NP-MRD: Showing NP-Card for 11-methoxyburnamine (NP0040916)

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Record Information

Version

2.0

Created at

2021-06-20 22:57:18 UTC

Updated at

2021-06-30 00:15:08 UTC

NP-MRD ID

NP0040916

Secondary Accession Numbers

None

Natural Product Identification

Common Name

11-methoxyburnamine

Provided By

JEOL Database JEOL Logo

Description

11-methoxyburnamine is found in Vinca herbacea L. 11-methoxyburnamine was first documented in 2011 (Boga, M., et al.).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306212100573D          

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M  END

     RDKit          3D

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M  END


  Mrv1652306212100573D          

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    5.1250    0.0714   -2.8143 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6811   -4.0774   -3.4659 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4311   -4.2897   -3.5948 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7024   -4.2505   -1.9848 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6051   -3.2051   -1.5418 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8679   -2.4421    0.3370 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1413   -0.9519    1.6617 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8949   -0.2515   -0.6406 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7046    0.6399    0.6250 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9329    2.1760   -1.1303 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2548   -0.3973   -2.1415 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7488    0.6732   -3.1166 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0915    1.9202   -3.4993 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0242    4.7605   -4.2383 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6882    5.3019   -2.7057 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6215    4.2397   -3.8211 H   0  0  0  0  0  0  0  0  0  0  0  0
 16 17  1  0  0  0  0
 12 15  1  0  0  0  0
 15 16  2  0  0  0  0
  5  4  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22  3  1  0  0  0  0
  3  4  1  0  0  0  0
  8 18  1  0  0  0  0
  3  2  2  0  0  0  0
 16  9  1  0  0  0  0
 20 46  1  1  0  0  0
 18 17  1  6  0  0  0
 23 22  1  0  0  0  0
  9 10  2  0  0  0  0
 12 13  1  0  0  0  0
  8  9  1  0  0  0  0
 13 14  1  0  0  0  0
  8 23  1  0  0  0  0
  8  7  1  1  0  0  0
 23 26  1  6  0  0  0
 18 20  1  0  0  0  0
 23 24  1  0  0  0  0
  6 19  1  0  0  0  0
  5  6  1  0  0  0  0
 18 19  1  0  0  0  0
  6  7  1  0  0  0  0
  2  1  1  0  0  0  0
  5 20  1  0  0  0  0
 24 25  1  0  0  0  0
 10 11  1  0  0  0  0
 26 28  1  0  0  0  0
 26 27  2  0  0  0  0
 11 12  2  0  0  0  0
 28 29  1  0  0  0  0
 17 45  1  0  0  0  0
 10 39  1  0  0  0  0
 11 40  1  0  0  0  0
 15 44  1  0  0  0  0
  6 36  1  1  0  0  0
  7 37  1  0  0  0  0
  7 38  1  0  0  0  0
 21 47  1  0  0  0  0
 21 48  1  0  0  0  0
 22 49  1  6  0  0  0
  4 34  1  0  0  0  0
  4 35  1  0  0  0  0
  2 33  1  0  0  0  0
 14 41  1  0  0  0  0
 14 42  1  0  0  0  0
 14 43  1  0  0  0  0
 24 50  1  0  0  0  0
 24 51  1  0  0  0  0
  1 30  1  0  0  0  0
  1 31  1  0  0  0  0
  1 32  1  0  0  0  0
 25 52  1  0  0  0  0
 29 53  1  0  0  0  0
 29 54  1  0  0  0  0
 29 55  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0040916

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC([H])([H])[C@@]1(C(=O)OC([H])([H])[H])[C@]2([H])\C(=C(\[H])C([H])([H])[H])C([H])([H])N3[C@@]4([H])O[C@@]5(N([H])C6=C([H])C(OC([H])([H])[H])=C([H])C([H])=C6[C@@]15C4([H])[H])[C@]3([H])C2([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C22H26N2O5/c1-4-12-10-24-17-8-15(12)20(11-25,19(26)28-3)21-9-18(24)29-22(17,21)23-16-7-13(27-2)5-6-14(16)21/h4-7,15,17-18,23,25H,8-11H2,1-3H3/b12-4-/t15-,17-,18-,20-,21-,22-/m0/s1

> <INCHI_KEY>
LWALTJMIUMAZGM-ZTBZFJLTSA-N

> <FORMULA>
C22H26N2O5

> <MOLECULAR_WEIGHT>
398.459

> <EXACT_MASS>
398.184171945

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
55

> <JCHEM_AVERAGE_POLARIZABILITY>
41.35039517476677

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl (1R,9S,11S,14E,15S,17S,19R)-14-ethylidene-19-(hydroxymethyl)-5-methoxy-18-oxa-2,12-diazahexacyclo[9.6.1.1^{9,15}.0^{1,9}.0^{3,8}.0^{12,17}]nonadeca-3,5,7-triene-19-carboxylate

