NP-MRD: Showing NP-Card for (4z)-7-(acetyloxy)-4-ethenyl-17-hydroxy-6,7,14-trimethyl-3,8-dioxo-2,9-dioxa-14-azatricyclo[9.5.1.0¹⁴,¹⁷]heptadeca-4,11-dien-14-ium (NP0216849)

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Record Information

Version

2.0

Created at

2022-09-05 16:58:42 UTC

Updated at

2022-09-05 16:58:42 UTC

NP-MRD ID

NP0216849

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(4z)-7-(acetyloxy)-4-ethenyl-17-hydroxy-6,7,14-trimethyl-3,8-dioxo-2,9-dioxa-14-azatricyclo[9.5.1.0¹⁴,¹⁷]heptadeca-4,11-dien-14-ium

Description

Clivorine belongs to the class of organic compounds known as tricarboxylic acids and derivatives. These are carboxylic acids containing exactly three carboxyl groups. (4z)-7-(acetyloxy)-4-ethenyl-17-hydroxy-6,7,14-trimethyl-3,8-dioxo-2,9-dioxa-14-azatricyclo[9.5.1.0¹⁴,¹⁷]heptadeca-4,11-dien-14-ium is found in Ligularia dentata and Ligularia hodgsonii. (4z)-7-(acetyloxy)-4-ethenyl-17-hydroxy-6,7,14-trimethyl-3,8-dioxo-2,9-dioxa-14-azatricyclo[9.5.1.0¹⁴,¹⁷]heptadeca-4,11-dien-14-ium was first documented in 2013 (PMID: 23937665). Based on a literature review a significant number of articles have been published on Clivorine (PMID: 35924956) (PMID: 32500835) (PMID: 31617262) (PMID: 31054999) (PMID: 28650983) (PMID: 27387401).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309052218582D          

 29 31  0  0  0  0            999 V2000
    6.7709    3.1074    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9824    2.8648    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7982    2.0606    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4026    1.4990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2184    0.6948    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4299    0.4522    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8228    0.1333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2709    0.8260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5828   -0.1877    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.2408    0.3100    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1388    1.1286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0008   -0.0110    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6386   -0.6709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2430   -1.2325    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8501   -0.9135    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2458   -0.3520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4572   -0.5946    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9619   -1.2543    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1814   -0.9871    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1943   -0.1622    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
    2.4058   -0.4048    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7199    0.5127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2152    1.1725    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0370    0.7712    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8255    1.0138    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0097    1.8180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4053    2.3796    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8529   -0.0330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6269   -0.8264    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  2  0  0  0  0
  7 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
  3 26  1  0  0  0  0
 26 27  2  0  0  0  0
 24 28  1  0  0  0  0
 17 28  1  0  0  0  0
 20 28  1  0  0  0  0
 28 29  1  0  0  0  0
M  CHG  1  20   1
M  END

