3056    2.2035 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0719    2.7645    3.0773 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0450   -1.7550   -2.4130 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8699   -0.1870   -2.6789 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.1944    0.2363    1.0689 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4643    1.6336   -0.8307 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4922    0.2368   -1.5099 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7267    1.1382    1.3170 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4831    4.7542    1.0247 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2442    5.2057   -0.1743 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6354    4.0771   -0.6105 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  3  2  1  6
  3  4  1  0
  3  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 11 12  1  1
 11 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 16 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 21 23  2  0
 19 24  1  0
 24 25  1  6
 24 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  1  0
 29 30  1  0
 30 31  1  0
 30 32  2  0
 28  3  1  0
 26  6  1  0
 24 10  1  0
 17 11  1  0
  1 33  1  0
  1 34  1  0
  2 35  1  0
  4 36  1  0
  4 37  1  0
  4 38  1  0
  5 39  1  0
  5 40  1  0
  7 41  1  0
 10 42  1  1
 12 43  1  0
 12 44  1  0
 12 45  1  0
 16 46  1  1
 17 47  1  1
 18 48  1  0
 19 49  1  6
 22 50  1  0
 22 51  1  0
 22 52  1  0
 25 53  1  0
 25 54  1  0
 25 55  1  0
 26 56  1  1
 27 57  1  0
 27 58  1  0
 28 59  1  1
 31 60  1  0
 31 61  1  0
 31 62  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       4.340  -0.440  -1.629  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.259  -0.813  -0.984  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.997  -0.296   0.384  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.281   0.077   1.050  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.173  -1.258   1.179  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.863  -1.471   0.471  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.504  -2.745   0.213  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.775  -2.902  -0.464  0.00  0.00           C+0
HETATM    9  O   UNK     0      -0.956  -3.845  -1.252  0.00  0.00           O+0
HETATM   10  C   UNK     0      -1.753  -1.855  -0.106  0.00  0.00           C+0
HETATM   11  C   UNK     0      -3.165  -2.113  -0.464  0.00  0.00           C+0
HETATM   12  C   UNK     0      -3.590  -3.502  -0.191  0.00  0.00           C+0
HETATM   13  C   UNK     0      -3.593  -1.692  -1.803  0.00  0.00           C+0
HETATM   14  O   UNK     0      -3.671  -2.323  -2.888  0.00  0.00           O+0
HETATM   15  O   UNK     0      -3.954  -0.331  -1.728  0.00  0.00           O+0
HETATM   16  C   UNK     0      -3.641   0.158  -0.438  0.00  0.00           C+0
HETATM   17  C   UNK     0      -3.952  -1.089   0.388  0.00  0.00           C+0
HETATM   18  O   UNK     0      -5.293  -1.355   0.285  0.00  0.00           O+0
HETATM   19  C   UNK     0      -2.197   0.583  -0.342  0.00  0.00           C+0
HETATM   20  O   UNK     0      -1.993   1.231   0.890  0.00  0.00           O+0
HETATM   21  C   UNK     0      -1.697   2.572   0.981  0.00  0.00           C+0
HETATM   22  C   UNK     0      -1.476   3.276   2.271  0.00  0.00           C+0
HETATM   23  O   UNK     0      -1.603   3.257  -0.068  0.00  0.00           O+0
HETATM   24  C   UNK     0      -1.216  -0.533  -0.607  0.00  0.00           C+0
HETATM   25  C   UNK     0      -1.055  -0.669  -2.101  0.00  0.00           C+0
HETATM   26  C   UNK     0       0.079  -0.285   0.103  0.00  0.00           C+0
HETATM   27  C   UNK     0       0.963   0.693  -0.628  0.00  0.00           C+0
HETATM   28  C   UNK     0       2.145   0.992   0.311  0.00  0.00           C+0
HETATM   29  O   UNK     0       2.903   2.085  -0.134  0.00  0.00           O+0
HETATM   30  C   UNK     0       3.089   3.219   0.632  0.00  0.00           C+0
HETATM   31  C   UNK     0       3.890   4.382   0.167  0.00  0.00           C+0
HETATM   32  O   UNK     0       2.557   3.268   1.772  0.00  0.00           O+0
HETATM   33  H   UNK     0       4.549  -0.802  -2.620  0.00  0.00           H+0
HETATM   34  H   UNK     0       5.034   0.238  -1.168  0.00  0.00           H+0
HETATM   35  H   UNK     0       2.575  -1.496  -1.469  0.00  0.00           H+0
HETATM   36  H   UNK     0       4.128   0.176   2.155  0.00  0.00           H+0
HETATM   37  H   UNK     0       4.586   1.082   0.642  0.00  0.00           H+0
HETATM   38  H   UNK     0       5.066  -0.691   0.871  0.00  0.00           H+0
HETATM   39  H   UNK     0       1.887  -0.750   2.142  0.00  0.00           H+0
HETATM   40  H   UNK     0       2.671  -2.223   1.363  0.00  0.00           H+0
HETATM   41  H   UNK     0       1.163  -3.562   0.494  0.00  0.00           H+0
HETATM   42  H   UNK     0      -1.733  -1.755   1.027  0.00  0.00           H+0
HETATM   43  H   UNK     0      -3.077  -3.988   0.660  0.00  0.00           H+0
HETATM   44  H   UNK     0      -3.479  -4.114  -1.131  0.00  0.00           H+0
HETATM   45  H   UNK     0      -4.680  -3.519   0.041  0.00  0.00           H+0
HETATM   46  H   UNK     0      -4.257   1.009  -0.141  0.00  0.00           H+0
HETATM   47  H   UNK     0      -3.555  -1.032   1.402  0.00  0.00           H+0
HETATM   48  H   UNK     0      -5.715  -1.695   1.106  0.00  0.00           H+0
HETATM   49  H   UNK     0      -2.060   1.339  -1.142  0.00  0.00           H+0
