NP-MRD: Showing NP-Card for pachyclavulide D (NP0031746)

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Record Information

Version

2.0

Created at

2021-06-19 22:44:33 UTC

Updated at

2021-06-30 00:00:31 UTC

NP-MRD ID

NP0031746

Secondary Accession Numbers

None

Natural Product Identification

Common Name

pachyclavulide D

Provided By

JEOL Database JEOL Logo

Description

(1S,2R,3R,5R,7S,8R,11R,12R,13S,14S,15S)-13-(acetyloxy)-7-chloro-12,15-dihydroxy-1,11,15-trimethyl-6-methylidene-10,16-dioxo-4,9-dioxatetracyclo[12.4.0.0³,⁵.0⁸,¹²]Octadec-17-en-2-yl acetate belongs to the class of organic compounds known as tricarboxylic acids and derivatives. These are carboxylic acids containing exactly three carboxyl groups. pachyclavulide D is found in Pachyclavularia violacea. pachyclavulide D was first documented in 2006 (Iwasaki, J., et al.). Based on a literature review very few articles have been published on (1S,2R,3R,5R,7S,8R,11R,12R,13S,14S,15S)-13-(acetyloxy)-7-chloro-12,15-dihydroxy-1,11,15-trimethyl-6-methylidene-10,16-dioxo-4,9-dioxatetracyclo[12.4.0.0³,⁵.0⁸,¹²]Octadec-17-en-2-yl acetate.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306202100443D          

 64 67  0  0  0  0            999 V2000
    0.4054   -3.4473   -1.8677 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4497   -2.4210   -2.0588 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4677   -1.5598   -3.3315 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7172   -2.0745   -4.5890 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -0.4853   -0.0208   -3.1202 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6570    0.5917   -4.4203 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0506    1.7472   -4.4954 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0893    2.4533   -5.4897 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6533    2.0690   -3.1599 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9728    2.8129   -3.3086 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7232    0.6916   -2.4637 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9200    0.0317   -2.8563 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6366    0.8786   -0.8826 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7507    0.9075   -0.4806 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3186    2.1254   -0.2310 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7782    1.9648    0.0668 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7280    3.1933   -0.2402 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5009   -0.1137   -0.0036 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.9525    0.4828    0.1849 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.0831    1.7470    1.0463 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5082    0.8249   -1.0970 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8640   -0.5782    0.7975 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.0467   -1.2529    2.2478 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9050   -0.6723    1.3711 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2085    0.3981    2.2397 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.5442   -2.3662    2.4461 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3737   -3.6829    2.7504 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0496   -3.9929    4.0508 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2563   -4.4960    2.0913 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2933   -1.7019    0.3249 C   0  0  2  0  0  0  0  0  0  0  0  0
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    2.4305    3.0057   -2.3343 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8120    3.7819   -3.7946 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6869    2.2623   -3.9302 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6841    0.4472   -2.3989 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0564    1.8669   -0.6854 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2556    2.9488    0.0735 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2525    1.3625   -0.7126 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9102    1.4982    1.0452 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6437   -1.0072   -0.6268 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1167    2.1164    1.0189 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8429    1.5760    2.0988 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.4148   -1.6643   -1.6031 H   0  0  0  0  0  0  0  0  0  0  0  0
 11 13  1  0  0  0  0
  9 10  1  0  0  0  0
 13 18  1  0  0  0  0
  7  8  2  0  0  0  0
 26 18  1  0  0  0  0
 28 29  1  0  0  0  0
 24 25  2  0  0  0  0
 29 30  1  0  0  0  0
 19 18  1  0  0  0  0
 30 31  1  0  0  0  0
 26 25  1  0  0  0  0
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  5 11  1  0  0  0  0
 13 14  1  0  0  0  0
 33 28  1  0  0  0  0
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 28 26  1  0  0  0  0
 15 16  1  0  0  0  0
  5  3  1  0  0  0  0
 30 32  2  0  0  0  0
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 22 19  1  0  0  0  0
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 31 60  1  0  0  0  0
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  1 36  1  0  0  0  0
  1 37  1  0  0  0  0
 21 53  1  0  0  0  0
M  END

     RDKit          3D

 64 67  0  0  0  0  0  0  0  0999 V2000
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M  END


