NP-MRD: Showing NP-Card for (1r,4z,7s,17r)-4-ethylidene-7-hydroxy-7-(hydroxymethyl)-6-methylidene-3,8-dioxo-2,9-dioxa-14-azatricyclo[9.5.1.0¹⁴,¹⁷]heptadec-11-en-14-ium-14-olate (NP0254495)

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Record Information

Version

2.0

Created at

2022-09-07 18:40:20 UTC

Updated at

2022-09-07 18:40:20 UTC

NP-MRD ID

NP0254495

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1r,4z,7s,17r)-4-ethylidene-7-hydroxy-7-(hydroxymethyl)-6-methylidene-3,8-dioxo-2,9-dioxa-14-azatricyclo[9.5.1.0¹⁴,¹⁷]heptadec-11-en-14-ium-14-olate

Description

Riddelliine N-oxide 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. Riddelliine N-oxide is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. (1r,4z,7s,17r)-4-ethylidene-7-hydroxy-7-(hydroxymethyl)-6-methylidene-3,8-dioxo-2,9-dioxa-14-azatricyclo[9.5.1.0¹⁴,¹⁷]heptadec-11-en-14-ium-14-olate was first documented in 2008 (PMID: 18842697). Based on a literature review a small amount of articles have been published on riddelliine N-oxide (PMID: 34669010) (PMID: 23937665) (PMID: 18395999).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309072220402D          

 26 28  0  0  1  0            999 V2000
    7.0069    0.9375    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
    6.8228    0.1333    0.0000 C   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 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0589   -2.0367    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8501   -0.9135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6660   -1.7177    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2458   -0.3520    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4572   -0.5946    0.0000 C   0  0  2  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 O   0  5  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 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0097    1.8180    0.0000 O   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
    5.9824    2.8648    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4026    1.4990    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.9849    2.0834    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2127    1.3431    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4827    0.5635    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8529   -0.0330    0.0000 C   0  0  2  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  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  4  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  6  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 20 22  1  0  0  0  0
  2 22  1  0  0  0  0
 22 23  1  6  0  0  0
 22 24  1  1  0  0  0
 24 25  1  0  0  0  0
 26 17  1  6  0  0  0
 10 26  1  0  0  0  0
 13 26  1  0  0  0  0
M  CHG  2  13   1  14  -1
M  END

     RDKit          3D

 49 51  0  0  0  0  0  0  0  0999 V2000
   -3.4843    0.7648    1.0437 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5545    0.1817    0.2772 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4414    0.8659   -0.1808 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9266    2.1192   -0.5416 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6358    3.2024   -0.6649 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0774    4.5149   -1.0444 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5417    2.1564   -0.8069 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9399    3.3021   -1.2241 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3768    1.0622   -0.6205 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9881    0.4871    0.4465 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.4279    1.0975    0.4999 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3489   -0.0417    0.0712 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5191   -1.1428   -0.2512 N   0  0  1  0  0  4  0  0  0  0  0  0
    3.1840   -1.2704   -1.5257 O   0  0  0  0  0  1  0  0  0  0  0  0
    3.8777   -2.4034    0.3889 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5223   -3.0466    0.4668 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6058   -2.0914    0.6094 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2242   -1.9624    0.7378 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8252   -2.7753    0.9177 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1271   -2.2997    0.7508 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9859   -2.9108    1.5121 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6990   -1.2814   -0.0888 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.0762   -1.3881   -1.3655 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1720   -1.5147   -0.3885 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6826   -0.5826   -1.2409 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3981   -0.8427    0.6222 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.3811    1.8119    1.3290 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3323    0.2216    1.3871 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7027    0.6266    0.6819 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1379    0.2688   -1.1259 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7345    3.1534   -0.4834 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9197    5.2831   -1.0229 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3561    4.9312   -0.3107 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7410    4.5626   -2.0991 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5424    0.8714    1.4250 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7061    1.3744    1.5150 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5456    1.8943   -0.2380 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0290    0.2724   -0.7456 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0241   -0.3524    0.9126 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3005   -2.1880    1.3722 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5508   -2.9521   -0.2923 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3535   -4.1153    0.4126 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0529   -1.4665   -0.2614 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1280   -1.2188    1.6031 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6890   -1.1431   -2.0850 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2142   -2.5556   -0.7892 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7064   -1.5470    0.5672 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3740   -1.0358   -1.8125 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8952   -0.8973    1.6595 H   0  0  0  0  0  0  0  0  0  0  0  0
  6  5  1  0
  5  4  2  0
  4  3  1  0
  3  2  1  0
  2  1  2  3
  2 22  1  0
 22 23  1  6
 22 24  1  0
 24 25  1  0
 22 20  1  0
 20 21  2  0
 20 19  1  0
 19 18  1  0
 18 17  1  0
 17 16  2  0
 16 15  1  0
 15 13  1  0
 13 14  1  6
 13 12  1  0
 12 11  1  0
 11 10  1  0
 10  9  1  0
  9  7  1  0
  7  8  2  0
 10 26  1  0
  7  4  1  0
 26 17  1  0
 26 13  1  0
  6 32  1  0
  6 33  1  0
  6 34  1  0
  5 31  1  0
  3 29  1  0
  3 30  1  0
  1 27  1  0
  1 28  1  0
 23 45  1  0
 24 46  1  0
 24 47  1  0
 25 48  1  0
 18 43  1  0
 18 44  1  0
 16 42  1  0
 15 40  1  0
 15 41  1  0
 12 38  1  0
 12 39  1  0
 11 36  1  0
 11 37  1  0
 10 35  1  1
 26 49  1  1
M  CHG  2  13   1  14  -1
M  END


