NP-MRD: Showing NP-Card for 19(Z)-Akuammidine (NP0077843)

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Record Information

Version

2.0

Created at

2022-04-28 22:59:44 UTC

Updated at

2022-04-28 22:59:44 UTC

NP-MRD ID

NP0077843

Secondary Accession Numbers

None

Natural Product Identification

Common Name

19(Z)-Akuammidine

Description

(Z)-Akuammidine belongs to the class of organic compounds known as macroline alkaloids. These are alkaloids with a structure that is based on the tetracyclic macroline skeleton. The macroline skeleton arises by scission of the C-21 to N-4 bond of the akuammilan skeleton, and mostly occurs in bisindole alkaloids. 19(Z)-Akuammidine is found in Gelsemium elegans and Gelsemium sempervirens. Based on a literature review very few articles have been published on (Z)-Akuammidine.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304292200592D          

 26 30  0  0  1  0            999 V2000
   -0.7779   -0.9460    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2774   -1.6159    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5479   -1.5269    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6659   -0.7074    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7543   -0.1239    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6531   -0.2971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2938    0.2226    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9861   -0.2262    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7828   -0.0121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3666   -0.5950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1537   -1.3921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3569   -1.6062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7731   -1.0233    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9493   -1.0671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3784   -1.7207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1913   -0.2975    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1732    0.0672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6957   -0.1259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3127    0.4218    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1468    1.2300    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9227   -2.1299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6905   -1.8280    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2142   -2.4385    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8950   -2.9045    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5298   -2.7951    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5930   -3.6176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  1  0  0  0
  5  4  1  6  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
  8 13  1  0  0  0  0
 13 14  1  0  0  0  0
  6 14  2  0  0  0  0
 14 15  1  0  0  0  0
  3 15  1  0  0  0  0
  5 16  1  0  0  0  0
  1 16  1  1  0  0  0
  4 17  1  0  0  0  0
 17 18  1  0  0  0  0
  1 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
  2 21  1  6  0  0  0
 21 22  1  0  0  0  0
  2 23  1  0  0  0  0
 23 24  2  0  0  0  0
 23 25  1  0  0  0  0
 25 26  1  0  0  0  0
M  END

     RDKit          3D

 50 54  0  0  0  0  0  0  0  0999 V2000
   -4.5955   -2.7999    0.1084 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9426   -1.5619   -0.4222 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6600   -1.3111   -0.2471 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7695   -2.2416    0.4909 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4971   -1.5354    0.6070 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0245   -1.4384   -0.7466 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8395   -0.5584   -1.6037 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0406   -0.0746   -0.7850 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5422    0.7014    0.4408 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.8032    0.9877    1.2616 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5029    1.7036    2.4165 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9325    1.9783    0.0670 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4539    3.0885    0.4289 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2262    2.1032   -0.6876 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7710    3.3872   -1.0189 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6408   -0.2226    1.2035 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7321    0.3224    1.4160 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7262   -0.1022    0.4032 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4083   -0.9372   -0.6288 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5081   -1.1336   -1.3664 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5232   -0.4565   -0.8487 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8561   -0.3391   -1.2464 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7144    0.4438   -0.5150 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2695    1.1062    0.5974 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9517    0.9746    0.9690 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0647    0.2008    0.2623 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8780   -3.6564    0.1467 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1238   -2.6375    1.0481 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3583   -3.0943   -0.6585 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5264   -0.8293   -0.9744 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5510   -3.1695   -0.0736 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1730   -2.5467    1.4725 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0065   -2.4910   -1.1350 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2771    0.2744   -2.0477 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2719   -1.1606   -2.4253 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7226    0.5227   -1.3987 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2472    0.0139    1.6220 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5285    1.5715    0.6819 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5406    1.5774    2.6248 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3450    3.8077   -0.1680 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4025    3.2443   -1.9248 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0496    4.0994   -1.3107 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0814   -0.4075    2.2196 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7568    1.4375    1.4842 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1547   -0.0245    2.4059 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5987   -1.7302   -2.2377 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2231   -0.8503   -2.1148 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7560    0.5500   -0.8056 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9417    1.7217    1.1736 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6018    1.4923    1.8393 H   0  0  0  0  0  0  0  0  0  0  0  0
 15 14  1  0
 14 12  1  0
 12 13  2  0
  9 12  1  0
  9 10  1  1
 10 11  1  0
  9 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 19  6  1  0
  6  7  1  0
  7  8  1  0
  8  3  1  0
  3  4  1  0
  4  5  1  0
  3  2  2  0
  2  1  1  0
  8  9  1  0
  5 16  1  0
 26 18  1  0
  5  6  1  0
 26 21  1  0
 15 40  1  0
 15 41  1  0
 15 42  1  0
 10 37  1  0
 10 38  1  0
 11 39  1  0
 16 43  1  1
 17 44  1  0
 17 45  1  0
 20 46  1  0
 22 47  1  0
 23 48  1  0
 24 49  1  0
 25 50  1  0
  6 33  1  6
  7 34  1  0
  7 35  1  0
  8 36  1  6
  4 31  1  0
  4 32  1  0
  2 30  1  0
  1 27  1  0
  1 28  1  0
  1 29  1  0
M  END


