NP-MRD: Showing NP-Card for 19(E)-11-methoxy-9,18-didemethoxygardneramine (NP0035908)

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Record Information

Version

2.0

Created at

2021-06-20 19:13:26 UTC

Updated at

2021-06-30 00:07:15 UTC

NP-MRD ID

NP0035908

Secondary Accession Numbers

None

Natural Product Identification

Common Name

19(E)-11-methoxy-9,18-didemethoxygardneramine

Provided By

JEOL Database JEOL Logo

Description

CHEBI:67512 Belongs to the class of organic compounds known as 3-alkylindoles. 3-Alkylindoles are compounds containing an indole moiety that carries an alkyl chain at the 3-position. 19(E)-11-methoxy-9,18-didemethoxygardneramine is found in Gardneria ovata. 19(E)-11-methoxy-9,18-didemethoxygardneramine was first documented in 2011 (Li, X. -N., et al.). Based on a literature review very few articles have been published on CHEBI:67512.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306202121133D          

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     RDKit          3D

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  Mrv1652306202121133D          

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    2.0945   -6.7024    0.3524 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8863   -5.4702   -0.0311 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5560   -4.0995    0.5438 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2251   -2.5347   -0.0326 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6228   -4.0438   -0.8682 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6347    0.9506   -2.1273 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3938    0.9907   -2.2098 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6358    1.2701   -0.6455 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3645    2.1843    3.1319 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5791    3.2236    2.0947 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0882    1.7102    3.0957 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5076    2.2670    0.6468 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2771    0.1399   -0.8718 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8356    1.0849   -0.6592 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9036   -1.6058   -0.1721 H   0  0  0  0  0  0  0  0  0  0  0  0
 28 27  1  0  0  0  0
  9 23  1  0  0  0  0
 12 11  2  0  0  0  0
 11 10  1  0  0  0  0
 10  9  2  0  0  0  0
  8 12  1  6  0  0  0
 28  5  1  0  0  0  0
 26 27  1  0  0  0  0
 26  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  6  7  1  0  0  0  0
  3  2  2  0  0  0  0
  8  7  1  0  0  0  0
  2  1  1  0  0  0  0
  8 28  1  0  0  0  0
 14 17  1  0  0  0  0
 26 25  1  0  0  0  0
  6 25  1  0  0  0  0
 25 24  1  0  0  0  0
 23 24  1  0  0  0  0
 14 15  1  0  0  0  0
 17 20  2  0  0  0  0
 20 21  1  0  0  0  0
 20 11  1  0  0  0  0
 21 22  1  0  0  0  0
  9  8  1  0  0  0  0
 15 16  1  0  0  0  0
 12 13  1  0  0  0  0
 17 18  1  0  0  0  0
 13 14  2  0  0  0  0
 18 19  1  0  0  0  0
  6  5  1  0  0  0  0
  7 36  1  0  0  0  0
  7 37  1  0  0  0  0
  6 35  1  1  0  0  0
 24 48  1  0  0  0  0
 24 49  1  0  0  0  0
 13 38  1  0  0  0  0
 28 54  1  6  0  0  0
 27 52  1  0  0  0  0
 27 53  1  0  0  0  0
 26 51  1  6  0  0  0
  4 33  1  0  0  0  0
  4 34  1  0  0  0  0
  2 32  1  0  0  0  0
  1 29  1  0  0  0  0
  1 30  1  0  0  0  0
  1 31  1  0  0  0  0
 25 50  1  1  0  0  0
 22 45  1  0  0  0  0
 22 46  1  0  0  0  0
 22 47  1  0  0  0  0
 16 39  1  0  0  0  0
 16 40  1  0  0  0  0
 16 41  1  0  0  0  0
 19 42  1  0  0  0  0
 19 43  1  0  0  0  0
 19 44  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0035908

