NP-MRD: Showing NP-Card for (9e)-9-ethylidene-7-(hydroxymethyl)-5-methyl-3,6,11-trioxa-15-azatetracyclo[10.5.1.0⁵,⁷.0¹⁵,¹⁸]octadec-1(17)-ene-4,10-dione (NP0218298)

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Record Information

Version

2.0

Created at

2022-09-05 18:55:06 UTC

Updated at

2022-09-05 18:55:06 UTC

NP-MRD ID

NP0218298

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(9e)-9-ethylidene-7-(hydroxymethyl)-5-methyl-3,6,11-trioxa-15-azatetracyclo[10.5.1.0⁵,⁷.0¹⁵,¹⁸]octadec-1(17)-ene-4,10-dione

Description

ERUCIFOLINE belongs to the class of organic compounds known as alkaloids and derivatives. These are naturally occurring chemical compounds that contain mostly basic nitrogen atoms. This group also includes some related compounds with neutral and even weakly acidic properties. Also some synthetic compounds of similar structure are attributed to alkaloids. In addition to carbon, hydrogen and nitrogen, alkaloids may also contain oxygen, sulfur and more rarely other elements such as chlorine, bromine, and phosphorus. (9e)-9-ethylidene-7-(hydroxymethyl)-5-methyl-3,6,11-trioxa-15-azatetracyclo[10.5.1.0⁵,⁷.0¹⁵,¹⁸]octadec-1(17)-ene-4,10-dione is found in Jacobaea aquatica and Jacobaea persoonii. (9e)-9-ethylidene-7-(hydroxymethyl)-5-methyl-3,6,11-trioxa-15-azatetracyclo[10.5.1.0⁵,⁷.0¹⁵,¹⁸]octadec-1(17)-ene-4,10-dione was first documented in 2017 (PMID: 28267991). Based on a literature review a small amount of articles have been published on ERUCIFOLINE (PMID: 30284188) (PMID: 35112977) (PMID: 34763859) (PMID: 29377789).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309052220552D          

 25 28  0  0  0  0            999 V2000
    6.8782    2.9653    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0803    2.7556    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8629    1.9598    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4435    1.3736    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2261    0.5777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8123    1.1583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6081    0.9409    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0240    0.7874    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8066   -0.0084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6024   -0.2258    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5892   -0.8043    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1697   -1.3905    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7913   -1.0139    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2108   -0.4278    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4129   -0.6374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8906   -1.2760    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1218   -0.9766    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1690   -0.1530    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7230    0.5411    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2453    1.1797    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0497    0.7446    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8476    0.9543    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0650    1.7501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4845    2.3363    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8323   -0.0512    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
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  5  8  1  0  0  0  0
  8  9  1  0  0  0  0
  5  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  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
 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
 15 25  1  0  0  0  0
 18 25  1  0  0  0  0
M  END

     RDKit          3D

 48 51  0  0  0  0  0  0  0  0999 V2000
    3.1521    3.4368    0.0158 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6956    3.2689    0.3013 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1557    2.2030    0.8717 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9936    1.0891    1.2660 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3880    0.0587    0.2740 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.1688    0.4391   -0.9680 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5284   -0.6415   -1.7573 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3456   -0.8609    1.0118 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1206   -1.3075    0.5272 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1224   -2.3011   -0.6163 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0804   -1.6271    1.5590 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5089   -1.8945    2.7139 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1979   -1.5930    1.1373 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9187   -2.3587    0.2380 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3658   -1.9302    0.2920 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5245   -2.4979   -0.0003 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6439   -1.5332    0.2745 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9904   -0.2424    0.3144 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7711    0.1658   -1.0678 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5837    1.0584   -0.9151 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6856    0.3878    0.1359 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1790    1.2400    1.0918 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3152    2.3016    1.0755 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7804    3.5105    1.2513 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6826   -0.5614    0.7726 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.4420    4.5060    0.2545 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3678    3.3332   -1.0660 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7936    2.8320    0.6679 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1013    4.1320   -0.0122 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4187    0.5316    2.0720 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9205    1.4127    1.8340 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6185    1.1262   -1.6213 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1587    0.8403   -0.6076 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4610   -0.9209   -1.6927 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5183   -3.2261   -0.3644 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6479   -1.9159   -1.5386 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1464   -2.7048   -0.7733 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8355   -3.4557    0.3765 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5715   -2.1534   -0.7954 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6225   -3.4987   -0.3759 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1321   -1.7776    1.2386 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3771   -1.5731   -0.5792 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6432    0.7406   -1.4509 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5419   -0.7108   -1.6954 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0396    1.2795   -1.8330 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9199    2.0253   -0.4722 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9200   -0.1400   -0.4904 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6125   -0.4925    1.8940 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  6
  6  7  1  0
  5  8  1  0
  8  9  1  0
  9 10  1  6
  9 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 18 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
 23  3  1  0
  9  5  1  0
 25 15  1  0
 25 18  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  2 29  1  0
  4 30  1  0
  4 31  1  0
  6 32  1  0
  6 33  1  0
  7 34  1  0
 10 35  1  0
 10 36  1  0
 10 37  1  0
 14 38  1  0
 14 39  1  0
 16 40  1  0
 17 41  1  0
 17 42  1  0
 19 43  1  0
 19 44  1  0
 20 45  1  0
 20 46  1  0
 21 47  1  6
 25 48  1  1
M  END


