NP-MRD: Showing NP-Card for (-)-jasplakinolide Z4 (NP0035803)

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Record Information

Version

2.0

Created at

2021-06-20 19:08:51 UTC

Updated at

2021-06-30 00:07:02 UTC

NP-MRD ID

NP0035803

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(-)-jasplakinolide Z4

Provided By

JEOL Database JEOL Logo

Description

(-)-Jasplakinolide Z4 is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. (-)-jasplakinolide Z4 is found in Jaspis splendens. (-)-jasplakinolide Z4 was first documented in 2011 (Watts, K. R., et al.). Based on a literature review very few articles have been published on (-)-jasplakinolide Z4.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306202121083D          

 75 76  0  0  0  0            999 V2000
   -5.6990    0.9629   -0.4299 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2778    1.4588   -0.4546 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4067    1.2527    0.5557 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6575    0.4823    1.8371 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.4097    1.3879    3.0441 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8667   -0.8446    1.8814 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3371   -0.7418    1.9332 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7010   -2.1148    1.7419 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9299   -0.2341    3.2011 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8700    2.2831   -1.6629 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.4664    1.5057   -2.9322 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.6248    0.7228   -3.5490 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2541    0.6026   -2.7086 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.3358   -0.5834   -0.4033 C   0  0  0  0  0  0  0  0  0  0  0  0
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    4.5802    1.1432    0.1310 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1210    0.3417    1.6158 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3547    5.1057    2.2877 H   0  0  0  0  0  0  0  0  0  0  0  0
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    0.0266    2.2106    2.9495 H   0  0  0  0  0  0  0  0  0  0  0  0
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 14 13  2  0  0  0  0
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  4 41  1  6  0  0  0
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  7 47  1  6  0  0  0
  9 51  1  0  0  0  0
  8 48  1  0  0  0  0
  8 49  1  0  0  0  0
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M  END

     RDKit          3D

 75 76  0  0  0  0  0  0  0  0999 V2000
   -5.6990    0.9629   -0.4299 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2778    1.4588   -0.4546 C   0  0  0  0  0  0  0  0  0  0  0  0
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 10 11  1  0
  6  7  1  0
 11 13  1  0
  7  9  1  0
 28 27  1  0
  7  8  1  0
 32 73  1  0
 31 72  1  0
 30 71  1  0
 29 70  1  0
 27 69  1  0
 23 67  1  0
 23 68  1  0
  4 41  1  6
  3 40  1  0
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  1 38  1  0
  1 39  1  0
 10 52  1  0
 10 53  1  0
 11 54  1  6
  6 45  1  0
  6 46  1  0
 15 58  1  0
 16 59  1  1
 22 66  1  6
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 35 75  1  0
  5 42  1  0
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 12 55  1  0
 12 56  1  0
 12 57  1  0
 21 63  1  0
 21 64  1  0
 21 65  1  0
 17 60  1  0
 17 61  1  0
 17 62  1  0
  7 47  1  6
  9 51  1  0
  8 48  1  0
  8 49  1  0
  8 50  1  0
M  END