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]\C(=C1/C([H])([H])N2[C@@]3([H])C([H])([H])[C@]45C(OC([H])([H])[C@@]3([H])[C@@]1([H])C([H])([H])[C@]24[H])=NC1=C5C([H])=C(OC([H])([H])[H])C(OC([H])([H])[H])=C1OC([H])([H])[H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C22H26N2O4/c1-5-11-9-24-15-8-22-14-7-16(25-2)19(26-3)20(27-4)18(14)23-21(22)28-10-13(15)12(11)6-17(22)24/h5,7,12-13,15,17H,6,8-10H2,1-4H3/b11-5-/t12-,13-,15-,17-,22+/m0/s1

> <INCHI_KEY>
KQEBWWUZXARNSU-GQGWNBIDSA-N

> <FORMULA>
C22H26N2O4

> <MOLECULAR_WEIGHT>
382.46

> <EXACT_MASS>
382.189257325

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
54

> <JCHEM_AVERAGE_POLARIZABILITY>
42.02856195965491

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,12S,13S,16E,17R,19S)-16-ethylidene-4,5,6-trimethoxy-10-oxa-8,14-diazahexacyclo[11.6.1.0^{1,9}.0^{2,7}.0^{12,17}.0^{14,19}]icosa-2(7),3,5,8-tetraene

> <ALOGPS_LOGP>
2.66

> <JCHEM_LOGP>
2.246493755

> <ALOGPS_LOGS>
-3.73

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
8.745513198091954

> <JCHEM_POLAR_SURFACE_AREA>
52.52000000000001

> <JCHEM_REFRACTIVITY>
107.51139999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.06e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,12S,13S,16E,17R,19S)-16-ethylidene-4,5,6-trimethoxy-10-oxa-8,14-diazahexacyclo[11.6.1.0^{1,9}.0^{2,7}.0^{12,17}.0^{14,19}]icosa-2(7),3,5,8-tetraene

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 54 59  0  0  0  0  0  0  0  0999 V2000
   -5.2795    2.2670    1.1324 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7811    0.8775    1.3664 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5102    0.4401    1.3112 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1384   -0.9979    1.5968 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6823   -1.1479    1.7608 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1415   -0.1929    2.7597 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3248   -0.5887    2.6571 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5146   -0.5256    1.1477 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1701    0.7899    0.7640 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2609    0.6927    0.0658 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5412   -0.6864   -0.0480 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5612   -1.4576    0.6012 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6162   -2.8443    0.6561 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6920   -3.4866    0.0443 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8756   -4.8459    0.0208 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8177   -5.6562    0.5142 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6909   -2.7113   -0.5946 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7263   -3.3685   -1.2317 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8290   -3.5092   -0.3378 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6237   -1.3026   -0.6689 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6520   -0.6933   -1.3373 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5481    0.7027   -1.5770 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6723    1.9826    1.0960 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2228    2.1925    2.2069 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4490    1.2786    2.3105 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.2741    1.2577    0.9938 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.5517    0.4658   -0.1123 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8995   -0.7713    0.5387 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.9486    2.2785    0.2666 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8470    2.6041    2.0056 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4833    2.9927    0.9561 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5620    0.1574    1.6111 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4769   -1.6448    0.7784 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6364   -1.3438    2.5107 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5287   -0.3916    3.7653 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9945    0.0638    3.2257 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4721   -1.6048    3.0482 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8265   -3.3850    1.1649 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6820   -5.5113    1.5909 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0945   -6.7024    0.3524 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8863   -5.4702   -0.0311 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5560   -4.0995    0.5438 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2251   -2.5347   -0.0326 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6228   -4.0438   -0.8682 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6347    0.9506   -2.1273 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3938    0.9907   -2.2098 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6358    1.2701   -0.6455 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3645    2.1843    3.1319 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5791    3.2236    2.0947 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0882    1.7102    3.0957 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5076    2.2670    0.6468 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2771    0.1399   -0.8718 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8356    1.0849   -0.6592 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9036   -1.6058   -0.1721 H   0  0  0  0  0  0  0  0  0  0  0  0
 28 27  1  0
  9 23  1  0
 12 11  2  0
 11 10  1  0
 10  9  2  0
  8 12  1  6
 28  5  1  0
 26 27  1  0
 26  3  1  0
  3  4  1  0
  4  5  1  0
  6  7  1  0
  3  2  2  0
  8  7  1  0
  2  1  1  0
  8 28  1  0
 14 17  1  0
 26 25  1  0
  6 25  1  0
 25 24  1  0
 23 24  1  0
 14 15  1  0
 17 20  2  0
 20 21  1  0
 20 11  1  0
 21 22  1  0
  9  8  1  0
 15 16  1  0
 12 13  1  0
 17 18  1  0
 13 14  2  0
 18 19  1  0
  6  5  1  0
  7 36  1  0
  7 37  1  0
  6 35  1  1
 24 48  1  0
 24 49  1  0
 13 38  1  0
 28 54  1  6
 27 52  1  0
 27 53  1  0
 26 51  1  6
  4 33  1  0
  4 34  1  0
  2 32  1  0
  1 29  1  0
  1 30  1  0
  1 31  1  0
 25 50  1  1
 22 45  1  0
 22 46  1  0
 22 47  1  0
 16 39  1  0
 16 40  1  0
 16 41  1  0
 19 42  1  0
 19 43  1  0
 19 44  1  0
M  END

