NP-MRD: Showing NP-Card for Eupalinin A (NP0044186)

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Record Information

Version

1.0

Created at

2021-11-12 23:55:01 UTC

Updated at

2021-11-26 17:46:23 UTC

NP-MRD ID

NP0044186

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Eupalinin A

Description

Eupalinin A 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. Eupalinin A is found in Eupatorium chinense and Eupatorium lindleyanum. It was first documented in 2008 (PMID: 17980607). Based on a literature review a significant number of articles have been published on eupalinin A (PMID: 34756847) (PMID: 34758548) (PMID: 34758547) (PMID: 19414401).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652311132100552D          

 30 32  0  0  1  0            999 V2000
    3.1597    2.2120    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4442    1.4376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2571    1.2967    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7855    1.9303    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5010    2.7047    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5416    0.5224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3544    0.3815    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0132   -0.1112    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2976   -0.8856    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.8260   -0.2520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6389   -0.3929    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.9234   -1.1673    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.4518   -0.5337    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3950   -1.8008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5821   -1.6600    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.0537   -2.2936    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2408   -2.1528    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9563   -1.3784    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.4847   -0.7448    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.0455   -0.0465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3522    0.7194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2456   -0.2485    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6120    0.2799    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1905   -1.0716    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3382   -3.0680    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8666   -2.4344    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6795   -2.5752    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2079   -1.9417    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9640   -3.3496    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7798    0.4200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  3  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
  9  8  1  1  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  6  0  0  0
 11 13  1  0  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
  9 19  1  0  0  0  0
 19 20  1  6  0  0  0
 20 21  2  0  0  0  0
 20 22  1  0  0  0  0
 22 23  2  0  0  0  0
 22 24  1  0  0  0  0
 18 24  1  1  0  0  0
 16 25  1  0  0  0  0
 15 26  1  1  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 27 29  1  0  0  0  0
 11 30  1  6  0  0  0
M  END

     RDKit          3D

 58 60  0  0  0  0  0  0  0  0999 V2000
   -1.7521   -0.9847    2.1900 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9811   -1.4029    1.2014 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7925   -2.7296    0.6484 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4762   -3.7426    1.0439 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1764   -2.6869   -0.2968 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9370   -1.4491   -0.2258 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1245   -1.7706    0.5715 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0765   -0.8993    0.7687 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2219   -1.4357    1.6297 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0895    0.4320    0.2557 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.4353    0.9371    0.4839 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6669    2.0500    1.2594 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0171    2.6101    1.5267 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7015    2.6544    1.7891 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8711    0.7292   -1.1946 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5622    1.4471   -1.3564 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1910    2.2454   -2.3792 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8090    0.8378   -2.3754 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3461    0.2832   -3.6722 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5161    0.4112   -1.9498 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8355    0.3516   -0.4922 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1973   -0.1007   -0.4540 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2388    0.6212    0.0614 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9819    1.7542    0.5316 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6181    0.1495    0.0939 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5593    0.9157    0.6144 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9804    0.4779    0.6695 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9872   -1.1748   -0.4468 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2992   -2.1834    0.2316 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0590   -0.5416    0.3676 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.3700   -1.6962    2.7143 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8011    0.0428    2.5103 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1338   -1.3452   -1.3073 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1924   -2.8053    1.0161 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6418   -2.3491    1.1933 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8120   -1.7163    2.6343 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9712   -0.6648    1.8041 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4702    1.1760    0.8526 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7578    1.7750    1.3764 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2509    3.3509    0.7587 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1330    2.9667    2.5612 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6047    1.5069   -1.6025 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0395   -0.1115   -1.8841 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0920    1.7561   -0.4062 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4317    0.4090   -3.7893 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7947    0.7011   -4.5489 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1609   -0.8242   -3.7140 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2807    1.1130   -2.3992 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7661   -0.5738   -2.3905 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8923    1.3687   -0.0233 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2778    1.8806    1.0061 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1146   -0.4204    1.3129 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3405    0.2290   -0.3700 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6012    1.2847    1.0886 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0540   -1.3507   -0.2593 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7733   -1.2613   -1.5374 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6234   -2.3150    1.1407 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4565    0.0674    1.1670 H   0  0  0  0  0  0  0  0  0  0  0  0
 27 26  1  0
 26 25  2  0
 25 28  1  0
 28 29  1  0
 25 23  1  0
 23 24  2  0
 23 22  1  0
 22 21  1  0
 21 20  1  0
 20 18  1  0
 18 16  1  0
 16 17  1  0
 16 15  1  0
 15 10  1  0
 10  8  1  0
  8  7  2  0
  7  6  1  0
  6 30  1  0
 30  2  1  0
  2  1  2  3
  2  3  1  0
  3  4  2  0
  3  5  1  0
  8  9  1  0
 10 11  1  0
 11 12  1  0
 12 14  2  0
 12 13  1  0
 18 19  1  6
 30 21  1  0
 17 18  1  0
  5  6  1  0
 27 52  1  0
 27 53  1  0
 27 54  1  0
 26 51  1  0
 28 55  1  0
 28 56  1  0
 29 57  1  0
 21 50  1  1
 20 48  1  0
 20 49  1  0
 16 44  1  1
 15 42  1  0
 15 43  1  0
 10 38  1  1
  7 34  1  0
  6 33  1  6
 30 58  1  1
  1 31  1  0
  1 32  1  0
  9 35  1  0
  9 36  1  0
  9 37  1  0
 13 39  1  0
 13 40  1  0
 13 41  1  0
 19 45  1  0
 19 46  1  0
 19 47  1  0
M  END