  Mrv1652309052220552D          

 25 28  0  0  0  0            999 V2000
    6.8782    2.9653    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0803    2.7556    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8629    1.9598    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4435    1.3736    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2261    0.5777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8123    1.1583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6081    0.9409    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0240    0.7874    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8066   -0.0084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6024   -0.2258    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5892   -0.8043    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1697   -1.3905    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7913   -1.0139    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2108   -0.4278    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4129   -0.6374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8906   -1.2760    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1218   -0.9766    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1690   -0.1530    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7230    0.5411    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2453    1.1797    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0497    0.7446    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8476    0.9543    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0650    1.7501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4845    2.3363    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8323   -0.0512    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
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  5  8  1  0  0  0  0
  8  9  1  0  0  0  0
  5  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  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
 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
 15 25  1  0  0  0  0
 18 25  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0218298

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C\C=C1/CC2(CO)OC2(C)C(=O)OCC2=CCN3CCC(OC1=O)C23

> <INCHI_IDENTIFIER>
InChI=1S/C18H23NO6/c1-3-11-8-18(10-20)17(2,25-18)16(22)23-9-12-4-6-19-7-5-13(14(12)19)24-15(11)21/h3-4,13-14,20H,5-10H2,1-2H3/b11-3+

> <INCHI_KEY>
NOQVBHHOUTTZGE-QDEBKDIKSA-N

> <FORMULA>
C18H23NO6

> <MOLECULAR_WEIGHT>
349.383

> <EXACT_MASS>
349.152537465

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
48

> <JCHEM_AVERAGE_POLARIZABILITY>
35.47947445033872

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(9E)-9-ethylidene-7-(hydroxymethyl)-5-methyl-3,6,11-trioxa-15-azatetracyclo[10.5.1.0^{5,7}.0^{15,18}]octadec-1(17)-ene-4,10-dione

> <JCHEM_LOGP>
0.5993564560000002

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.241914151680543

> <JCHEM_PKA_STRONGEST_BASIC>
7.136071275188414

> <JCHEM_POLAR_SURFACE_AREA>
88.6

> <JCHEM_REFRACTIVITY>
88.96829999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(9E)-9-ethylidene-7-(hydroxymethyl)-5-methyl-3,6,11-trioxa-15-azatetracyclo[10.5.1.0^{5,7}.0^{15,18}]octadec-1(17)-ene-4,10-dione

> <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      12.839   5.535   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      11.350   5.144   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      10.944   3.658   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      12.028   2.564   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      11.622   1.078   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      12.716   2.162   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      14.202   1.756   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0      13.111   1.470   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      12.706  -0.016   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      14.191  -0.422   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      12.300  -1.501   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      13.384  -2.596   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0      10.810  -1.893   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       9.727  -0.798   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.237  -1.190   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       7.262  -2.382   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.827  -1.823   0.000  0.00  0.00           C+0
HETATM   18  N   UNK     0       5.915  -0.286   0.000  0.00  0.00           N+0
HETATM   19  C   UNK     0       5.083   1.010   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.058   2.202   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       7.559   1.390   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       9.049   1.781   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       9.455   3.267   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       8.371   4.361   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       7.154  -0.096   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   23                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    8    9                                             
CONECT    6    5    7                                                       
CONECT    7    6                                                            
CONECT    8    5    9                                                       
CONECT    9    8    5   10   11                                             
CONECT   10    9                                                            
CONECT   11    9   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   25                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   25                                                  
CONECT   19   18   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   15   18                                                  
MASTER        0    0    0    0    0    0    0    0   25    0   56    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₈H₂₃NO₆