> <ALOGPS_LOGP>
1.94

> <JCHEM_LOGP>
1.4698428776666668

> <ALOGPS_LOGS>
-2.31

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.825358195049425

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.20570924398132

> <JCHEM_PKA_STRONGEST_BASIC>
4.676099246508954

> <JCHEM_POLAR_SURFACE_AREA>
80.26

> <JCHEM_REFRACTIVITY>
107.03739999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.96e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl (1R,9S,11S,14E,15S,17S,19R)-14-ethylidene-19-(hydroxymethyl)-5-methoxy-18-oxa-2,12-diazahexacyclo[9.6.1.1^{9,15}.0^{1,9}.0^{3,8}.0^{12,17}]nonadeca-3,5,7-triene-19-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 55 60  0  0  0  0  0  0  0  0999 V2000
   -1.6951    4.9389   -0.5833 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3692    4.1390    0.6354 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1563    2.8105    0.7473 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0144    2.2240    2.1422 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3690    0.9296    2.2300 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.0980    0.9417    2.2053 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7214    1.7068    1.0282 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2399    0.8758   -0.1867 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3354    0.1297   -0.9256 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4349    0.6238   -1.6037 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2541   -0.2897   -2.2711 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9721   -1.6693   -2.2649 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8591   -2.4273   -2.9835 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6387   -3.8321   -2.9948 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8620   -2.1543   -1.5668 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0726   -1.2512   -0.8776 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9009   -1.5577   -0.1528 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.6566   -0.3502    0.5958 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4312   -0.3923    1.8193 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7334   -0.0591    1.1727 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.7251    0.4839    0.1525 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1896    1.8137   -0.4110 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1765    1.5515   -1.1498 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0895    0.6466   -2.4107 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2608    1.0290   -3.1377 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7685    2.8589   -1.7049 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7527    3.4371   -1.2625 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0718    3.3084   -2.7931 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6322    4.4698   -3.4137 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8693    5.6171   -0.8151 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5856    5.5464   -0.3907 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9091    4.3280   -1.4610 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3512    4.7402    1.5459 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5138    2.9313    2.8164 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0291    2.1064    2.5467 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5423    1.1968    3.1715 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8154    1.6707    1.1096 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4395    2.7602    1.0288 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6620    1.6848   -1.6288 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1250    0.0714   -2.8143 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6811   -4.0774   -3.4659 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4311   -4.2897   -3.5948 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7024   -4.2505   -1.9848 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6051   -3.2051   -1.5418 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8679   -2.4421    0.3370 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1413   -0.9519    1.6617 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8949   -0.2515   -0.6406 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7046    0.6399    0.6250 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9329    2.1760   -1.1303 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2548   -0.3973   -2.1415 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7488    0.6732   -3.1166 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0915    1.9202   -3.4993 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0242    4.7605   -4.2383 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6882    5.3019   -2.7057 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6215    4.2397   -3.8211 H   0  0  0  0  0  0  0  0  0  0  0  0
 16 17  1  0
 12 15  1  0
 15 16  2  0
  5  4  1  0
 20 21  1  0
 21 22  1  0
 22  3  1  0
  3  4  1  0
  8 18  1  0
  3  2  2  0
 16  9  1  0
 20 46  1  1
 18 17  1  6
 23 22  1  0
  9 10  2  0
 12 13  1  0
  8  9  1  0
 13 14  1  0
  8 23  1  0
  8  7  1  1
 23 26  1  6
 18 20  1  0
 23 24  1  0
  6 19  1  0
  5  6  1  0
 18 19  1  0
  6  7  1  0
  2  1  1  0
  5 20  1  0
 24 25  1  0
 10 11  1  0
 26 28  1  0
 26 27  2  0
 11 12  2  0
 28 29  1  0
 17 45  1  0
 10 39  1  0
 11 40  1  0
 15 44  1  0
  6 36  1  1
  7 37  1  0
  7 38  1  0
 21 47  1  0
 21 48  1  0
 22 49  1  6
  4 34  1  0
  4 35  1  0
  2 33  1  0
 14 41  1  0
 14 42  1  0
 14 43  1  0
 24 50  1  0
 24 51  1  0
  1 30  1  0
  1 31  1  0
  1 32  1  0
 25 52  1  0
 29 53  1  0
 29 54  1  0
 29 55  1  0
M  END

