NP-MRD: Showing NP-Card for Junceellolide H (NP0026751)

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Record Information

Version

2.0

Created at

2021-06-19 18:33:36 UTC

Updated at

2021-06-29 23:52:29 UTC

NP-MRD ID

NP0026751

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Junceellolide H

Provided By

JEOL Database JEOL Logo

Description

Junceellolide H is found in Junceella fragilis. Junceellolide H was first documented in 2003 (Sung, P.-J., et al.). Based on a literature review very few articles have been published on (1R)-1,5,8aalpha,12-Tetramethyl-8alpha,9beta,13alpha-trihydroxy-1,2,3aalpha,6,7,8,8a,9,10,12abeta,13,13a-dodecahydro-1beta,13abeta-epoxybenzo[4,5]cyclodeca[1,2-b]furan-2-one.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306192120333D          

 54 57  0  0  0  0            999 V2000
   -2.3704    0.8735   -1.4797 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8759    1.0004   -1.2984 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2031    1.8113   -2.1381 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2891    1.8797   -2.2330 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9386    0.6537   -1.5788 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7633   -0.4603   -2.4584 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3815    0.3739   -0.1382 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6663    1.6756    0.6875 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2238   -0.7908    0.5263 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8480   -0.9666    1.8973 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3785   -2.1888   -0.1212 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4913   -3.3444    0.3701 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1633   -3.5150   -0.3296 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.2790   -2.4494    1.4909 C   0  0  2  0  0  0  0  0  0  0  0  0
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   -3.2074   -2.4564    2.7567 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0824   -2.8222    3.5242 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1015   -1.0913    2.2032 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.5876    0.1123    2.9297 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.5631    1.9083   -3.2949 H   0  0  0  0  0  0  0  0  0  0  0  0
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  4  3  1  0  0  0  0
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  3  2  2  0  0  0  0
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  8 37  1  0  0  0  0
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M  END

     RDKit          3D

 54 57  0  0  0  0  0  0  0  0999 V2000
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    1.3815    0.3739   -0.1382 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6663    1.6756    0.6875 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2238   -0.7908    0.5263 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8480   -0.9666    1.8973 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.0292   -3.1715    0.1977 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.5876    0.1123    2.9297 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


  Mrv1652306192120333D          

 54 57  0  0  0  0            999 V2000
   -2.3704    0.8735   -1.4797 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8759    1.0004   -1.2984 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2031    1.8113   -2.1381 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2891    1.8797   -2.2330 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9386    0.6537   -1.5788 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7633   -0.4603   -2.4584 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3815    0.3739   -0.1382 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6663    1.6756    0.6875 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2238   -0.7908    0.5263 C   0  0  1  0  0  0  0  0  0  0  0  0
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    1.5631    1.9083   -3.2949 H   0  0  0  0  0  0  0  0  0  0  0  0
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    2.5950   -1.4170    2.3387 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3969   -2.5052    0.1557 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4114   -2.1619   -1.2083 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3764   -3.3139    1.4572 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0513   -4.2770    0.2058 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8258   -3.5658   -2.3755 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6909   -5.1631   -1.6061 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7596   -4.3032   -2.1330 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9333   -3.3777   -0.3754 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3757   -2.3815    2.0992 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9666    0.3026    3.8107 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6179   -0.0392    3.2676 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5806    1.0102    2.3041 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6517    1.0138    1.1034 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5237   -0.2407    2.3002 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2828   -0.8902   -0.6589 H   0  0  0  0  0  0  0  0  0  0  0  0
 11 12  1  0  0  0  0
 16 15  1  0  0  0  0
 13 15  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 26  7  1  0  0  0  0
  2  1  1  0  0  0  0
  5  6  1  0  0  0  0
  7  9  1  0  0  0  0
 26 54  1  6  0  0  0
 26 24  1  0  0  0  0
 23 20  1  0  0  0  0
 24 23  1  0  0  0  0
 20 18  1  0  0  0  0
 23 16  1  0  0  0  0
 16 17  1  0  0  0  0
 11  9  1  0  0  0  0
 23 22  1  6  0  0  0
 20 22  1  0  0  0  0
 18 17  1  0  0  0  0
 26  2  1  0  0  0  0
 18 19  2  0  0  0  0
  7  5  1  0  0  0  0
 20 21  1  1  0  0  0
  5  4  1  0  0  0  0
  9 10  1  0  0  0  0
  4  3  1  0  0  0  0
  7  8  1  1  0  0  0
  3  2  2  0  0  0  0
 24 25  1  0  0  0  0
  9 38  1  1  0  0  0
 24 52  1  6  0  0  0
 16 48  1  1  0  0  0
 11 40  1  0  0  0  0
 11 41  1  0  0  0  0
 12 42  1  0  0  0  0
 12 43  1  0  0  0  0
  5 33  1  1  0  0  0
  4 31  1  0  0  0  0
  4 32  1  0  0  0  0
  3 30  1  0  0  0  0
 15 47  1  0  0  0  0
 14 44  1  0  0  0  0
 14 45  1  0  0  0  0
 14 46  1  0  0  0  0
  1 27  1  0  0  0  0
  1 28  1  0  0  0  0
  1 29  1  0  0  0  0
  6 34  1  0  0  0  0
 21 49  1  0  0  0  0
 21 50  1  0  0  0  0
 21 51  1  0  0  0  0
 10 39  1  0  0  0  0
  8 35  1  0  0  0  0
  8 36  1  0  0  0  0
  8 37  1  0  0  0  0
 25 53  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0026751