Average Mass

349.3830 Da

Monoisotopic Mass

349.15254 Da

IUPAC Name

(9E)-9-ethylidene-7-(hydroxymethyl)-5-methyl-3,6,11-trioxa-15-azatetracyclo[10.5.1.0^{5,7}.0^{15,18}]octadec-1(17)-ene-4,10-dione

Traditional Name

(9E)-9-ethylidene-7-(hydroxymethyl)-5-methyl-3,6,11-trioxa-15-azatetracyclo[10.5.1.0^{5,7}.0^{15,18}]octadec-1(17)-ene-4,10-dione

CAS Registry Number

Not Available

SMILES

C\C=C1/CC2(CO)OC2(C)C(=O)OCC2=CCN3CCC(OC1=O)C23

InChI Identifier

InChI=1S/C18H23NO6/c1-3-11-8-18(10-20)17(2,25-18)16(22)23-9-12-4-6-19-7-5-13(14(12)19)24-15(11)21/h3-4,13-14,20H,5-10H2,1-2H3/b11-3+

InChI Key

NOQVBHHOUTTZGE-QDEBKDIKSA-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
Jacobaea aquatica	LOTUS Database	35616633
Jacobaea persoonii	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as alkaloids and derivatives. These are naturally occurring chemical compounds that contain mostly basic nitrogen atoms. This group also includes some related compounds with neutral and even weakly acidic properties. Also some synthetic compounds of similar structure are attributed to alkaloids. In addition to carbon, hydrogen and nitrogen, alkaloids may also contain oxygen, sulfur and more rarely other elements such as chlorine, bromine, and phosphorus.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Not Available

Sub Class

Not Available

Direct Parent

Alkaloids and derivatives

Alternative Parents

Substituents

Senecionan-skeleton
Alkaloid or derivatives
Pyrrolizine
Dicarboxylic acid or derivatives
N-alkylpyrrolidine
Pyrrolidine
Pyrroline
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Amino acid or derivatives
Carboxylic acid ester
Lactone
Tertiary aliphatic amine
Tertiary amine
Carboxylic acid derivative
Dialkyl ether
Oxirane
Ether
Oxacycle
Azacycle
Organoheterocyclic compound
Amine
Organic nitrogen compound
Organic oxide
Organopnictogen compound
Hydrocarbon derivative
Organonitrogen compound
Organooxygen compound
Primary alcohol
Organic oxygen compound
Carbonyl group
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	0.6	ChemAxon
pKa (Strongest Acidic)	14.24	ChemAxon
pKa (Strongest Basic)	7.14	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	88.6 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	88.97 m³·mol⁻¹	ChemAxon
Polarizability	35.48 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