  Mrv1652306202121083D          

 75 76  0  0  0  0            999 V2000
   -5.6990    0.9629   -0.4299 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2778    1.4588   -0.4546 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4067    1.2527    0.5557 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6575    0.4823    1.8371 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.4097    1.3879    3.0441 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8667   -0.8446    1.8814 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3371   -0.7418    1.9332 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7010   -2.1148    1.7419 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9299   -0.2341    3.2011 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8700    2.2831   -1.6629 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.4664    1.5057   -2.9322 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.6248    0.7228   -3.5490 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2541    0.6026   -2.7086 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2723   -0.6130   -2.8806 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1118    1.2716   -2.3425 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.1495    0.5872   -2.0747 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9767    0.4887   -3.3495 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8939    1.4074   -0.9996 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5556    2.5806   -0.7847 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9406    0.8195   -0.2937 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3358   -0.5834   -0.4033 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5710    1.6380    0.7783 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.0400    1.2924    1.0745 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.7450    2.3691    1.8500 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3336    3.5136    1.3527 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4185    4.0681   -0.4653 Br  0  0  0  0  0  0  0  0  0  0  0  0
    5.8666    4.2274    2.3845 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.6395    3.5781    3.5734 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9984    3.9363    4.8784 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6285    3.0720    5.9121 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9292    1.8977    5.6478 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5803    1.5541    4.3365 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9392    2.4078    3.2727 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6905    1.4280    2.0256 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6875    2.3406    2.1930 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7431    0.4356    2.7516 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -6.3230    1.5081   -1.1456 H   0  0  0  0  0  0  0  0  0  0  0  0
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    0.0519   -0.2010    3.1978 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.9180   -0.1326   -2.9331 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3364    0.3252   -4.5287 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.0926   -0.4042   -1.6825 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1953    1.4840   -3.7535 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4388   -0.0706   -4.1223 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9346   -0.0098   -3.1751 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3633   -0.6310   -0.7737 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7074   -1.1550   -1.0839 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2815   -1.0536    0.5816 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5054    2.6940    0.4884 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5802    1.1432    0.1310 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1210    0.3417    1.6158 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3547    5.1057    2.2877 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5429    4.8511    5.0884 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8898    3.3213    6.9381 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6470    1.2393    6.4659 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0305    0.6351    4.1508 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0266    2.2106    2.9495 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4923    3.0472    1.4907 H   0  0  0  0  0  0  0  0  0  0  0  0
 14 13  2  0  0  0  0
 27 25  1  0  0  0  0
 25 24  2  0  0  0  0
 24 33  1  0  0  0  0
 29 28  1  0  0  0  0
 13 15  1  0  0  0  0
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 16 18  1  0  0  0  0
 19 18  2  0  0  0  0
 24 23  1  0  0  0  0
  6  4  1  0  0  0  0
 33 28  2  0  0  0  0
 32 31  2  0  0  0  0
 18 20  1  0  0  0  0
 20 22  1  0  0  0  0
 22 34  1  0  0  0  0
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 34 36  2  0  0  0  0
  1  2  1  0  0  0  0
 34 35  1  0  0  0  0
 33 32  1  0  0  0  0
  4  5  1  0  0  0  0
 31 30  1  0  0  0  0
 11 12  1  0  0  0  0
 22 23  1  0  0  0  0
 20 21  1  0  0  0  0
 30 29  2  0  0  0  0
 16 17  1  0  0  0  0
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 28 27  1  0  0  0  0
  7  8  1  0  0  0  0
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 17 60  1  0  0  0  0
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 17 62  1  0  0  0  0
  7 47  1  6  0  0  0
  9 51  1  0  0  0  0
  8 48  1  0  0  0  0
  8 49  1  0  0  0  0
  8 50  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0035803

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]O[C@@]([H])(C([H])([H])[H])C([H])([H])[C@]([H])(C(\[H])=C(/C([H])([H])[H])C([H])([H])[C@@]([H])(C(=O)N([H])[C@]([H])(C(=O)N(C([H])([H])[H])[C@@]([H])(C(=O)N([H])[H])C([H])([H])C1=C(Br)N([H])C2=C1C([H])=C([H])C([H])=C2[H])C([H])([H])[H])C([H])([H])[H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C27H39BrN4O4/c1-15(11-16(2)13-18(4)33)12-17(3)26(35)30-19(5)27(36)32(6)23(25(29)34)14-21-20-9-7-8-10-22(20)31-24(21)28/h7-11,16-19,23,31,33H,12-14H2,1-6H3,(H2,29,34)(H,30,35)/b15-11+/t16-,17-,18-,19-,23+/m0/s1

> <INCHI_KEY>
XWCIEJNXKGXQCZ-YZTGKPPRSA-N

> <FORMULA>
C27H39BrN4O4

> <MOLECULAR_WEIGHT>
563.537

> <EXACT_MASS>
562.215469

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
75

> <JCHEM_AVERAGE_POLARIZABILITY>
57.24817878042248

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S,4E,6R,8S)-N-[(1S)-1-{[(1R)-2-(2-bromo-1H-indol-3-yl)-1-carbamoylethyl](methyl)carbamoyl}ethyl]-8-hydroxy-2,4,6-trimethylnon-4-enamide

