NP-MRD: Showing NP-Card for (1r,4z,6s,7r,11z)-4-ethylidene-7-hydroxy-6,7,14-trimethyl-2,9-dioxa-14-azabicyclo[9.5.1]heptadec-11-ene-3,8,17-trione (NP0186478)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-04 02:20:44 UTC

Updated at

2022-09-04 02:20:44 UTC

NP-MRD ID

NP0186478

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1r,4z,6s,7r,11z)-4-ethylidene-7-hydroxy-6,7,14-trimethyl-2,9-dioxa-14-azabicyclo[9.5.1]heptadec-11-ene-3,8,17-trione

Description

Senkirkine belongs to the class of organic compounds known as macrolides and analogues. These are organic compounds containing a lactone ring of at least twelve members. (1r,4z,6s,7r,11z)-4-ethylidene-7-hydroxy-6,7,14-trimethyl-2,9-dioxa-14-azabicyclo[9.5.1]heptadec-11-ene-3,8,17-trione is found in Chersodoma jodopappa, Farfugium japonicum, Gynura procumbens, Packera anonyma, Packera glabella, Petasites hybridus, Petasites japonicus, Petasites pyrenaicus, Petasites spurius, Senecio deferens, Senecio gallicus, Senecio glaucus, Senecio inaequidens, Jacobaea vulgaris, Senecio leptolobus, Senecio rodriguezii, Senecio vernalis, Telanthophora grandifolia and Tussilago farfara. (1r,4z,6s,7r,11z)-4-ethylidene-7-hydroxy-6,7,14-trimethyl-2,9-dioxa-14-azabicyclo[9.5.1]heptadec-11-ene-3,8,17-trione was first documented in 2017 (PMID: 28165832). Based on a literature review a significant number of articles have been published on Senkirkine (PMID: 34185104) (PMID: 34581050) (PMID: 33774095) (PMID: 32419051) (PMID: 35700647) (PMID: 34297098).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309042204202D          

 26 27  0  0  1  0            999 V2000
    3.7062   -0.9335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6208   -0.7138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5249   -0.2991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3498   -0.2867    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7730   -0.9949    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.6381   -0.8554    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3712   -1.7155    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.1904   -2.0632    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4531   -2.6007    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5463   -1.7278    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9670   -1.2243    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1446   -2.4484    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3197   -2.4608    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8965   -1.7526    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1392   -2.0797    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3723   -1.7755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0452   -1.0181    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1803   -1.0313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3494   -0.2512    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1068    0.0759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8751   -0.3238    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.2768    0.3968    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1017    0.4091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4757    1.1979    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2983   -1.0320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2755   -0.8484    0.0000 O   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
  5  6  1  6  0  0  0
  5  7  1  0  0  0  0
  7  8  1  6  0  0  0
  7  9  1  1  0  0  0
  7 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
 21 20  1  1  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
  3 23  1  0  0  0  0
 23 24  2  0  0  0  0
 21 25  1  0  0  0  0
 14 25  1  0  0  0  0
 25 26  2  0  0  0  0
M  END

