NP-MRD: Showing NP-Card for methyl (12r,13s,14z)-14-ethylidene-12-(hydroxymethyl)-1,10-diazatetracyclo[11.2.2.0³,¹¹.0⁴,⁹]heptadeca-3(11),4,6,8-tetraene-12-carboxylate (NP0294192)

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Record Information

Version

2.0

Created at

2022-09-10 02:36:59 UTC

Updated at

2022-09-10 02:36:59 UTC

NP-MRD ID

NP0294192

Secondary Accession Numbers

None

Natural Product Identification

Common Name

methyl (12r,13s,14z)-14-ethylidene-12-(hydroxymethyl)-1,10-diazatetracyclo[11.2.2.0³,¹¹.0⁴,⁹]heptadeca-3(11),4,6,8-tetraene-12-carboxylate

Description

Vallesamine belongs to the class of organic compounds known as vallesaman alkaloids. These are alkaloids with a structure that is based on the vallesaman skeleton, a tetracyclic compound that contains a piperidine ring fused to an indole. methyl (12r,13s,14z)-14-ethylidene-12-(hydroxymethyl)-1,10-diazatetracyclo[11.2.2.0³,¹¹.0⁴,⁹]heptadeca-3(11),4,6,8-tetraene-12-carboxylate is found in Alstonia angustiloba, Alstonia scholaris, Tabernaemontana cymosa, Tabernaemontana markgrafiana and Tabernaemontana pandacaqui. methyl (12r,13s,14z)-14-ethylidene-12-(hydroxymethyl)-1,10-diazatetracyclo[11.2.2.0³,¹¹.0⁴,⁹]heptadeca-3(11),4,6,8-tetraene-12-carboxylate was first documented in 2021 (PMID: 34325978). Based on a literature review a small amount of articles have been published on Vallesamine (PMID: 35176533) (PMID: 35888731) (PMID: 32891813).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309102204372D          

 25 28  0  0  1  0            999 V2000
    8.7008    0.9533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1809    1.5939    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3662    1.4641    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1744    0.6617    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4714    0.2300    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.4643    0.9143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6187    1.5600    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9345    2.1671    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.1321    2.3589    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.5331    2.9262    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7250    3.7286    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5251    3.0843    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0933    3.7873    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3498    3.1067    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7815    2.4037    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4291    1.9272    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7252    2.3576    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.0984    1.8212    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2804    1.9281    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7788    1.2731    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0952    0.5112    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9133    0.4043    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4149    1.0593    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2373    1.1248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6690    0.4218    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
  8  7  1  1  0  0  0
  3  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  1  0  0  0
 10 11  1  0  0  0  0
  9 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
  9 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 18 23  1  0  0  0  0
 23 24  1  0  0  0  0
 16 24  2  0  0  0  0
 24 25  1  0  0  0  0
  5 25  1  0  0  0  0
M  END

     RDKit          3D

 49 52  0  0  0  0  0  0  0  0999 V2000
   -3.6472   -1.2773    1.6511 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0607   -0.3373    0.6558 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0290   -0.6505   -0.1071 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4117   -1.9707    0.0057 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4707   -2.3385   -0.9629 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4654   -1.7026   -2.2189 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3086   -0.4784   -2.3552 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4634    0.2950   -1.0865 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2896    1.0504   -0.6163 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2086    1.9282   -1.7433 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8494    2.7079   -2.1694 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7571    1.9890    0.4526 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2411    2.0474    1.5895 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8120    2.8402    0.1832 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3188    3.7588    1.1326 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8401    0.2320   -0.1359 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8100    0.9799    0.4186 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8399    0.2172    0.8555 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0426    0.5309    1.4833 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9439   -0.4439    1.8357 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6255   -1.7541    1.5499 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4267   -2.0549    0.9253 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5224   -1.0718    0.5722 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2768   -1.0570   -0.0448 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8381   -2.4529   -0.3989 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9420   -1.4468    2.4975 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6055   -0.8748    1.9989 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8866   -2.2693    1.1748 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4801    0.6665    0.5255 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1850   -2.7963    0.0643 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9409   -2.0100    1.0359 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5767   -1.4193   -2.4885 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7837   -2.4335   -2.9996 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3507   -0.8029   -2.6535 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9861    0.1920   -3.1704 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2693    1.0625   -1.2948 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5879    1.2874   -2.5602 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0783    2.5392   -1.4095 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5218    3.4928   -2.7089 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9064    4.5192    0.5790 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5056    4.2374    1.7224 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9892    3.2745    1.8676 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8452    2.0357    0.5388 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2877    1.5612    1.7054 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8940   -0.2010    2.3313 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2775   -2.5764    1.7935 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1809   -3.0815    0.7031 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5235   -2.8242   -1.2044 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8514   -3.1195    0.4799 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  1
  9 10  1  0
 10 11  1  0
  9  8  1  0
  8  7  1  0
  7  6  1  0
  6  5  1  0
  5  4  1  0
  4  3  1  0
  3  2  2  0
  2  1  1  0
  5 25  1  0
 25 24  1  0
 24 16  2  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 16  9  1  0
 23 18  1  0
  3  8  1  0
 23 24  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
  8 36  1  6
  7 34  1  0
  7 35  1  0
  6 32  1  0
  6 33  1  0
  4 30  1  0
  4 31  1  0
  2 29  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
 25 48  1  0
 25 49  1  0
 17 43  1  0
 19 44  1  0
 20 45  1  0
 21 46  1  0
 22 47  1  0
M  END