  Mrv1652306202100443D          

 64 67  0  0  0  0            999 V2000
    0.4054   -3.4473   -1.8677 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4497   -2.4210   -2.0588 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4677   -1.5598   -3.3315 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7172   -2.0745   -4.5890 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -0.4853   -0.0208   -3.1202 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6570    0.5917   -4.4203 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0506    1.7472   -4.4954 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0893    2.4533   -5.4897 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6533    2.0690   -3.1599 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9728    2.8129   -3.3086 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7232    0.6916   -2.4637 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9200    0.0317   -2.8563 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6366    0.8786   -0.8826 C   0  0  1  0  0  0  0  0  0  0  0  0
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    1.5009   -0.1137   -0.0036 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.9525    0.4828    0.1849 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.0831    1.7470    1.0463 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5082    0.8249   -1.0970 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8640   -0.5782    0.7975 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.3560   -1.2876    1.9775 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0467   -1.2529    2.2478 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9050   -0.6723    1.3711 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2085    0.3981    2.2397 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0515   -1.9232    1.1488 C   0  0  1  0  0  0  0  0  0  0  0  0
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    0.2563   -4.4960    2.0913 O   0  0  0  0  0  0  0  0  0  0  0  0
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    0.3236   -4.1011   -1.0022 H   0  0  0  0  0  0  0  0  0  0  0  0
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    2.4305    3.0057   -2.3343 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8120    3.7819   -3.7946 H   0  0  0  0  0  0  0  0  0  0  0  0
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    2.6841    0.4472   -2.3989 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0564    1.8669   -0.6854 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2556    2.9488    0.0735 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2525    1.3625   -0.7126 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9102    1.4982    1.0452 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6437   -1.0072   -0.6268 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1167    2.1164    1.0189 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8429    1.5760    2.0988 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4675    2.5705    0.6749 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4815    0.6985   -1.0088 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0813   -1.7830    2.6119 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7431   -1.7428    3.1747 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2235    0.1378    3.3055 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6742    1.3811    2.1459 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8450    0.5201    1.9834 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5588   -2.7088    0.6956 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5655   -3.4405    4.8600 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9668   -5.0640    4.2561 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1099   -3.7350    3.9887 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9587   -0.9763    0.7739 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4148   -1.6643   -1.6031 H   0  0  0  0  0  0  0  0  0  0  0  0
 11 13  1  0  0  0  0
  9 10  1  0  0  0  0
 13 18  1  0  0  0  0
  7  8  2  0  0  0  0
 26 18  1  0  0  0  0
 28 29  1  0  0  0  0
 24 25  2  0  0  0  0
 29 30  1  0  0  0  0
 19 18  1  0  0  0  0
 30 31  1  0  0  0  0
 26 25  1  0  0  0  0
 26 27  1  1  0  0  0
  5 11  1  0  0  0  0
 13 14  1  0  0  0  0
 33 28  1  0  0  0  0
 14 15  1  0  0  0  0
 28 26  1  0  0  0  0
 15 16  1  0  0  0  0
  5  3  1  0  0  0  0
 30 32  2  0  0  0  0
  2 35  1  0  0  0  0
 15 17  2  0  0  0  0
 24 22  1  0  0  0  0
 18 49  1  6  0  0  0
 11  9  1  0  0  0  0
 19 20  1  0  0  0  0
  9  7  1  0  0  0  0
  2  1  2  3  0  0  0
 22 19  1  0  0  0  0
  7  6  1  0  0  0  0
 22 23  2  0  0  0  0
 19 21  1  6  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
 33 35  1  0  0  0  0
 11 12  1  1  0  0  0
 33 34  1  0  0  0  0
 35 34  1  0  0  0  0
  5  6  1  0  0  0  0
 13 45  1  6  0  0  0
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  3 38  1  6  0  0  0
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  5 39  1  1  0  0  0
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  1 36  1  0  0  0  0
  1 37  1  0  0  0  0
 21 53  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0031746

