NP-MRD: Showing NP-Card for (1r,4e,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 (NP0150535)

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Record Information

Version

2.0

Created at

2022-09-02 06:40:05 UTC

Updated at

2022-09-02 06:40:05 UTC

NP-MRD ID

NP0150535

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1r,4e,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

Neosenkirkine 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,4e,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 Packera anonyma, Senecio inaequidens, Senecio leptolobus, Telanthophora grandifolia and Tussilago farfara. (1r,4e,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 2004 (PMID: 15595537). Based on a literature review very few articles have been published on Neosenkirkine (PMID: 23738446).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309022208402D          

 26 27  0  0  1  0            999 V2000
    4.8812   -1.7778    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6992   -0.8134    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
    7.6447   -0.8904    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
    7.2120   -2.0300    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5668   -2.6198    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
    4.9089   -1.2470    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
    1.1849   -1.0310    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
    5.4945    1.1870    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
    5.2953   -0.9048    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
   -2.8209    3.0044    1.7827 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9671    3.1668    0.5759 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4785    2.1200   -0.0837 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8410    0.7642    0.4635 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2765   -0.1334   -0.6648 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.6308    0.2618   -1.1930 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2511   -1.5869   -0.3929 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.6851   -2.0786   -0.2182 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7960   -2.2433   -1.5616 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4083   -2.0219    0.7446 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7442   -1.5578    1.8671 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3767   -2.8293    0.6577 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9014   -2.9723    0.2663 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6517   -1.8371   -0.3111 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8978   -2.0537    0.2277 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0620   -1.1626    0.6082 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6539    0.2014    0.7263 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8217    0.7767    2.0186 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7595    1.0543   -0.3694 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7027    1.1214   -1.3871 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2967    0.7392   -0.9019 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3465    1.4111   -1.6500 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6407    2.2644   -1.2675 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8774    3.2808   -1.9788 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2786   -0.7631   -1.1639 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8498   -0.8589   -2.3434 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3750    2.3276    2.5246 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8142    2.5826    1.4547 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0298    3.9859    2.2052 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7210    4.1708    0.2021 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9502    0.4204    0.9804 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6627    0.8245    1.1756 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5636    0.0822   -1.4972 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6788    1.3786   -1.3633 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8588   -0.2186   -2.1624 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4708    0.0465   -0.5118 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6267   -3.1820   -0.1005 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1681   -1.5912    0.6482 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3081   -1.8935   -1.1039 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2049   -3.1169   -1.6802 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9750   -3.9185   -0.3645 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4438   -3.3590    1.2074 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0318   -3.0990    0.4038 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5300   -1.6021    1.4943 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7981   -1.2280   -0.2199 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8004    1.8993    1.8952 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0470    0.4363    2.7225 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8319    0.5018    2.3929 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7281    0.8092   -0.9054 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9735    2.0945    0.0274 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9791    0.5305   -2.2871 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6216    2.1787   -1.7610 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2448    0.8715    0.1715 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  6
  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


  Mrv1652309022208402D          

 26 27  0  0  1  0            999 V2000
    4.8812   -1.7778    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6992   -0.8134    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
    7.6447   -0.8904    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
    7.2120   -2.0300    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5668   -2.6198    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
    4.9089   -1.2470    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
    1.1849   -1.0310    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
    5.4945    1.1870    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
    5.2953   -0.9048    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>
NP0150535

> <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-JIAZNLDYSA-N

> <FORMULA>
C19H27NO6

> <MOLECULAR_WEIGHT>
365.426

> <EXACT_MASS>
365.183837593

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
53

> <JCHEM_AVERAGE_POLARIZABILITY>
37.454393226792845

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,4E,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

> <ALOGPS_LOGP>
1.49

> <JCHEM_LOGP>
1.892650938666667

> <ALOGPS_LOGS>
-1.83

> <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

> <ALOGPS_SOLUBILITY>
5.46e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,4E,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                                 02-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-SEP-22         0                                  
HETATM    1  C   UNK     0       9.112  -3.319   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.772  -1.518   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      14.270  -1.662   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      13.462  -3.789   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      12.258  -4.890   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       9.163  -2.328   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       2.212  -1.924   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      10.256   2.216   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       9.885  -1.689   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
Senkirkine	MeSH
Senkirkine, (15E)-isomer	MeSH

Chemical Formula

C₁₉H₂₇NO₆

Average Mass

365.4260 Da

Monoisotopic Mass

365.18384 Da

IUPAC Name

(1R,4E,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,4E,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-JIAZNLDYSA-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
Packera anonyma	LOTUS Database	35616633
Senecio inaequidens	LOTUS Database	35616633
Senecio leptolobus	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
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Tertiary alcohol
Tertiary aliphatic amine
Tertiary amine
Lactone
Ketone
Carboxylic acid ester
Amino acid or derivatives
Oxacycle
Azacycle
Organoheterocyclic compound
Carboxylic acid derivative
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Carbonyl group
Amine
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	1.49	ALOGPS
logP	1.89	ChemAxon
logS	-1.8	ALOGPS
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	37.45 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

C00026217

Chemspider ID

68894724

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

134714985

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Mroczek T, Ndjoko K, Glowniak K, Hostettmann K: On-line structure characterization of pyrrolizidine alkaloids in Onosma stellulatum and Emilia coccinea by liquid chromatography-ion-trap mass spectrometry. J Chromatogr A. 2004 Nov 12;1056(1-2):91-7. [PubMed:15595537 ]
Tidjani S, Okusa PN, Zellagui A, Banuls LM, Stevigny C, Duez P, Rhouati S: Analysis of pyrrolizidine alkaloids and evaluation of some biological activities of Algerian Senecio delphinifolius (Asteraceae). Nat Prod Commun. 2013 Apr;8(4):439-40. [PubMed:23738446 ]
LOTUS database [Link]

Showing NP-Card for (1r,4e,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 (NP0150535)

MOL for NP0150535 ((1r,4e,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 NP0150535 ((1r,4e,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 NP0150535 ((1r,4e,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 NP0150535 ((1r,4e,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 NP0150535 ((1r,4e,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 NP0150535 ((1r,4e,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 NP0150535 ((1r,4e,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 NP0150535 ((1r,4e,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 NP0150535 ((1r,4e,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 NP0150535 ((1r,4e,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)