HEADER    PROTEIN                                 20-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-JUN-21         0                                  
HETATM    1  C   UNK     0      -5.279   2.267   1.132  0.00  0.00           C+0
HETATM    2  C   UNK     0      -4.781   0.878   1.366  0.00  0.00           C+0
HETATM    3  C   UNK     0      -3.510   0.440   1.311  0.00  0.00           C+0
HETATM    4  C   UNK     0      -3.138  -0.998   1.597  0.00  0.00           C+0
HETATM    5  N   UNK     0      -1.682  -1.148   1.761  0.00  0.00           N+0
HETATM    6  C   UNK     0      -1.141  -0.193   2.760  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.325  -0.589   2.657  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.515  -0.526   1.148  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.170   0.790   0.764  0.00  0.00           C+0
HETATM   10  N   UNK     0       2.261   0.693   0.066  0.00  0.00           N+0
HETATM   11  C   UNK     0       2.541  -0.686  -0.048  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.561  -1.458   0.601  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.616  -2.844   0.656  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.692  -3.487   0.044  0.00  0.00           C+0
HETATM   15  O   UNK     0       2.876  -4.846   0.021  0.00  0.00           O+0
HETATM   16  C   UNK     0       1.818  -5.656   0.514  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.691  -2.711  -0.595  0.00  0.00           C+0
HETATM   18  O   UNK     0       4.726  -3.369  -1.232  0.00  0.00           O+0
HETATM   19  C   UNK     0       5.829  -3.509  -0.338  0.00  0.00           C+0
HETATM   20  C   UNK     0       3.624  -1.303  -0.669  0.00  0.00           C+0
HETATM   21  O   UNK     0       4.652  -0.693  -1.337  0.00  0.00           O+0
HETATM   22  C   UNK     0       4.548   0.703  -1.577  0.00  0.00           C+0
HETATM   23  O   UNK     0       0.672   1.983   1.096  0.00  0.00           O+0
HETATM   24  C   UNK     0      -0.223   2.192   2.207  0.00  0.00           C+0
HETATM   25  C   UNK     0      -1.449   1.279   2.311  0.00  0.00           C+0
HETATM   26  C   UNK     0      -2.274   1.258   0.994  0.00  0.00           C+0
HETATM   27  C   UNK     0      -1.552   0.466  -0.112  0.00  0.00           C+0
HETATM   28  C   UNK     0      -0.900  -0.771   0.539  0.00  0.00           C+0
HETATM   29  H   UNK     0      -5.949   2.279   0.267  0.00  0.00           H+0
HETATM   30  H   UNK     0      -5.847   2.604   2.006  0.00  0.00           H+0
HETATM   31  H   UNK     0      -4.483   2.993   0.956  0.00  0.00           H+0
HETATM   32  H   UNK     0      -5.562   0.157   1.611  0.00  0.00           H+0
HETATM   33  H   UNK     0      -3.477  -1.645   0.778  0.00  0.00           H+0
HETATM   34  H   UNK     0      -3.636  -1.344   2.511  0.00  0.00           H+0
HETATM   35  H   UNK     0      -1.529  -0.392   3.765  0.00  0.00           H+0
HETATM   36  H   UNK     0       0.995   0.064   3.226  0.00  0.00           H+0
HETATM   37  H   UNK     0       0.472  -1.605   3.048  0.00  0.00           H+0
HETATM   38  H   UNK     0       0.827  -3.385   1.165  0.00  0.00           H+0
HETATM   39  H   UNK     0       1.682  -5.511   1.591  0.00  0.00           H+0
HETATM   40  H   UNK     0       2.095  -6.702   0.352  0.00  0.00           H+0
HETATM   41  H   UNK     0       0.886  -5.470  -0.031  0.00  0.00           H+0
HETATM   42  H   UNK     0       5.556  -4.099   0.544  0.00  0.00           H+0
HETATM   43  H   UNK     0       6.225  -2.535  -0.033  0.00  0.00           H+0
HETATM   44  H   UNK     0       6.623  -4.044  -0.868  0.00  0.00           H+0
HETATM   45  H   UNK     0       3.635   0.951  -2.127  0.00  0.00           H+0
HETATM   46  H   UNK     0       5.394   0.991  -2.210  0.00  0.00           H+0
HETATM   47  H   UNK     0       4.636   1.270  -0.646  0.00  0.00           H+0
HETATM   48  H   UNK     0       0.365   2.184   3.132  0.00  0.00           H+0
HETATM   49  H   UNK     0      -0.579   3.224   2.095  0.00  0.00           H+0
HETATM   50  H   UNK     0      -2.088   1.710   3.096  0.00  0.00           H+0
HETATM   51  H   UNK     0      -2.508   2.267   0.647  0.00  0.00           H+0
HETATM   52  H   UNK     0      -2.277   0.140  -0.872  0.00  0.00           H+0
