NP-MRD: Showing NP-Card for methyl (13r,15s)-15-ethyl-11-methyl-1,11-diazatetracyclo[13.3.1.0⁴,¹².0⁵,¹⁰]nonadeca-4(12),5,7,9-tetraene-13-carboxylate (NP0176623)

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Record Information

Version

2.0

Created at

2022-09-03 14:19:09 UTC

Updated at

2022-09-03 14:19:09 UTC

NP-MRD ID

NP0176623

Secondary Accession Numbers

None

Natural Product Identification

Common Name

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

Description

Vincaminoreine 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 (13r,15s)-15-ethyl-11-methyl-1,11-diazatetracyclo[13.3.1.0⁴,¹².0⁵,¹⁰]nonadeca-4(12),5,7,9-tetraene-13-carboxylate is found in Vinca minor. methyl (13r,15s)-15-ethyl-11-methyl-1,11-diazatetracyclo[13.3.1.0⁴,¹².0⁵,¹⁰]nonadeca-4(12),5,7,9-tetraene-13-carboxylate was first documented in 2011 (PMID: 24250413). Based on a literature review very few articles have been published on Vincaminoreine.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309032216192D          

 26 29  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
    4.6619    1.4458    0.0000 C   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  2  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
 12 14  1  0  0  0  0
 14 15  2  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  2  0  0  0  0
 10 19  1  0  0  0  0
 14 19  1  0  0  0  0
 11 20  1  0  0  0  0
 20 21  1  1  0  0  0
 21 22  2  0  0  0  0
 21 23  1  0  0  0  0
 23 24  1  0  0  0  0
 20 25  1  0  0  0  0
  3 25  1  0  0  0  0
  7 26  1  0  0  0  0
  3 26  1  0  0  0  0
M  END

     RDKit          3D

 56 59  0  0  0  0  0  0  0  0999 V2000
    3.2094   -0.2158    2.6778 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4990    0.2562    1.2923 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2407    0.0542    0.3775 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6907    0.5594   -0.9197 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3591   -0.5540   -1.7601 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2465   -1.5060   -2.1454 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5994   -1.9035   -0.9588 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.2079   -2.0627   -0.9303 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6103   -0.9315   -1.4544 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5554   -0.4582   -0.4138 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3713    0.5001    0.5358 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5315    0.5658    1.2287 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8000    1.4744    2.3613 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4571   -0.2974    0.7814 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7561   -0.5787    1.1707 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4863   -1.5383    0.5139 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9084   -2.2147   -0.5349 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6156   -1.9189   -0.9050 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8509   -0.9521   -0.2590 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0626    1.2714    0.6943 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0394    2.4139   -0.1943 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4060    3.5533    0.2821 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2178    2.4634   -1.5558 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0896    3.6386   -2.3296 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0831    0.4792    1.1003 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2312   -1.4943    0.2499 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0879    0.7015    3.3246 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0967   -0.7514    3.1015 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3544   -0.8913    2.7617 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3463   -0.2855    0.8948 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7005    1.3460    1.2452 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5514    1.2994   -0.8030 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9749    0.9521   -1.6342 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1955   -1.0063   -1.2589 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6871   -0.0492   -2.6914 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6849   -2.3814   -2.6979 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5475   -0.9834   -2.8167 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0857   -2.2760    0.1410 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0280   -3.0482   -1.4349 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1871   -1.3795   -2.3368 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0421   -0.1393   -1.9376 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5984    1.0793    2.9848 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0753    2.4902    1.9811 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8697    1.5231    2.9667 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1649   -0.0243    1.9955 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5230   -1.7732    0.8133 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5007   -2.9745   -1.0473 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1922   -2.4700   -1.7341 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3281    1.8705    1.6800 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9997    4.2551   -2.1967 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7519    4.2420   -1.8917 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1771    3.4438   -3.3731 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5912   -0.4675    1.5519 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4556    0.9092    2.1108 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6539   -1.8978    1.1038 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2387   -1.9172    0.2929 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  3  2  1  1
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7 26  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 20  1  0
 20 25  1  0
 20 21  1  0
 21 22  2  0
 21 23  1  0
 23 24  1  0
 11 12  1  0
 12 13  1  0
 12 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 26  3  1  0
 19 10  1  0
 25  3  1  0
 19 14  1  0
  1 27  1  0
  1 28  1  0
  1 29  1  0
  2 30  1  0
  2 31  1  0
  4 32  1  0
  4 33  1  0
  5 34  1  0
  5 35  1  0
  6 36  1  0
  6 37  1  0
 26 55  1  0
 26 56  1  0
  8 38  1  0
  8 39  1  0
  9 40  1  0
  9 41  1  0
 20 49  1  1
 25 53  1  0
 25 54  1  0
 24 50  1  0
 24 51  1  0
 24 52  1  0
 13 42  1  0
 13 43  1  0
 13 44  1  0
 15 45  1  0
 16 46  1  0
 17 47  1  0
 18 48  1  0
M  END