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]O[C@@]1([H])C([H])([H])C([H])=C(C([H])([H])[H])[C@]2([H])[C@]([H])(O[H])[C@]34O[C@]3(C(=O)O[C@@]4([H])\C([H])=C(C([H])([H])[H])/C([H])([H])C([H])([H])[C@]([H])(O[H])[C@@]12C([H])([H])[H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C20H28O6/c1-10-5-7-12(21)18(3)13(22)8-6-11(2)15(18)16(23)20-14(9-10)25-17(24)19(20,4)26-20/h6,9,12-16,21-23H,5,7-8H2,1-4H3/b10-9-/t12-,13-,14-,15+,16-,18-,19-,20-/m0/s1

> <INCHI_KEY>
ALWWZYJXKOQZBH-ZYMUOCAQSA-N

> <FORMULA>
C20H28O6

> <MOLECULAR_WEIGHT>
364.438

> <EXACT_MASS>
364.188588622

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
54

> <JCHEM_AVERAGE_POLARIZABILITY>
37.869696060237324

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,2S,3S,7S,8S,9S,12Z,14S,17R)-2,7,9-trihydroxy-4,8,12,17-tetramethyl-15,18-dioxatetracyclo[12.4.0.0^{1,17}.0^{3,8}]octadeca-4,12-dien-16-one

> <ALOGPS_LOGP>
1.18

> <JCHEM_LOGP>
0.926322815666666

> <ALOGPS_LOGS>
-2.22

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.328664429434284

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.418915902413907

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9743161732924985

> <JCHEM_POLAR_SURFACE_AREA>
99.52

> <JCHEM_REFRACTIVITY>
94.6946

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.21e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2S,3S,7S,8S,9S,12Z,14S,17R)-2,7,9-trihydroxy-4,8,12,17-tetramethyl-15,18-dioxatetracyclo[12.4.0.0^{1,17}.0^{3,8}]octadeca-4,12-dien-16-one