HEADER    PROTEIN                                 21-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   21-JUN-21         0                                  
HETATM    1  C   UNK     0      -1.695   4.939  -0.583  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.369   4.139   0.635  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.156   2.811   0.747  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.014   2.224   2.142  0.00  0.00           C+0
HETATM    5  N   UNK     0      -0.369   0.930   2.230  0.00  0.00           N+0
HETATM    6  C   UNK     0       1.098   0.942   2.205  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.721   1.707   1.028  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.240   0.876  -0.187  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.335   0.130  -0.926  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.435   0.624  -1.604  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.254  -0.290  -2.271  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.972  -1.669  -2.265  0.00  0.00           C+0
HETATM   13  O   UNK     0       4.859  -2.427  -2.983  0.00  0.00           O+0
HETATM   14  C   UNK     0       4.639  -3.832  -2.995  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.862  -2.154  -1.567  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.073  -1.251  -0.878  0.00  0.00           C+0
HETATM   17  N   UNK     0       0.901  -1.558  -0.153  0.00  0.00           N+0
HETATM   18  C   UNK     0       0.657  -0.350   0.596  0.00  0.00           C+0
HETATM   19  O   UNK     0       1.431  -0.392   1.819  0.00  0.00           O+0
HETATM   20  C   UNK     0      -0.733  -0.059   1.173  0.00  0.00           C+0
HETATM   21  C   UNK     0      -1.725   0.484   0.153  0.00  0.00           C+0
HETATM   22  C   UNK     0      -1.190   1.814  -0.411  0.00  0.00           C+0
HETATM   23  C   UNK     0       0.177   1.552  -1.150  0.00  0.00           C+0
HETATM   24  C   UNK     0      -0.090   0.647  -2.411  0.00  0.00           C+0
HETATM   25  O   UNK     0      -1.261   1.029  -3.138  0.00  0.00           O+0
HETATM   26  C   UNK     0       0.769   2.859  -1.705  0.00  0.00           C+0
HETATM   27  O   UNK     0       1.753   3.437  -1.262  0.00  0.00           O+0
HETATM   28  O   UNK     0       0.072   3.308  -2.793  0.00  0.00           O+0
HETATM   29  C   UNK     0       0.632   4.470  -3.414  0.00  0.00           C+0
HETATM   30  H   UNK     0      -0.869   5.617  -0.815  0.00  0.00           H+0
HETATM   31  H   UNK     0      -2.586   5.546  -0.391  0.00  0.00           H+0
HETATM   32  H   UNK     0      -1.909   4.328  -1.461  0.00  0.00           H+0
HETATM   33  H   UNK     0      -1.351   4.740   1.546  0.00  0.00           H+0
HETATM   34  H   UNK     0      -0.514   2.931   2.816  0.00  0.00           H+0
HETATM   35  H   UNK     0      -2.029   2.106   2.547  0.00  0.00           H+0
HETATM   36  H   UNK     0       1.542   1.197   3.172  0.00  0.00           H+0
HETATM   37  H   UNK     0       2.815   1.671   1.110  0.00  0.00           H+0
HETATM   38  H   UNK     0       1.440   2.760   1.029  0.00  0.00           H+0
HETATM   39  H   UNK     0       3.662   1.685  -1.629  0.00  0.00           H+0
HETATM   40  H   UNK     0       5.125   0.071  -2.814  0.00  0.00           H+0
HETATM   41  H   UNK     0       3.681  -4.077  -3.466  0.00  0.00           H+0
HETATM   42  H   UNK     0       5.431  -4.290  -3.595  0.00  0.00           H+0
HETATM   43  H   UNK     0       4.702  -4.250  -1.985  0.00  0.00           H+0
HETATM   44  H   UNK     0       2.605  -3.205  -1.542  0.00  0.00           H+0
HETATM   45  H   UNK     0       0.868  -2.442   0.337  0.00  0.00           H+0
HETATM   46  H   UNK     0      -1.141  -0.952   1.662  0.00  0.00           H+0
HETATM   47  H   UNK     0      -1.895  -0.252  -0.641  0.00  0.00           H+0
HETATM   48  H   UNK     0      -2.705   0.640   0.625  0.00  0.00           H+0
HETATM   49  H   UNK     0      -1.933   2.176  -1.130  0.00  0.00           H+0
HETATM   50  H   UNK     0      -0.255  -0.397  -2.142  0.00  0.00           H+0
HETATM   51  H   UNK     0       0.749   0.673  -3.117  0.00  0.00           H+0
HETATM   52  H   UNK     0      -1.091   1.920  -3.499  0.00  0.00           H+0
HETATM   53  H   UNK     0      -0.024   4.761  -4.238  0.00  0.00           H+0
HETATM   54  H   UNK     0       0.688   5.302  -2.706  0.00  0.00           H+0
HETATM   55  H   UNK     0       1.621   4.240  -3.821  0.00  0.00           H+0
CONECT    1    2   30   31   32                                             
CONECT    2    3    1   33                                                  
CONECT    3   22    4    2                                                  
CONECT    4    5    3   34   35                                             
CONECT    5    4    6   20                                                  
CONECT    6   19    5    7   36                                             
CONECT    7    8    6   37   38                                             
CONECT    8   18    9   23    7                                             
CONECT    9   16   10    8                                                  
CONECT   10    9   11   39                                                  
CONECT   11   10   12   40                                                  
CONECT   12   15   13   11                                                  
CONECT   13   12   14                                                       
CONECT   14   13   41   42   43                                             
CONECT   15   12   16   44                                                  
CONECT   16   17   15    9                                                  
CONECT   17   16   18   45                                                  
CONECT   18    8   17   20   19                                             
CONECT   19    6   18                                                       
CONECT   20   21   46   18    5                                             
CONECT   21   20   22   47   48                                             
CONECT   22   21    3   23   49                                             
CONECT   23   22    8   26   24                                             
CONECT   24   23   25   50   51                                             
CONECT   25   24   52                                                       
CONECT   26   23   28   27                                                  
CONECT   27   26                                                            
CONECT   28   26   29                                                       
CONECT   29   28   53   54   55                                             
CONECT   30    1                                                            
CONECT   31    1                                                            
CONECT   32    1                                                            
CONECT   33    2                                                            
CONECT   34    4                                                            
CONECT   35    4                                                            
CONECT   36    6                                                            
CONECT   37    7                                                            
CONECT   38    7                                                            
CONECT   39   10                                                            
CONECT   40   11                                                            
CONECT   41   14                                                            
CONECT   42   14                                                            
CONECT   43   14                                                            
CONECT   44   15                                                            
CONECT   45   17                                                            
CONECT   46   20                                                            
CONECT   47   21                                                            
CONECT   48   21                                                            
CONECT   49   22                                                            
CONECT   50   24                                                            
CONECT   51   24                                                            
CONECT   52   25                                                            
CONECT   53   29                                                            
CONECT   54   29                                                            
CONECT   55   29                                                            
MASTER        0    0    0    0    0    0    0    0   55    0  120    0
END