> <ALOGPS_LOGP>
3.48

> <JCHEM_LOGP>
2.959266791666667

> <ALOGPS_LOGS>
-5.30

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.915886513393602

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.763338383750916

> <JCHEM_PKA_STRONGEST_BASIC>
-0.9043821176158585

> <JCHEM_POLAR_SURFACE_AREA>
128.52

> <JCHEM_REFRACTIVITY>
145.5688

> <JCHEM_ROTATABLE_BOND_COUNT>
12

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.83e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S,4E,6R,8S)-N-[(1S)-1-{[(1R)-2-(2-bromo-1H-indol-3-yl)-1-carbamoylethyl](methyl)carbamoyl}ethyl]-8-hydroxy-2,4,6-trimethylnon-4-enamide

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 75 76  0  0  0  0  0  0  0  0999 V2000
   -5.6990    0.9629   -0.4299 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2778    1.4588   -0.4546 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4067    1.2527    0.5557 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6575    0.4823    1.8371 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.4097    1.3879    3.0441 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8667   -0.8446    1.8814 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3371   -0.7418    1.9332 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7010   -2.1148    1.7419 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9299   -0.2341    3.2011 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8700    2.2831   -1.6629 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.5710    1.6380    0.7783 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.0400    1.2924    1.0745 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7450    2.3691    1.8500 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3336    3.5136    1.3527 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4185    4.0681   -0.4653 Br  0  0  0  0  0  0  0  0  0  0  0  0
    5.8666    4.2274    2.3845 N   0  0  0  0  0  0  0  0  0  0  0  0
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    0.0519   -0.2010    3.1978 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6900    2.9707   -1.9108 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0432    2.9467   -1.3760 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1561    2.2510   -3.6784 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9180   -0.1326   -2.9331 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3364    0.3252   -4.5287 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4997    1.3644   -3.6949 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1254    2.2721   -2.1734 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0926   -0.4042   -1.6825 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1953    1.4840   -3.7535 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4388   -0.0706   -4.1223 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9346   -0.0098   -3.1751 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3633   -0.6310   -0.7737 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7074   -1.1550   -1.0839 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2815   -1.0536    0.5816 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5054    2.6940    0.4884 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5802    1.1432    0.1310 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1210    0.3417    1.6158 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3547    5.1057    2.2877 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5429    4.8511    5.0884 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8898    3.3213    6.9381 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6470    1.2393    6.4659 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0305    0.6351    4.1508 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0266    2.2106    2.9495 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4923    3.0472    1.4907 H   0  0  0  0  0  0  0  0  0  0  0  0
 14 13  2  0
 27 25  1  0
 25 24  2  0
 24 33  1  0
 29 28  1  0
 13 15  1  0
 15 16  1  0
 16 18  1  0
 19 18  2  0
 24 23  1  0
  6  4  1  0
 33 28  2  0
 32 31  2  0
 18 20  1  0
 20 22  1  0
 22 34  1  0
  4  3  1  0
  3  2  2  0
 34 36  2  0
  1  2  1  0
 34 35  1  0
 33 32  1  0
  4  5  1  0
 31 30  1  0
 11 12  1  0
 22 23  1  0
 20 21  1  0
 30 29  2  0
 16 17  1  0
  2 10  1  0
 25 26  1  0
 10 11  1  0
  6  7  1  0
 11 13  1  0
  7  9  1  0
 28 27  1  0
  7  8  1  0
 32 73  1  0
 31 72  1  0
 30 71  1  0
 29 70  1  0
 27 69  1  0
 23 67  1  0
 23 68  1  0
  4 41  1  6
  3 40  1  0
  1 37  1  0
  1 38  1  0
  1 39  1  0
 10 52  1  0
 10 53  1  0
 11 54  1  6
  6 45  1  0
  6 46  1  0
 15 58  1  0
 16 59  1  1
 22 66  1  6
 35 74  1  0
 35 75  1  0
  5 42  1  0
  5 43  1  0
  5 44  1  0
 12 55  1  0
 12 56  1  0
 12 57  1  0
 21 63  1  0
 21 64  1  0
 21 65  1  0
 17 60  1  0
 17 61  1  0
 17 62  1  0
  7 47  1  6
  9 51  1  0
  8 48  1  0
  8 49  1  0
  8 50  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      -5.699   0.963  -0.430  0.00  0.00           C+0
HETATM    2  C   UNK     0      -4.278   1.459  -0.455  0.00  0.00           C+0
HETATM    3  C   UNK     0      -3.407   1.253   0.556  0.00  0.00           C+0
HETATM    4  C   UNK     0      -3.658   0.482   1.837  0.00  0.00           C+0
HETATM    5  C   UNK     0      -3.410   1.388   3.044  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.867  -0.845   1.881  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.337  -0.742   1.933  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.701  -2.115   1.742  0.00  0.00           C+0