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 54 57  0  0  0  0  0  0  0  0999 V2000
   -2.3704    0.8735   -1.4797 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8759    1.0004   -1.2984 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2031    1.8113   -2.1381 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2891    1.8797   -2.2330 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9386    0.6537   -1.5788 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7633   -0.4603   -2.4584 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3815    0.3739   -0.1382 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6663    1.6756    0.6875 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2238   -0.7908    0.5263 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8480   -0.9666    1.8973 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3785   -2.1888   -0.1212 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4913   -3.3444    0.3701 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1633   -3.5150   -0.3296 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2314   -4.1725   -1.6854 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0292   -3.1715    0.1977 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2790   -2.4494    1.4909 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1994   -3.2425    2.2750 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2074   -2.4564    2.7567 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0824   -2.8222    3.5242 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1015   -1.0913    2.2032 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.5876    0.1123    2.9297 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2024   -1.0171    0.7710 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8781   -1.0855    1.3315 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0095    0.1290    1.1343 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2819    0.3177    2.3392 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1810    0.1046   -0.2221 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.6439   -0.1775   -1.6128 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7225    1.4032   -2.3724 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9166    1.2914   -0.6305 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7433    2.4206   -2.8614 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6398    2.8137   -1.7819 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5631    1.9083   -3.2949 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0208    0.8251   -1.5284 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8275   -0.4880   -2.7287 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6636    1.5181    1.7681 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9394    2.4667    0.4772 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6628    2.0711    0.4550 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2480   -0.3894    0.5663 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5950   -1.4170    2.3387 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3969   -2.5052    0.1557 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4114   -2.1619   -1.2083 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3764   -3.3139    1.4572 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0513   -4.2770    0.2058 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8258   -3.5658   -2.3755 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6909   -5.1631   -1.6061 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7596   -4.3032   -2.1330 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9333   -3.3777   -0.3754 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3757   -2.3815    2.0992 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9666    0.3026    3.8107 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6179   -0.0392    3.2676 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5806    1.0102    2.3041 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6517    1.0138    1.1034 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5237   -0.2407    2.3002 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2828   -0.8902   -0.6589 H   0  0  0  0  0  0  0  0  0  0  0  0
 11 12  1  0
 16 15  1  0
 13 15  2  0
 12 13  1  0
 13 14  1  0
 26  7  1  0
  2  1  1  0
  5  6  1  0
  7  9  1  0
 26 54  1  6
 26 24  1  0
 23 20  1  0
 24 23  1  0
 20 18  1  0
 23 16  1  0
 16 17  1  0
 11  9  1  0
 23 22  1  6
 20 22  1  0
 18 17  1  0
 26  2  1  0
 18 19  2  0
  7  5  1  0
 20 21  1  1
  5  4  1  0
  9 10  1  0
  4  3  1  0
  7  8  1  1
  3  2  2  0
 24 25  1  0
  9 38  1  1
 24 52  1  6
 16 48  1  1
 11 40  1  0
 11 41  1  0
 12 42  1  0
 12 43  1  0
  5 33  1  1
  4 31  1  0
  4 32  1  0
  3 30  1  0
 15 47  1  0
 14 44  1  0
 14 45  1  0
 14 46  1  0
  1 27  1  0
  1 28  1  0
  1 29  1  0
  6 34  1  0
 21 49  1  0
 21 50  1  0
 21 51  1  0
 10 39  1  0
  8 35  1  0
  8 36  1  0
  8 37  1  0
 25 53  1  0
M  END