     RDKit          3D

 57 59  0  0  0  0  0  0  0  0999 V2000
   -0.3260    4.5787    1.1974 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1638    3.5817    1.0572 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9829    2.4954    0.0875 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9188    1.5555    0.0653 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8553    0.4074   -0.8666 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.8034    0.7035   -2.0323 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3781   -0.8659   -0.2297 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.5718   -1.8691   -1.3248 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6528   -0.6273    0.3823 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3740   -1.5889    1.0306 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7023   -1.3433    1.6707 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9191   -2.7581    1.1094 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3755   -1.2621    0.7809 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7780   -1.4903    1.9419 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0794   -1.3661    0.4396 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5616   -2.0976   -0.5481 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0182   -1.7349   -0.4838 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0831   -2.5276   -0.3454 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3123   -1.6278   -0.3408 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6939   -0.5085    0.3229 N   0  0  1  0  0  4  0  0  0  0  0  0
    3.3395   -0.8617    1.6544 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2562    0.7722    0.1539 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0074    1.6315    0.4388 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8183    0.7503   -0.0041 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0464    1.4245   -0.9805 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1925    2.4796   -0.8042 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3857    3.5860   -1.4511 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5322   -0.3906   -0.5820 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.0548   -0.0643   -1.8310 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5579    4.6471    0.5900 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4859    5.3628    1.9189 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0324    3.5629    1.6914 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7721    1.5855    0.7302 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8617    0.2348   -1.3120 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9356    1.7983   -2.1562 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3488    0.2849   -2.9378 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7745    0.2090   -1.8780 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3791   -2.9109   -1.0023 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0097   -1.5838   -2.2271 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6412   -1.8415   -1.6249 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3234   -2.2698    1.4987 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6358   -1.1704    2.7482 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2579   -0.5334    1.1522 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2690   -1.8586   -1.5893 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4683   -3.1875   -0.4481 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1414   -3.6058   -0.2493 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1191   -2.0753    0.2377 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5333   -1.4277   -1.3939 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2970   -1.1494    1.7833 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9501   -1.7540    1.9818 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6263   -0.0525    2.3606 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5864    0.8922   -0.8951 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0064    1.0813    0.8942 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0519    2.4976   -0.2528 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9313    1.9024    1.4908 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1884    0.5521    0.8581 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3105   -0.1722   -2.4778 H   0  0  0  0  0  0  0  0  0  0  0  0
  6  5  1  0
  5  4  1  0
  4  3  2  0
  3  2  1  0
  2  1  2  0
  3 26  1  0
 26 27  2  0
 26 25  1  0
 25 24  1  0
 24 23  1  0
 23 22  1  0
 22 20  1  0
 20 21  1  1
 20 19  1  0
 19 18  1  0
 18 17  2  0
 17 16  1  0
 16 15  1  0
 15 13  1  0
 13 14  2  0
 13  7  1  0
  7  8  1  0
  7  9  1  1
  9 10  1  0
 10 11  1  0
 10 12  2  0
 17 28  1  0
 28 29  1  6
  7  5  1  0
 28 24  1  0
 28 20  1  0
  6 35  1  0
  6 36  1  0
  6 37  1  0
  5 34  1  6
  4 33  1  0
  2 32  1  0
  1 30  1  0
  1 31  1  0
 24 56  1  1
 23 54  1  0
 23 55  1  0
 22 52  1  0
 22 53  1  0
 21 49  1  0
 21 50  1  0
 21 51  1  0
 19 47  1  0
 19 48  1  0
 18 46  1  0
 16 44  1  0
 16 45  1  0
  8 38  1  0
  8 39  1  0
  8 40  1  0
 11 41  1  0
 11 42  1  0
 11 43  1  0
 29 57  1  0
M  CHG  1  20   1
M  END


  Mrv1652309052218582D          

 29 31  0  0  0  0            999 V2000
    6.7709    3.1074    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9824    2.8648    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7982    2.0606    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4026    1.4990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2184    0.6948    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4299    0.4522    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8228    0.1333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2709    0.8260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5828   -0.1877    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.2408    0.3100    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1388    1.1286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0008   -0.0110    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6386   -0.6709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2430   -1.2325    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8501   -0.9135    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2458   -0.3520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4572   -0.5946    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9619   -1.2543    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1814   -0.9871    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1943   -0.1622    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
    2.4058   -0.4048    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7199    0.5127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2152    1.1725    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0370    0.7712    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8255    1.0138    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0097    1.8180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4053    2.3796    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8529   -0.0330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6269   -0.8264    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  2  0  0  0  0
  7 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
  3 26  1  0  0  0  0
 26 27  2  0  0  0  0
 24 28  1  0  0  0  0
 17 28  1  0  0  0  0
 20 28  1  0  0  0  0
 28 29  1  0  0  0  0
M  CHG  1  20   1
M  END
> <DATABASE_ID>
NP0216849

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1\C=C(C=C)/C(=O)OC2CC[N+]3(C)CC=C(COC(=O)C1(C)OC(C)=O)C23O

> <INCHI_IDENTIFIER>
InChI=1S/C21H28NO7/c1-6-15-11-13(2)20(4,29-14(3)23)19(25)27-12-16-7-9-22(5)10-8-17(21(16,22)26)28-18(15)24/h6-7,11,13,17,26H,1,8-10,12H2,2-5H3/q+1/b15-11-