     RDKit          3D

 53 54  0  0  0  0  0  0  0  0999 V2000
   -2.3952    3.7979   -0.6624 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9121    2.4081   -0.7034 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1819    1.3283   -1.0716 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9320    0.0816   -1.0265 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1592   -0.6326    0.2816 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.0314    0.1392    1.2088 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7970   -0.9521    0.8031 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1747   -1.7950   -0.2111 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4030    0.3486    1.0558 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5986   -1.6044    2.0828 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5238   -2.1591    2.6848 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3244   -1.5716    2.5920 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9127   -1.8606    2.1349 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6540   -1.0164    1.2009 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3592   -1.9801    0.5344 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0630   -2.1874   -0.7742 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6925   -0.9009   -1.0591 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.7423   -0.5453   -0.2277 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8930    0.0396   -1.6912 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6844    1.3633   -1.0447 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3842    1.3715   -0.1922 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3984    1.1179   -1.0740 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8122    1.6598   -1.4774 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8475    2.6418   -2.3737 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7240    0.4034    0.9241 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2142    1.1962    1.8430 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5115    4.3304   -1.6203 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8805    4.3741    0.1162 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3112    3.7226   -0.3585 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9646    2.3003   -0.4092 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0255    0.2592   -1.3490 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6613   -0.6446   -1.8520 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6985   -1.5713    0.0198 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4253   -0.4976    2.0510 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5932    1.0738    1.5940 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9561    0.4163    0.6476 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3577   -1.4267   -0.8169 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7938   -2.7962    0.1817 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9000   -2.2276   -0.9844 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6328    0.6404    1.9443 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8690   -2.9424    1.7681 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5385   -2.0811    3.0771 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4593   -2.8949    1.1033 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4147   -2.5183   -1.5820 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9313   -2.8917   -0.6271 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6490   -0.2498   -0.8341 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5888    0.2814    0.4826 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0785   -1.4178    0.3722 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8666   -0.4086   -1.8560 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2715    0.2012   -2.7450 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5255    1.7637   -0.4853 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4543    2.0986   -1.8480 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4362    2.4149    0.2529 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  5  7  1  0
  7  8  1  0
  7  9  1  1
  7 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 17 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  2  0
 21 25  1  0
 25 26  2  0
 23  3  1  0
 25 14  1  0
  1 27  1  0
  1 28  1  0
  1 29  1  0
  2 30  1  0
  4 31  1  0
  4 32  1  0
  5 33  1  6
  6 34  1  0
  6 35  1  0
  6 36  1  0
  8 37  1  0
  8 38  1  0
  8 39  1  0
  9 40  1  0
 13 41  1  0
 13 42  1  0
 15 43  1  0
 16 44  1  0
 16 45  1  0
 18 46  1  0
 18 47  1  0
 18 48  1  0
 19 49  1  0
 19 50  1  0
 20 51  1  0
 20 52  1  0
 21 53  1  1
M  END


  Mrv1652309042204202D          

 26 27  0  0  1  0            999 V2000
    3.7062   -0.9335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6208   -0.7138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5249   -0.2991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3498   -0.2867    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7730   -0.9949    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.6381   -0.8554    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3712   -1.7155    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.1904   -2.0632    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4531   -2.6007    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5463   -1.7278    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9670   -1.2243    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1446   -2.4484    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3197   -2.4608    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8965   -1.7526    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1392   -2.0797    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3723   -1.7755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0452   -1.0181    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1803   -1.0313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3494   -0.2512    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1068    0.0759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8751   -0.3238    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.2768    0.3968    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1017    0.4091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4757    1.1979    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2983   -1.0320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2755   -0.8484    0.0000 O   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
  5  6  1  6  0  0  0
  5  7  1  0  0  0  0
  7  8  1  6  0  0  0
  7  9  1  1  0  0  0
  7 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
 21 20  1  1  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
  3 23  1  0  0  0  0
 23 24  2  0  0  0  0
 21 25  1  0  0  0  0
 14 25  1  0  0  0  0
 25 26  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0186478

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C\C=C1\C[C@H](C)[C@@](C)(O)C(=O)OC\C2=C\CN(C)CC[C@@H](OC1=O)C2=O

> <INCHI_IDENTIFIER>
InChI=1S/C19H27NO6/c1-5-13-10-12(2)19(3,24)18(23)25-11-14-6-8-20(4)9-7-15(16(14)21)26-17(13)22/h5-6,12,15,24H,7-11H2,1-4H3/b13-5-,14-6-/t12-,15+,19+/m0/s1

> <INCHI_KEY>
HPDHKHMHQGCNPE-AVAFHTDCSA-N

> <FORMULA>
C19H27NO6

> <MOLECULAR_WEIGHT>
365.426

> <EXACT_MASS>
365.183837593

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
53

> <JCHEM_AVERAGE_POLARIZABILITY>
37.46014530476201

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,4Z,6S,7R,11Z)-4-ethylidene-7-hydroxy-6,7,14-trimethyl-2,9-dioxa-14-azabicyclo[9.5.1]heptadec-11-ene-3,8,17-trione