  Mrv1652309032216192D          

 26 29  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
    4.6619    1.4458    0.0000 C   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  2  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
 12 14  1  0  0  0  0
 14 15  2  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  2  0  0  0  0
 10 19  1  0  0  0  0
 14 19  1  0  0  0  0
 11 20  1  0  0  0  0
 20 21  1  1  0  0  0
 21 22  2  0  0  0  0
 21 23  1  0  0  0  0
 23 24  1  0  0  0  0
 20 25  1  0  0  0  0
  3 25  1  0  0  0  0
  7 26  1  0  0  0  0
  3 26  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0176623

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC[C@@]12CCCN(C1)CCC1=C([C@@H](C2)C(=O)OC)N(C)C2=CC=CC=C12

> <INCHI_IDENTIFIER>
InChI=1S/C22H30N2O2/c1-4-22-11-7-12-24(15-22)13-10-17-16-8-5-6-9-19(16)23(2)20(17)18(14-22)21(25)26-3/h5-6,8-9,18H,4,7,10-15H2,1-3H3/t18-,22+/m1/s1

> <INCHI_KEY>
AULRJVXQWYCCSG-GCJKJVERSA-N

> <FORMULA>
C22H30N2O2

> <MOLECULAR_WEIGHT>
354.494

> <EXACT_MASS>
354.230728214

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
56

> <JCHEM_AVERAGE_POLARIZABILITY>
41.26735016976552

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <JCHEM_LOGP>
3.901985499333333

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
8.461620496822514

> <JCHEM_POLAR_SURFACE_AREA>
34.47

> <JCHEM_REFRACTIVITY>
105.0771

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

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

> <JCHEM_VEBER_RULE>
1

$$$$

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       8.702   2.699   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.596   0.104   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      11.132   0.212   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      11.994  -1.065   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      11.319  -2.449   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       9.782  -2.557   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       8.921  -1.280   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.904   1.443   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       6.388   2.905   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       7.896   3.217   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       5.364   4.055   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       5.848   5.517   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       4.301   1.377   0.000  0.00  0.00           C+0
HETATM   26  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   25   26                                             
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8   26                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   19                                                  
CONECT   11   10   12   20                                                  
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15   19                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   10   14                                                  
CONECT   20   11   21   25                                                  
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24                                                       
CONECT   24   23                                                            
CONECT   25   20    3                                                       
CONECT   26    7    3                                                       
MASTER        0    0    0    0    0    0    0    0   26    0   58    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₂H₃₀N₂O₂

Average Mass

354.4940 Da

Monoisotopic Mass

354.23073 Da

IUPAC Name

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

Traditional Name

methyl (13R,15S)-15-ethyl-11-methyl-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([C@@H](C2)C(=O)OC)N(C)C2=CC=CC=C12

InChI Identifier

InChI=1S/C22H30N2O2/c1-4-22-11-7-12-24(15-22)13-10-17-16-8-5-6-9-19(16)23(2)20(17)18(14-22)21(25)26-3/h5-6,8-9,18H,4,7,10-15H2,1-3H3/t18-,22+/m1/s1