> <INCHI_KEY>
NEHWGXHBNGZJNY-PTNGSMBKSA-N

> <FORMULA>
C21H28NO7

> <MOLECULAR_WEIGHT>
406.454

> <EXACT_MASS>
406.186028666

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
57

> <JCHEM_AVERAGE_POLARIZABILITY>
41.31929483626723

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
1

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(4Z)-7-(acetyloxy)-4-ethenyl-17-hydroxy-6,7,14-trimethyl-3,8-dioxo-2,9-dioxa-14-azatricyclo[9.5.1.0^{14,17}]heptadeca-4,11-dien-14-ium

> <JCHEM_LOGP>
-2.571020618805078

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.51943863135318

> <JCHEM_PKA_STRONGEST_BASIC>
-4.758597542646119

> <JCHEM_POLAR_SURFACE_AREA>
99.13000000000001

> <JCHEM_REFRACTIVITY>
115.9831

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(4Z)-7-(acetyloxy)-4-ethenyl-17-hydroxy-6,7,14-trimethyl-3,8-dioxo-2,9-dioxa-14-azatricyclo[9.5.1.0^{14,17}]heptadeca-4,11-dien-14-ium

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 05-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   05-SEP-22         0                                  
HETATM    1  C   UNK     0      12.639   5.800   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      11.167   5.348   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      10.823   3.846   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      11.951   2.798   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      11.608   1.297   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      10.136   0.844   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      12.736   0.249   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      13.572   1.542   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      14.155  -0.350   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      15.383   0.579   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      15.192   2.107   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      16.801  -0.021   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      12.392  -1.252   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      13.520  -2.301   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0      10.920  -1.705   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       9.792  -0.657   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       8.320  -1.110   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       7.396  -2.341   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.939  -1.843   0.000  0.00  0.00           C+0
HETATM   20  N   UNK     0       5.963  -0.303   0.000  0.00  0.00           N+1
HETATM   21  C   UNK     0       4.491  -0.756   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       5.077   0.957   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       6.002   2.189   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       7.536   1.440   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       9.008   1.892   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       9.351   3.394   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       8.223   4.442   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       7.192  -0.062   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       6.770  -1.543   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   26                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8    9   13                                             
CONECT    8    7                                                            
CONECT    9    7   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10                                                            
CONECT   13    7   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   28                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21   22   28                                             
CONECT   21   20                                                            
CONECT   22   20   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25   28                                                  
CONECT   25   24   26                                                       
CONECT   26   25    3   27                                                  
CONECT   27   26                                                            
CONECT   28   24   17   20   29                                             
CONECT   29   28                                                            
MASTER        0    0    0    0    0    0    0    0   29    0   62    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₁H₂₈NO₇

Average Mass

406.4540 Da

Monoisotopic Mass

406.18603 Da

IUPAC Name

(4Z)-7-(acetyloxy)-4-ethenyl-17-hydroxy-6,7,14-trimethyl-3,8-dioxo-2,9-dioxa-14-azatricyclo[9.5.1.0^{14,17}]heptadeca-4,11-dien-14-ium

Traditional Name

(4Z)-7-(acetyloxy)-4-ethenyl-17-hydroxy-6,7,14-trimethyl-3,8-dioxo-2,9-dioxa-14-azatricyclo[9.5.1.0^{14,17}]heptadeca-4,11-dien-14-ium

CAS Registry Number

Not Available

SMILES

CC1\C=C(C=C)/C(=O)OC2CC[N+]3(C)CC=C(COC(=O)C1(C)OC(C)=O)C23O

InChI Identifier

InChI=1S/C21H28NO7/c1-6-15-11-13(2)20(4,29-14(3)23)19(25)27-12-16-7-9-22(5)10-8-17(21(16,22)26)28-18(15)24/h6-7,11,13,17,26H,1,8-10,12H2,2-5H3/q+1/b15-11-

InChI Key

NEHWGXHBNGZJNY-PTNGSMBKSA-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, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, 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
Ligularia dentata	LOTUS Database	35616633
Ligularia hodgsonii	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as tricarboxylic acids and derivatives. These are carboxylic acids containing exactly three carboxyl groups.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Tricarboxylic acids and derivatives