  Mrv1652309102204372D          

 25 28  0  0  1  0            999 V2000
    8.7008    0.9533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1809    1.5939    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3662    1.4641    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1744    0.6617    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4714    0.2300    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.4643    0.9143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6187    1.5600    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9345    2.1671    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.1321    2.3589    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.5331    2.9262    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7250    3.7286    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5251    3.0843    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0933    3.7873    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3498    3.1067    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7815    2.4037    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4291    1.9272    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7252    2.3576    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.0984    1.8212    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2804    1.9281    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7788    1.2731    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0952    0.5112    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9133    0.4043    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4149    1.0593    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2373    1.1248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6690    0.4218    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
  8  7  1  1  0  0  0
  3  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  1  0  0  0
 10 11  1  0  0  0  0
  9 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
  9 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 18 23  1  0  0  0  0
 23 24  1  0  0  0  0
 16 24  2  0  0  0  0
 24 25  1  0  0  0  0
  5 25  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0294192

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)[C@]1(CO)[C@H]2CCN(C\C2=C/C)CC2=C1NC1=CC=CC=C21

> <INCHI_IDENTIFIER>
InChI=1S/C20H24N2O3/c1-3-13-10-22-9-8-16(13)20(12-23,19(24)25-2)18-15(11-22)14-6-4-5-7-17(14)21-18/h3-7,16,21,23H,8-12H2,1-2H3/b13-3+/t16-,20+/m0/s1

> <INCHI_KEY>
JZKSIYFJGCTTET-QMBIXULJSA-N

> <FORMULA>
C20H24N2O3

> <MOLECULAR_WEIGHT>
340.423

> <EXACT_MASS>
340.178692641

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
49

> <JCHEM_AVERAGE_POLARIZABILITY>
37.06101851266283

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl (12R,13S,14Z)-14-ethylidene-12-(hydroxymethyl)-1,10-diazatetracyclo[11.2.2.0^{3,11}.0^{4,9}]heptadeca-3(11),4,6,8-tetraene-12-carboxylate