  Mrv1652311132100552D          

 30 32  0  0  1  0            999 V2000
    3.1597    2.2120    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4442    1.4376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2571    1.2967    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7855    1.9303    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5010    2.7047    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5416    0.5224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3544    0.3815    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0132   -0.1112    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2976   -0.8856    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.8260   -0.2520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6389   -0.3929    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.9234   -1.1673    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.4518   -0.5337    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3950   -1.8008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5821   -1.6600    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.0537   -2.2936    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2408   -2.1528    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9563   -1.3784    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.4847   -0.7448    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.0455   -0.0465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3522    0.7194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2456   -0.2485    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6120    0.2799    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1905   -1.0716    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3382   -3.0680    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8666   -2.4344    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6795   -2.5752    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2079   -1.9417    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9640   -3.3496    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7798    0.4200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  3  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
  9  8  1  1  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  6  0  0  0
 11 13  1  0  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
  9 19  1  0  0  0  0
 19 20  1  6  0  0  0
 20 21  2  0  0  0  0
 20 22  1  0  0  0  0
 22 23  2  0  0  0  0
 22 24  1  0  0  0  0
 18 24  1  1  0  0  0
 16 25  1  0  0  0  0
 15 26  1  1  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 27 29  1  0  0  0  0
 11 30  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0044186

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C22H28O8/c1-6-14(10-23)21(26)29-17-9-22(5)18(30-22)8-15(27-13(4)24)11(2)7-16-19(17)12(3)20(25)28-16/h6-7,15-19,23H,3,8-10H2,1-2,4-5H3/b11-7-,14-6+/t15-,16+,17+,18+,19-,22+/m0/s1

> <INCHI_KEY>
RDZDKJXIRQNZFT-WMFZWANKSA-N

> <FORMULA>
C22H28O8

> <MOLECULAR_WEIGHT>
420.458

> <EXACT_MASS>
420.178417862

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
58

> <JCHEM_AVERAGE_POLARIZABILITY>
42.95261678819962

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,2R,4R,6R,8S,9Z,11R)-8-(acetyloxy)-4,9-dimethyl-14-methylidene-13-oxo-5,12-dioxatricyclo[9.3.0.0^{4,6}]tetradec-9-en-2-yl (2E)-2-(hydroxymethyl)but-2-enoate