> <JCHEM_LOGP>
1.892650938666667

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
16.46158691948702

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.370715373334395

> <JCHEM_PKA_STRONGEST_BASIC>
6.959298126672541

> <JCHEM_POLAR_SURFACE_AREA>
93.13999999999999

> <JCHEM_REFRACTIVITY>
96.97629999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1R,4Z,6S,7R,11Z)-4-ethylidene-7-hydroxy-6,7,14-trimethyl-2,9-dioxa-14-azabicyclo[9.5.1]heptadec-11-ene-3,8,17-trione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 04-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-22         0                                  
HETATM    1  C   UNK     0       6.918  -1.743   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.626  -1.332   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      10.313  -0.558   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      11.853  -0.535   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      12.643  -1.857   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      14.258  -1.597   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      11.893  -3.202   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      13.422  -3.851   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      12.046  -4.855   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      10.353  -3.225   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       9.272  -2.285   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       9.603  -4.570   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       8.063  -4.593   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.274  -3.272   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.860  -3.882   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.428  -3.314   0.000  0.00  0.00           C+0
HETATM   17  N   UNK     0       3.818  -1.900   0.000  0.00  0.00           N+0
HETATM   18  C   UNK     0       2.203  -1.925   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.386  -0.469   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.799   0.142   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       7.233  -0.604   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       7.983   0.741   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       9.523   0.764   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      10.221   2.236   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       8.023  -1.926   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       9.848  -1.584   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   23                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8    9   10                                             
CONECT    8    7                                                            
CONECT    9    7                                                            
CONECT   10    7   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   25                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22   25                                                  
CONECT   22   21   23                                                       
CONECT   23   22    3   24                                                  
CONECT   24   23                                                            
CONECT   25   21   14   26                                                  
CONECT   26   25                                                            
MASTER        0    0    0    0    0    0    0    0   26    0   54    0
END

View in JSmol

Synonyms

Value	Source
Neosenkirkine	MeSH
Senkirkine, (15E)-isomer	MeSH

Chemical Formula

C₁₉H₂₇NO₆

Average Mass

365.4260 Da

Monoisotopic Mass

365.18384 Da

IUPAC Name

(1R,4Z,6S,7R,11Z)-4-ethylidene-7-hydroxy-6,7,14-trimethyl-2,9-dioxa-14-azabicyclo[9.5.1]heptadec-11-ene-3,8,17-trione

Traditional Name

(1R,4Z,6S,7R,11Z)-4-ethylidene-7-hydroxy-6,7,14-trimethyl-2,9-dioxa-14-azabicyclo[9.5.1]heptadec-11-ene-3,8,17-trione

CAS Registry Number

Not Available

SMILES

C\C=C1\C[C@H](C)[C@@](C)(O)C(=O)OC\C2=C\CN(C)CC[C@@H](OC1=O)C2=O

InChI Identifier

InChI=1S/C19H27NO6/c1-5-13-10-12(2)19(3,24)18(23)25-11-14-6-8-20(4)9-7-15(16(14)21)26-17(13)22/h5-6,12,15,24H,7-11H2,1-4H3/b13-5-,14-6-/t12-,15+,19+/m0/s1

InChI Key

HPDHKHMHQGCNPE-AVAFHTDCSA-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
Chersodoma jodopappa	LOTUS Database	35616633
Farfugium japonicum	LOTUS Database	35616633
Gynura procumbens	LOTUS Database	35616633
Packera anonyma	LOTUS Database	35616633
Packera glabella	LOTUS Database	35616633
Petasites hybridus	LOTUS Database	35616633
Petasites japonicus	LOTUS Database	35616633
Petasites pyrenaicus	LOTUS Database	35616633
Petasites spurius	LOTUS Database	35616633
Senecio deferens	LOTUS Database	35616633
Senecio gallicus	LOTUS Database	35616633
Senecio glaucus	LOTUS Database	35616633
Senecio inaequidens	LOTUS Database	35616633
Senecio jacobaea	LOTUS Database	35616633
Senecio leptolobus	LOTUS Database	35616633
Senecio rodriguezii	LOTUS Database	35616633
Senecio vernalis	LOTUS Database	35616633
Telanthophora grandifolia	LOTUS Database	35616633
Tussilago farfara	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as macrolides and analogues. These are organic compounds containing a lactone ring of at least twelve members.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Macrolides and analogues