> <JCHEM_LOGP>
1.8017152039999997

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
15.347438349148096

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.617419632539828

> <JCHEM_PKA_STRONGEST_BASIC>
7.1249535533693145

> <JCHEM_POLAR_SURFACE_AREA>
65.56

> <JCHEM_REFRACTIVITY>
98.0236

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
methyl (12R,13S,14Z)-14-ethylidene-12-(hydroxymethyl)-1,10-diazatetracyclo[11.2.2.0^{3,11}.0^{4,9}]heptadeca-3(11),4,6,8-tetraene-12-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 10-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-SEP-22         0                                  
HETATM    1  C   UNK     0      16.241   1.779   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      15.271   2.975   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      13.750   2.733   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      13.392   1.235   0.000  0.00  0.00           C+0
HETATM    5  N   UNK     0      12.080   0.429   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0      12.067   1.707   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      12.355   2.912   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      12.944   4.045   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      11.447   4.403   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      10.329   5.462   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      10.687   6.960   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      12.180   5.757   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      11.374   7.070   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0      13.720   5.799   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      14.525   4.487   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      10.134   3.597   0.000  0.00  0.00           C+0
HETATM   17  N   UNK     0       8.820   4.401   0.000  0.00  0.00           N+0
HETATM   18  C   UNK     0       7.650   3.400   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       6.123   3.599   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.187   2.376   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       5.778   0.954   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       7.305   0.755   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       8.241   1.977   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       9.776   2.100   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      10.582   0.787   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    8                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   25                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    3    9                                                  
CONECT    9    8   10   12   16                                             
CONECT   10    9   11                                                       
CONECT   11   10                                                            
CONECT   12    9   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14                                                            
CONECT   16    9   17   24                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19   23                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   18   24                                                  
CONECT   24   23   16   25                                                  
CONECT   25   24    5                                                       
MASTER        0    0    0    0    0    0    0    0   25    0   56    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₀H₂₄N₂O₃

Average Mass

340.4230 Da

Monoisotopic Mass

340.17869 Da

IUPAC Name

methyl (12R,13S,14Z)-14-ethylidene-12-(hydroxymethyl)-1,10-diazatetracyclo[11.2.2.0^{3,11}.0^{4,9}]heptadeca-3(11),4,6,8-tetraene-12-carboxylate

Traditional Name

methyl (12R,13S,14Z)-14-ethylidene-12-(hydroxymethyl)-1,10-diazatetracyclo[11.2.2.0^{3,11}.0^{4,9}]heptadeca-3(11),4,6,8-tetraene-12-carboxylate

CAS Registry Number

Not Available

SMILES

COC(=O)[C@]1(CO)[C@H]2CCN(C\C2=C/C)CC2=C1NC1=CC=CC=C21

InChI Identifier

InChI=1S/C20H24N2O3/c1-3-13-10-22-9-8-16(13)20(12-23,19(24)25-2)18-15(11-22)14-6-4-5-7-17(14)21-18/h3-7,16,21,23H,8-12H2,1-2H3/b13-3+/t16-,20+/m0/s1

InChI Key

JZKSIYFJGCTTET-QMBIXULJSA-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
Alstonia angustiloba	LOTUS Database	35616633
Alstonia scholaris	LOTUS Database	35616633
Tabernaemontana cymosa	LOTUS Database	35616633
Tabernaemontana markgrafiana	LOTUS Database	35616633
Tabernaemontana pandacaqui	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as vallesaman alkaloids. These are alkaloids with a structure that is based on the vallesaman skeleton, a tetracyclic compound that contains a piperidine ring fused to an indole.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Vallesaman alkaloids

Sub Class

Not Available

Direct Parent

Vallesaman alkaloids

Alternative Parents

Substituents

Vallesaman-skeleton
3-alkylindole
Indole
Indole or derivatives
Beta-hydroxy acid
Aralkylamine
Hydroxy acid
Piperidine
Benzenoid
Heteroaromatic compound
Pyrrole
Methyl ester
Amino acid or derivatives
Carboxylic acid ester
Tertiary amine
Tertiary aliphatic amine
Azacycle
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organoheterocyclic compound
Organooxygen compound
Organonitrogen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Amine
Carbonyl group
Organic nitrogen compound
Primary alcohol
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	1.8	ChemAxon
pKa (Strongest Acidic)	14.62	ChemAxon
pKa (Strongest Basic)	7.12	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	65.56 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	98.02 m³·mol⁻¹	ChemAxon
Polarizability	37.06 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

