NP-MRD: Showing NP-Card for (1r,17s)-4-ethyl-7,17-dihydroxy-7,14-dimethyl-6-methylidene-3,8-dioxo-2,9-dioxa-14-azatricyclo[9.5.1.0¹⁴,¹⁷]heptadec-11-en-14-ium (NP0175827)

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Record Information

Version

2.0

Created at

2022-09-03 13:23:31 UTC

Updated at

2022-09-03 13:23:31 UTC

NP-MRD ID

NP0175827

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1r,17s)-4-ethyl-7,17-dihydroxy-7,14-dimethyl-6-methylidene-3,8-dioxo-2,9-dioxa-14-azatricyclo[9.5.1.0¹⁴,¹⁷]heptadec-11-en-14-ium

Description

Emiline 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. (1r,17s)-4-ethyl-7,17-dihydroxy-7,14-dimethyl-6-methylidene-3,8-dioxo-2,9-dioxa-14-azatricyclo[9.5.1.0¹⁴,¹⁷]heptadec-11-en-14-ium is found in Emilia sonchifolia. (1r,17s)-4-ethyl-7,17-dihydroxy-7,14-dimethyl-6-methylidene-3,8-dioxo-2,9-dioxa-14-azatricyclo[9.5.1.0¹⁴,¹⁷]heptadec-11-en-14-ium was first documented in 2019 (PMID: 30375240). Based on a literature review very few articles have been published on Emiline (PMID: 34539789).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309032215232D          

 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 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7199    0.5127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2152    1.1725    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0370    0.7712    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8255    1.0138    0.0000 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  0  0  0  0  0  0  0  0  0  0
    6.9849    2.0834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2127    1.3431    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
    3.6269   -0.8264    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  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  0  0  0  0
 22 24  1  0  0  0  0
 17 25  1  0  0  0  0
 10 25  1  0  0  0  0
 13 25  1  0  0  0  0
 25 26  1  1  0  0  0
M  CHG  1  13   1
M  END

     RDKit          3D

 54 56  0  0  0  0  0  0  0  0999 V2000
    3.2144    0.5897    1.2010 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8531    0.5246   -0.0573 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5538   -0.7964   -0.6637 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5164   -1.5318    0.1534 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0473   -2.8731    0.6323 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4355   -3.7785   -0.4912 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3219   -1.7428   -0.7104 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4665   -2.6111   -1.6138 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8155   -1.0185   -0.4899 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4775   -0.8445    0.7218 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.6800   -1.8042    0.8484 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9148   -0.8837    0.7521 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3661    0.2341    0.1045 N   0  0  1  0  0  4  0  0  0  0  0  0
   -3.0757    0.0772   -1.2861 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9440    1.5310    0.3146 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7123    2.3515   -0.0445 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6363    1.6503    0.3209 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1658    1.9815    0.2014 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2717    1.5352   -1.0370 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4587    1.7803   -1.6507 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5264    2.0497   -2.8779 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7352    1.7402   -0.8941 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.9136    2.9929   -0.0488 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8439    1.7211   -1.7719 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1405    0.4357    0.9056 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.5510    0.6136    2.2227 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3176   -0.2604    1.8595 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4309    1.5586    1.6349 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2516   -0.6993   -1.7267 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5220   -1.3774   -0.6849 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2559   -0.9597    1.0848 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2698   -3.3789    1.2276 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9184   -2.7348    1.3032 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7104   -3.2393   -1.4277 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6242   -4.4936   -0.7453 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3212   -4.4255   -0.2216 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7760   -1.0486    1.5648 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6820   -2.4882   -0.0140 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7045   -2.2873    1.8265 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2304   -0.6274    1.7645 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7085   -1.4190    0.1965 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8837   -0.9811   -1.5839 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0163    0.3562   -1.8471 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3085    0.7778   -1.6303 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6874    1.7349   -0.4604 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2825    1.7346    1.3269 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7627    3.3282   -0.5135 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0901    3.0779    0.3457 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3365    1.5062    1.0657 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2604    3.0197    0.8254 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6205    3.8744   -0.6844 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9787    3.1403    0.2047 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1733    0.8057   -1.9061 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5375    1.5819    2.4737 H   0  0  0  0  0  0  0  0  0  0  0  0
  6  5  1  0
  5  4  1  0
  4  3  1  0
  3  2  1  0
  2  1  2  3
  2 22  1  0
 22 23  1  0
 22 24  1  6
 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 25  1  0
 25 26  1  1
  7  4  1  0
 25 17  1  0
 25 13  1  0
  6 34  1  0
  6 35  1  0
  6 36  1  0
  5 32  1  0
  5 33  1  0
  4 31  1  1
  3 29  1  0
  3 30  1  0
  1 27  1  0
  1 28  1  0
 23 50  1  0
 23 51  1  0
 23 52  1  0
 24 53  1  0
 18 48  1  0
 18 49  1  0
 16 47  1  0
 15 45  1  0
 15 46  1  0
 14 42  1  0
 14 43  1  0
 14 44  1  0
 12 40  1  0
 12 41  1  0
 11 38  1  0
 11 39  1  0
 10 37  1  1
 26 54  1  0
M  CHG  1  13   1
M  END