HETATM    9  O   UNK     0      -0.930  -0.234   3.201  0.00  0.00           O+0
HETATM   10  C   UNK     0      -3.870   2.283  -1.663  0.00  0.00           C+0
HETATM   11  C   UNK     0      -3.466   1.506  -2.932  0.00  0.00           C+0
HETATM   12  C   UNK     0      -4.625   0.723  -3.549  0.00  0.00           C+0
HETATM   13  C   UNK     0      -2.254   0.603  -2.709  0.00  0.00           C+0
HETATM   14  O   UNK     0      -2.272  -0.613  -2.881  0.00  0.00           O+0
HETATM   15  N   UNK     0      -1.112   1.272  -2.342  0.00  0.00           N+0
HETATM   16  C   UNK     0       0.150   0.587  -2.075  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.977   0.489  -3.349  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.894   1.407  -1.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       0.556   2.581  -0.785  0.00  0.00           O+0
HETATM   20  N   UNK     0       1.941   0.820  -0.294  0.00  0.00           N+0
HETATM   21  C   UNK     0       2.336  -0.583  -0.403  0.00  0.00           C+0
HETATM   22  C   UNK     0       2.571   1.638   0.778  0.00  0.00           C+0
HETATM   23  C   UNK     0       4.040   1.292   1.075  0.00  0.00           C+0
HETATM   24  C   UNK     0       4.745   2.369   1.850  0.00  0.00           C+0
HETATM   25  C   UNK     0       5.334   3.514   1.353  0.00  0.00           C+0
HETATM   26 Br   UNK     0       5.418   4.068  -0.465  0.00  0.00          Br+0
HETATM   27  N   UNK     0       5.867   4.227   2.385  0.00  0.00           N+0
HETATM   28  C   UNK     0       5.640   3.578   3.573  0.00  0.00           C+0
HETATM   29  C   UNK     0       5.998   3.936   4.878  0.00  0.00           C+0
HETATM   30  C   UNK     0       5.628   3.072   5.912  0.00  0.00           C+0
HETATM   31  C   UNK     0       4.929   1.898   5.648  0.00  0.00           C+0
HETATM   32  C   UNK     0       4.580   1.554   4.337  0.00  0.00           C+0
HETATM   33  C   UNK     0       4.939   2.408   3.273  0.00  0.00           C+0
HETATM   34  C   UNK     0       1.690   1.428   2.026  0.00  0.00           C+0
HETATM   35  N   UNK     0       0.688   2.341   2.193  0.00  0.00           N+0
HETATM   36  O   UNK     0       1.743   0.436   2.752  0.00  0.00           O+0
HETATM   37  H   UNK     0      -6.162   1.111   0.550  0.00  0.00           H+0
HETATM   38  H   UNK     0      -6.323   1.508  -1.146  0.00  0.00           H+0
HETATM   39  H   UNK     0      -5.738  -0.100  -0.685  0.00  0.00           H+0
HETATM   40  H   UNK     0      -2.405   1.674   0.468  0.00  0.00           H+0
HETATM   41  H   UNK     0      -4.713   0.192   1.889  0.00  0.00           H+0
HETATM   42  H   UNK     0      -2.412   1.837   3.028  0.00  0.00           H+0
HETATM   43  H   UNK     0      -4.133   2.212   3.059  0.00  0.00           H+0
HETATM   44  H   UNK     0      -3.524   0.831   3.980  0.00  0.00           H+0
HETATM   45  H   UNK     0      -3.154  -1.438   1.002  0.00  0.00           H+0
HETATM   46  H   UNK     0      -3.209  -1.404   2.763  0.00  0.00           H+0
HETATM   47  H   UNK     0      -0.967  -0.066   1.157  0.00  0.00           H+0
HETATM   48  H   UNK     0      -0.954  -2.537   0.765  0.00  0.00           H+0
HETATM   49  H   UNK     0      -1.029  -2.810   2.522  0.00  0.00           H+0
HETATM   50  H   UNK     0       0.389  -2.050   1.820  0.00  0.00           H+0
HETATM   51  H   UNK     0       0.052  -0.201   3.198  0.00  0.00           H+0
HETATM   52  H   UNK     0      -4.690   2.971  -1.911  0.00  0.00           H+0
HETATM   53  H   UNK     0      -3.043   2.947  -1.376  0.00  0.00           H+0
HETATM   54  H   UNK     0      -3.156   2.251  -3.678  0.00  0.00           H+0
HETATM   55  H   UNK     0      -4.918  -0.133  -2.933  0.00  0.00           H+0
HETATM   56  H   UNK     0      -4.336   0.325  -4.529  0.00  0.00           H+0
HETATM   57  H   UNK     0      -5.500   1.364  -3.695  0.00  0.00           H+0
HETATM   58  H   UNK     0      -1.125   2.272  -2.173  0.00  0.00           H+0
HETATM   59  H   UNK     0      -0.093  -0.404  -1.683  0.00  0.00           H+0
HETATM   60  H   UNK     0       1.195   1.484  -3.753  0.00  0.00           H+0
HETATM   61  H   UNK     0       0.439  -0.071  -4.122  0.00  0.00           H+0
HETATM   62  H   UNK     0       1.935  -0.010  -3.175  0.00  0.00           H+0
HETATM   63  H   UNK     0       3.363  -0.631  -0.774  0.00  0.00           H+0
HETATM   64  H   UNK     0       1.707  -1.155  -1.084  0.00  0.00           H+0
HETATM   65  H   UNK     0       2.281  -1.054   0.582  0.00  0.00           H+0
HETATM   66  H   UNK     0       2.505   2.694   0.488  0.00  0.00           H+0
HETATM   67  H   UNK     0       4.580   1.143   0.131  0.00  0.00           H+0
HETATM   68  H   UNK     0       4.121   0.342   1.616  0.00  0.00           H+0
HETATM   69  H   UNK     0       6.355   5.106   2.288  0.00  0.00           H+0
HETATM   70  H   UNK     0       6.543   4.851   5.088  0.00  0.00           H+0
HETATM   71  H   UNK     0       5.890   3.321   6.938  0.00  0.00           H+0
HETATM   72  H   UNK     0       4.647   1.239   6.466  0.00  0.00           H+0
HETATM   73  H   UNK     0       4.030   0.635   4.151  0.00  0.00           H+0
HETATM   74  H   UNK     0       0.027   2.211   2.950  0.00  0.00           H+0
HETATM   75  H   UNK     0       0.492   3.047   1.491  0.00  0.00           H+0
CONECT    1    2   37   38   39                                             
CONECT    2    3    1   10                                                  