Direct Parent

Tricarboxylic acids and derivatives

Alternative Parents

Substituents

Tricarboxylic acid or derivatives
Pyrrolizine
N-alkylpyrrolidine
Pyrrolidine
Tetraalkylammonium salt
Pyrroline
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Carboxylic acid ester
Lactone
Alkanolamine
Oxacycle
Azacycle
Organoheterocyclic compound
Organic nitrogen compound
Carbonyl group
Organic salt
Hydrocarbon derivative
Organic oxide
Organooxygen compound
Organonitrogen compound
Organopnictogen compound
Organic oxygen compound
Organic cation
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	-2.6	ChemAxon
pKa (Strongest Acidic)	10.52	ChemAxon
pKa (Strongest Basic)	-4.8	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	99.13 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	115.98 m³·mol⁻¹	ChemAxon
Polarizability	41.32 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	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

C00002082

Chemspider ID

4516111

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5363807

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Xia Q, Zhao Y, Von Tungeln LS, Doerge DR, Lin G, Cai L, Fu PP: Pyrrolizidine alkaloid-derived DNA adducts as a common biological biomarker of pyrrolizidine alkaloid-induced tumorigenicity. Chem Res Toxicol. 2013 Sep 16;26(9):1384-96. doi: 10.1021/tx400241c. Epub 2013 Aug 26. [PubMed:23937665 ]
Wu H, Fan D, Cheng J: Development and Validation of an UHPLC-MS/MS Method for the Determination of 32 Pyrrolizidine Alkaloids in Chinese Wild Honey. J AOAC Int. 2022 Dec 22;106(1):56-64. doi: 10.1093/jaoacint/qsac094. [PubMed:35924956 ]
Song Z, He Y, Ma J, Fu PP, Lin G: Pulmonary toxicity is a common phenomenon of toxic pyrrolizidine alkaloids. J Environ Sci Health C Toxicol Carcinog. 2020;38(2):124-140. doi: 10.1080/26896583.2020.1743608. Epub 2020 Apr 27. [PubMed:32500835 ]
Pingili RB, Challa SR, Pawar AK, Toleti V, Kodali T, Koppula S: A systematic review on hepatoprotective activity of quercetin against various drugs and toxic agents: Evidence from preclinical studies. Phytother Res. 2020 Jan;34(1):5-32. doi: 10.1002/ptr.6503. Epub 2019 Oct 15. [PubMed:31617262 ]
Lu Y, Ma J, Lin G: Development of a two-layer transwell co-culture model for the in vitro investigation of pyrrolizidine alkaloid-induced hepatic sinusoidal damage. Food Chem Toxicol. 2019 Jul;129:391-398. doi: 10.1016/j.fct.2019.04.057. Epub 2019 May 2. [PubMed:31054999 ]
Liu W, Li X, Zhou B, Fang S, Ho W, Chen H, Liang H, Ye L, Tang J: Differential induction of apoptosis and autophagy by pyrrolizidine alkaloid clivorine in human hepatoma Huh-7.5 cells and its toxic implication. PLoS One. 2017 Jun 26;12(6):e0179379. doi: 10.1371/journal.pone.0179379. eCollection 2017. [PubMed:28650983 ]
Xiong A, Yan AL, Bi CW, Lam KY, Chan GK, Lau KK, Dong TT, Lin H, Yang L, Wang Z, Tsim KW: Clivorine, an otonecine pyrrolizidine alkaloid from Ligularia species, impairs neuronal differentiation via NGF-induced signaling pathway in cultured PC12 cells. Phytomedicine. 2016 Aug 15;23(9):931-8. doi: 10.1016/j.phymed.2016.06.006. Epub 2016 Jun 10. [PubMed:27387401 ]
Ji LL, Sheng YC, Zheng ZY, Shi L, Wang ZT: The involvement of p62-Keap1-Nrf2 antioxidative signaling pathway and JNK in the protection of natural flavonoid quercetin against hepatotoxicity. Free Radic Biol Med. 2015 Aug;85:12-23. doi: 10.1016/j.freeradbiomed.2015.03.035. Epub 2015 Apr 14. [PubMed:25881548 ]
Ji L, Ma Y, Wang Z, Cai Z, Pang C, Wang Z: Quercetin prevents pyrrolizidine alkaloid clivorine-induced liver injury in mice by elevating body defense capacity. PLoS One. 2014 Jun 6;9(6):e98970. doi: 10.1371/journal.pone.0098970. eCollection 2014. [PubMed:24905073 ]
Li YH, Kan WL, Li N, Lin G: Assessment of pyrrolizidine alkaloid-induced toxicity in an in vitro screening model. J Ethnopharmacol. 2013 Nov 25;150(2):560-7. doi: 10.1016/j.jep.2013.09.010. Epub 2013 Sep 14. [PubMed:24045176 ]
LOTUS database [Link]

