NP-MRD: Showing NP-Card for 8beta-(5-Acetoxy-tiglinoyloxy)-2-oxo-ludartin (NP0063691)

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Record Information

Version

1.0

Created at

2022-04-28 08:03:33 UTC

Updated at

2022-04-28 08:03:33 UTC

NP-MRD ID

NP0063691

Secondary Accession Numbers

None

Natural Product Identification

Common Name

8beta-(5-Acetoxy-tiglinoyloxy)-2-oxo-ludartin

Description

(1S,2S,6R,7R,12S,14S)-9,14-dimethyl-5-methylidene-4,11-dioxo-3,13-dioxatetracyclo[8.4.0.0²,⁶.0¹²,¹⁴]Tetradec-9-en-7-yl (2E)-2-[(acetyloxy)methyl]but-2-enoate belongs to the class of organic compounds known as germacranolides and derivatives. These are sesquiterpene lactones with a structure based on the germacranolide skeleton, characterized by a gamma lactone fused to a 1,7-dimethylcyclodec-1-ene moiety. 8beta-(5-Acetoxy-tiglinoyloxy)-2-oxo-ludartin is found in Lasiolaena santosii. It was first documented in 2022 (PMID: 35483916). Based on a literature review a significant number of articles have been published on (1S,2S,6R,7R,12S,14S)-9,14-dimethyl-5-methylidene-4,11-dioxo-3,13-dioxatetracyclo[8.4.0.0²,⁶.0¹²,¹⁴]Tetradec-9-en-7-yl (2E)-2-[(acetyloxy)methyl]but-2-enoate (PMID: 35483915) (PMID: 35483914) (PMID: 35483913) (PMID: 35483912).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282210032D          

 30 33  0  0  1  0            999 V2000
    4.9177   -0.6302    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.2264   -0.1799    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5845   -0.6982    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.8791   -1.4688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4603   -2.1796    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6435   -2.2953    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0437   -1.7289    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1126   -0.9067    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7984   -0.4481    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5740    0.3458    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7497    0.3778    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2910    1.0636    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4645   -0.3963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6706   -0.6206    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2731   -2.0235    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1429   -2.8381    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7833   -3.3582    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3723   -3.1327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2421   -3.9474    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5285   -4.2420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2681   -2.6126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0387   -2.9072    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6792   -2.3872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4498   -2.6818    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5490   -1.5725    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9190   -2.8653    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7030   -1.4268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2214   -2.0686    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9620    0.1936    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7780    0.5126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  1  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  3  9  1  0  0  0  0
  9 10  1  6  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
  8 13  1  1  0  0  0
 13 14  2  0  0  0  0
  7 15  1  1  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 18 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 23 25  1  0  0  0  0
  5 26  1  0  0  0  0
  4 27  1  0  0  0  0
  1 27  1  0  0  0  0
 27 28  2  0  0  0  0
  2 29  1  0  0  0  0
  1 29  1  6  0  0  0
  2 30  1  1  0  0  0
M  END