  Mrv1652309032215232D          

 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 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7199    0.5127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2152    1.1725    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0370    0.7712    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8255    1.0138    0.0000 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  0  0  0  0  0  0  0  0  0  0
    6.9849    2.0834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2127    1.3431    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
    3.6269   -0.8264    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  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  0  0  0  0
 22 24  1  0  0  0  0
 17 25  1  0  0  0  0
 10 25  1  0  0  0  0
 13 25  1  0  0  0  0
 25 26  1  1  0  0  0
M  CHG  1  13   1
M  END
> <DATABASE_ID>
NP0175827

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCC1CC(=C)C(C)(O)C(=O)OCC2=CC[N+]3(C)CC[C@@H](OC1=O)[C@@]23O

> <INCHI_IDENTIFIER>
InChI=1S/C19H28NO6/c1-5-13-10-12(2)18(3,23)17(22)25-11-14-6-8-20(4)9-7-15(19(14,20)24)26-16(13)21/h6,13,15,23-24H,2,5,7-11H2,1,3-4H3/q+1/t13?,15-,18?,19+,20?/m1/s1

> <INCHI_KEY>
NJNQFHVIXUJHSN-GTFIEPSHSA-N

> <FORMULA>
C19H28NO6

> <MOLECULAR_WEIGHT>
366.433

> <EXACT_MASS>
366.191114046

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
54

> <JCHEM_AVERAGE_POLARIZABILITY>
37.94639755389457

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
1

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
0.97

> <JCHEM_LOGP>
-3.061571157805079

> <ALOGPS_LOGS>
-3.72

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
12.059439059265488

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.50733358068884

> <JCHEM_PKA_STRONGEST_BASIC>
-4.090589124667805

> <JCHEM_POLAR_SURFACE_AREA>
93.06

> <JCHEM_REFRACTIVITY>
105.6121

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.60e-02 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 03-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-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  C   UNK     0       4.491  -0.756   0.000  0.00  0.00           C+0
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  C   UNK     0      13.038   3.889   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      13.464   2.507   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       7.192  -0.062   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       6.770  -1.543   0.000  0.00  0.00           O+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   25                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   15   25                                             
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   25                                                  
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                                                            
CONECT   25   17   10   13   26                                             
CONECT   26   25                                                            
MASTER        0    0    0    0    0    0    0    0   26    0   56    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₉H₂₈NO₆

Average Mass

366.4330 Da

Monoisotopic Mass

366.19111 Da

IUPAC Name

(1R,17S)-4-ethyl-7,17-dihydroxy-7,14-dimethyl-6-methylidene-3,8-dioxo-2,9-dioxa-14-azatricyclo[9.5.1.0^{14,17}]heptadec-11-en-14-ium

Traditional Name

(1R,17S)-4-ethyl-7,17-dihydroxy-7,14-dimethyl-6-methylidene-3,8-dioxo-2,9-dioxa-14-azatricyclo[9.5.1.0^{14,17}]heptadec-11-en-14-ium

CAS Registry Number

Not Available

SMILES

CCC1CC(=C)C(C)(O)C(=O)OCC2=CC[N+]3(C)CC[C@@H](OC1=O)[C@@]23O

InChI Identifier

InChI=1S/C19H28NO6/c1-5-13-10-12(2)18(3,23)17(22)25-11-14-6-8-20(4)9-7-15(19(14,20)24)26-16(13)21/h6,13,15,23-24H,2,5,7-11H2,1,3-4H3/q+1/t13?,15-,18?,19+,20?/m1/s1