CONECT    3    4    2   40                                                  
CONECT    4    6    3    5   41                                             
CONECT    5    4   42   43   44                                             
CONECT    6    4    7   45   46                                             
CONECT    7    6    9    8   47                                             
CONECT    8    7   48   49   50                                             
CONECT    9    7   51                                                       
CONECT   10    2   11   52   53                                             
CONECT   11   12   10   13   54                                             
CONECT   12   11   55   56   57                                             
CONECT   13   14   15   11                                                  
CONECT   14   13                                                            
CONECT   15   13   16   58                                                  
CONECT   16   15   18   17   59                                             
CONECT   17   16   60   61   62                                             
CONECT   18   16   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   22   21                                                  
CONECT   21   20   63   64   65                                             
CONECT   22   20   34   23   66                                             
CONECT   23   24   22   67   68                                             
CONECT   24   25   33   23                                                  
CONECT   25   27   24   26                                                  
CONECT   26   25                                                            
CONECT   27   25   28   69                                                  
CONECT   28   29   33   27                                                  
CONECT   29   28   30   70                                                  
CONECT   30   31   29   71                                                  
CONECT   31   32   30   72                                                  
CONECT   32   31   33   73                                                  
CONECT   33   24   28   32                                                  
CONECT   34   22   36   35                                                  
CONECT   35   34   74   75                                                  
CONECT   36   34                                                            
CONECT   37    1                                                            
CONECT   38    1                                                            
CONECT   39    1                                                            
CONECT   40    3                                                            
CONECT   41    4                                                            
CONECT   42    5                                                            
CONECT   43    5                                                            
CONECT   44    5                                                            
CONECT   45    6                                                            
CONECT   46    6                                                            
CONECT   47    7                                                            
CONECT   48    8                                                            
CONECT   49    8                                                            
CONECT   50    8                                                            
CONECT   51    9                                                            
CONECT   52   10                                                            
CONECT   53   10                                                            
CONECT   54   11                                                            
CONECT   55   12                                                            
CONECT   56   12                                                            
CONECT   57   12                                                            
CONECT   58   15                                                            
CONECT   59   16                                                            
CONECT   60   17                                                            
CONECT   61   17                                                            
CONECT   62   17                                                            
CONECT   63   21                                                            
CONECT   64   21                                                            
CONECT   65   21                                                            
CONECT   66   22                                                            
CONECT   67   23                                                            
CONECT   68   23                                                            
CONECT   69   27                                                            
CONECT   70   29                                                            
CONECT   71   30                                                            
CONECT   72   31                                                            
CONECT   73   32                                                            
CONECT   74   35                                                            
CONECT   75   35                                                            
MASTER        0    0    0    0    0    0    0    0   75    0  152    0
END