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]O[C@]12[C@@]([H])(OC(=O)[C@]1([H])C([H])([H])[H])[C@@]([H])(Cl)C(=C([H])[H])[C@@]1([H])O[C@@]1([H])[C@]([H])(OC(=O)C([H])([H])[H])[C@]1(C([H])=C([H])C(=O)[C@](O[H])(C([H])([H])[H])[C@]1([H])[C@]2([H])OC(=O)C([H])([H])[H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C24H29ClO10/c1-9-14(25)18-24(31,10(2)21(29)35-18)20(33-12(4)27)17-22(5,8-7-13(28)23(17,6)30)19(32-11(3)26)16-15(9)34-16/h7-8,10,14-20,30-31H,1H2,2-6H3/t10-,14-,15+,16+,17+,18-,19-,20-,22-,23+,24-/m0/s1

> <INCHI_KEY>
ZMZWRXWIJZDCCP-PWLJAXAPSA-N

> <FORMULA>
C24H29ClO10

> <MOLECULAR_WEIGHT>
512.94

> <EXACT_MASS>
512.1449248

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
64

> <JCHEM_AVERAGE_POLARIZABILITY>
48.70968231212169

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,2R,3R,5R,7S,8R,11R,12R,13S,14S,15S)-2-(acetyloxy)-7-chloro-12,15-dihydroxy-1,11,15-trimethyl-6-methylidene-10,16-dioxo-4,9-dioxatetracyclo[12.4.0.0^{3,5}.0^{8,12}]octadec-17-en-13-yl acetate