InChI Key

NJNQFHVIXUJHSN-GTFIEPSHSA-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
Emilia sonchifolia	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
Tetraalkylammonium salt
Pyrrolidine
Pyrroline
Quaternary ammonium salt
Tertiary alcohol
Carboxylic acid ester
Lactone
Azacycle
Oxacycle
Carboxylic acid derivative
Alkanolamine
Organoheterocyclic compound
Organic oxygen compound
Alcohol
Organooxygen compound
Organonitrogen compound
Hydrocarbon derivative
Organic oxide
Carbonyl group
Organic nitrogen compound
Organic cation
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	0.97	ALOGPS
logP	-3.1	ChemAxon
logS	-3.7	ALOGPS
pKa (Strongest Acidic)	10.51	ChemAxon
pKa (Strongest Basic)	-4.1	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	93.06 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	105.61 m³·mol⁻¹	ChemAxon
Polarizability	37.95 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

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

101710314

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

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 ]
Mezache N, Derbre S, Laouer H, Richomme P, Seraphin D, Akkal S: Senecipyrrolidine, an unusual pyrrolidine alkaloid isolated from Jacobaea gigantea (Desf.) Pelser (Asteraceae). Nat Prod Res. 2019 Aug;33(15):2182-2191. doi: 10.1080/14786419.2018.1493584. Epub 2018 Oct 30. [PubMed:30375240 ]
LOTUS database [Link]

Showing NP-Card for (1r,17s)-4-ethyl-7,17-dihydroxy-7,14-dimethyl-6-methylidene-3,8-dioxo-2,9-dioxa-14-azatricyclo[9.5.1.0¹⁴,¹⁷]heptadec-11-en-14-ium (NP0175827)

MOL for NP0175827 ((1r,17s)-4-ethyl-7,17-dihydroxy-7,14-dimethyl-6-methylidene-3,8-dioxo-2,9-dioxa-14-azatricyclo[9.5.1.0¹⁴,¹⁷]heptadec-11-en-14-ium)

3D MOL for NP0175827 ((1r,17s)-4-ethyl-7,17-dihydroxy-7,14-dimethyl-6-methylidene-3,8-dioxo-2,9-dioxa-14-azatricyclo[9.5.1.0¹⁴,¹⁷]heptadec-11-en-14-ium)

3D SDF for NP0175827 ((1r,17s)-4-ethyl-7,17-dihydroxy-7,14-dimethyl-6-methylidene-3,8-dioxo-2,9-dioxa-14-azatricyclo[9.5.1.0¹⁴,¹⁷]heptadec-11-en-14-ium)

3D-SDF for NP0175827 ((1r,17s)-4-ethyl-7,17-dihydroxy-7,14-dimethyl-6-methylidene-3,8-dioxo-2,9-dioxa-14-azatricyclo[9.5.1.0¹⁴,¹⁷]heptadec-11-en-14-ium)

PDB for NP0175827 ((1r,17s)-4-ethyl-7,17-dihydroxy-7,14-dimethyl-6-methylidene-3,8-dioxo-2,9-dioxa-14-azatricyclo[9.5.1.0¹⁴,¹⁷]heptadec-11-en-14-ium)

3D PDB for NP0175827 ((1r,17s)-4-ethyl-7,17-dihydroxy-7,14-dimethyl-6-methylidene-3,8-dioxo-2,9-dioxa-14-azatricyclo[9.5.1.0¹⁴,¹⁷]heptadec-11-en-14-ium)

SMILES for NP0175827 ((1r,17s)-4-ethyl-7,17-dihydroxy-7,14-dimethyl-6-methylidene-3,8-dioxo-2,9-dioxa-14-azatricyclo[9.5.1.0¹⁴,¹⁷]heptadec-11-en-14-ium)

INCHI for NP0175827 ((1r,17s)-4-ethyl-7,17-dihydroxy-7,14-dimethyl-6-methylidene-3,8-dioxo-2,9-dioxa-14-azatricyclo[9.5.1.0¹⁴,¹⁷]heptadec-11-en-14-ium)

Structure for NP0175827 ((1r,17s)-4-ethyl-7,17-dihydroxy-7,14-dimethyl-6-methylidene-3,8-dioxo-2,9-dioxa-14-azatricyclo[9.5.1.0¹⁴,¹⁷]heptadec-11-en-14-ium)

3D Structure for NP0175827 ((1r,17s)-4-ethyl-7,17-dihydroxy-7,14-dimethyl-6-methylidene-3,8-dioxo-2,9-dioxa-14-azatricyclo[9.5.1.0¹⁴,¹⁷]heptadec-11-en-14-ium)