95639789

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

137628476

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Wei X, Vrieling K, Mulder PPJ, Klinkhamer PGL: Methyl Jasmonate Changes the Composition and Distribution Rather than the Concentration of Defence Compounds: a Study on Pyrrolizidine Alkaloids. J Chem Ecol. 2019 Feb;45(2):136-145. doi: 10.1007/s10886-018-1020-7. Epub 2018 Oct 4. [PubMed:30284188 ]
Liu X, Klinkhamer PGL, Vrieling K: The effect of structurally related metabolites on insect herbivores: A case study on pyrrolizidine alkaloids and western flower thrips. Phytochemistry. 2017 Jun;138:93-103. doi: 10.1016/j.phytochem.2017.02.027. Epub 2017 Mar 6. [PubMed:28267991 ]
Bandini TB, Spisso BF: Detection, dietary exposure assessment and risk evaluation of quinolones and pyrrolizidine alkaloids in commercial honey from Brazil. Food Addit Contam Part B Surveill. 2022 Jun;15(2):89-97. doi: 10.1080/19393210.2022.2028310. Epub 2022 Feb 3. [PubMed:35112977 ]
Wei X, Klinkhamer PGL, Mulder PPJ, van der Veen-van Wijk K, Vrieling K: Seasonal variation in defence compounds: A case study on pyrrolizidine alkaloids of clones of Jacobaea vulgaris, Jacobaea aquatica and their hybrids. Plant Sci. 2021 Dec;313:111067. doi: 10.1016/j.plantsci.2021.111067. Epub 2021 Sep 25. [PubMed:34763859 ]
Gottschalk C, Ostertag J, Meyer K, Gehring K, Thyssen S, Gareis M: Influence of grass pellet production on pyrrolizidine alkaloids occurring in Senecio aquaticus-infested grassland. Food Addit Contam Part A Chem Anal Control Expo Risk Assess. 2018 Apr;35(4):750-759. doi: 10.1080/19440049.2018.1430901. Epub 2018 Feb 23. [PubMed:29377789 ]
LOTUS database [Link]

Showing NP-Card for (9e)-9-ethylidene-7-(hydroxymethyl)-5-methyl-3,6,11-trioxa-15-azatetracyclo[10.5.1.0⁵,⁷.0¹⁵,¹⁸]octadec-1(17)-ene-4,10-dione (NP0218298)

MOL for NP0218298 ((9e)-9-ethylidene-7-(hydroxymethyl)-5-methyl-3,6,11-trioxa-15-azatetracyclo[10.5.1.0⁵,⁷.0¹⁵,¹⁸]octadec-1(17)-ene-4,10-dione)

3D MOL for NP0218298 ((9e)-9-ethylidene-7-(hydroxymethyl)-5-methyl-3,6,11-trioxa-15-azatetracyclo[10.5.1.0⁵,⁷.0¹⁵,¹⁸]octadec-1(17)-ene-4,10-dione)

3D SDF for NP0218298 ((9e)-9-ethylidene-7-(hydroxymethyl)-5-methyl-3,6,11-trioxa-15-azatetracyclo[10.5.1.0⁵,⁷.0¹⁵,¹⁸]octadec-1(17)-ene-4,10-dione)

3D-SDF for NP0218298 ((9e)-9-ethylidene-7-(hydroxymethyl)-5-methyl-3,6,11-trioxa-15-azatetracyclo[10.5.1.0⁵,⁷.0¹⁵,¹⁸]octadec-1(17)-ene-4,10-dione)

PDB for NP0218298 ((9e)-9-ethylidene-7-(hydroxymethyl)-5-methyl-3,6,11-trioxa-15-azatetracyclo[10.5.1.0⁵,⁷.0¹⁵,¹⁸]octadec-1(17)-ene-4,10-dione)

3D PDB for NP0218298 ((9e)-9-ethylidene-7-(hydroxymethyl)-5-methyl-3,6,11-trioxa-15-azatetracyclo[10.5.1.0⁵,⁷.0¹⁵,¹⁸]octadec-1(17)-ene-4,10-dione)

SMILES for NP0218298 ((9e)-9-ethylidene-7-(hydroxymethyl)-5-methyl-3,6,11-trioxa-15-azatetracyclo[10.5.1.0⁵,⁷.0¹⁵,¹⁸]octadec-1(17)-ene-4,10-dione)

INCHI for NP0218298 ((9e)-9-ethylidene-7-(hydroxymethyl)-5-methyl-3,6,11-trioxa-15-azatetracyclo[10.5.1.0⁵,⁷.0¹⁵,¹⁸]octadec-1(17)-ene-4,10-dione)

Structure for NP0218298 ((9e)-9-ethylidene-7-(hydroxymethyl)-5-methyl-3,6,11-trioxa-15-azatetracyclo[10.5.1.0⁵,⁷.0¹⁵,¹⁸]octadec-1(17)-ene-4,10-dione)

3D Structure for NP0218298 ((9e)-9-ethylidene-7-(hydroxymethyl)-5-methyl-3,6,11-trioxa-15-azatetracyclo[10.5.1.0⁵,⁷.0¹⁵,¹⁸]octadec-1(17)-ene-4,10-dione)