     RDKit          3D

 54 57  0  0  0  0  0  0  0  0999 V2000
   -0.3157   -3.0035    1.4795 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3502   -2.2333    1.2942 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6722   -2.4975    1.9066 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9550   -3.4485    2.6771 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5545   -1.4933    1.4712 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7566   -0.3642    1.0984 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.3933    0.4516    0.0397 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.6775    1.7766   -0.0128 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4877    2.0587    0.4619 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1215    3.4937    0.2089 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5041    1.2057    1.1741 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3628   -0.0902    0.3949 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9139   -0.6566    0.5626 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8662   -0.6942   -0.4327 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5450   -0.1868   -1.5369 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1953   -1.2960   -0.2232 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5108   -1.8251    0.9504 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8019   -2.4428    1.2501 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1855   -1.3170   -1.3108 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5216   -0.0085   -1.7567 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4445    0.0989   -2.7779 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8844    1.4043   -3.3375 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9472   -0.9310   -3.2707 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5109   -1.0114    0.5061 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.6215    2.6576   -0.6906 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2492    3.6405   -1.3824 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0179    2.1836   -0.4112 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.5073    1.0505   -1.0045 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7940    0.8827    0.2451 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.6502    0.3594    1.3436 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4002   -3.8896    2.1105 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6605   -2.8593    1.0550 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5641    0.2284    1.9868 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2348    0.0217   -0.9918 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9273    3.6709   -0.8766 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2343    3.7588    0.8207 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0009    4.0867    0.5609 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4979    1.6993    1.1186 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7200    1.0597    2.2311 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3680    0.2778   -0.6849 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7510   -1.7863    1.7202 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6442   -1.6920    1.2801 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7705   -2.8849    2.2645 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0672   -3.2727    0.5622 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7747   -1.8358   -2.2222 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1193   -1.7846   -0.9819 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0084    1.4126   -3.2268 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6982    1.4619   -4.4204 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5187    2.2596   -2.7631 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8663   -1.3612   -0.5160 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6858    2.9442    0.0293 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8614   -0.7379    1.2243 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3002    0.6114    2.3524 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6613    0.8473    1.2384 H   0  0  0  0  0  0  0  0  0  0  0  0
 18 17  1  0
 17 16  2  0
 16 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 21 23  2  0
 16 14  1  0
 14 15  2  0
 14 13  1  0
 13 12  1  0
 12 11  1  0
 11  9  1  0
  9 10  1  0
  9  8  2  0
  8  7  1  0
  7  6  1  0
  6  5  1  0
  5  3  1  0
  3  4  2  0
  3  2  1  0
  2  1  2  3
  2 24  1  0
  7 29  1  0
 29 30  1  1
 29 28  1  0
 28 27  1  0
 27 25  1  0
 25 26  2  0
 24 12  1  0
 27 29  1  0
 25  8  1  0
 24  6  1  0
 18 42  1  0
 18 43  1  0
 18 44  1  0
 17 41  1  0
 19 45  1  0
 19 46  1  0
 22 47  1  0
 22 48  1  0
 22 49  1  0
 12 40  1  6
 11 38  1  0
 11 39  1  0
 10 35  1  0
 10 36  1  0
 10 37  1  0
  7 34  1  6
  6 33  1  1
  1 31  1  0
  1 32  1  0
 24 50  1  6
 30 52  1  0
 30 53  1  0
 30 54  1  0
 27 51  1  1
M  END


  Mrv1652304282210032D          

 30 33  0  0  1  0            999 V2000
    4.9177   -0.6302    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.2264   -0.1799    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5845   -0.6982    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.8791   -1.4688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4603   -2.1796    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6435   -2.2953    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0437   -1.7289    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1126   -0.9067    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7984   -0.4481    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5740    0.3458    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7497    0.3778    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2910    1.0636    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4645   -0.3963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6706   -0.6206    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2731   -2.0235    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1429   -2.8381    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7833   -3.3582    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3723   -3.1327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2421   -3.9474    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5285   -4.2420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2681   -2.6126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0387   -2.9072    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6792   -2.3872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4498   -2.6818    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5490   -1.5725    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9190   -2.8653    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7030   -1.4268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2214   -2.0686    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9620    0.1936    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7780    0.5126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  1  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  3  9  1  0  0  0  0
  9 10  1  6  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
  8 13  1  1  0  0  0
 13 14  2  0  0  0  0
  7 15  1  1  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 18 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 23 25  1  0  0  0  0
  5 26  1  0  0  0  0
  4 27  1  0  0  0  0
  1 27  1  0  0  0  0
 27 28  2  0  0  0  0
  2 29  1  0  0  0  0
  1 29  1  6  0  0  0
  2 30  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0063691

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C\C=C(/COC(C)=O)C(=O)O[C@@H]1CC(C)=C2[C@@H]([C@H]3OC(=O)C(=C)[C@H]13)[C@]1(C)O[C@@H]1C2=O

> <INCHI_IDENTIFIER>
InChI=1S/C22H24O8/c1-6-12(8-27-11(4)23)21(26)28-13-7-9(2)14-16(22(5)19(30-22)17(14)24)18-15(13)10(3)20(25)29-18/h6,13,15-16,18-19H,3,7-8H2,1-2,4-5H3/b12-6+/t13-,15-,16+,18+,19-,22+/m1/s1

> <INCHI_KEY>
SZOZPUPPJCQDKE-RPOQHKDZSA-N

> <FORMULA>
C22H24O8

> <MOLECULAR_WEIGHT>
416.426

> <EXACT_MASS>
416.147117733

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
54

> <JCHEM_AVERAGE_POLARIZABILITY>
41.7098073901911

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,2S,6R,7R,12S,14S)-9,14-dimethyl-5-methylidene-4,11-dioxo-3,13-dioxatetracyclo[8.4.0.0^{2,6}.0^{12,14}]tetradec-9-en-7-yl (2E)-2-[(acetyloxy)methyl]but-2-enoate