  Mrv1652304292200592D          

 26 30  0  0  1  0            999 V2000
   -0.7779   -0.9460    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2774   -1.6159    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5479   -1.5269    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6659   -0.7074    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7543   -0.1239    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6531   -0.2971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2938    0.2226    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9861   -0.2262    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7828   -0.0121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3666   -0.5950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1537   -1.3921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3569   -1.6062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7731   -1.0233    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9493   -1.0671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3784   -1.7207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1913   -0.2975    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1732    0.0672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6957   -0.1259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3127    0.4218    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1468    1.2300    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9227   -2.1299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6905   -1.8280    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2142   -2.4385    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8950   -2.9045    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5298   -2.7951    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5930   -3.6176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  1  0  0  0
  5  4  1  6  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
  8 13  1  0  0  0  0
 13 14  1  0  0  0  0
  6 14  2  0  0  0  0
 14 15  1  0  0  0  0
  3 15  1  0  0  0  0
  5 16  1  0  0  0  0
  1 16  1  1  0  0  0
  4 17  1  0  0  0  0
 17 18  1  0  0  0  0
  1 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
  2 21  1  6  0  0  0
 21 22  1  0  0  0  0
  2 23  1  0  0  0  0
 23 24  2  0  0  0  0
 23 25  1  0  0  0  0
 25 26  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0077843

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)[C@]1(CO)[C@@H]2CC3=C(NC4=CC=CC=C34)[C@@H]3C[C@H]1\C(CN23)=C\C

> <INCHI_IDENTIFIER>
InChI=1S/C21H24N2O3/c1-3-12-10-23-17-9-15(12)21(11-24,20(25)26-2)18(23)8-14-13-6-4-5-7-16(13)22-19(14)17/h3-7,15,17-18,22,24H,8-11H2,1-2H3/b12-3+/t15-,17-,18-,21-/m0/s1

> <INCHI_KEY>
RCEFXZXHYFOPIE-DNTDCJNWSA-N

> <FORMULA>
C21H24N2O3

> <MOLECULAR_WEIGHT>
352.434

> <EXACT_MASS>
352.178692641

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
50

> <JCHEM_AVERAGE_POLARIZABILITY>
38.588629758393836

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl (1S,12S,13S,14S,15Z)-15-ethylidene-13-(hydroxymethyl)-3,17-diazapentacyclo[12.3.1.0^{2,10}.0^{4,9}.0^{12,17}]octadeca-2(10),4,6,8-tetraene-13-carboxylate

> <ALOGPS_LOGP>
2.63

> <JCHEM_LOGP>
2.0383856056666665

> <ALOGPS_LOGS>
-2.92

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.418616498293758

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.685886597791662

> <JCHEM_PKA_STRONGEST_BASIC>
5.958648677287678

> <JCHEM_POLAR_SURFACE_AREA>
65.56

> <JCHEM_REFRACTIVITY>
100.15

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.29e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl (1S,12S,13S,14S,15Z)-15-ethylidene-13-(hydroxymethyl)-3,17-diazapentacyclo[12.3.1.0^{2,10}.0^{4,9}.0^{12,17}]octadeca-2(10),4,6,8-tetraene-13-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 29-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-APR-22         0                                  
HETATM    1  C   UNK     0      -1.452  -1.766   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.518  -3.016   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.023  -2.850   0.000  0.00  0.00           C+0
HETATM    4  N   UNK     0       1.243  -1.321   0.000  0.00  0.00           N+0
HETATM    5  C   UNK     0       1.408  -0.231   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.086  -0.555   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0       4.282   0.416   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0       5.574  -0.422   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.061  -0.023   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.151  -1.111   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.754  -2.599   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.266  -2.998   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.177  -1.910   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.639  -1.992   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.573  -3.212   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -0.357  -0.555   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.323   0.125   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -1.299  -0.235   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -2.450   0.787   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -2.141   2.296   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -1.722  -3.976   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      -3.156  -3.412   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      -0.400  -4.552   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      -1.671  -5.422   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0       0.989  -5.217   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       1.107  -6.753   0.000  0.00  0.00           C+0
CONECT    1    2   16   18                                                  
CONECT    2    1    3   21   23                                             
CONECT    3    2    4   15                                                  
CONECT    4    3    5   17                                                  
CONECT    5    4    6   16                                                  
CONECT    6    5    7   14                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   13                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12    8   14                                                  
CONECT   14   13    6   15                                                  
CONECT   15   14    3                                                       
CONECT   16    5    1                                                       
CONECT   17    4   18                                                       
CONECT   18   17    1   19                                                  
CONECT   19   18   20                                                       
CONECT   20   19                                                            
CONECT   21    2   22                                                       
CONECT   22   21                                                            
CONECT   23    2   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26                                                       
CONECT   26   25                                                            
MASTER        0    0    0    0    0    0    0    0   26    0   60    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₁H₂₄N₂O₃