> <ALOGPS_LOGP>
1.81

> <JCHEM_LOGP>
0.7489085633333323

> <ALOGPS_LOGS>
-3.19

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.041722627120198

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.262119929293156

> <JCHEM_PKA_STRONGEST_BASIC>
-3.704040437861374

> <JCHEM_POLAR_SURFACE_AREA>
148.96000000000004

> <JCHEM_REFRACTIVITY>
118.3569

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.28e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2R,3R,5R,7S,8R,11R,12R,13S,14S,15S)-2-(acetyloxy)-7-chloro-12,15-dihydroxy-1,11,15-trimethyl-6-methylidene-10,16-dioxo-4,9-dioxatetracyclo[12.4.0.0^{3,5}.0^{8,12}]octadec-17-en-13-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 64 67  0  0  0  0  0  0  0  0999 V2000
    0.4054   -3.4473   -1.8677 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4497   -2.4210   -2.0588 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4677   -1.5598   -3.3315 C   0  0  2  0  0  0  0  0  0  0  0  0
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   -0.4853   -0.0208   -3.1202 C   0  0  2  0  0  0  0  0  0  0  0  0
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    0.0893    2.4533   -5.4897 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6533    2.0690   -3.1599 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9728    2.8129   -3.3086 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7232    0.6916   -2.4637 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9200    0.0317   -2.8563 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6366    0.8786   -0.8826 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7507    0.9075   -0.4806 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3186    2.1254   -0.2310 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.9525    0.4828    0.1849 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.0831    1.7470    1.0463 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5082    0.8249   -1.0970 O   0  0  0  0  0  0  0  0  0  0  0  0
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    5.0057   -0.7765    0.3881 O   0  0  0  0  0  0  0  0  0  0  0  0
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    2.0467   -1.2529    2.2478 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9050   -0.6723    1.3711 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2085    0.3981    2.2397 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0515   -1.9232    1.1488 C   0  0  1  0  0  0  0  0  0  0  0  0
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    0.2563   -4.4960    2.0913 O   0  0  0  0  0  0  0  0  0  0  0  0
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    0.3236   -4.1011   -1.0022 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.4186   -1.7976   -3.8276 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4120    0.2363   -2.5969 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0757    2.7201   -2.6661 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4305    3.0057   -2.3343 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.9102    1.4982    1.0452 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6437   -1.0072   -0.6268 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1167    2.1164    1.0189 H   0  0  0  0  0  0  0  0  0  0  0  0
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    4.4815    0.6985   -1.0088 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0813   -1.7830    2.6119 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.9668   -5.0640    4.2561 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.9587   -0.9763    0.7739 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4148   -1.6643   -1.6031 H   0  0  0  0  0  0  0  0  0  0  0  0
 11 13  1  0
  9 10  1  0
 13 18  1  0
  7  8  2  0
 26 18  1  0
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 29 30  1  0
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 30 31  1  0
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 13 14  1  0
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 14 15  1  0
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 30 32  2  0
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 18 49  1  6
 11  9  1  0
 19 20  1  0
  9  7  1  0
  2  1  2  3
 22 19  1  0
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 22 23  2  0
 19 21  1  6
  2  3  1  0
  3  4  1  0
 33 35  1  0
 11 12  1  1
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  5  6  1  0
 13 45  1  6
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 20 52  1  0
  1 36  1  0
  1 37  1  0
 21 53  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       0.405  -3.447  -1.868  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.450  -2.421  -2.059  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.468  -1.560  -3.332  0.00  0.00           C+0
HETATM    4 Cl   UNK     0       0.717  -2.075  -4.589  0.00  0.00          Cl+0
HETATM    5  C   UNK     0      -0.485  -0.021  -3.120  0.00  0.00           C+0
HETATM    6  O   UNK     0      -0.657   0.592  -4.420  0.00  0.00           O+0
HETATM    7  C   UNK     0       0.051   1.747  -4.495  0.00  0.00           C+0
HETATM    8  O   UNK     0       0.089   2.453  -5.490  0.00  0.00           O+0
HETATM    9  C   UNK     0       0.653   2.069  -3.160  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.973   2.813  -3.309  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.723   0.692  -2.464  0.00  0.00           C+0
HETATM   12  O   UNK     0       1.920   0.032  -2.856  0.00  0.00           O+0
HETATM   13  C   UNK     0       0.637   0.879  -0.883  0.00  0.00           C+0
HETATM   14  O   UNK     0      -0.751   0.908  -0.481  0.00  0.00           O+0
HETATM   15  C   UNK     0      -1.319   2.125  -0.231  0.00  0.00           C+0
HETATM   16  C   UNK     0      -2.778   1.965   0.067  0.00  0.00           C+0
HETATM   17  O   UNK     0      -0.728   3.193  -0.240  0.00  0.00           O+0
HETATM   18  C   UNK     0       1.501  -0.114  -0.004  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.953   0.483   0.185  0.00  0.00           C+0
HETATM   20  C   UNK     0       3.083   1.747   1.046  0.00  0.00           C+0
HETATM   21  O   UNK     0       3.508   0.825  -1.097  0.00  0.00           O+0
HETATM   22  C   UNK     0       3.864  -0.578   0.798  0.00  0.00           C+0
HETATM   23  O   UNK     0       5.006  -0.777   0.388  0.00  0.00           O+0
HETATM   24  C   UNK     0       3.356  -1.288   1.978  0.00  0.00           C+0
HETATM   25  C   UNK     0       2.047  -1.253   2.248  0.00  0.00           C+0
HETATM   26  C   UNK     0       0.905  -0.672   1.371  0.00  0.00           C+0
HETATM   27  C   UNK     0       0.209   0.398   2.240  0.00  0.00           C+0
HETATM   28  C   UNK     0      -0.052  -1.923   1.149  0.00  0.00           C+0
HETATM   29  O   UNK     0      -0.544  -2.366   2.446  0.00  0.00           O+0
HETATM   30  C   UNK     0      -0.374  -3.683   2.750  0.00  0.00           C+0
HETATM   31  C   UNK     0      -1.050  -3.993   4.051  0.00  0.00           C+0
HETATM   32  O   UNK     0       0.256  -4.496   2.091  0.00  0.00           O+0
HETATM   33  C   UNK     0      -1.293  -1.702   0.325  0.00  0.00           C+0
HETATM   34  O   UNK     0      -1.919  -2.960  -0.016  0.00  0.00           O+0