HEADER    PROTEIN                                 19-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-JUN-21         0                                  
HETATM    1  C   UNK     0      -2.370   0.874  -1.480  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.876   1.000  -1.298  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.203   1.811  -2.138  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.289   1.880  -2.233  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.939   0.654  -1.579  0.00  0.00           C+0
HETATM    6  O   UNK     0       1.763  -0.460  -2.458  0.00  0.00           O+0
HETATM    7  C   UNK     0       1.381   0.374  -0.138  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.666   1.676   0.688  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.224  -0.791   0.526  0.00  0.00           C+0
HETATM   10  O   UNK     0       1.848  -0.967   1.897  0.00  0.00           O+0
HETATM   11  C   UNK     0       2.378  -2.189  -0.121  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.491  -3.344   0.370  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.163  -3.515  -0.330  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.231  -4.173  -1.685  0.00  0.00           C+0
HETATM   15  C   UNK     0      -1.029  -3.172   0.198  0.00  0.00           C+0
HETATM   16  C   UNK     0      -1.279  -2.449   1.491  0.00  0.00           C+0
HETATM   17  O   UNK     0      -2.199  -3.243   2.275  0.00  0.00           O+0
HETATM   18  C   UNK     0      -3.207  -2.456   2.757  0.00  0.00           C+0
HETATM   19  O   UNK     0      -4.082  -2.822   3.524  0.00  0.00           O+0
HETATM   20  C   UNK     0      -3.102  -1.091   2.203  0.00  0.00           C+0
HETATM   21  C   UNK     0      -3.588   0.112   2.930  0.00  0.00           C+0
HETATM   22  O   UNK     0      -3.202  -1.017   0.771  0.00  0.00           O+0
HETATM   23  C   UNK     0      -1.878  -1.085   1.331  0.00  0.00           C+0
HETATM   24  C   UNK     0      -1.010   0.129   1.134  0.00  0.00           C+0
HETATM   25  O   UNK     0      -0.282   0.318   2.339  0.00  0.00           O+0
HETATM   26  C   UNK     0      -0.181   0.105  -0.222  0.00  0.00           C+0
HETATM   27  H   UNK     0      -2.644  -0.178  -1.613  0.00  0.00           H+0
HETATM   28  H   UNK     0      -2.723   1.403  -2.372  0.00  0.00           H+0
HETATM   29  H   UNK     0      -2.917   1.291  -0.631  0.00  0.00           H+0
HETATM   30  H   UNK     0      -0.743   2.421  -2.861  0.00  0.00           H+0
HETATM   31  H   UNK     0       1.640   2.814  -1.782  0.00  0.00           H+0
HETATM   32  H   UNK     0       1.563   1.908  -3.295  0.00  0.00           H+0
HETATM   33  H   UNK     0       3.021   0.825  -1.528  0.00  0.00           H+0
HETATM   34  H   UNK     0       0.828  -0.488  -2.729  0.00  0.00           H+0
HETATM   35  H   UNK     0       1.664   1.518   1.768  0.00  0.00           H+0
HETATM   36  H   UNK     0       0.939   2.467   0.477  0.00  0.00           H+0
HETATM   37  H   UNK     0       2.663   2.071   0.455  0.00  0.00           H+0
HETATM   38  H   UNK     0       3.248  -0.389   0.566  0.00  0.00           H+0
HETATM   39  H   UNK     0       2.595  -1.417   2.339  0.00  0.00           H+0
HETATM   40  H   UNK     0       3.397  -2.505   0.156  0.00  0.00           H+0
HETATM   41  H   UNK     0       2.411  -2.162  -1.208  0.00  0.00           H+0
HETATM   42  H   UNK     0       1.376  -3.314   1.457  0.00  0.00           H+0
HETATM   43  H   UNK     0       2.051  -4.277   0.206  0.00  0.00           H+0
HETATM   44  H   UNK     0       0.826  -3.566  -2.376  0.00  0.00           H+0
HETATM   45  H   UNK     0       0.691  -5.163  -1.606  0.00  0.00           H+0
HETATM   46  H   UNK     0      -0.760  -4.303  -2.133  0.00  0.00           H+0
HETATM   47  H   UNK     0      -1.933  -3.378  -0.375  0.00  0.00           H+0
HETATM   48  H   UNK     0      -0.376  -2.381   2.099  0.00  0.00           H+0
HETATM   49  H   UNK     0      -2.967   0.303   3.811  0.00  0.00           H+0
HETATM   50  H   UNK     0      -4.618  -0.039   3.268  0.00  0.00           H+0
HETATM   51  H   UNK     0      -3.581   1.010   2.304  0.00  0.00           H+0
HETATM   52  H   UNK     0      -1.652   1.014   1.103  0.00  0.00           H+0
HETATM   53  H   UNK     0       0.524  -0.241   2.300  0.00  0.00           H+0
HETATM   54  H   UNK     0      -0.283  -0.890  -0.659  0.00  0.00           H+0
CONECT    1    2   27   28   29                                             
CONECT    2    1   26    3                                                  
CONECT    3    4    2   30                                                  
CONECT    4    5    3   31   32                                             
CONECT    5    6    7    4   33                                             
CONECT    6    5   34                                                       
CONECT    7   26    9    5    8                                             
CONECT    8    7   35   36   37                                             
CONECT    9    7   11   10   38                                             
CONECT   10    9   39                                                       
CONECT   11   12    9   40   41                                             
CONECT   12   11   13   42   43                                             
CONECT   13   15   12   14                                                  
CONECT   14   13   44   45   46                                             
CONECT   15   16   13   47                                                  
CONECT   16   15   23   17   48                                             
CONECT   17   16   18                                                       
CONECT   18   20   17   19                                                  
CONECT   19   18                                                            
CONECT   20   23   18   22   21                                             
CONECT   21   20   49   50   51                                             
CONECT   22   23   20                                                       
CONECT   23   20   24   16   22                                             
CONECT   24   26   23   25   52                                             
CONECT   25   24   53                                                       
CONECT   26    7   54   24    2                                             
CONECT   27    1                                                            
CONECT   28    1                                                            
CONECT   29    1                                                            
CONECT   30    3                                                            
CONECT   31    4                                                            
CONECT   32    4                                                            
CONECT   33    5                                                            
CONECT   34    6                                                            
CONECT   35    8                                                            
CONECT   36    8                                                            
CONECT   37    8                                                            
CONECT   38    9                                                            
CONECT   39   10                                                            
CONECT   40   11                                                            
CONECT   41   11                                                            
CONECT   42   12                                                            
CONECT   43   12                                                            
CONECT   44   14                                                            
CONECT   45   14                                                            
CONECT   46   14                                                            
CONECT   47   15                                                            
CONECT   48   16                                                            
CONECT   49   21                                                            
CONECT   50   21                                                            
CONECT   51   21                                                            
CONECT   52   24                                                            
CONECT   53   25                                                            
CONECT   54   26                                                            
MASTER        0    0    0    0    0    0    0    0   54    0  114    0
END

