NP-MRD: Showing NP-Card for methyl (13s,15s)-15-ethyl-1,11-diazatetracyclo[13.3.1.0⁴,¹².0⁵,¹⁰]nonadeca-4(12),5,7,9-tetraene-13-carboxylate (NP0163746)

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Record Information

Version

2.0

Created at

2022-09-02 22:28:05 UTC

Updated at

2022-09-02 22:28:05 UTC

NP-MRD ID

NP0163746

Secondary Accession Numbers

None

Natural Product Identification

Common Name

methyl (13s,15s)-15-ethyl-1,11-diazatetracyclo[13.3.1.0⁴,¹².0⁵,¹⁰]nonadeca-4(12),5,7,9-tetraene-13-carboxylate

Description

Epivincadine belongs to the class of organic compounds known as quebrachamine alkaloids. These are alkaloids with a structure based on the quebrachamine skeleton, a tetracyclic compound that is derived by fission of the 7,21 bond of the aspidospermidine skeleton. Some quebrachamine alkaloids lack the C-16 methoxycarbonyl group. methyl (13s,15s)-15-ethyl-1,11-diazatetracyclo[13.3.1.0⁴,¹².0⁵,¹⁰]nonadeca-4(12),5,7,9-tetraene-13-carboxylate is found in Amsonia tabernaemontana and Vinca minor. Based on a literature review very few articles have been published on epivincadine.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309032200282D          

 25 28  0  0  1  0            999 V2000
    1.7365    1.6320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2639    0.9558    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6131    0.2084    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7600    0.0169    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4521   -0.7699    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0107   -1.4037    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8778   -1.2916    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7080   -1.5522    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5271   -1.2917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9622   -0.5711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8188    0.2414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5472    0.6288    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.1407    0.0558    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9637    0.1134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4251   -0.5705    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0636   -1.3120    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2406   -1.3697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7792   -0.6858    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1628    0.7730    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4221    1.5562    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2301    1.7232    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8736    2.1724    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1329    2.9556    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3039    0.7374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8176   -0.5289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  3  2  1  6  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
  7  8  1  0  0  0  0
  8  9  1  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  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 10 18  1  0  0  0  0
 13 18  1  0  0  0  0
 11 19  1  0  0  0  0
 19 20  1  6  0  0  0
 20 21  2  0  0  0  0
 20 22  1  0  0  0  0
 22 23  1  0  0  0  0
 19 24  1  0  0  0  0
  3 24  1  0  0  0  0
  7 25  1  0  0  0  0
  3 25  1  0  0  0  0
M  END

     RDKit          3D

 53 56  0  0  0  0  0  0  0  0999 V2000
   -2.6721   -0.2999   -2.9564 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2295    0.1241   -1.6389 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1658    0.0917   -0.5271 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.8377    0.5261    0.7022 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6240   -0.6702    1.2731 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5397   -1.5448    1.9257 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5495   -1.7661    0.9582 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2638   -2.1376    1.3355 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6243   -1.0469    1.8784 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5470   -0.5156    0.8425 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2947    0.5198    0.0094 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3820    0.6804   -0.7713 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3358   -0.2290   -0.4632 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6058   -0.4839   -0.9566 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4005   -1.4946   -0.4606 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8700   -2.2525    0.5629 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6001   -2.0111    1.0691 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8317   -0.9881    0.5462 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0010    1.3066    0.0132 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3601    2.7290   -0.2774 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1365    3.2654   -1.2986 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1972    3.4796    0.5032 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4932    4.8337    0.1604 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9567    0.7944   -0.9776 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8126   -1.3978   -0.3768 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4088    0.6133   -3.5307 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4416   -0.8300   -3.5790 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7345   -0.8888   -2.8761 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5710    1.1803   -1.6845 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0945   -0.4885   -1.4020 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2432    0.8634    1.5401 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5788    1.3324    0.4640 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1758   -1.2045    0.5055 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3070   -0.2552    2.0344 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0429   -2.5038    2.1739 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2315   -1.0500    2.8533 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3256   -3.0229    2.0363 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2740   -2.5539    0.4366 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2067   -1.5232    2.7244 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0828   -0.2222    2.3380 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5197    1.3927   -1.5245 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9918    0.1293   -1.7598 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3962   -1.6978   -0.8442 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4214   -3.0581    1.0058 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2034   -2.6336    1.8872 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3222    1.3070    1.0644 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0026    5.2759    1.0358 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1970    4.8335   -0.6943 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5931    5.3851   -0.1594 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2791    1.6397   -1.6596 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3676    0.1392   -1.6911 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6135   -2.0476   -0.7801 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9067   -1.6243   -0.9900 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  3  2  1  6
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7 25  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 11 19  1  0
 19 24  1  0
 19 20  1  0
 20 21  2  0
 20 22  1  0
 22 23  1  0
 25  3  1  0
 18 10  1  0
 24  3  1  0
 18 13  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  2 29  1  0
  2 30  1  0
  4 31  1  0
  4 32  1  0
  5 33  1  0
  5 34  1  0
  6 35  1  0
  6 36  1  0
 25 52  1  0
 25 53  1  0
  8 37  1  0
  8 38  1  0
  9 39  1  0
  9 40  1  0
 12 41  1  0
 14 42  1  0
 15 43  1  0
 16 44  1  0
 17 45  1  0
 19 46  1  1
 24 50  1  0
 24 51  1  0
 23 47  1  0
 23 48  1  0
 23 49  1  0
M  END