  Mrv1652309072220402D          

 26 28  0  0  1  0            999 V2000
    7.0069    0.9375    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
    6.8228    0.1333    0.0000 C   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 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0589   -2.0367    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8501   -0.9135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6660   -1.7177    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2458   -0.3520    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4572   -0.5946    0.0000 C   0  0  2  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 O   0  5  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 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0097    1.8180    0.0000 O   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
    5.9824    2.8648    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4026    1.4990    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.9849    2.0834    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2127    1.3431    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4827    0.5635    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8529   -0.0330    0.0000 C   0  0  2  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  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  4  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  6  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 20 22  1  0  0  0  0
  2 22  1  0  0  0  0
 22 23  1  6  0  0  0
 22 24  1  1  0  0  0
 24 25  1  0  0  0  0
 26 17  1  6  0  0  0
 10 26  1  0  0  0  0
 13 26  1  0  0  0  0
M  CHG  2  13   1  14  -1
M  END
> <DATABASE_ID>
NP0254495

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C\C=C1\CC(=C)[C@](O)(CO)C(=O)OCC2=CC[N+]3([O-])CC[C@@H](OC1=O)[C@@H]23

> <INCHI_IDENTIFIER>
InChI=1S/C18H23NO7/c1-3-12-8-11(2)18(23,10-20)17(22)25-9-13-4-6-19(24)7-5-14(15(13)19)26-16(12)21/h3-4,14-15,20,23H,2,5-10H2,1H3/b12-3-/t14-,15-,18-,19?/m1/s1

> <INCHI_KEY>
NPENPMDVCQGSSO-AHPXGCJSSA-N

> <FORMULA>
C18H23NO7

> <MOLECULAR_WEIGHT>
365.382

> <EXACT_MASS>
365.147452085

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
49

> <JCHEM_AVERAGE_POLARIZABILITY>
35.82916110753211

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,4Z,7S,17R)-4-ethylidene-7-hydroxy-7-(hydroxymethyl)-6-methylidene-3,8-dioxo-2,9-dioxa-14-azatricyclo[9.5.1.0^{14,17}]heptadec-11-en-14-ium-14-olate