RDKit          3D

54 57  0  0  0  0  0  0  0  0999 V2000
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    2.6628    2.0711    0.4550 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2480   -0.3894    0.5663 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5950   -1.4170    2.3387 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3969   -2.5052    0.1557 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4114   -2.1619   -1.2083 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3764   -3.3139    1.4572 H   0  0  0  0  0  0  0  0  0  0  0  0
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    0.8258   -3.5658   -2.3755 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6909   -5.1631   -1.6061 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7596   -4.3032   -2.1330 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9333   -3.3777   -0.3754 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3757   -2.3815    2.0992 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9666    0.3026    3.8107 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6179   -0.0392    3.2676 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5806    1.0102    2.3041 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6517    1.0138    1.1034 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5237   -0.2407    2.3002 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2828   -0.8902   -0.6589 H   0  0  0  0  0  0  0  0  0  0  0  0
 11 12  1  0
 16 15  1  0
 13 15  2  0
 12 13  1  0
 13 14  1  0
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  2  1  1  0
  5  6  1  0
  7  9  1  0
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 23 20  1  0
 24 23  1  0
 20 18  1  0
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 26  2  1  0
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 20 21  1  1
  5  4  1  0
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  3  2  2  0
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  9 38  1  1
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  5 33  1  1
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  3 30  1  0
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  1 27  1  0
  1 28  1  0
  1 29  1  0
  6 34  1  0
 21 49  1  0
 21 50  1  0
 21 51  1  0
 10 39  1  0
  8 35  1  0
  8 36  1  0
  8 37  1  0
 25 53  1  0
M  END

