NP-MRD: Showing NP-Card for Akunolide B (S)-MTPA ester at C-9 (NP0332016)

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Record Information

Version

2.0

Created at

2023-10-24 04:00:51 UTC

Updated at

2025-06-11 05:41:05 UTC

NP-MRD ID

NP0332016

Natural Product DOI

https://doi.org/10.57994/1144

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Akunolide B (S)-MTPA ester at C-9

Description

Akunolide B (S)-MTPA ester at C-9 belongs to the class of organic compounds known as benzylethers. These are aromatic ethers with the general formula ROCR' (R = alkyl, aryl; R'=benzene). Based on a literature review very few articles have been published on Akunolide B (S)-MTPA ester at C-9.

Structure

MOL SDF PDB SMILES InChI


  Mrv2104 10242304002D          

 65 68  0  0  1  0            999 V2000
    5.7327    0.1007    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5428    0.2566    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.0829   -0.3671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6033    0.2731    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8038   -0.7684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8129   -1.1466    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.3530   -1.7702    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0829   -2.5498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6230   -3.1734    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3530   -3.9530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8931   -4.5766    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6230   -5.3562    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1631   -5.9798    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8931   -6.7594    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4332   -7.3830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0028   -1.3025    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4627   -0.6789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6525   -0.8348    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1124   -0.2111    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.9226   -0.0552    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3023   -0.3671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5944   -0.7906    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5965   -1.1378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7622    0.2566    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9521    0.1007    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4120    0.7243    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1420   -0.0552    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6019    0.5684    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0618    1.1921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3318    1.9716    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2083    2.5952    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0184    2.4393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1420    2.1275    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4120    2.9071    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2221    3.0630    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6820    1.5039    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4922    1.6598    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2221    0.8802    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0323    1.0361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8424    1.1921    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.1124    1.9716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9226    2.1275    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.1926    2.9071    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6525    3.5307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9226    4.3103    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.7021    4.0402    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3258    4.5803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1430    4.5803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4131    5.3599    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    3.8730    3.8008    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    3.3635    4.8503    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    5.1926    5.0898    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6525    5.7135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9226    6.4930    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7327    6.6489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2728    6.0253    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0028    5.2457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8424    3.3748    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4627    1.5039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2728    1.6598    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.5428    2.4393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8129    1.0361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6525    1.3480    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3825    0.5684    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2229    0.1105    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  3  5  1  0  0  0  0
  6  3  1  0  0  0  0
  6  7  1  1  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
  6 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 19 18  1  0  0  0  0
 19 20  1  6  0  0  0
 19 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  1  0  0  0  0
 24 21  1  0  0  0  0
 24 25  1  0  0  0  0
 26 25  1  0  0  0  0
 26 27  1  1  0  0  0
 26 28  1  0  0  0  0
 28 29  1  0  0  0  0
 30 29  1  0  0  0  0
 30 31  1  1  0  0  0
 31 32  1  0  0  0  0
 33 30  1  0  0  0  0
 33 34  1  6  0  0  0
 34 35  1  0  0  0  0
 33 36  1  0  0  0  0
 36 26  1  0  0  0  0
 36 37  1  1  0  0  0
 24 38  1  6  0  0  0
 24 39  1  0  0  0  0
 40 39  1  0  0  0  0
 40 41  1  0  0  0  0
 42 41  1  0  0  0  0
 42 43  1  6  0  0  0
 43 44  1  0  0  0  0
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 45 46  1  1  0  0  0
 46 47  1  0  0  0  0
 45 48  1  0  0  0  0
 48 49  1  0  0  0  0
 48 50  1  0  0  0  0
 48 51  1  0  0  0  0
 45 52  1  0  0  0  0
 52 53  2  0  0  0  0
 53 54  1  0  0  0  0
 54 55  2  0  0  0  0
 55 56  1  0  0  0  0
 56 57  2  0  0  0  0
 52 57  1  0  0  0  0
 44 58  2  0  0  0  0
 42 59  1  0  0  0  0
 60 59  1  0  0  0  0
 60 61  1  6  0  0  0
 60 62  1  0  0  0  0
  2 62  1  0  0  0  0
 40 63  1  6  0  0  0
 40 64  1  0  0  0  0
 19 64  1  0  0  0  0
 17 65  2  0  0  0  0
M  END