HETATM   35  C   UNK     0      -1.557  -2.123  -1.115  0.00  0.00           C+0
HETATM   36  H   UNK     0       0.324  -4.101  -1.002  0.00  0.00           H+0
HETATM   37  H   UNK     0       1.195  -3.708  -2.565  0.00  0.00           H+0
HETATM   38  H   UNK     0      -1.419  -1.798  -3.828  0.00  0.00           H+0
HETATM   39  H   UNK     0      -1.412   0.236  -2.597  0.00  0.00           H+0
HETATM   40  H   UNK     0      -0.076   2.720  -2.666  0.00  0.00           H+0
HETATM   41  H   UNK     0       2.430   3.006  -2.334  0.00  0.00           H+0
HETATM   42  H   UNK     0       1.812   3.782  -3.795  0.00  0.00           H+0
HETATM   43  H   UNK     0       2.687   2.262  -3.930  0.00  0.00           H+0
HETATM   44  H   UNK     0       2.684   0.447  -2.399  0.00  0.00           H+0
HETATM   45  H   UNK     0       1.056   1.867  -0.685  0.00  0.00           H+0
HETATM   46  H   UNK     0      -3.256   2.949   0.074  0.00  0.00           H+0
HETATM   47  H   UNK     0      -3.252   1.363  -0.713  0.00  0.00           H+0
HETATM   48  H   UNK     0      -2.910   1.498   1.045  0.00  0.00           H+0
HETATM   49  H   UNK     0       1.644  -1.007  -0.627  0.00  0.00           H+0
HETATM   50  H   UNK     0       4.117   2.116   1.019  0.00  0.00           H+0
HETATM   51  H   UNK     0       2.843   1.576   2.099  0.00  0.00           H+0
HETATM   52  H   UNK     0       2.467   2.571   0.675  0.00  0.00           H+0
HETATM   53  H   UNK     0       4.481   0.699  -1.009  0.00  0.00           H+0
HETATM   54  H   UNK     0       4.081  -1.783   2.612  0.00  0.00           H+0
HETATM   55  H   UNK     0       1.743  -1.743   3.175  0.00  0.00           H+0
HETATM   56  H   UNK     0       0.224   0.138   3.305  0.00  0.00           H+0
HETATM   57  H   UNK     0       0.674   1.381   2.146  0.00  0.00           H+0
HETATM   58  H   UNK     0      -0.845   0.520   1.983  0.00  0.00           H+0
HETATM   59  H   UNK     0       0.559  -2.709   0.696  0.00  0.00           H+0
HETATM   60  H   UNK     0      -0.566  -3.441   4.860  0.00  0.00           H+0
HETATM   61  H   UNK     0      -0.967  -5.064   4.256  0.00  0.00           H+0
HETATM   62  H   UNK     0      -2.110  -3.735   3.989  0.00  0.00           H+0
HETATM   63  H   UNK     0      -1.959  -0.976   0.774  0.00  0.00           H+0
HETATM   64  H   UNK     0      -2.415  -1.664  -1.603  0.00  0.00           H+0
CONECT    1    2   36   37                                                  
CONECT    2   35    1    3                                                  
CONECT    3    5    2    4   38                                             
CONECT    4    3                                                            
CONECT    5   11    3    6   39                                             
CONECT    6    7    5                                                       
CONECT    7    8    9    6                                                  
CONECT    8    7                                                            
CONECT    9   10   11    7   40                                             
CONECT   10    9   41   42   43                                             
CONECT   11   13    5    9   12                                             
CONECT   12   11   44                                                       
CONECT   13   11   18   14   45                                             
CONECT   14   13   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15   46   47   48                                             
CONECT   17   15                                                            
CONECT   18   13   26   19   49                                             
CONECT   19   18   20   22   21                                             
CONECT   20   19   50   51   52                                             
CONECT   21   19   53                                                       
CONECT   22   24   19   23                                                  
CONECT   23   22                                                            
CONECT   24   25   22   54                                                  
CONECT   25   24   26   55                                                  
CONECT   26   18   25   27   28                                             
CONECT   27   26   56   57   58                                             
CONECT   28   29   33   26   59                                             
CONECT   29   28   30                                                       
CONECT   30   29   31   32                                                  
CONECT   31   30   60   61   62                                             
CONECT   32   30                                                            
CONECT   33   28   35   34   63                                             
CONECT   34   33   35                                                       
CONECT   35    2   33   34   64                                             
CONECT   36    1                                                            
CONECT   37    1                                                            
CONECT   38    3                                                            
CONECT   39    5                                                            
CONECT   40    9                                                            
CONECT   41   10                                                            
CONECT   42   10                                                            
CONECT   43   10                                                            
CONECT   44   12                                                            
CONECT   45   13                                                            
CONECT   46   16                                                            
CONECT   47   16                                                            
CONECT   48   16                                                            
CONECT   49   18                                                            
CONECT   50   20                                                            
CONECT   51   20                                                            
CONECT   52   20                                                            
CONECT   53   21                                                            
CONECT   54   24                                                            
CONECT   55   25                                                            
CONECT   56   27                                                            
CONECT   57   27                                                            
CONECT   58   27                                                            
CONECT   59   28                                                            
CONECT   60   31                                                            
CONECT   61   31                                                            
CONECT   62   31                                                            
CONECT   63   33                                                            
CONECT   64   35                                                            
MASTER        0    0    0    0    0    0    0    0   64    0  134    0
END