HETATM   53  H   UNK     0      -0.836   1.085  -0.659  0.00  0.00           H+0
HETATM   54  H   UNK     0      -0.904  -1.606  -0.172  0.00  0.00           H+0
CONECT    1    2   29   30   31                                             
CONECT    2    3    1   32                                                  
CONECT    3   26    4    2                                                  
CONECT    4    3    5   33   34                                             
CONECT    5   28    4    6                                                  
CONECT    6    7   25    5   35                                             
CONECT    7    6    8   36   37                                             
CONECT    8   12    7   28    9                                             
CONECT    9   23   10    8                                                  
CONECT   10   11    9                                                       
CONECT   11   12   10   20                                                  
CONECT   12   11    8   13                                                  
CONECT   13   12   14   38                                                  
CONECT   14   17   15   13                                                  
CONECT   15   14   16                                                       
CONECT   16   15   39   40   41                                             
CONECT   17   14   20   18                                                  
CONECT   18   17   19                                                       
CONECT   19   18   42   43   44                                             
CONECT   20   17   21   11                                                  
CONECT   21   20   22                                                       
CONECT   22   21   45   46   47                                             
CONECT   23    9   24                                                       
CONECT   24   25   23   48   49                                             
CONECT   25   26    6   24   50                                             
CONECT   26   27    3   25   51                                             
CONECT   27   28   26   52   53                                             
CONECT   28   27    5    8   54                                             
CONECT   29    1                                                            
CONECT   30    1                                                            
CONECT   31    1                                                            
CONECT   32    2                                                            
CONECT   33    4                                                            
CONECT   34    4                                                            
CONECT   35    6                                                            
CONECT   36    7                                                            
CONECT   37    7                                                            
CONECT   38   13                                                            
CONECT   39   16                                                            
CONECT   40   16                                                            
CONECT   41   16                                                            
CONECT   42   19                                                            
CONECT   43   19                                                            
CONECT   44   19                                                            
CONECT   45   22                                                            
CONECT   46   22                                                            
CONECT   47   22                                                            
CONECT   48   24                                                            
CONECT   49   24                                                            
CONECT   50   25                                                            
CONECT   51   26                                                            
CONECT   52   27                                                            
CONECT   53   27                                                            
CONECT   54   28                                                            
MASTER        0    0    0    0    0    0    0    0   54    0  118    0
END