RDKit          3D

55 60  0  0  0  0  0  0  0  0999 V2000
   -1.6951    4.9389   -0.5833 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3692    4.1390    0.6354 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1563    2.8105    0.7473 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0144    2.2240    2.1422 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3690    0.9296    2.2300 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.0980    0.9417    2.2053 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7214    1.7068    1.0282 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2399    0.8758   -0.1867 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3354    0.1297   -0.9256 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4349    0.6238   -1.6037 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2541   -0.2897   -2.2711 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9721   -1.6693   -2.2649 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8591   -2.4273   -2.9835 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6387   -3.8321   -2.9948 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8620   -2.1543   -1.5668 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0726   -1.2512   -0.8776 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9009   -1.5577   -0.1528 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.6566   -0.3502    0.5958 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4312   -0.3923    1.8193 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7334   -0.0591    1.1727 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.7251    0.4839    0.1525 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1896    1.8137   -0.4110 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1765    1.5515   -1.1498 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0895    0.6466   -2.4107 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2608    1.0290   -3.1377 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7685    2.8589   -1.7049 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7527    3.4371   -1.2625 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0718    3.3084   -2.7931 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6322    4.4698   -3.4137 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8693    5.6171   -0.8151 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5856    5.5464   -0.3907 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9091    4.3280   -1.4610 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3512    4.7402    1.5459 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5138    2.9313    2.8164 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0291    2.1064    2.5467 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5423    1.1968    3.1715 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8154    1.6707    1.1096 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4395    2.7602    1.0288 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6620    1.6848   -1.6288 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1250    0.0714   -2.8143 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6811   -4.0774   -3.4659 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4311   -4.2897   -3.5948 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7024   -4.2505   -1.9848 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6051   -3.2051   -1.5418 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8679   -2.4421    0.3370 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1413   -0.9519    1.6617 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8949   -0.2515   -0.6406 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7046    0.6399    0.6250 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9329    2.1760   -1.1303 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2548   -0.3973   -2.1415 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7488    0.6732   -3.1166 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0915    1.9202   -3.4993 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0242    4.7605   -4.2383 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6882    5.3019   -2.7057 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6215    4.2397   -3.8211 H   0  0  0  0  0  0  0  0  0  0  0  0
 16 17  1  0
 12 15  1  0
 15 16  2  0
  5  4  1  0
 20 21  1  0
 21 22  1  0
 22  3  1  0
  3  4  1  0
  8 18  1  0
  3  2  2  0
 16  9  1  0
 20 46  1  1
 18 17  1  6
 23 22  1  0
  9 10  2  0
 12 13  1  0
  8  9  1  0
 13 14  1  0
  8 23  1  0
  8  7  1  1
 23 26  1  6
 18 20  1  0
 23 24  1  0
  6 19  1  0
  5  6  1  0
 18 19  1  0
  6  7  1  0
  2  1  1  0
  5 20  1  0
 24 25  1  0
 10 11  1  0
 26 28  1  0
 26 27  2  0
 11 12  2  0
 28 29  1  0
 17 45  1  0
 10 39  1  0
 11 40  1  0
 15 44  1  0
  6 36  1  1
  7 37  1  0
  7 38  1  0
 21 47  1  0
 21 48  1  0
 22 49  1  6
  4 34  1  0
  4 35  1  0
  2 33  1  0
 14 41  1  0
 14 42  1  0
 14 43  1  0
 24 50  1  0
 24 51  1  0
  1 30  1  0
  1 31  1  0
  1 32  1  0
 25 52  1  0
 29 53  1  0
 29 54  1  0
 29 55  1  0
M  END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₂H₂₆N₂O₅