> <ALOGPS_LOGP>
1.26

> <JCHEM_LOGP>
1.5671157476666666

> <ALOGPS_LOGS>
-3.47

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.886291686266247

> <JCHEM_PKA_STRONGEST_BASIC>
-2.848536016427132

> <JCHEM_POLAR_SURFACE_AREA>
111.66

> <JCHEM_REFRACTIVITY>
106.46189999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.42e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2R,4R,6R,8S,9Z,11R)-8-(acetyloxy)-4,9-dimethyl-14-methylidene-13-oxo-5,12-dioxatricyclo[9.3.0.0^{4,6}]tetradec-9-en-2-yl (2E)-2-(hydroxymethyl)but-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 13-NOV-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   13-NOV-21         0                                  
HETATM    1  C   UNK     0       5.898   4.129   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.429   2.683   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       7.947   2.421   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.933   3.603   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       8.402   5.049   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       8.478   0.975   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       9.995   0.712   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0       7.491  -0.208   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       8.022  -1.653   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.009  -0.470   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      10.526  -0.733   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      11.057  -2.179   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      12.043  -0.996   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      10.071  -3.362   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.553  -3.099   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       7.567  -4.281   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.050  -4.019   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.519  -2.573   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       6.505  -1.390   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.685  -0.087   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       6.257   1.343   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       4.192  -0.464   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       3.009   0.523   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       4.089  -2.000   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       8.098  -5.727   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       9.084  -4.544   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      10.602  -4.807   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      11.588  -3.624   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      11.133  -6.253   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      10.789   0.784   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    6                                                  
CONECT    4    3    5                                                       
CONECT    5    4                                                            
CONECT    6    3    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9    8   10   19                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   13   30                                             
CONECT   12   11   13   14                                                  
CONECT   13   12   11                                                       
CONECT   14   12   15                                                       
CONECT   15   14   16   26                                                  
CONECT   16   15   17   25                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19   24                                                  
CONECT   19   18    9   20                                                  
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   18                                                       
CONECT   25   16                                                            
CONECT   26   15   27                                                       
CONECT   27   26   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27                                                            
CONECT   30   11                                                            
MASTER        0    0    0    0    0    0    0    0   30    0   64    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₂H₂₈O₈

Average Mass

420.4580 Da

Monoisotopic Mass

420.17842 Da

IUPAC Name

(1R,2R,4R,6R,8S,9Z,11R)-8-(acetyloxy)-4,9-dimethyl-14-methylidene-13-oxo-5,12-dioxatricyclo[9.3.0.0^{4,6}]tetradec-9-en-2-yl (2E)-2-(hydroxymethyl)but-2-enoate

Traditional Name

(1R,2R,4R,6R,8S,9Z,11R)-8-(acetyloxy)-4,9-dimethyl-14-methylidene-13-oxo-5,12-dioxatricyclo[9.3.0.0^{4,6}]tetradec-9-en-2-yl (2E)-2-(hydroxymethyl)but-2-enoate

CAS Registry Number

Not Available

SMILES

C\C=C(/CO)C(=O)O[C@@H]1C[C@@]2(C)O[C@@H]2C[C@H](OC(C)=O)\C(C)=C/[C@H]2OC(=O)C(=C)[C@H]12

InChI Identifier

InChI=1S/C22H28O8/c1-6-14(10-23)21(26)29-17-9-22(5)18(30-22)8-15(27-13(4)24)11(2)7-16-19(17)12(3)20(25)28-16/h6-7,15-19,23H,3,8-10H2,1-2,4-5H3/b11-7-,14-6+/t15-,16+,17+,18+,19-,22+/m0/s1