RDKit          3D

54 59  0  0  0  0  0  0  0  0999 V2000
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   -4.7811    0.8775    1.3664 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5102    0.4401    1.3112 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1384   -0.9979    1.5968 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6823   -1.1479    1.7608 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1415   -0.1929    2.7597 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3248   -0.5887    2.6571 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5146   -0.5256    1.1477 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1701    0.7899    0.7640 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2609    0.6927    0.0658 N   0  0  0  0  0  0  0  0  0  0  0  0
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    1.5612   -1.4576    0.6012 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6162   -2.8443    0.6561 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6920   -3.4866    0.0443 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8756   -4.8459    0.0208 O   0  0  0  0  0  0  0  0  0  0  0  0
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    3.6909   -2.7113   -0.5946 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7263   -3.3685   -1.2317 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8290   -3.5092   -0.3378 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6237   -1.3026   -0.6689 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6520   -0.6933   -1.3373 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5481    0.7027   -1.5770 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6723    1.9826    1.0960 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2228    2.1925    2.2069 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4490    1.2786    2.3105 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.2741    1.2577    0.9938 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.5517    0.4658   -0.1123 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8995   -0.7713    0.5387 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.9486    2.2785    0.2666 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8470    2.6041    2.0056 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4833    2.9927    0.9561 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5620    0.1574    1.6111 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4769   -1.6448    0.7784 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6364   -1.3438    2.5107 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5287   -0.3916    3.7653 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9945    0.0638    3.2257 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4721   -1.6048    3.0482 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8265   -3.3850    1.1649 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6820   -5.5113    1.5909 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0945   -6.7024    0.3524 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8863   -5.4702   -0.0311 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5560   -4.0995    0.5438 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2251   -2.5347   -0.0326 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6228   -4.0438   -0.8682 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6347    0.9506   -2.1273 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3938    0.9907   -2.2098 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6358    1.2701   -0.6455 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3645    2.1843    3.1319 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5791    3.2236    2.0947 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0882    1.7102    3.0957 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5076    2.2670    0.6468 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2771    0.1399   -0.8718 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8356    1.0849   -0.6592 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9036   -1.6058   -0.1721 H   0  0  0  0  0  0  0  0  0  0  0  0
 28 27  1  0
  9 23  1  0
 12 11  2  0
 11 10  1  0
 10  9  2  0
  8 12  1  6
 28  5  1  0
 26 27  1  0
 26  3  1  0
  3  4  1  0
  4  5  1  0
  6  7  1  0
  3  2  2  0
  8  7  1  0
  2  1  1  0
  8 28  1  0
 14 17  1  0
 26 25  1  0
  6 25  1  0
 25 24  1  0
 23 24  1  0
 14 15  1  0
 17 20  2  0
 20 21  1  0
 20 11  1  0
 21 22  1  0
  9  8  1  0
 15 16  1  0
 12 13  1  0
 17 18  1  0
 13 14  2  0
 18 19  1  0
  6  5  1  0
  7 36  1  0
  7 37  1  0
  6 35  1  1
 24 48  1  0
 24 49  1  0
 13 38  1  0
 28 54  1  6
 27 52  1  0
 27 53  1  0
 26 51  1  6
  4 33  1  0
  4 34  1  0
  2 32  1  0
  1 29  1  0
  1 30  1  0
  1 31  1  0
 25 50  1  1
 22 45  1  0
 22 46  1  0
 22 47  1  0
 16 39  1  0
 16 40  1  0
 16 41  1  0
 19 42  1  0
 19 43  1  0
 19 44  1  0
M  END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₂H₂₆N₂O₄