  Mrv1652309032200282D          

 25 28  0  0  1  0            999 V2000
    1.7365    1.6320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2639    0.9558    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6131    0.2084    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7600    0.0169    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4521   -0.7699    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0107   -1.4037    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8778   -1.2916    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7080   -1.5522    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5271   -1.2917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9622   -0.5711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8188    0.2414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5472    0.6288    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.1407    0.0558    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9637    0.1134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4251   -0.5705    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0636   -1.3120    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2406   -1.3697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7792   -0.6858    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1628    0.7730    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4221    1.5562    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2301    1.7232    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8736    2.1724    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1329    2.9556    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3039    0.7374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8176   -0.5289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  3  2  1  6  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
  7  8  1  0  0  0  0
  8  9  1  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  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 10 18  1  0  0  0  0
 13 18  1  0  0  0  0
 11 19  1  0  0  0  0
 19 20  1  6  0  0  0
 20 21  2  0  0  0  0
 20 22  1  0  0  0  0
 22 23  1  0  0  0  0
 19 24  1  0  0  0  0
  3 24  1  0  0  0  0
  7 25  1  0  0  0  0
  3 25  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0163746

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC[C@@]12CCCN(C1)CCC1=C(NC3=CC=CC=C13)[C@H](C2)C(=O)OC

> <INCHI_IDENTIFIER>
InChI=1S/C21H28N2O2/c1-3-21-10-6-11-23(14-21)12-9-16-15-7-4-5-8-18(15)22-19(16)17(13-21)20(24)25-2/h4-5,7-8,17,22H,3,6,9-14H2,1-2H3/t17-,21-/m0/s1

> <INCHI_KEY>
JFLTVMWSBAMWAW-UWJYYQICSA-N

> <FORMULA>
C21H28N2O2

> <MOLECULAR_WEIGHT>
340.467

> <EXACT_MASS>
340.21507815

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
53

> <JCHEM_AVERAGE_POLARIZABILITY>
39.022515873396905

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl (13S,15S)-15-ethyl-1,11-diazatetracyclo[13.3.1.0^{4,12}.0^{5,10}]nonadeca-4(12),5,7,9-tetraene-13-carboxylate

> <ALOGPS_LOGP>
3.97

> <JCHEM_LOGP>
3.6783094336666666

> <ALOGPS_LOGS>
-4.24

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
15.485028492517415

> <JCHEM_PKA_STRONGEST_BASIC>
8.52530565440095

> <JCHEM_POLAR_SURFACE_AREA>
45.33

> <JCHEM_REFRACTIVITY>
100.18039999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.98e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl (13S,15S)-15-ethyl-1,11-diazatetracyclo[13.3.1.0^{4,12}.0^{5,10}]nonadeca-4(12),5,7,9-tetraene-13-carboxylate

> <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       3.241   3.046   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.359   1.784   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.011   0.389   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.419   0.032   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.844  -1.437   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.887  -2.620   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0       3.505  -2.411   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0       5.055  -2.897   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.584  -2.411   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.396  -1.066   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.128   0.451   0.000  0.00  0.00           C+0
HETATM   12  N   UNK     0       8.488   1.174   0.000  0.00  0.00           N+0
HETATM   13  C   UNK     0       9.596   0.104   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      11.132   0.212   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      11.994  -1.065   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      11.319  -2.449   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       9.782  -2.557   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       8.921  -1.280   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.904   1.443   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.388   2.905   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       7.896   3.217   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       5.364   4.055   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       5.848   5.517   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       4.301   1.377   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       3.393  -0.987   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   24   25                                             
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8   25                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   18                                                  
CONECT   11   10   12   19                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   18                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   10   13                                                  
CONECT   19   11   20   24                                                  
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23                                                       
CONECT   23   22                                                            
CONECT   24   19    3                                                       
CONECT   25    7    3                                                       
MASTER        0    0    0    0    0    0    0    0   25    0   56    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₁H₂₈N₂O₂

Average Mass

340.4670 Da

Monoisotopic Mass

340.21508 Da

IUPAC Name

methyl (13S,15S)-15-ethyl-1,11-diazatetracyclo[13.3.1.0^{4,12}.0^{5,10}]nonadeca-4(12),5,7,9-tetraene-13-carboxylate