Average Mass

352.4340 Da

Monoisotopic Mass

352.17869 Da

IUPAC Name

methyl (1S,12S,13S,14S,15Z)-15-ethylidene-13-(hydroxymethyl)-3,17-diazapentacyclo[12.3.1.0^{2,10}.0^{4,9}.0^{12,17}]octadeca-2(10),4,6,8-tetraene-13-carboxylate

Traditional Name

methyl (1S,12S,13S,14S,15Z)-15-ethylidene-13-(hydroxymethyl)-3,17-diazapentacyclo[12.3.1.0^{2,10}.0^{4,9}.0^{12,17}]octadeca-2(10),4,6,8-tetraene-13-carboxylate

CAS Registry Number

Not Available

SMILES

COC(=O)[C@]1(CO)[C@@H]2CC3=C(NC4=CC=CC=C34)[C@@H]3C[C@H]1\C(CN23)=C\C

InChI Identifier

InChI=1S/C21H24N2O3/c1-3-12-10-23-17-9-15(12)21(11-24,20(25)26-2)18(23)8-14-13-6-4-5-7-16(13)22-19(14)17/h3-7,15,17-18,22,24H,8-11H2,1-2H3/b12-3+/t15-,17-,18-,21-/m0/s1

InChI Key

RCEFXZXHYFOPIE-DNTDCJNWSA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Gelsemium elegans	Plant	KNApSAcK
Gelsemium sempervirens	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as macroline alkaloids. These are alkaloids with a structure that is based on the tetracyclic macroline skeleton. The macroline skeleton arises by scission of the C-21 to N-4 bond of the akuammilan skeleton, and mostly occurs in bisindole alkaloids.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Macroline alkaloids

Sub Class

Not Available

Direct Parent

Macroline alkaloids

Alternative Parents

Substituents

Macroline skeleton
Corynanthean skeleton
Vobasan skeleton
Pyridoindole
Beta-carboline
3-alkylindole
Piperidinecarboxylic acid
Indole or derivatives
Indole
Quinuclidine
Beta-hydroxy acid
Aralkylamine
Benzenoid
Hydroxy acid
Piperidine
Heteroaromatic compound
Methyl ester
1,3-aminoalcohol
Pyrrole
Amino acid or derivatives
Carboxylic acid ester
Tertiary aliphatic amine
Tertiary amine
Monocarboxylic acid or derivatives
Organoheterocyclic compound
Azacycle
Carboxylic acid derivative
Organonitrogen compound
Hydrocarbon derivative
Organic oxide
Alcohol
Carbonyl group
Organopnictogen compound
Organic oxygen compound
Organooxygen compound
Amine
Organic nitrogen compound
Primary alcohol
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic 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	2.63	ALOGPS
logP	2.04	ChemAxon
logS	-2.9	ALOGPS
pKa (Strongest Acidic)	14.69	ChemAxon
pKa (Strongest Basic)	5.96	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	65.56 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	100.15 m³·mol⁻¹	ChemAxon
Polarizability	38.59 Å³	ChemAxon
Number of Rings	5	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

C00041252

Chemspider ID

62954674

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

13946380

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for 19(Z)-Akuammidine (NP0077843)

MOL for NP0077843 (19(Z)-Akuammidine)

3D MOL for NP0077843 (19(Z)-Akuammidine)

3D SDF for NP0077843 (19(Z)-Akuammidine)

3D-SDF for NP0077843 (19(Z)-Akuammidine)

PDB for NP0077843 (19(Z)-Akuammidine)

3D PDB for NP0077843 (19(Z)-Akuammidine)

SMILES for NP0077843 (19(Z)-Akuammidine)

INCHI for NP0077843 (19(Z)-Akuammidine)

Structure for NP0077843 (19(Z)-Akuammidine)

3D Structure for NP0077843 (19(Z)-Akuammidine)