InChI Key

RDZDKJXIRQNZFT-WMFZWANKSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 150 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 250 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 175 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 225 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 125 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, Chloroform-d, 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
Eupatorium chinense	LOTUS Database	35616633
Eupatorium lindleyanum	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
Beta-hydroxy acid
Fatty acid ester
Gamma butyrolactone
Fatty acyl
Hydroxy acid
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Tetrahydrofuran
Carboxylic acid ester
Lactone
Organoheterocyclic compound
Oxacycle
Ether
Oxirane
Dialkyl ether
Carboxylic acid derivative
Hydrocarbon derivative
Organic oxide
Alcohol
Carbonyl group
Organic oxygen compound
Organooxygen compound
Primary alcohol
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	1.26	ALOGPS
logP	1.57	ChemAxon
logS	-3.5	ALOGPS
pKa (Strongest Acidic)	14.89	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	111.66 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	106.46 m³·mol⁻¹	ChemAxon
Polarizability	42.95 Å³	ChemAxon
Number of Rings	3	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

C00011864

Chemspider ID

23320091

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

44452656

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

McDonagh MS, Wagner J, Ahmed AY, Morasco B, Kansagara D, Chou R: Living Systematic Review on Cannabis and Other Plant-Based Treatments for Chronic Pain - Quarterly Progress Report/Addendum: September 2021. 2020 Dec. [PubMed:34756847 ]
Zhang WB, Yang QB, Wu SF, Lu SH, Cheng M, Sheng Y, Zhang QC, Yang LF, Yu L, Yan SX: [Application of diffusion-weighted magnetic resonance imaging in evaluating the efficacy of radiotherapy and chemotherapy for esophageal cancer]. Zhonghua Yi Xue Za Zhi. 2021 Nov 9;101(41):3427-3430. doi: 10.3760/cma.j.cn112137-20210709-01544. [PubMed:34758548 ]
Sun Y, Wang DM, Yu H, Liu C, Ji TY, Wang S, Wu Y, Liu XY, Jiang YW, Cai LX, Liu QZ: [The screening of potential biological markers of seizure onset zone in focal cortical dysplasia based on bioinformatics analysis]. Zhonghua Yi Xue Za Zhi. 2021 Nov 9;101(41):3422-3426. doi: 10.3760/cma.j.cn112137-20210331-00779. [PubMed:34758547 ]
Itoh T, Ohguchi K, Nozawa Y, Akao Y: Intracellular glutathione regulates sesquiterpene lactone-induced conversion of autophagy to apoptosis in human leukemia HL60 cells. Anticancer Res. 2009 Apr;29(4):1449-57. [PubMed:19414401 ]
Itoh T, Ito Y, Ohguchi K, Ohyama M, Iinuma M, Otsuki Y, Nozawa Y, Akao Y: Eupalinin A isolated from Eupatorium chinense L. induces autophagocytosis in human leukemia HL60 cells. Bioorg Med Chem. 2008 Jan 15;16(2):721-31. doi: 10.1016/j.bmc.2007.10.033. Epub 2007 Oct 17. [PubMed:17980607 ]
Ito Kazuo, Sakakibara Yoshihisa, Haruna Mitsumasa, Lee Kuo-Hsiung (1979). FOUR NEW GERMACRANOLIDES FROM EUPATORIUM LINDLEYANUM DC. CHEMISTRY LETTERS, Vol.8, No.12, pp. 1469-1472, 1979. DOI: 10.1246/cl.1979.1469. CHEMISTRY LETTERS.

Showing NP-Card for Eupalinin A (NP0044186)

MOL for NP0044186 (Eupalinin A)

3D MOL for NP0044186 (Eupalinin A)

3D SDF for NP0044186 (Eupalinin A)

3D-SDF for NP0044186 (Eupalinin A)

PDB for NP0044186 (Eupalinin A)

3D PDB for NP0044186 (Eupalinin A)

SMILES for NP0044186 (Eupalinin A)

INCHI for NP0044186 (Eupalinin A)

Structure for NP0044186 (Eupalinin A)

3D Structure for NP0044186 (Eupalinin A)