HETATM   50  H   UNK     0      -0.414   3.358   2.538  0.00  0.00           H+0
HETATM   51  H   UNK     0      -1.883   4.306   2.204  0.00  0.00           H+0
HETATM   52  H   UNK     0      -2.072   2.765   3.077  0.00  0.00           H+0
HETATM   53  H   UNK     0      -1.045  -1.755  -2.413  0.00  0.00           H+0
HETATM   54  H   UNK     0      -1.870  -0.187  -2.679  0.00  0.00           H+0
HETATM   55  H   UNK     0      -0.132  -0.261  -2.515  0.00  0.00           H+0
HETATM   56  H   UNK     0      -0.194   0.236   1.069  0.00  0.00           H+0
HETATM   57  H   UNK     0       0.464   1.634  -0.831  0.00  0.00           H+0
HETATM   58  H   UNK     0       1.492   0.237  -1.510  0.00  0.00           H+0
HETATM   59  H   UNK     0       1.727   1.138   1.317  0.00  0.00           H+0
HETATM   60  H   UNK     0       4.483   4.754   1.025  0.00  0.00           H+0
HETATM   61  H   UNK     0       3.244   5.206  -0.174  0.00  0.00           H+0
HETATM   62  H   UNK     0       4.635   4.077  -0.611  0.00  0.00           H+0
CONECT    1    2   33   34                                                  
CONECT    2    1    3   35                                                  
CONECT    3    2    4    5   28                                             
CONECT    4    3   36   37   38                                             
CONECT    5    3    6   39   40                                             
CONECT    6    5    7   26                                                  
CONECT    7    6    8   41                                                  
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   24   42                                             
CONECT   11   10   12   13   17                                             
CONECT   12   11   43   44   45                                             
CONECT   13   11   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16   15   17   19   46                                             
CONECT   17   16   18   11   47                                             
CONECT   18   17   48                                                       
CONECT   19   16   20   24   49                                             
CONECT   20   19   21                                                       
CONECT   21   20   22   23                                                  
CONECT   22   21   50   51   52                                             
CONECT   23   21                                                            
CONECT   24   19   25   26   10                                             
CONECT   25   24   53   54   55                                             
CONECT   26   24   27    6   56                                             
CONECT   27   26   28   57   58                                             
CONECT   28   27   29    3   59                                             
CONECT   29   28   30                                                       
CONECT   30   29   31   32                                                  
CONECT   31   30   60   61   62                                             
CONECT   32   30                                                            
CONECT   33    1                                                            
CONECT   34    1                                                            
CONECT   35    2                                                            
CONECT   36    4                                                            
CONECT   37    4                                                            
CONECT   38    4                                                            
CONECT   39    5                                                            
CONECT   40    5                                                            
CONECT   41    7                                                            
CONECT   42   10                                                            
CONECT   43   12                                                            
CONECT   44   12                                                            
CONECT   45   12                                                            
CONECT   46   16                                                            
CONECT   47   17                                                            
CONECT   48   18                                                            
CONECT   49   19                                                            
CONECT   50   22                                                            
CONECT   51   22                                                            
CONECT   52   22                                                            
CONECT   53   25                                                            
CONECT   54   25                                                            
CONECT   55   25                                                            
CONECT   56   26                                                            
CONECT   57   27                                                            
CONECT   58   27                                                            
CONECT   59   28                                                            
CONECT   60   31                                                            
CONECT   61   31                                                            
CONECT   62   31                                                            
MASTER        0    0    0    0    0    0    0    0   62    0  130    0
END