RDKit          3D

64 67  0  0  0  0  0  0  0  0999 V2000
    0.4054   -3.4473   -1.8677 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4497   -2.4210   -2.0588 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.7172   -2.0745   -4.5890 Cl  0  0  0  0  0  0  0  0  0  0  0  0
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    0.0506    1.7472   -4.4954 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0893    2.4533   -5.4897 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6533    2.0690   -3.1599 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9728    2.8129   -3.3086 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7232    0.6916   -2.4637 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9200    0.0317   -2.8563 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6366    0.8786   -0.8826 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7507    0.9075   -0.4806 O   0  0  0  0  0  0  0  0  0  0  0  0
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    1.5009   -0.1137   -0.0036 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.9525    0.4828    0.1849 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.0831    1.7470    1.0463 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5082    0.8249   -1.0970 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8640   -0.5782    0.7975 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0057   -0.7765    0.3881 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3560   -1.2876    1.9775 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0467   -1.2529    2.2478 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9050   -0.6723    1.3711 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2085    0.3981    2.2397 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0515   -1.9232    1.1488 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5442   -2.3662    2.4461 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3737   -3.6829    2.7504 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0496   -3.9929    4.0508 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2563   -4.4960    2.0913 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2933   -1.7019    0.3249 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.9185   -2.9598   -0.0156 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5573   -2.1230   -1.1155 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3236   -4.1011   -1.0022 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1946   -3.7085   -2.5651 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4186   -1.7976   -3.8276 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4120    0.2363   -2.5969 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0757    2.7201   -2.6661 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4305    3.0057   -2.3343 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8120    3.7819   -3.7946 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6869    2.2623   -3.9302 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6841    0.4472   -2.3989 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0564    1.8669   -0.6854 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2556    2.9488    0.0735 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2525    1.3625   -0.7126 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9102    1.4982    1.0452 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6437   -1.0072   -0.6268 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1167    2.1164    1.0189 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8429    1.5760    2.0988 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4675    2.5705    0.6749 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4815    0.6985   -1.0088 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0813   -1.7830    2.6119 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7431   -1.7428    3.1747 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2235    0.1378    3.3055 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6742    1.3811    2.1459 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8450    0.5201    1.9834 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5588   -2.7088    0.6956 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5655   -3.4405    4.8600 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9668   -5.0640    4.2561 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1099   -3.7350    3.9887 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9587   -0.9763    0.7739 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4148   -1.6643   -1.6031 H   0  0  0  0  0  0  0  0  0  0  0  0
 11 13  1  0
  9 10  1  0
 13 18  1  0
  7  8  2  0
 26 18  1  0
 28 29  1  0
 24 25  2  0
 29 30  1  0
 19 18  1  0
 30 31  1  0
 26 25  1  0
 26 27  1  1
  5 11  1  0
 13 14  1  0
 33 28  1  0
 14 15  1  0
 28 26  1  0
 15 16  1  0
  5  3  1  0
 30 32  2  0
  2 35  1  0
 15 17  2  0
 24 22  1  0
 18 49  1  6
 11  9  1  0
 19 20  1  0
  9  7  1  0
  2  1  2  3
 22 19  1  0
  7  6  1  0
 22 23  2  0
 19 21  1  6
  2  3  1  0
  3  4  1  0
 33 35  1  0
 11 12  1  1
 33 34  1  0
 35 34  1  0
  5  6  1  0
 13 45  1  6
 28 59  1  6
 33 63  1  1
  3 38  1  6
 35 64  1  6
 24 54  1  0
 25 55  1  0
  5 39  1  1
  9 40  1  1
 12 44  1  0
 10 41  1  0
 10 42  1  0
 10 43  1  0
 31 60  1  0
 31 61  1  0
 31 62  1  0
 27 56  1  0
 27 57  1  0
 27 58  1  0
 16 46  1  0
 16 47  1  0
 16 48  1  0
 20 50  1  0
 20 51  1  0
 20 52  1  0
  1 36  1  0
  1 37  1  0
 21 53  1  0
M  END