> <JCHEM_LOGP>
-0.7971146156666651

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.925297525455708

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.107270780939992

> <JCHEM_PKA_STRONGEST_BASIC>
2.817080939005572

> <JCHEM_POLAR_SURFACE_AREA>
116.12

> <JCHEM_REFRACTIVITY>
92.69569999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1R,4Z,7S,17R)-4-ethylidene-7-hydroxy-7-(hydroxymethyl)-6-methylidene-3,8-dioxo-2,9-dioxa-14-azatricyclo[9.5.1.0^{14,17}]heptadec-11-en-14-ium-14-olate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 07-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-SEP-22         0                                  
HETATM    1  C   UNK     0      13.080   1.750   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      11.608   1.297   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      12.736   0.249   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      12.392  -1.252   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      13.520  -2.301   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      13.177  -3.802   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      10.920  -1.705   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      10.577  -3.206   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0       9.792  -0.657   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       8.320  -1.110   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.396  -2.341   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.939  -1.843   0.000  0.00  0.00           C+0
HETATM   13  N   UNK     0       5.963  -0.303   0.000  0.00  0.00           N+1
HETATM   14  O   UNK     0       4.491  -0.756   0.000  0.00  0.00           O-1
HETATM   15  C   UNK     0       5.077   0.957   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.002   2.189   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       7.536   1.440   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       9.008   1.892   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       9.351   3.394   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      10.823   3.846   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      11.167   5.348   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      11.951   2.798   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      13.038   3.889   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      13.464   2.507   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      13.968   1.052   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       7.192  -0.062   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   22                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    7                                                  
CONECT    5    4    6                                                       
CONECT    6    5                                                            
CONECT    7    4    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10                                                       
CONECT   10    9   11   26                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   15   26                                             
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   26                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20    2   23   24                                             
CONECT   23   22                                                            
CONECT   24   22   25                                                       
CONECT   25   24                                                            
CONECT   26   17   10   13                                                  
MASTER        0    0    0    0    0    0    0    0   26    0   56    0
END

View in JSmol

Synonyms

Value	Source
(15Z)-12,18-Dihydroxy-13,19-didehydrosenecionan-11,16-dione 4-oxide	ChEBI

Chemical Formula

C₁₈H₂₃NO₇

Average Mass

365.3820 Da

Monoisotopic Mass

365.14745 Da

IUPAC Name

(1R,4Z,7S,17R)-4-ethylidene-7-hydroxy-7-(hydroxymethyl)-6-methylidene-3,8-dioxo-2,9-dioxa-14-azatricyclo[9.5.1.0^{14,17}]heptadec-11-en-14-ium-14-olate

Traditional Name

(1R,4Z,7S,17R)-4-ethylidene-7-hydroxy-7-(hydroxymethyl)-6-methylidene-3,8-dioxo-2,9-dioxa-14-azatricyclo[9.5.1.0^{14,17}]heptadec-11-en-14-ium-14-olate

CAS Registry Number

Not Available

SMILES

C\C=C1\CC(=C)[C@](O)(CO)C(=O)OCC2=CC[N+]3([O-])CC[C@@H](OC1=O)[C@@H]23

InChI Identifier

InChI=1S/C18H23NO7/c1-3-12-8-11(2)18(23,10-20)17(22)25-9-13-4-6-19(24)7-5-14(15(13)19)26-16(12)21/h3-4,14-15,20,23H,2,5-10H2,1H3/b12-3-/t14-,15-,18-,19?/m1/s1

InChI Key

NPENPMDVCQGSSO-AHPXGCJSSA-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

Not Available

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
Trialkyl amine oxide
Pyrrolidine
Pyrroline
Tertiary alcohol
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Carboxylic acid ester
1,2-diol
Lactone
Oxacycle
N-oxide
Azacycle
Organoheterocyclic compound
Trisubstituted n-oxide
Carboxylic acid derivative
Hydrocarbon derivative
Primary alcohol
Organooxygen compound
Organonitrogen compound
Organic oxide
Organic oxygen compound
Organic nitrogen compound
Organic salt
Alcohol
Organopnictogen compound
Organic zwitterion
Carbonyl group
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	-0.8	ChemAxon
pKa (Strongest Acidic)	11.11	ChemAxon
pKa (Strongest Basic)	2.82	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	116.12 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	92.7 m³·mol⁻¹	ChemAxon
Polarizability	35.83 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