RDKit          3D

62 65  0  0  0  0  0  0  0  0999 V2000
    4.3396   -0.4403   -1.6293 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2590   -0.8130   -0.9837 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9973   -0.2962    0.3843 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2805    0.0765    1.0501 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1729   -1.2583    1.1792 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8626   -1.4706    0.4713 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5042   -2.7451    0.2130 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7748   -2.9015   -0.4641 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9557   -3.8454   -1.2520 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7527   -1.8551   -0.1057 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.1649   -2.1126   -0.4641 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.5903   -3.5024   -0.1905 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5932   -1.6924   -1.8033 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6711   -2.3229   -2.8882 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9538   -0.3307   -1.7283 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6412    0.1581   -0.4384 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.9519   -1.0893    0.3882 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.2932   -1.3554    0.2853 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1971    0.5825   -0.3420 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.9929    1.2313    0.8899 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6968    2.5721    0.9812 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4761    3.2759    2.2705 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6033    3.2571   -0.0684 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2158   -0.5326   -0.6067 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0551   -0.6686   -2.1014 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0790   -0.2854    0.1032 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9627    0.6933   -0.6276 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1452    0.9915    0.3113 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.9027    2.0851   -0.1339 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0888    3.2192    0.6322 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8902    4.3823    0.1673 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5568    3.2684    1.7717 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5486   -0.8018   -2.6197 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0338    0.2381   -1.1679 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5750   -1.4965   -1.4687 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1279    0.1756    2.1552 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5858    1.0818    0.6419 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0665   -0.6908    0.8706 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8866   -0.7502    2.1420 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6711   -2.2226    1.3633 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1633   -3.5622    0.4941 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7331   -1.7545    1.0269 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0769   -3.9881    0.6597 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4791   -4.1143   -1.1310 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6798   -3.5189    0.0412 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2570    1.0089   -0.1413 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5554   -1.0321    1.4020 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7149   -1.6951    1.1057 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0599    1.3393   -1.1424 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4144    3.3584    2.5383 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8829    4.3056    2.2035 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0719    2.7645    3.0773 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0450   -1.7550   -2.4130 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8699   -0.1870   -2.6789 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1316   -0.2606   -2.5152 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1944    0.2363    1.0689 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4643    1.6336   -0.8307 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4922    0.2368   -1.5099 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7267    1.1382    1.3170 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4831    4.7542    1.0247 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2442    5.2057   -0.1743 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6354    4.0771   -0.6105 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  3  2  1  6
  3  4  1  0
  3  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 11 12  1  1
 11 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 16 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 21 23  2  0
 19 24  1  0
 24 25  1  6
 24 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  1  0
 29 30  1  0
 30 31  1  0
 30 32  2  0
 28  3  1  0
 26  6  1  0
 24 10  1  0
 17 11  1  0
  1 33  1  0
  1 34  1  0
  2 35  1  0
  4 36  1  0
  4 37  1  0
  4 38  1  0
  5 39  1  0
  5 40  1  0
  7 41  1  0
 10 42  1  1
 12 43  1  0
 12 44  1  0
 12 45  1  0
 16 46  1  1
 17 47  1  1
 18 48  1  0
 19 49  1  6
 22 50  1  0
 22 51  1  0
 22 52  1  0
 25 53  1  0
 25 54  1  0
 25 55  1  0
 26 56  1  1
 27 57  1  0
 27 58  1  0
 28 59  1  1
 31 60  1  0
 31 61  1  0
 31 62  1  0
M  END