Traditional Name

methyl (13S,15S)-15-ethyl-1,11-diazatetracyclo[13.3.1.0^{4,12}.0^{5,10}]nonadeca-4(12),5,7,9-tetraene-13-carboxylate

CAS Registry Number

Not Available

SMILES

CC[C@@]12CCCN(C1)CCC1=C(NC3=CC=CC=C13)[C@H](C2)C(=O)OC

InChI Identifier

InChI=1S/C21H28N2O2/c1-3-21-10-6-11-23(14-21)12-9-16-15-7-4-5-8-18(15)22-19(16)17(13-21)20(24)25-2/h4-5,7-8,17,22H,3,6,9-14H2,1-2H3/t17-,21-/m0/s1

InChI Key

JFLTVMWSBAMWAW-UWJYYQICSA-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
Amsonia tabernaemontana	LOTUS Database	35616633
Vinca minor	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as quebrachamine alkaloids. These are alkaloids with a structure based on the quebrachamine skeleton, a tetracyclic compound that is derived by fission of the 7,21 bond of the aspidospermidine skeleton. Some quebrachamine alkaloids lack the C-16 methoxycarbonyl group.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Quebrachamine alkaloids

Sub Class

Not Available

Direct Parent

Quebrachamine alkaloids

Alternative Parents

Substituents

Quebrachamine skeleton
3-alkylindole
Indole
Indole or derivatives
Aralkylamine
Piperidine
Benzenoid
Heteroaromatic compound
Pyrrole
Methyl ester
Carboxylic acid ester
Tertiary aliphatic amine
Tertiary amine
Amino acid or derivatives
Organoheterocyclic compound
Azacycle
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Carbonyl group
Organic nitrogen compound
Amine
Organic oxygen compound
Organonitrogen compound
Organooxygen compound
Organic oxide
Hydrocarbon derivative
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	3.97	ALOGPS
logP	3.68	ChemAxon
logS	-4.2	ALOGPS
pKa (Strongest Acidic)	15.49	ChemAxon
pKa (Strongest Basic)	8.53	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	45.33 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	100.18 m³·mol⁻¹	ChemAxon
Polarizability	39.02 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

C00024486

Chemspider ID

8490687

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10315222

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for methyl (13s,15s)-15-ethyl-1,11-diazatetracyclo[13.3.1.0⁴,¹².0⁵,¹⁰]nonadeca-4(12),5,7,9-tetraene-13-carboxylate (NP0163746)

MOL for NP0163746 (methyl (13s,15s)-15-ethyl-1,11-diazatetracyclo[13.3.1.0⁴,¹².0⁵,¹⁰]nonadeca-4(12),5,7,9-tetraene-13-carboxylate)

3D MOL for NP0163746 (methyl (13s,15s)-15-ethyl-1,11-diazatetracyclo[13.3.1.0⁴,¹².0⁵,¹⁰]nonadeca-4(12),5,7,9-tetraene-13-carboxylate)

3D SDF for NP0163746 (methyl (13s,15s)-15-ethyl-1,11-diazatetracyclo[13.3.1.0⁴,¹².0⁵,¹⁰]nonadeca-4(12),5,7,9-tetraene-13-carboxylate)

3D-SDF for NP0163746 (methyl (13s,15s)-15-ethyl-1,11-diazatetracyclo[13.3.1.0⁴,¹².0⁵,¹⁰]nonadeca-4(12),5,7,9-tetraene-13-carboxylate)

PDB for NP0163746 (methyl (13s,15s)-15-ethyl-1,11-diazatetracyclo[13.3.1.0⁴,¹².0⁵,¹⁰]nonadeca-4(12),5,7,9-tetraene-13-carboxylate)

3D PDB for NP0163746 (methyl (13s,15s)-15-ethyl-1,11-diazatetracyclo[13.3.1.0⁴,¹².0⁵,¹⁰]nonadeca-4(12),5,7,9-tetraene-13-carboxylate)

SMILES for NP0163746 (methyl (13s,15s)-15-ethyl-1,11-diazatetracyclo[13.3.1.0⁴,¹².0⁵,¹⁰]nonadeca-4(12),5,7,9-tetraene-13-carboxylate)

INCHI for NP0163746 (methyl (13s,15s)-15-ethyl-1,11-diazatetracyclo[13.3.1.0⁴,¹².0⁵,¹⁰]nonadeca-4(12),5,7,9-tetraene-13-carboxylate)

Structure for NP0163746 (methyl (13s,15s)-15-ethyl-1,11-diazatetracyclo[13.3.1.0⁴,¹².0⁵,¹⁰]nonadeca-4(12),5,7,9-tetraene-13-carboxylate)

3D Structure for NP0163746 (methyl (13s,15s)-15-ethyl-1,11-diazatetracyclo[13.3.1.0⁴,¹².0⁵,¹⁰]nonadeca-4(12),5,7,9-tetraene-13-carboxylate)