Average Mass

398.4590 Da

Monoisotopic Mass

398.18417 Da

IUPAC Name

methyl (1R,9S,11S,14E,15S,17S,19R)-14-ethylidene-19-(hydroxymethyl)-5-methoxy-18-oxa-2,12-diazahexacyclo[9.6.1.1^{9,15}.0^{1,9}.0^{3,8}.0^{12,17}]nonadeca-3,5,7-triene-19-carboxylate

Traditional Name

methyl (1R,9S,11S,14E,15S,17S,19R)-14-ethylidene-19-(hydroxymethyl)-5-methoxy-18-oxa-2,12-diazahexacyclo[9.6.1.1^{9,15}.0^{1,9}.0^{3,8}.0^{12,17}]nonadeca-3,5,7-triene-19-carboxylate

CAS Registry Number

Not Available

SMILES

[H]OC([H])([H])[C@@]1(C(=O)OC([H])([H])[H])[C@]2([H])\C(=C(\[H])C([H])([H])[H])C([H])([H])N3[C@@]4([H])O[C@@]5(N([H])C6=C([H])C(OC([H])([H])[H])=C([H])C([H])=C6[C@@]15C4([H])[H])[C@]3([H])C2([H])[H]

InChI Identifier

InChI=1S/C22H26N2O5/c1-4-12-10-24-17-8-15(12)20(11-25,19(26)28-3)21-9-18(24)29-22(17,21)23-16-7-13(27-2)5-6-14(16)21/h4-7,15,17-18,23,25H,8-11H2,1-3H3/b12-4-/t15-,17-,18-,20-,21-,22-/m0/s1

InChI Key

LWALTJMIUMAZGM-ZTBZFJLTSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Vinca herbacea L.	JEOL database	Boga, M., et al, Phyto. Lett. 4, 399 (2011)

Chemical Taxonomy

Classification

Not classified

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	1.94	ALOGPS
logP	1.47	ChemAxon
logS	-2.3	ALOGPS
pKa (Strongest Acidic)	11.21	ChemAxon
pKa (Strongest Basic)	4.68	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	80.26 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	107.04 m³·mol⁻¹	ChemAxon
Polarizability	41.35 Å³	ChemAxon
Number of Rings	6	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

Not Available

References

General References

Boga, M., et al. (2011). Boga, M., et al, Phyto. Lett. 4, 399 (2011). Phyto. Lett..

Showing NP-Card for 11-methoxyburnamine (NP0040916)

MOL for NP0040916 (11-methoxyburnamine)

3D MOL for NP0040916 (11-methoxyburnamine)

3D SDF for NP0040916 (11-methoxyburnamine)

3D-SDF for NP0040916 (11-methoxyburnamine)

PDB for NP0040916 (11-methoxyburnamine)

3D PDB for NP0040916 (11-methoxyburnamine)

SMILES for NP0040916 (11-methoxyburnamine)

INCHI for NP0040916 (11-methoxyburnamine)

Structure for NP0040916 (11-methoxyburnamine)

3D Structure for NP0040916 (11-methoxyburnamine)