View in JSmol View NMR Assignments

Synonyms

Value	Source
(1S,2S,7S,8S,10R,11S,12S,13S,16S)-8-(Acetyloxy)-7-ethenyl-16-hydroxy-1,7,11-trimethyl-3,15-dioxo-14-oxatetracyclo[11.2.1.0,.0,]hexadec-4-en-12-yl acetic acid	Generator

Chemical Formula

C₂₄H₃₀O₈

Average Mass

446.4960 Da

Monoisotopic Mass

446.19407 Da

IUPAC Name

(1S,2S,7S,8S,10R,11S,12S,13S,16S)-8-(acetyloxy)-7-ethenyl-16-hydroxy-1,7,11-trimethyl-3,15-dioxo-14-oxatetracyclo[11.2.1.0^{2,11}.0^{5,10}]hexadec-4-en-12-yl acetate

Traditional Name

(1S,2S,7S,8S,10R,11S,12S,13S,16S)-8-(acetyloxy)-7-ethenyl-16-hydroxy-1,7,11-trimethyl-3,15-dioxo-14-oxatetracyclo[11.2.1.0^{2,11}.0^{5,10}]hexadec-4-en-12-yl acetate

CAS Registry Number

Not Available

SMILES

CC(=O)O[C@H]1C[C@@H]2C(C[C@@]1(C)C=C)=CC(=O)[C@@H]1[C@@]3(C)[C@H](O)[C@H](OC3=O)[C@@H](OC(C)=O)[C@@]21C

InChI Identifier

InChI=1S/C24H30O8/c1-7-22(4)10-13-8-15(27)18-23(5,14(13)9-16(22)30-11(2)25)20(31-12(3)26)17-19(28)24(18,6)21(29)32-17/h7-8,14,16-20,28H,1,9-10H2,2-6H3/t14-,16+,17+,18+,19-,20-,22-,23+,24+/m1/s1

InChI Key

LIOQTLKMMDOYDZ-RHMXXYPNSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 150 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 250 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 175 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 225 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 125 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, Chloroform-d, 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
Didymella chenopodii	LOTUS Database	35616633
Phoma	NPAtlas	23786488

Chemical Taxonomy

Classification

Not classified

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	1.36	ALOGPS
logP	1.59	ChemAxon
logS	-3.9	ALOGPS
pKa (Strongest Acidic)	13.33	ChemAxon
pKa (Strongest Basic)	-3.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	116.2 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	111.39 m³·mol⁻¹	ChemAxon
Polarizability	45.67 Å³	ChemAxon
Number of Rings	4	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

NPA014501

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

29784867

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

71746067

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Cimmino A, Andolfi A, Zonno MC, Avolio F, Santini A, Tuzi A, Berestetskyi A, Vurro M, Evidente A: Chenopodolin: a phytotoxic unrearranged ent-pimaradiene diterpene produced by Phoma chenopodicola, a fungal pathogen for Chenopodium album biocontrol. J Nat Prod. 2013 Jul 26;76(7):1291-7. doi: 10.1021/np400218z. Epub 2013 Jun 20. [PubMed:23786488 ]

Showing NP-Card for Chenopodolin (NP0011862)

MOL for NP0011862 (Chenopodolin)

3D MOL for NP0011862 (Chenopodolin)

3D SDF for NP0011862 (Chenopodolin)

3D-SDF for NP0011862 (Chenopodolin)

PDB for NP0011862 (Chenopodolin)

3D PDB for NP0011862 (Chenopodolin)

SMILES for NP0011862 (Chenopodolin)

INCHI for NP0011862 (Chenopodolin)

Structure for NP0011862 (Chenopodolin)

3D Structure for NP0011862 (Chenopodolin)