InChI Key

AULRJVXQWYCCSG-GCJKJVERSA-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
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
N-alkylindole
Indole
Indole or derivatives
Aralkylamine
N-methylpyrrole
Piperidine
Substituted pyrrole
Benzenoid
Heteroaromatic compound
Pyrrole
Methyl ester
Tertiary aliphatic amine
Tertiary amine
Carboxylic acid ester
Amino acid or derivatives
Organoheterocyclic compound
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Azacycle
Hydrocarbon derivative
Organic oxygen compound
Organic nitrogen compound
Amine
Organic oxide
Organonitrogen compound
Organooxygen compound
Carbonyl group
Organopnictogen compound
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	3.9	ChemAxon
pKa (Strongest Basic)	8.46	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	34.47 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	105.08 m³·mol⁻¹	ChemAxon
Polarizability	41.27 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	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

12444831

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Farahanikia B, Akbarzadeh T, Jahangirzadeh A, Yassa N, Shams Ardekani MR, Mirnezami T, Hadjiakhoondi A, Khanavi M: Phytochemical Investigation of Vinca minor Cultivated in Iran. Iran J Pharm Res. 2011 Fall;10(4):777-85. [PubMed:24250413 ]
LOTUS database [Link]

Showing NP-Card for methyl (13r,15s)-15-ethyl-11-methyl-1,11-diazatetracyclo[13.3.1.0⁴,¹².0⁵,¹⁰]nonadeca-4(12),5,7,9-tetraene-13-carboxylate (NP0176623)

MOL for NP0176623 (methyl (13r,15s)-15-ethyl-11-methyl-1,11-diazatetracyclo[13.3.1.0⁴,¹².0⁵,¹⁰]nonadeca-4(12),5,7,9-tetraene-13-carboxylate)

3D MOL for NP0176623 (methyl (13r,15s)-15-ethyl-11-methyl-1,11-diazatetracyclo[13.3.1.0⁴,¹².0⁵,¹⁰]nonadeca-4(12),5,7,9-tetraene-13-carboxylate)

3D SDF for NP0176623 (methyl (13r,15s)-15-ethyl-11-methyl-1,11-diazatetracyclo[13.3.1.0⁴,¹².0⁵,¹⁰]nonadeca-4(12),5,7,9-tetraene-13-carboxylate)

3D-SDF for NP0176623 (methyl (13r,15s)-15-ethyl-11-methyl-1,11-diazatetracyclo[13.3.1.0⁴,¹².0⁵,¹⁰]nonadeca-4(12),5,7,9-tetraene-13-carboxylate)

PDB for NP0176623 (methyl (13r,15s)-15-ethyl-11-methyl-1,11-diazatetracyclo[13.3.1.0⁴,¹².0⁵,¹⁰]nonadeca-4(12),5,7,9-tetraene-13-carboxylate)

3D PDB for NP0176623 (methyl (13r,15s)-15-ethyl-11-methyl-1,11-diazatetracyclo[13.3.1.0⁴,¹².0⁵,¹⁰]nonadeca-4(12),5,7,9-tetraene-13-carboxylate)

SMILES for NP0176623 (methyl (13r,15s)-15-ethyl-11-methyl-1,11-diazatetracyclo[13.3.1.0⁴,¹².0⁵,¹⁰]nonadeca-4(12),5,7,9-tetraene-13-carboxylate)

INCHI for NP0176623 (methyl (13r,15s)-15-ethyl-11-methyl-1,11-diazatetracyclo[13.3.1.0⁴,¹².0⁵,¹⁰]nonadeca-4(12),5,7,9-tetraene-13-carboxylate)

Structure for NP0176623 (methyl (13r,15s)-15-ethyl-11-methyl-1,11-diazatetracyclo[13.3.1.0⁴,¹².0⁵,¹⁰]nonadeca-4(12),5,7,9-tetraene-13-carboxylate)

3D Structure for NP0176623 (methyl (13r,15s)-15-ethyl-11-methyl-1,11-diazatetracyclo[13.3.1.0⁴,¹².0⁵,¹⁰]nonadeca-4(12),5,7,9-tetraene-13-carboxylate)