  Mrv2104 10242304002D          

 65 68  0  0  1  0            999 V2000
    5.7327    0.1007    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5428    0.2566    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.0829   -0.3671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6033    0.2731    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8038   -0.7684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8129   -1.1466    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.3530   -1.7702    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0829   -2.5498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6230   -3.1734    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3530   -3.9530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8931   -4.5766    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6230   -5.3562    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1631   -5.9798    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8931   -6.7594    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4332   -7.3830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0028   -1.3025    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4627   -0.6789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6525   -0.8348    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1124   -0.2111    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.9226   -0.0552    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3023   -0.3671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5944   -0.7906    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.7622    0.2566    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
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    1.4120    0.7243    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1420   -0.0552    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6019    0.5684    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0618    1.1921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3318    1.9716    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2083    2.5952    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0184    2.4393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1420    2.1275    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4120    2.9071    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2221    3.0630    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6820    1.5039    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4922    1.6598    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2221    0.8802    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0323    1.0361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8424    1.1921    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.1124    1.9716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9226    2.1275    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.1926    2.9071    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6525    3.5307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9226    4.3103    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.7021    4.0402    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3258    4.5803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1430    4.5803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4131    5.3599    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    3.8730    3.8008    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    3.3635    4.8503    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    5.1926    5.0898    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6525    5.7135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9226    6.4930    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7327    6.6489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2728    6.0253    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0028    5.2457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8424    3.3748    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4627    1.5039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2728    1.6598    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.5428    2.4393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8129    1.0361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6525    1.3480    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3825    0.5684    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2229    0.1105    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  3  5  1  0  0  0  0
  6  3  1  0  0  0  0
  6  7  1  1  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
  6 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 19 18  1  0  0  0  0
 19 20  1  6  0  0  0
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 24 38  1  6  0  0  0
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 52 57  1  0  0  0  0
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 42 59  1  0  0  0  0
 60 59  1  0  0  0  0
 60 61  1  6  0  0  0
 60 62  1  0  0  0  0
  2 62  1  0  0  0  0
 40 63  1  6  0  0  0
 40 64  1  0  0  0  0
 19 64  1  0  0  0  0
 17 65  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0332016

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@]12C[C@]([H])(O[C@]3([H])OC[C@@H](OC)[C@H](OC)[C@H]3O)C(C)(C)[C@]([H])(CC(=O)O[C@H](\C=C\C=C\CCCC=C)C(C)(C)[C@H](O)C[C@@H](C)C[C@H](C1)OC(=O)[C@@](OC)(C1=CC=CC=C1)C(F)(F)F)O2

> <INCHI_IDENTIFIER>
InChI=1S/C46H67F3O12/c1-10-11-12-13-14-15-19-22-35-43(3,4)34(50)24-29(2)23-31(59-42(53)45(56-9,46(47,48)49)30-20-17-16-18-21-30)25-32-26-36(44(5,6)37(58-32)27-38(51)60-35)61-41-39(52)40(55-8)33(54-7)28-57-41/h10,14-22,29,31-37,39-41,50,52H,1,11-13,23-28H2,2-9H3/b15-14+,22-19+/t29-,31+,32+,33+,34+,35+,36-,37-,39+,40-,41-,45-/m0/s1

> <INCHI_KEY>
LIKDNMNUQAQUTG-HKSXHFJLSA-N

> <FORMULA>
C46H67F3O12

> <MOLECULAR_WEIGHT>
869.025

> <EXACT_MASS>
868.458462086

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
128

> <JCHEM_AVERAGE_POLARIZABILITY>
91.0689921131109

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,5R,7R,9R,11R,13R,15S)-7-hydroxy-15-{[(2S,3R,4R,5R)-3-hydroxy-4,5-dimethoxyoxan-2-yl]oxy}-6,6,9,16,16-pentamethyl-5-[(1E,3E)-nona-1,3,8-trien-1-yl]-3-oxo-4,17-dioxabicyclo[11.3.1]heptadecan-11-yl (2S)-3,3,3-trifluoro-2-methoxy-2-phenylpropanoate