Sub Class

Not Available

Direct Parent

Macrolides and analogues

Alternative Parents

Substituents

Macrolide
Alpha-acyloxy ketone
Dicarboxylic acid or derivatives
Tertiary alcohol
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Amino acid or derivatives
Carboxylic acid ester
Ketone
Lactone
Tertiary amine
Tertiary aliphatic amine
Carboxylic acid derivative
Oxacycle
Azacycle
Organoheterocyclic compound
Organic oxide
Organooxygen compound
Organonitrogen compound
Organic oxygen compound
Alcohol
Amine
Organic nitrogen compound
Carbonyl group
Hydrocarbon derivative
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	1.89	ChemAxon
pKa (Strongest Acidic)	12.37	ChemAxon
pKa (Strongest Basic)	6.96	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	93.14 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	96.98 m³·mol⁻¹	ChemAxon
Polarizability	37.46 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00002119

Chemspider ID

57257208

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

102004936

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Buchmueller J, Sprenger H, Ebmeyer J, Rasinger JD, Creutzenberg O, Schaudien D, Hengstler JG, Guenther G, Braeuning A, Hessel-Pras S: Pyrrolizidine alkaloid-induced transcriptomic changes in rat lungs in a 28-day subacute feeding study. Arch Toxicol. 2021 Aug;95(8):2785-2796. doi: 10.1007/s00204-021-03108-x. Epub 2021 Jun 29. [PubMed:34185104 ]
Adefegha SA, Oboh G, Okeke BM, Oyeleye SI: Comparative Effects of Alkaloid Extracts from Aframomum melegueta (Alligator Pepper) and Aframomum danielli (Bastered Melegueta) on Enzymes Relevant to Erectile Dysfunction. J Diet Suppl. 2017 Sep 3;14(5):542-552. doi: 10.1080/19390211.2016.1272661. Epub 2017 Feb 6. [PubMed:28165832 ]
Zan K, Zhou Y, Li YL, Wang Y, Liu LN, Jin HY, Zuo TT, Ma SC: [Simultaneous determination of six pyrrolizidine alkaloids in different parts of Emilia sonchifolia by UPLC-MS/MS]. Zhongguo Zhong Yao Za Zhi. 2021 Sep;46(17):4456-4461. doi: 10.19540/j.cnki.cjcmm.20210623.202. [PubMed:34581050 ]
Zhang Y, Yang FF, Chen H, Qi YD, Si JY, Wu Q, Liao YH: Analysis of pyrrolizidine alkaloids in Eupatorium fortunei Turcz. and their in vitro neurotoxicity. Food Chem Toxicol. 2021 May;151:112151. doi: 10.1016/j.fct.2021.112151. Epub 2021 Mar 25. [PubMed:33774095 ]
Ebmeyer J, Rasinger JD, Hengstler JG, Schaudien D, Creutzenberg O, Lampen A, Braeuning A, Hessel-Pras S: Hepatotoxic pyrrolizidine alkaloids induce DNA damage response in rat liver in a 28-day feeding study. Arch Toxicol. 2020 May;94(5):1739-1751. doi: 10.1007/s00204-020-02779-2. Epub 2020 May 17. [PubMed:32419051 ]
Xiao Y, Yi H, Wang G, Chen S, Li X, Wu Q, Zhang S, Deng K, He Y, Yang X: Electrochemiluminescence sensor for point-of-care detection of pyrrolizidine alkaloids. Talanta. 2022 Nov 1;249:123645. doi: 10.1016/j.talanta.2022.123645. Epub 2022 Jun 1. [PubMed:35700647 ]
Jeong SH, Choi EY, Kim J, Lee C, Kang J, Cho S, Ko KY: LC-ESI-MS/MS Simultaneous Analysis Method Coupled with Cation-Exchange Solid-Phase Extraction for Determination of Pyrrolizidine Alkaloids on Five Kinds of Herbal Medicines. J AOAC Int. 2021 Dec 11;104(6):1514-1525. doi: 10.1093/jaoacint/qsab098. [PubMed:34297098 ]
Klevenhusen F, These A, Taenzer J, Weiss K, Pieper R: Effects of ensiling conditions on pyrrolizidine alkaloid degradation in silages mixed with two different Senecio spp. Arch Anim Nutr. 2022 Apr;76(2):93-111. doi: 10.1080/1745039X.2022.2084321. Epub 2022 Jun 29. [PubMed:35766237 ]