> <ALOGPS_LOGP>
2.25

> <JCHEM_LOGP>
1.9330042039999993

> <ALOGPS_LOGS>
-3.47

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
19.077282122892342

> <JCHEM_PKA_STRONGEST_BASIC>
-4.279807993535766

> <JCHEM_POLAR_SURFACE_AREA>
105.2

> <JCHEM_REFRACTIVITY>
103.35409999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.41e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2S,6R,7R,12S,14S)-9,14-dimethyl-5-methylidene-4,11-dioxo-3,13-dioxatetracyclo[8.4.0.0^{2,6}.0^{12,14}]tetradec-9-en-7-yl (2E)-2-[(acetyloxy)methyl]but-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0       9.180  -1.176   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       7.889  -0.336   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.691  -1.303   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.241  -2.742   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.459  -4.069   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.934  -4.285   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.815  -3.227   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.944  -1.693   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.224  -0.836   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       4.805   0.646   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       3.266   0.705   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       2.410   1.985   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       2.734  -0.740   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.252  -1.159   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       2.376  -3.777   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       2.133  -5.298   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       3.329  -6.269   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       0.695  -5.848   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.452  -7.368   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -0.987  -7.918   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -0.501  -4.877   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      -1.939  -5.427   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      -3.134  -4.456   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      -4.573  -5.006   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      -2.891  -2.935   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       7.315  -5.349   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       8.779  -2.663   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       9.747  -3.861   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0       9.262   0.361   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       7.052   0.957   0.000  0.00  0.00           C+0
CONECT    1    2   27   29                                                  
CONECT    2    1    3   29   30                                             
CONECT    3    2    4    9                                                  
CONECT    4    3    5   27                                                  
CONECT    5    4    6   26                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   15                                                  
CONECT    8    7    9   13                                                  
CONECT    9    8    3   10                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11    8   14                                                  
CONECT   14   13                                                            
CONECT   15    7   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19   21                                                  
CONECT   19   18   20                                                       
CONECT   20   19                                                            
CONECT   21   18   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23                                                            
CONECT   26    5                                                            
CONECT   27    4    1   28                                                  
CONECT   28   27                                                            
CONECT   29    2    1                                                       
CONECT   30    2                                                            
MASTER        0    0    0    0    0    0    0    0   30    0   66    0
END

View in JSmol

Synonyms

Value	Source
(1S,2S,6R,7R,12S,14S)-9,14-Dimethyl-5-methylidene-4,11-dioxo-3,13-dioxatetracyclo[8.4.0.0,.0,]tetradec-9-en-7-yl (2E)-2-[(acetyloxy)methyl]but-2-enoic acid	Generator

Chemical Formula

C₂₂H₂₄O₈

Average Mass

416.4260 Da

Monoisotopic Mass

416.14712 Da

IUPAC Name

(1S,2S,6R,7R,12S,14S)-9,14-dimethyl-5-methylidene-4,11-dioxo-3,13-dioxatetracyclo[8.4.0.0^{2,6}.0^{12,14}]tetradec-9-en-7-yl (2E)-2-[(acetyloxy)methyl]but-2-enoate

Traditional Name

(1S,2S,6R,7R,12S,14S)-9,14-dimethyl-5-methylidene-4,11-dioxo-3,13-dioxatetracyclo[8.4.0.0^{2,6}.0^{12,14}]tetradec-9-en-7-yl (2E)-2-[(acetyloxy)methyl]but-2-enoate

CAS Registry Number

Not Available

SMILES

C\C=C(/COC(C)=O)C(=O)O[C@@H]1CC(C)=C2[C@@H]([C@H]3OC(=O)C(=C)[C@H]13)[C@]1(C)O[C@@H]1C2=O

InChI Identifier

InChI=1S/C22H24O8/c1-6-12(8-27-11(4)23)21(26)28-13-7-9(2)14-16(22(5)19(30-22)17(14)24)18-15(13)10(3)20(25)29-18/h6,13,15-16,18-19H,3,7-8H2,1-2,4-5H3/b12-6+/t13-,15-,16+,18+,19-,22+/m1/s1

InChI Key

SZOZPUPPJCQDKE-RPOQHKDZSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Lasiolaena santosii	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as germacranolides and derivatives. These are sesquiterpene lactones with a structure based on the germacranolide skeleton, characterized by a gamma lactone fused to a 1,7-dimethylcyclodec-1-ene moiety.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Germacranolides and derivatives

Alternative Parents

Substituents

Germacranolide
Sesquiterpenoid
Tricarboxylic acid or derivatives
Fatty acid ester
Fatty acyl
Oxane
Gamma butyrolactone
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Tetrahydrofuran
Lactone
Ketone
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Ether
Oxirane
Dialkyl ether
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen 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	2.25	ALOGPS
logP	1.93	ChemAxon
logS	-3.5	ALOGPS
pKa (Strongest Acidic)	19.08	ChemAxon
pKa (Strongest Basic)	-4.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	105.2 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	103.35 m³·mol⁻¹	ChemAxon
Polarizability	41.71 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	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