RDKit          3D

75 76  0  0  0  0  0  0  0  0999 V2000
   -5.6990    0.9629   -0.4299 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2778    1.4588   -0.4546 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4067    1.2527    0.5557 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6575    0.4823    1.8371 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.4097    1.3879    3.0441 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8667   -0.8446    1.8814 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3371   -0.7418    1.9332 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7010   -2.1148    1.7419 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9299   -0.2341    3.2011 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8700    2.2831   -1.6629 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4664    1.5057   -2.9322 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.6248    0.7228   -3.5490 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2541    0.6026   -2.7086 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2723   -0.6130   -2.8806 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1118    1.2716   -2.3425 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.1495    0.5872   -2.0747 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9767    0.4887   -3.3495 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8939    1.4074   -0.9996 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5556    2.5806   -0.7847 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9406    0.8195   -0.2937 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3358   -0.5834   -0.4033 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5710    1.6380    0.7783 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.0400    1.2924    1.0745 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7450    2.3691    1.8500 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3336    3.5136    1.3527 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4185    4.0681   -0.4653 Br  0  0  0  0  0  0  0  0  0  0  0  0
    5.8666    4.2274    2.3845 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.6395    3.5781    3.5734 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9984    3.9363    4.8784 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6285    3.0720    5.9121 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9292    1.8977    5.6478 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5803    1.5541    4.3365 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9392    2.4078    3.2727 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6905    1.4280    2.0256 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6875    2.3406    2.1930 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7431    0.4356    2.7516 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1621    1.1114    0.5503 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3230    1.5081   -1.1456 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7384   -0.1003   -0.6850 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4052    1.6743    0.4677 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7132    0.1916    1.8886 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4116    1.8368    3.0278 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1331    2.2115    3.0594 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5239    0.8313    3.9802 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1541   -1.4376    1.0025 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2093   -1.4042    2.7626 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9674   -0.0656    1.1570 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9540   -2.5372    0.7647 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0291   -2.8103    2.5222 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3889   -2.0501    1.8199 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0519   -0.2010    3.1978 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6900    2.9707   -1.9108 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0432    2.9467   -1.3760 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1561    2.2510   -3.6784 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9180   -0.1326   -2.9331 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3364    0.3252   -4.5287 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4997    1.3644   -3.6949 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1254    2.2721   -2.1734 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0926   -0.4042   -1.6825 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1953    1.4840   -3.7535 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4388   -0.0706   -4.1223 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9346   -0.0098   -3.1751 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3633   -0.6310   -0.7737 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7074   -1.1550   -1.0839 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2815   -1.0536    0.5816 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5054    2.6940    0.4884 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5802    1.1432    0.1310 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1210    0.3417    1.6158 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3547    5.1057    2.2877 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5429    4.8511    5.0884 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8898    3.3213    6.9381 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6470    1.2393    6.4659 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0305    0.6351    4.1508 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0266    2.2106    2.9495 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4923    3.0472    1.4907 H   0  0  0  0  0  0  0  0  0  0  0  0
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  8 48  1  0
  8 49  1  0
  8 50  1  0
M  END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₇H₃₉BrN₄O₄