View in JSmol

Synonyms

Value	Source
(1R)-1,5,8Aalpha,12-tetramethyl-8a,9b,13a-trihydroxy-1,2,3aalpha,6,7,8,8a,9,10,12abeta,13,13a-dodecahydro-1b,13abeta-epoxybenzo[4,5]cyclodeca[1,2-b]furan-2-one	Generator
(1R)-1,5,8Aalpha,12-tetramethyl-8α,9β,13α-trihydroxy-1,2,3aalpha,6,7,8,8a,9,10,12abeta,13,13a-dodecahydro-1β,13abeta-epoxybenzo[4,5]cyclodeca[1,2-b]furan-2-one	Generator

Chemical Formula

C₂₀H₂₈O₆

Average Mass

364.4380 Da

Monoisotopic Mass

364.18859 Da

IUPAC Name

(1R,2S,3S,7S,8S,9S,12Z,14S,17R)-2,7,9-trihydroxy-4,8,12,17-tetramethyl-15,18-dioxatetracyclo[12.4.0.0^{1,17}.0^{3,8}]octadeca-4,12-dien-16-one

Traditional Name

(1R,2S,3S,7S,8S,9S,12Z,14S,17R)-2,7,9-trihydroxy-4,8,12,17-tetramethyl-15,18-dioxatetracyclo[12.4.0.0^{1,17}.0^{3,8}]octadeca-4,12-dien-16-one

CAS Registry Number

Not Available

SMILES

[H]O[C@@]1([H])C([H])([H])C([H])=C(C([H])([H])[H])[C@]2([H])[C@]([H])(O[H])[C@]34O[C@]3(C(=O)O[C@@]4([H])\C([H])=C(C([H])([H])[H])/C([H])([H])C([H])([H])[C@]([H])(O[H])[C@@]12C([H])([H])[H])C([H])([H])[H]

InChI Identifier

InChI=1S/C20H28O6/c1-10-5-7-12(21)18(3)13(22)8-6-11(2)15(18)16(23)20-14(9-10)25-17(24)19(20,4)26-20/h6,9,12-16,21-23H,5,7-8H2,1-4H3/b10-9-/t12-,13-,14-,15+,16-,18-,19-,20-/m0/s1

InChI Key

ALWWZYJXKOQZBH-ZYMUOCAQSA-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
Junceella fragilis	JEOL database	Sung, P.-J., et al, Chem. Pharm. Bull. 51, 1429 (2003)

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as diterpene lactones. These are diterpenoids containing a lactone moiety.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Diterpene lactones

Alternative Parents

Substituents

Diterpene lactone
Diterpenoid
Briarane diterpenoid
Para-dioxane
Gamma butyrolactone
Oxolane
Carboxylic acid ester
Lactone
Secondary alcohol
Monocarboxylic acid or derivatives
Oxacycle
Ether
Oxirane
Dialkyl ether
Carboxylic acid derivative
Organoheterocyclic compound
Polyol
Organooxygen compound
Alcohol
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Carbonyl group
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

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

Predicted Properties

Property	Value	Source
logP	1.18	ALOGPS
logP	0.93	ChemAxon
logS	-2.2	ALOGPS
pKa (Strongest Acidic)	13.42	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	99.52 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	94.69 m³·mol⁻¹	ChemAxon
Polarizability	37.87 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

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

10207662

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

21589221

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Sung, P.-J., et al. (2003). Sung, P.-J., et al, Chem. Pharm. Bull. 51, 1429 (2003). Chem. Pharm. Bull..

Showing NP-Card for Junceellolide H (NP0026751)

MOL for NP0026751 (Junceellolide H)

3D MOL for NP0026751 (Junceellolide H)

3D SDF for NP0026751 (Junceellolide H)

3D-SDF for NP0026751 (Junceellolide H)

PDB for NP0026751 (Junceellolide H)

3D PDB for NP0026751 (Junceellolide H)

SMILES for NP0026751 (Junceellolide H)

INCHI for NP0026751 (Junceellolide H)

Structure for NP0026751 (Junceellolide H)

3D Structure for NP0026751 (Junceellolide H)