Not Available

Chemspider ID

4944586

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

6440301

PDB ID

Not Available

ChEBI ID

136421

Good Scents ID

Not Available

References

General References

Widjaja F, Wesseling S, Rietjens IMCM: Physiologically based kinetic modelling predicts the in vivo relative potency of riddelliine N-oxide compared to riddelliine in rat to be dose dependent. Arch Toxicol. 2022 Jan;96(1):135-151. doi: 10.1007/s00204-021-03179-w. Epub 2021 Oct 20. [PubMed:34669010 ]
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 ]
Yan J, Xia Q, Chou MW, Fu PP: Metabolic activation of retronecine and retronecine N-oxide - formation of DHP-derived DNA adducts. Toxicol Ind Health. 2008 Apr;24(3):181-8. doi: 10.1177/0748233708093727. [PubMed:18842697 ]
Xia Q, Yan J, Chou MW, Fu PP: Formation of DHP-derived DNA adducts from metabolic activation of the prototype heliotridine-type pyrrolizidine alkaloid, heliotrine. Toxicol Lett. 2008 May 5;178(2):77-82. doi: 10.1016/j.toxlet.2008.02.008. Epub 2008 Mar 4. [PubMed:18395999 ]
LOTUS database [Link]

Showing NP-Card for (1r,4z,7s,17r)-4-ethylidene-7-hydroxy-7-(hydroxymethyl)-6-methylidene-3,8-dioxo-2,9-dioxa-14-azatricyclo[9.5.1.0¹⁴,¹⁷]heptadec-11-en-14-ium-14-olate (NP0254495)

MOL for NP0254495 ((1r,4z,7s,17r)-4-ethylidene-7-hydroxy-7-(hydroxymethyl)-6-methylidene-3,8-dioxo-2,9-dioxa-14-azatricyclo[9.5.1.0¹⁴,¹⁷]heptadec-11-en-14-ium-14-olate)

3D MOL for NP0254495 ((1r,4z,7s,17r)-4-ethylidene-7-hydroxy-7-(hydroxymethyl)-6-methylidene-3,8-dioxo-2,9-dioxa-14-azatricyclo[9.5.1.0¹⁴,¹⁷]heptadec-11-en-14-ium-14-olate)

3D SDF for NP0254495 ((1r,4z,7s,17r)-4-ethylidene-7-hydroxy-7-(hydroxymethyl)-6-methylidene-3,8-dioxo-2,9-dioxa-14-azatricyclo[9.5.1.0¹⁴,¹⁷]heptadec-11-en-14-ium-14-olate)

3D-SDF for NP0254495 ((1r,4z,7s,17r)-4-ethylidene-7-hydroxy-7-(hydroxymethyl)-6-methylidene-3,8-dioxo-2,9-dioxa-14-azatricyclo[9.5.1.0¹⁴,¹⁷]heptadec-11-en-14-ium-14-olate)

PDB for NP0254495 ((1r,4z,7s,17r)-4-ethylidene-7-hydroxy-7-(hydroxymethyl)-6-methylidene-3,8-dioxo-2,9-dioxa-14-azatricyclo[9.5.1.0¹⁴,¹⁷]heptadec-11-en-14-ium-14-olate)

3D PDB for NP0254495 ((1r,4z,7s,17r)-4-ethylidene-7-hydroxy-7-(hydroxymethyl)-6-methylidene-3,8-dioxo-2,9-dioxa-14-azatricyclo[9.5.1.0¹⁴,¹⁷]heptadec-11-en-14-ium-14-olate)

SMILES for NP0254495 ((1r,4z,7s,17r)-4-ethylidene-7-hydroxy-7-(hydroxymethyl)-6-methylidene-3,8-dioxo-2,9-dioxa-14-azatricyclo[9.5.1.0¹⁴,¹⁷]heptadec-11-en-14-ium-14-olate)

INCHI for NP0254495 ((1r,4z,7s,17r)-4-ethylidene-7-hydroxy-7-(hydroxymethyl)-6-methylidene-3,8-dioxo-2,9-dioxa-14-azatricyclo[9.5.1.0¹⁴,¹⁷]heptadec-11-en-14-ium-14-olate)

Structure for NP0254495 ((1r,4z,7s,17r)-4-ethylidene-7-hydroxy-7-(hydroxymethyl)-6-methylidene-3,8-dioxo-2,9-dioxa-14-azatricyclo[9.5.1.0¹⁴,¹⁷]heptadec-11-en-14-ium-14-olate)

3D Structure for NP0254495 ((1r,4z,7s,17r)-4-ethylidene-7-hydroxy-7-(hydroxymethyl)-6-methylidene-3,8-dioxo-2,9-dioxa-14-azatricyclo[9.5.1.0¹⁴,¹⁷]heptadec-11-en-14-ium-14-olate)