View in JSmol

Synonyms

Value	Source
(1S,2R,3R,5R,7S,8R,11R,12R,13S,14S,15S)-13-(Acetyloxy)-7-chloro-12,15-dihydroxy-1,11,15-trimethyl-6-methylidene-10,16-dioxo-4,9-dioxatetracyclo[12.4.0.0,.0,]octadec-17-en-2-yl acetic acid	Generator

Chemical Formula

C₂₄H₂₉ClO₁₀

Average Mass

512.9400 Da

Monoisotopic Mass

512.14492 Da

IUPAC Name

(1S,2R,3R,5R,7S,8R,11R,12R,13S,14S,15S)-2-(acetyloxy)-7-chloro-12,15-dihydroxy-1,11,15-trimethyl-6-methylidene-10,16-dioxo-4,9-dioxatetracyclo[12.4.0.0^{3,5}.0^{8,12}]octadec-17-en-13-yl acetate

Traditional Name

(1S,2R,3R,5R,7S,8R,11R,12R,13S,14S,15S)-2-(acetyloxy)-7-chloro-12,15-dihydroxy-1,11,15-trimethyl-6-methylidene-10,16-dioxo-4,9-dioxatetracyclo[12.4.0.0^{3,5}.0^{8,12}]octadec-17-en-13-yl acetate

CAS Registry Number

Not Available

SMILES

[H]O[C@]12[C@@]([H])(OC(=O)[C@]1([H])C([H])([H])[H])[C@@]([H])(Cl)C(=C([H])[H])[C@@]1([H])O[C@@]1([H])[C@]([H])(OC(=O)C([H])([H])[H])[C@]1(C([H])=C([H])C(=O)[C@](O[H])(C([H])([H])[H])[C@]1([H])[C@]2([H])OC(=O)C([H])([H])[H])C([H])([H])[H]

InChI Identifier

InChI=1S/C24H29ClO10/c1-9-14(25)18-24(31,10(2)21(29)35-18)20(33-12(4)27)17-22(5,8-7-13(28)23(17,6)30)19(32-11(3)26)16-15(9)34-16/h7-8,10,14-20,30-31H,1H2,2-6H3/t10-,14-,15+,16+,17+,18-,19-,20-,22-,23+,24-/m0/s1

InChI Key

ZMZWRXWIJZDCCP-PWLJAXAPSA-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
Pachyclavularia violacea	JEOL database	Iwasaki, J., et al, J. Nat. Prod. 69, 2 (2006)

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as tricarboxylic acids and derivatives. These are carboxylic acids containing exactly three carboxyl groups.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Tricarboxylic acids and derivatives

Direct Parent

Tricarboxylic acids and derivatives

Alternative Parents

Substituents

Tricarboxylic acid or derivatives
Cyclohexenone
Acyloin
Gamma butyrolactone
Tertiary alcohol
Tetrahydrofuran
Carboxylic acid ester
Ketone
Lactone
Cyclic ketone
Ether
Oxirane
Dialkyl ether
Oxacycle
Organoheterocyclic compound
Organooxygen compound
Organochloride
Organohalogen compound
Alcohol
Organic oxide
Organic oxygen compound
Carbonyl group
Alkyl halide
Hydrocarbon derivative
Alkyl chloride
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	1.81	ALOGPS
logP	0.75	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Acidic)	12.26	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	148.96 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	118.36 m³·mol⁻¹	ChemAxon
Polarizability	48.71 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

9859663

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11684935

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Iwasaki, J., et al. (2006). Iwasaki, J., et al, J. Nat. Prod. 69, 2 (2006) . J. Nat. Prod..

Showing NP-Card for pachyclavulide D (NP0031746)

MOL for NP0031746 (pachyclavulide D)

3D MOL for NP0031746 (pachyclavulide D)

3D SDF for NP0031746 (pachyclavulide D)

3D-SDF for NP0031746 (pachyclavulide D)

PDB for NP0031746 (pachyclavulide D)

3D PDB for NP0031746 (pachyclavulide D)

SMILES for NP0031746 (pachyclavulide D)

INCHI for NP0031746 (pachyclavulide D)

Structure for NP0031746 (pachyclavulide D)

3D Structure for NP0031746 (pachyclavulide D)