Kamiya Y, Miura T, Kato A, Murayama N, Shimizu M, Yamazaki H: Plasma Concentration Profiles for Hepatotoxic Pyrrolizidine Alkaloid Senkirkine in Humans Extrapolated from Rat Data Sets Using a Simplified Physiologically Based Pharmacokinetic Model. Drug Metab Bioanal Lett. 2022;15(1):64-69. doi: 10.2174/1872312801666211220110055. [PubMed:34931973 ]
Yang M, Tan D, Lu A, Qin L, Wang C, Ling H, Lu Y, He Y: Identification and Simultaneous Determination of the Main Toxical Pyrrolizidine Alkaloids in a Compound Prescription of Traditional Chinese Medicine: Qianbai Biyan Tablet. Int J Anal Chem. 2021 Sep 9;2021:5209618. doi: 10.1155/2021/5209618. eCollection 2021. [PubMed:34539789 ]
Kisielius V, Hama JR, Skrbic N, Hansen HCB, Strobel BW, Rasmussen LH: The invasive butterbur contaminates stream and seepage water in groundwater wells with toxic pyrrolizidine alkaloids. Sci Rep. 2020 Nov 13;10(1):19784. doi: 10.1038/s41598-020-76586-1. [PubMed:33188248 ]
Li X, He X, Chen S, Guo X, Bryant MS, Guo L, Manjanatha MG, Zhou T, Witt KL, Mei N: Evaluation of pyrrolizidine alkaloid-induced genotoxicity using metabolically competent TK6 cell lines. Food Chem Toxicol. 2020 Nov;145:111662. doi: 10.1016/j.fct.2020.111662. Epub 2020 Aug 13. [PubMed:32798647 ]
Klevenhusen F, Pieper R, Winter J, Ronczka S, Speer K: Stability of pyrrolizidine alkaloids from Senecio vernalis in grass silage under different ensilage conditions. J Sci Food Agric. 2019 Nov;99(14):6649-6654. doi: 10.1002/jsfa.9963. Epub 2019 Sep 2. [PubMed:31368529 ]
He X, Xia Q, Gamboa da Costa G, Lin G, Fu PP: 1-Formyl-7-hydroxy-6,7-dihydro-5 H-pyrrolizine (1-CHO-DHP): A Potential Proximate Carcinogenic Metabolite of Pyrrolizidine Alkaloids. Chem Res Toxicol. 2019 Jun 17;32(6):1193-1203. doi: 10.1021/acs.chemrestox.9b00038. Epub 2019 Jun 3. [PubMed:31120748 ]
Kitajima M, Okabe K, Yoshida M, Nakabayashi R, Saito K, Kogure N, Takayama H: New otonecine-type pyrrolizidine alkaloid from Petasites japonicus. J Nat Med. 2019 Jun;73(3):602-607. doi: 10.1007/s11418-019-01285-9. Epub 2019 Feb 19. [PubMed:30784002 ]
Ebmeyer J, Behrend J, Lorenz M, Gunther G, Reif R, Hengstler JG, Braeuning A, Lampen A, Hessel-Pras S: Pyrrolizidine alkaloid-induced alterations of prostanoid synthesis in human endothelial cells. Chem Biol Interact. 2019 Jan 25;298:104-111. doi: 10.1016/j.cbi.2018.11.007. Epub 2018 Nov 19. [PubMed:30465738 ]
Muluneh F, Hakkinen MR, El-Dairi R, Pasanen M, Juvonen RO: New glutathione conjugate of pyrrolizidine alkaloids produced by human cytosolic enzyme-dependent reactions in vitro. Rapid Commun Mass Spectrom. 2018 Aug 30;32(16):1344-1352. doi: 10.1002/rcm.8173. [PubMed:29788543 ]
Waizenegger J, Braeuning A, Templin M, Lampen A, Hessel-Pras S: Structure-dependent induction of apoptosis by hepatotoxic pyrrolizidine alkaloids in the human hepatoma cell line HepaRG: Single versus repeated exposure. Food Chem Toxicol. 2018 Apr;114:215-226. doi: 10.1016/j.fct.2018.02.036. Epub 2018 Feb 16. [PubMed:29458164 ]
Cheng X, Liao M, Diao X, Sun Y, Zhang L: Screening and identification of metabolites of two kinds of main active ingredients and hepatotoxic pyrrolizidine alkaloids in rat after lavage Farfarae Flos extract by UHPLC-Q-TOF-MS mass spectrometry. Biomed Chromatogr. 2018 Feb;32(2). doi: 10.1002/bmc.4047. Epub 2017 Aug 18. [PubMed:28702943 ]
LOTUS database [Link]