Showing NP-Card for (4z)-7-(acetyloxy)-4-ethenyl-17-hydroxy-6,7,14-trimethyl-3,8-dioxo-2,9-dioxa-14-azatricyclo[9.5.1.0¹⁴,¹⁷]heptadeca-4,11-dien-14-ium (NP0216849)

MOL for NP0216849 ((4z)-7-(acetyloxy)-4-ethenyl-17-hydroxy-6,7,14-trimethyl-3,8-dioxo-2,9-dioxa-14-azatricyclo[9.5.1.0¹⁴,¹⁷]heptadeca-4,11-dien-14-ium)

3D MOL for NP0216849 ((4z)-7-(acetyloxy)-4-ethenyl-17-hydroxy-6,7,14-trimethyl-3,8-dioxo-2,9-dioxa-14-azatricyclo[9.5.1.0¹⁴,¹⁷]heptadeca-4,11-dien-14-ium)

3D SDF for NP0216849 ((4z)-7-(acetyloxy)-4-ethenyl-17-hydroxy-6,7,14-trimethyl-3,8-dioxo-2,9-dioxa-14-azatricyclo[9.5.1.0¹⁴,¹⁷]heptadeca-4,11-dien-14-ium)

3D-SDF for NP0216849 ((4z)-7-(acetyloxy)-4-ethenyl-17-hydroxy-6,7,14-trimethyl-3,8-dioxo-2,9-dioxa-14-azatricyclo[9.5.1.0¹⁴,¹⁷]heptadeca-4,11-dien-14-ium)

PDB for NP0216849 ((4z)-7-(acetyloxy)-4-ethenyl-17-hydroxy-6,7,14-trimethyl-3,8-dioxo-2,9-dioxa-14-azatricyclo[9.5.1.0¹⁴,¹⁷]heptadeca-4,11-dien-14-ium)

3D PDB for NP0216849 ((4z)-7-(acetyloxy)-4-ethenyl-17-hydroxy-6,7,14-trimethyl-3,8-dioxo-2,9-dioxa-14-azatricyclo[9.5.1.0¹⁴,¹⁷]heptadeca-4,11-dien-14-ium)

SMILES for NP0216849 ((4z)-7-(acetyloxy)-4-ethenyl-17-hydroxy-6,7,14-trimethyl-3,8-dioxo-2,9-dioxa-14-azatricyclo[9.5.1.0¹⁴,¹⁷]heptadeca-4,11-dien-14-ium)

INCHI for NP0216849 ((4z)-7-(acetyloxy)-4-ethenyl-17-hydroxy-6,7,14-trimethyl-3,8-dioxo-2,9-dioxa-14-azatricyclo[9.5.1.0¹⁴,¹⁷]heptadeca-4,11-dien-14-ium)

Structure for NP0216849 ((4z)-7-(acetyloxy)-4-ethenyl-17-hydroxy-6,7,14-trimethyl-3,8-dioxo-2,9-dioxa-14-azatricyclo[9.5.1.0¹⁴,¹⁷]heptadeca-4,11-dien-14-ium)

3D Structure for NP0216849 ((4z)-7-(acetyloxy)-4-ethenyl-17-hydroxy-6,7,14-trimethyl-3,8-dioxo-2,9-dioxa-14-azatricyclo[9.5.1.0¹⁴,¹⁷]heptadeca-4,11-dien-14-ium)