163106077

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Uchida Y, Kan H, Sakurai K, Horimoto Y, Hayashi E, Iida A, Okamura N, Oishi K, Matsukawa N: APOE varepsilon4 dose associates with increased brain iron and beta-amyloid via blood-brain barrier dysfunction. J Neurol Neurosurg Psychiatry. 2022 Apr 28. pii: jnnp-2021-328519. doi: 10.1136/jnnp-2021-328519. [PubMed:35483916 ]
Cacciaguerra L, Pagani E, Radaelli M, Mesaros S, Martinelli V, Ivanovic J, Drulovic J, Filippi M, Rocca MA: MR T2-relaxation time as an indirect measure of brain water content and disease activity in NMOSD. J Neurol Neurosurg Psychiatry. 2022 Apr 28. pii: jnnp-2022-328956. doi: 10.1136/jnnp-2022-328956. [PubMed:35483915 ]
Broomfield NM, West R, Barber M, Quinn TJ, Gillespie D, Walters M, House A: TEARS: a longitudinal investigation of the prevalence, psychological associations and trajectory of poststroke emotionalism. J Neurol Neurosurg Psychiatry. 2022 Apr 28. pii: jnnp-2022-329042. doi: 10.1136/jnnp-2022-329042. [PubMed:35483914 ]
Khankari J, Yu Y, Ouyang J, Hussein R, Do HM, Heit JJ, Zaharchuk G: Automated detection of arterial landmarks and vascular occlusions in patients with acute stroke receiving digital subtraction angiography using deep learning. J Neurointerv Surg. 2022 Apr 28. pii: neurintsurg-2021-018638. doi: 10.1136/neurintsurg-2021-018638. [PubMed:35483913 ]
Adeeb N, Dibas M, Diestro JDB, Phan K, Cuellar-Saenz HH, Sweid A, Lay SV, Guenego A, Aslan A, Renieri L, Sundararajan SH, Saliou G, Mohlenbruch M, Regenhardt RW, Vranic JE, Lylyk I, Foreman PM, Vachhani JA, Zupancic V, Hafeez MU, Rutledge C, Waqas M, Tutino VM, Rabinov JD, Ren Y, Schirmer CM, Piano M, Kuhn AL, Michelozzi C, Elens S, Starke RM, Hassan A, Salehani A, Brehm A, MohammedAli M, Jones J, Psychogios M, Spears J, Lubicz B, Panni P, Puri AS, Pero G, Griessenauer CJ, Asadi H, Siddiqui A, Ducruet A, Albuquerque FC, Du R, Kan P, Kalousek V, Lylyk P, Stapleton CJ, Boddu S, Knopman J, Aziz-Sultan MA, Limbucci N, Jabbour P, Cognard C, Patel AB, Dmytriw AA: Comparing treatment outcomes of various intracranial bifurcation aneurysms locations using the Woven EndoBridge (WEB) device. J Neurointerv Surg. 2022 Apr 28. pii: neurintsurg-2022-018694. doi: 10.1136/neurintsurg-2022-018694. [PubMed:35483912 ]

Showing NP-Card for 8beta-(5-Acetoxy-tiglinoyloxy)-2-oxo-ludartin (NP0063691)

MOL for NP0063691 (8beta-(5-Acetoxy-tiglinoyloxy)-2-oxo-ludartin)

3D MOL for NP0063691 (8beta-(5-Acetoxy-tiglinoyloxy)-2-oxo-ludartin)

3D SDF for NP0063691 (8beta-(5-Acetoxy-tiglinoyloxy)-2-oxo-ludartin)

3D-SDF for NP0063691 (8beta-(5-Acetoxy-tiglinoyloxy)-2-oxo-ludartin)

PDB for NP0063691 (8beta-(5-Acetoxy-tiglinoyloxy)-2-oxo-ludartin)

3D PDB for NP0063691 (8beta-(5-Acetoxy-tiglinoyloxy)-2-oxo-ludartin)

SMILES for NP0063691 (8beta-(5-Acetoxy-tiglinoyloxy)-2-oxo-ludartin)

INCHI for NP0063691 (8beta-(5-Acetoxy-tiglinoyloxy)-2-oxo-ludartin)

Structure for NP0063691 (8beta-(5-Acetoxy-tiglinoyloxy)-2-oxo-ludartin)

3D Structure for NP0063691 (8beta-(5-Acetoxy-tiglinoyloxy)-2-oxo-ludartin)