Average Mass

563.5370 Da

Monoisotopic Mass

562.21547 Da

IUPAC Name

(2S,4E,6R,8S)-N-[(1S)-1-{[(1R)-2-(2-bromo-1H-indol-3-yl)-1-carbamoylethyl](methyl)carbamoyl}ethyl]-8-hydroxy-2,4,6-trimethylnon-4-enamide

Traditional Name

(2S,4E,6R,8S)-N-[(1S)-1-{[(1R)-2-(2-bromo-1H-indol-3-yl)-1-carbamoylethyl](methyl)carbamoyl}ethyl]-8-hydroxy-2,4,6-trimethylnon-4-enamide

CAS Registry Number

Not Available

SMILES

[H]O[C@@]([H])(C([H])([H])[H])C([H])([H])[C@]([H])(C(\[H])=C(/C([H])([H])[H])C([H])([H])[C@@]([H])(C(=O)N([H])[C@]([H])(C(=O)N(C([H])([H])[H])[C@@]([H])(C(=O)N([H])[H])C([H])([H])C1=C(Br)N([H])C2=C1C([H])=C([H])C([H])=C2[H])C([H])([H])[H])C([H])([H])[H])C([H])([H])[H]

InChI Identifier

InChI=1S/C27H39BrN4O4/c1-15(11-16(2)13-18(4)33)12-17(3)26(35)30-19(5)27(36)32(6)23(25(29)34)14-21-20-9-7-8-10-22(20)31-24(21)28/h7-11,16-19,23,31,33H,12-14H2,1-6H3,(H2,29,34)(H,30,35)/b15-11+/t16-,17-,18-,19-,23+/m0/s1

InChI Key

XWCIEJNXKGXQCZ-YZTGKPPRSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, CD₃OD, 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
Jaspis splendens	JEOL database	Watts, K. R., et al, J. Nat. Prod. 74, 341 (2011)

Chemical Taxonomy

Classification

Not classified

Physical Properties

State

Not Available

Experimental Properties

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

Predicted Properties

Property	Value	Source
logP	3.48	ALOGPS
logP	2.96	ChemAxon
logS	-5.3	ALOGPS
pKa (Strongest Acidic)	12.76	ChemAxon
pKa (Strongest Basic)	-0.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	128.52 Å²	ChemAxon
Rotatable Bond Count	12	ChemAxon
Refractivity	145.57 m³·mol⁻¹	ChemAxon
Polarizability	57.25 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	No	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

26344173

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

68277

Good Scents ID

Not Available

References

General References

Watts, K. R., et al. (2011). Watts, K. R., et al, J. Nat. Prod. 74, 341 (2011). J. Nat. Prod..

Showing NP-Card for (-)-jasplakinolide Z4 (NP0035803)

MOL for NP0035803 ((-)-jasplakinolide Z4)

3D MOL for NP0035803 ((-)-jasplakinolide Z4)

3D SDF for NP0035803 ((-)-jasplakinolide Z4)

3D-SDF for NP0035803 ((-)-jasplakinolide Z4)

PDB for NP0035803 ((-)-jasplakinolide Z4)

3D PDB for NP0035803 ((-)-jasplakinolide Z4)

SMILES for NP0035803 ((-)-jasplakinolide Z4)

INCHI for NP0035803 ((-)-jasplakinolide Z4)

Structure for NP0035803 ((-)-jasplakinolide Z4)

3D Structure for NP0035803 ((-)-jasplakinolide Z4)