Showing NP-Card for (1r,4z,6s,7r,11z)-4-ethylidene-7-hydroxy-6,7,14-trimethyl-2,9-dioxa-14-azabicyclo[9.5.1]heptadec-11-ene-3,8,17-trione (NP0186478)

MOL for NP0186478 ((1r,4z,6s,7r,11z)-4-ethylidene-7-hydroxy-6,7,14-trimethyl-2,9-dioxa-14-azabicyclo[9.5.1]heptadec-11-ene-3,8,17-trione)

3D MOL for NP0186478 ((1r,4z,6s,7r,11z)-4-ethylidene-7-hydroxy-6,7,14-trimethyl-2,9-dioxa-14-azabicyclo[9.5.1]heptadec-11-ene-3,8,17-trione)

3D SDF for NP0186478 ((1r,4z,6s,7r,11z)-4-ethylidene-7-hydroxy-6,7,14-trimethyl-2,9-dioxa-14-azabicyclo[9.5.1]heptadec-11-ene-3,8,17-trione)

3D-SDF for NP0186478 ((1r,4z,6s,7r,11z)-4-ethylidene-7-hydroxy-6,7,14-trimethyl-2,9-dioxa-14-azabicyclo[9.5.1]heptadec-11-ene-3,8,17-trione)

PDB for NP0186478 ((1r,4z,6s,7r,11z)-4-ethylidene-7-hydroxy-6,7,14-trimethyl-2,9-dioxa-14-azabicyclo[9.5.1]heptadec-11-ene-3,8,17-trione)

3D PDB for NP0186478 ((1r,4z,6s,7r,11z)-4-ethylidene-7-hydroxy-6,7,14-trimethyl-2,9-dioxa-14-azabicyclo[9.5.1]heptadec-11-ene-3,8,17-trione)

SMILES for NP0186478 ((1r,4z,6s,7r,11z)-4-ethylidene-7-hydroxy-6,7,14-trimethyl-2,9-dioxa-14-azabicyclo[9.5.1]heptadec-11-ene-3,8,17-trione)

INCHI for NP0186478 ((1r,4z,6s,7r,11z)-4-ethylidene-7-hydroxy-6,7,14-trimethyl-2,9-dioxa-14-azabicyclo[9.5.1]heptadec-11-ene-3,8,17-trione)

Structure for NP0186478 ((1r,4z,6s,7r,11z)-4-ethylidene-7-hydroxy-6,7,14-trimethyl-2,9-dioxa-14-azabicyclo[9.5.1]heptadec-11-ene-3,8,17-trione)

3D Structure for NP0186478 ((1r,4z,6s,7r,11z)-4-ethylidene-7-hydroxy-6,7,14-trimethyl-2,9-dioxa-14-azabicyclo[9.5.1]heptadec-11-ene-3,8,17-trione)