Average Mass

382.4600 Da

Monoisotopic Mass

382.18926 Da

IUPAC Name

(1R,12S,13S,16E,17R,19S)-16-ethylidene-4,5,6-trimethoxy-10-oxa-8,14-diazahexacyclo[11.6.1.0^{1,9}.0^{2,7}.0^{12,17}.0^{14,19}]icosa-2(7),3,5,8-tetraene

Traditional Name

(1R,12S,13S,16E,17R,19S)-16-ethylidene-4,5,6-trimethoxy-10-oxa-8,14-diazahexacyclo[11.6.1.0^{1,9}.0^{2,7}.0^{12,17}.0^{14,19}]icosa-2(7),3,5,8-tetraene

CAS Registry Number

Not Available

SMILES

[H]\C(=C1/C([H])([H])N2[C@@]3([H])C([H])([H])[C@]45C(OC([H])([H])[C@@]3([H])[C@@]1([H])C([H])([H])[C@]24[H])=NC1=C5C([H])=C(OC([H])([H])[H])C(OC([H])([H])[H])=C1OC([H])([H])[H])C([H])([H])[H]

InChI Identifier

InChI=1S/C22H26N2O4/c1-5-11-9-24-15-8-22-14-7-16(25-2)19(26-3)20(27-4)18(14)23-21(22)28-10-13(15)12(11)6-17(22)24/h5,7,12-13,15,17H,6,8-10H2,1-4H3/b11-5-/t12-,13-,15-,17-,22+/m0/s1

InChI Key

KQEBWWUZXARNSU-GQGWNBIDSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, CD₃OD, 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
Gardneria ovata	JEOL database	Li, X. -N., et al, J. Nat. Prod. 74, 1073 (2011)

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 3-alkylindoles. 3-Alkylindoles are compounds containing an indole moiety that carries an alkyl chain at the 3-position.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Indoles and derivatives

Sub Class

Indoles

Direct Parent

3-alkylindoles

Alternative Parents

Substituents

3-alkylindole
Indolizidine
Anisole
Quinuclidine
Alkyl aryl ether
Oxepane
Aralkylamine
Piperidine
N-alkylpyrrolidine
Benzenoid
Pyrrolidine
Tertiary amine
Tertiary aliphatic amine
Organic 1,3-dipolar compound
Azacycle
Oxacycle
Ether
Propargyl-type 1,3-dipolar organic compound
Organic nitrogen compound
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Organopnictogen compound
Organic oxygen compound
Amine
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

tropane alkaloid (CHEBI:67512 )

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	2.66	ALOGPS
logP	2.25	ChemAxon
logS	-3.7	ALOGPS
pKa (Strongest Basic)	8.75	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	52.52 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	107.51 m³·mol⁻¹	ChemAxon
Polarizability	42.03 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

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

26399065

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

54582101

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Li, X. -N., et al. (2011). Li, X. -N., et al, J. Nat. Prod. 74, 1073 (2011). J. Nat. Prod..

Showing NP-Card for 19(E)-11-methoxy-9,18-didemethoxygardneramine (NP0035908)

MOL for NP0035908 (19(E)-11-methoxy-9,18-didemethoxygardneramine)

3D MOL for NP0035908 (19(E)-11-methoxy-9,18-didemethoxygardneramine)

3D SDF for NP0035908 (19(E)-11-methoxy-9,18-didemethoxygardneramine)

3D-SDF for NP0035908 (19(E)-11-methoxy-9,18-didemethoxygardneramine)

PDB for NP0035908 (19(E)-11-methoxy-9,18-didemethoxygardneramine)

3D PDB for NP0035908 (19(E)-11-methoxy-9,18-didemethoxygardneramine)

SMILES for NP0035908 (19(E)-11-methoxy-9,18-didemethoxygardneramine)

INCHI for NP0035908 (19(E)-11-methoxy-9,18-didemethoxygardneramine)

Structure for NP0035908 (19(E)-11-methoxy-9,18-didemethoxygardneramine)

3D Structure for NP0035908 (19(E)-11-methoxy-9,18-didemethoxygardneramine)