> <JCHEM_LOGP>
7.922412354999999

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.623871898321825

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.36332976576365

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9643697292818763

> <JCHEM_POLAR_SURFACE_AREA>
148.44

> <JCHEM_REFRACTIVITY>
222.09919999999994

> <JCHEM_ROTATABLE_BOND_COUNT>
16

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(1S,5R,7R,9R,11R,13R,15S)-7-hydroxy-15-{[(2S,3R,4R,5R)-3-hydroxy-4,5-dimethoxyoxan-2-yl]oxy}-6,6,9,16,16-pentamethyl-5-[(1E,3E)-nona-1,3,8-trien-1-yl]-3-oxo-4,17-dioxabicyclo[11.3.1]heptadecan-11-yl (2S)-3,3,3-trifluoro-2-methoxy-2-phenylpropanoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-OCT-23   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-OCT-23         0                                  
HETATM    1  O   UNK     0      10.701   0.188   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      12.213   0.479   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      13.221  -0.685   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      14.193   0.510   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      14.567  -1.434   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      12.717  -2.140   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      13.726  -3.304   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      13.221  -4.760   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      14.230  -5.924   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      13.726  -7.379   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      14.734  -8.543   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      14.230  -9.998   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      15.238 -11.162   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      14.734 -12.618   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      15.742 -13.782   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      11.205  -2.431   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      10.197  -1.267   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       8.685  -1.558   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       7.677  -0.394   0.000  0.00  0.00           C+0
HETATM   20  H   UNK     0       9.189  -0.103   0.000  0.00  0.00           H+0
HETATM   21  C   UNK     0       6.164  -0.685   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       4.843  -1.476   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       6.714  -2.124   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       5.156   0.479   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       3.644   0.188   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       2.636   1.352   0.000  0.00  0.00           C+0
HETATM   27  H   UNK     0       2.132  -0.103   0.000  0.00  0.00           H+0
HETATM   28  O   UNK     0       1.123   1.061   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       0.115   2.225   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       0.619   3.680   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      -0.389   4.844   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0      -1.901   4.553   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       2.132   3.971   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       2.636   5.427   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0       4.148   5.718   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       3.140   2.807   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0       4.652   3.098   0.000  0.00  0.00           O+0
HETATM   38  H   UNK     0       4.148   1.643   0.000  0.00  0.00           H+0
HETATM   39  C   UNK     0       5.660   1.934   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0       7.172   2.225   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0       7.677   3.680   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0       9.189   3.971   0.000  0.00  0.00           C+0
HETATM   43  O   UNK     0       9.693   5.427   0.000  0.00  0.00           O+0
HETATM   44  C   UNK     0       8.685   6.591   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0       9.189   8.046   0.000  0.00  0.00           C+0
HETATM   46  O   UNK     0      10.644   7.542   0.000  0.00  0.00           O+0
HETATM   47  C   UNK     0      11.808   8.550   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0       7.734   8.550   0.000  0.00  0.00           C+0
HETATM   49  F   UNK     0       8.238  10.005   0.000  0.00  0.00           F+0
HETATM   50  F   UNK     0       7.230   7.095   0.000  0.00  0.00           F+0
HETATM   51  F   UNK     0       6.278   9.054   0.000  0.00  0.00           F+0
HETATM   52  C   UNK     0       9.693   9.501   0.000  0.00  0.00           C+0
HETATM   53  C   UNK     0       8.685  10.665   0.000  0.00  0.00           C+0
HETATM   54  C   UNK     0       9.189  12.120   0.000  0.00  0.00           C+0
HETATM   55  C   UNK     0      10.701  12.411   0.000  0.00  0.00           C+0
HETATM   56  C   UNK     0      11.709  11.247   0.000  0.00  0.00           C+0
HETATM   57  C   UNK     0      11.205   9.792   0.000  0.00  0.00           C+0
HETATM   58  O   UNK     0       7.172   6.300   0.000  0.00  0.00           O+0
HETATM   59  C   UNK     0      10.197   2.807   0.000  0.00  0.00           C+0
HETATM   60  C   UNK     0      11.709   3.098   0.000  0.00  0.00           C+0
HETATM   61  C   UNK     0      12.213   4.553   0.000  0.00  0.00           C+0
HETATM   62  C   UNK     0      12.717   1.934   0.000  0.00  0.00           C+0
HETATM   63  H   UNK     0       8.685   2.516   0.000  0.00  0.00           H+0
HETATM   64  O   UNK     0       8.181   1.061   0.000  0.00  0.00           O+0
HETATM   65  O   UNK     0       9.749   0.206   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   62                                                  
CONECT    3    2    4    5    6                                             
CONECT    4    3                                                            
CONECT    5    3                                                            
CONECT    6    3    7   16                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14                                                            
CONECT   16    6   17                                                       
CONECT   17   16   18   65                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20   21   64                                             
CONECT   20   19                                                            
CONECT   21   19   22   23   24                                             
CONECT   22   21                                                            
CONECT   23   21                                                            
CONECT   24   21   25   38   39                                             
CONECT   25   24   26                                                       
CONECT   26   25   27   28   36                                             
CONECT   27   26                                                            
CONECT   28   26   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   31   33                                                  
CONECT   31   30   32                                                       
CONECT   32   31                                                            
CONECT   33   30   34   36                                                  
CONECT   34   33   35                                                       
CONECT   35   34                                                            
CONECT   36   33   26   37                                                  
CONECT   37   36                                                            
CONECT   38   24                                                            
CONECT   39   24   40                                                       
CONECT   40   39   41   63   64                                             
CONECT   41   40   42                                                       
CONECT   42   41   43   59                                                  
CONECT   43   42   44                                                       
CONECT   44   43   45   58                                                  
CONECT   45   44   46   48   52                                             
CONECT   46   45   47                                                       
CONECT   47   46                                                            
CONECT   48   45   49   50   51                                             
CONECT   49   48                                                            
CONECT   50   48                                                            
CONECT   51   48                                                            
CONECT   52   45   53   57                                                  
CONECT   53   52   54                                                       
CONECT   54   53   55                                                       
CONECT   55   54   56                                                       
CONECT   56   55   57                                                       
CONECT   57   56   52                                                       
CONECT   58   44                                                            
CONECT   59   42   60                                                       
CONECT   60   59   61   62                                                  
CONECT   61   60                                                            
CONECT   62   60    2                                                       
CONECT   63   40                                                            
CONECT   64   40   19                                                       
CONECT   65   17                                                            
MASTER        0    0    0    0    0    0    0    0   65    0  136    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₄₆H₆₇F₃O₁₂