C00025979

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

101286269

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Li R, Zhao YL, Qin F, Zhao Y, Xiao XR, Cao WY, Fan MR, Wang SG, Wu Y, Wang B, Fan CZ, Guo ZN, Yang QN, Zhang WT, Li XG, Li F, Luo XD, Gao R: The clinical population pharmacokinetics, metabolomics and therapeutic analysis of alkaloids from Alstonia scholaris leaves in acute bronchitis patients. Phytomedicine. 2022 Feb 5;98:153979. doi: 10.1016/j.phymed.2022.153979. [PubMed:35176533 ]
Mitra S, Prova SR, Sultana SA, Das R, Nainu F, Emran TB, Tareq AM, Uddin MS, Alqahtani AM, Dhama K, Simal-Gandara J: Therapeutic potential of indole alkaloids in respiratory diseases: A comprehensive review. Phytomedicine. 2021 Sep;90:153649. doi: 10.1016/j.phymed.2021.153649. Epub 2021 Jul 15. [PubMed:34325978 ]
Mahar R, Manivel N, Kanojiya S, Mishra DK, Shukla SK: Assessment of Tissue Specific Distribution and Seasonal Variation of Alkaloids in Alstonia scholaris. Metabolites. 2022 Jun 30;12(7):607. doi: 10.3390/metabo12070607. [PubMed:35888731 ]
Spiegler V, Greiffer L, Jacobtorweihen J, Asase A, Lanvers-Kaminsky C, Hempel G, Agyare C, Hensel A: In vitro screening of plant extracts traditionally used as cancer remedies in Ghana - 15-Hydroxyangustilobine A as the active principle in Alstonia boonei leaves. J Ethnopharmacol. 2021 Jan 30;265:113359. doi: 10.1016/j.jep.2020.113359. Epub 2020 Sep 3. [PubMed:32891813 ]
LOTUS database [Link]

Showing NP-Card for methyl (12r,13s,14z)-14-ethylidene-12-(hydroxymethyl)-1,10-diazatetracyclo[11.2.2.0³,¹¹.0⁴,⁹]heptadeca-3(11),4,6,8-tetraene-12-carboxylate (NP0294192)

MOL for NP0294192 (methyl (12r,13s,14z)-14-ethylidene-12-(hydroxymethyl)-1,10-diazatetracyclo[11.2.2.0³,¹¹.0⁴,⁹]heptadeca-3(11),4,6,8-tetraene-12-carboxylate)

3D MOL for NP0294192 (methyl (12r,13s,14z)-14-ethylidene-12-(hydroxymethyl)-1,10-diazatetracyclo[11.2.2.0³,¹¹.0⁴,⁹]heptadeca-3(11),4,6,8-tetraene-12-carboxylate)

3D SDF for NP0294192 (methyl (12r,13s,14z)-14-ethylidene-12-(hydroxymethyl)-1,10-diazatetracyclo[11.2.2.0³,¹¹.0⁴,⁹]heptadeca-3(11),4,6,8-tetraene-12-carboxylate)

3D-SDF for NP0294192 (methyl (12r,13s,14z)-14-ethylidene-12-(hydroxymethyl)-1,10-diazatetracyclo[11.2.2.0³,¹¹.0⁴,⁹]heptadeca-3(11),4,6,8-tetraene-12-carboxylate)

PDB for NP0294192 (methyl (12r,13s,14z)-14-ethylidene-12-(hydroxymethyl)-1,10-diazatetracyclo[11.2.2.0³,¹¹.0⁴,⁹]heptadeca-3(11),4,6,8-tetraene-12-carboxylate)

3D PDB for NP0294192 (methyl (12r,13s,14z)-14-ethylidene-12-(hydroxymethyl)-1,10-diazatetracyclo[11.2.2.0³,¹¹.0⁴,⁹]heptadeca-3(11),4,6,8-tetraene-12-carboxylate)

SMILES for NP0294192 (methyl (12r,13s,14z)-14-ethylidene-12-(hydroxymethyl)-1,10-diazatetracyclo[11.2.2.0³,¹¹.0⁴,⁹]heptadeca-3(11),4,6,8-tetraene-12-carboxylate)

INCHI for NP0294192 (methyl (12r,13s,14z)-14-ethylidene-12-(hydroxymethyl)-1,10-diazatetracyclo[11.2.2.0³,¹¹.0⁴,⁹]heptadeca-3(11),4,6,8-tetraene-12-carboxylate)

Structure for NP0294192 (methyl (12r,13s,14z)-14-ethylidene-12-(hydroxymethyl)-1,10-diazatetracyclo[11.2.2.0³,¹¹.0⁴,⁹]heptadeca-3(11),4,6,8-tetraene-12-carboxylate)

3D Structure for NP0294192 (methyl (12r,13s,14z)-14-ethylidene-12-(hydroxymethyl)-1,10-diazatetracyclo[11.2.2.0³,¹¹.0⁴,⁹]heptadeca-3(11),4,6,8-tetraene-12-carboxylate)