Average Mass

869.0250 Da

Monoisotopic Mass

868.45846 Da

IUPAC Name

(1S,5R,7R,9R,11R,13R,15S)-7-hydroxy-15-{[(2S,3R,4R,5R)-3-hydroxy-4,5-dimethoxyoxan-2-yl]oxy}-6,6,9,16,16-pentamethyl-5-[(1E,3E)-nona-1,3,8-trien-1-yl]-3-oxo-4,17-dioxabicyclo[11.3.1]heptadecan-11-yl (2S)-3,3,3-trifluoro-2-methoxy-2-phenylpropanoate

Traditional Name

CAS Registry Number

Not Available

SMILES

[H][C@]12C[C@]([H])(O[C@]3([H])OC[C@@H](OC)[C@H](OC)[C@H]3O)C(C)(C)[C@]([H])(CC(=O)O[C@H](\C=C\C=C\CCCC=C)C(C)(C)[C@H](O)C[C@@H](C)C[C@H](C1)OC(=O)[C@@](OC)(C1=CC=CC=C1)C(F)(F)F)O2

InChI Identifier

InChI=1S/C46H67F3O12/c1-10-11-12-13-14-15-19-22-35-43(3,4)34(50)24-29(2)23-31(59-42(53)45(56-9,46(47,48)49)30-20-17-16-18-21-30)25-32-26-36(44(5,6)37(58-32)27-38(51)60-35)61-41-39(52)40(55-8)33(54-7)28-57-41/h10,14-22,29,31-37,39-41,50,52H,1,11-13,23-28H2,2-9H3/b15-14+,22-19+/t29-,31+,32+,33+,34+,35+,36-,37-,39+,40-,41-,45-/m0/s1

InChI Key

LIKDNMNUQAQUTG-HKSXHFJLSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
COSY NMR	[¹H, ¹H] NMR Spectrum (2D, 396 MHz, CD3OD, experimental)	caopengran16@126.com	Not Available	Not Available	2024-02-27	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 396 MHz, CD3OD, experimental)	caopengran16@126.com	Not Available	Not Available	2024-02-27	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

Chemical Taxonomy

Description

This compound belongs to the class of organic compounds known as benzylethers. These are aromatic ethers with the general formula ROCR' (R = alkyl, aryl; R'=benzene).

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Benzylethers

Direct Parent

Benzylethers

Alternative Parents

Substituents

Benzylether
Fatty acid ester
Fatty acyl
Oxane
Monosaccharide
Dicarboxylic acid or derivatives
Secondary alcohol
Lactone
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Ether
Dialkyl ether
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organofluoride
Organohalogen compound
Alkyl halide
Alkyl fluoride
Alcohol
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

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

Predicted Properties

Property	Value	Source
logP	7.92	ChemAxon
pKa (Strongest Acidic)	12.36	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	148.44 Å²	ChemAxon
Rotatable Bond Count	16	ChemAxon
Refractivity	222.1 m³·mol⁻¹	ChemAxon
Polarizability	91.07 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

DOI: 10.1021/acs.jnatprod.3c00742

Showing NP-Card for Akunolide B (S)-MTPA ester at C-9 (NP0332016)

MOL for NP0332016 (Akunolide B (S)-MTPA ester at C-9)

3D MOL for NP0332016 (Akunolide B (S)-MTPA ester at C-9)

3D SDF for NP0332016 (Akunolide B (S)-MTPA ester at C-9)

3D-SDF for NP0332016 (Akunolide B (S)-MTPA ester at C-9)

PDB for NP0332016 (Akunolide B (S)-MTPA ester at C-9)

3D PDB for NP0332016 (Akunolide B (S)-MTPA ester at C-9)

SMILES for NP0332016 (Akunolide B (S)-MTPA ester at C-9)

INCHI for NP0332016 (Akunolide B (S)-MTPA ester at C-9)

Structure for NP0332016 (Akunolide B (S)-MTPA ester at C-9)

3D Structure for NP0332016 (Akunolide B (S)-MTPA ester at C-9)