NP-MRD: Showing NP-Card for 12-methoxyicajine (NP0041593)

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Record Information

Version

2.0

Created at

2021-06-20 23:28:07 UTC

Updated at

2021-06-30 00:16:12 UTC

NP-MRD ID

NP0041593

Secondary Accession Numbers

None

Natural Product Identification

Common Name

12-methoxyicajine

Provided By

JEOL Database JEOL Logo

Description

Vomicine methyl ether belongs to the class of organic compounds known as carbazoles. Carbazoles are compounds containing a three ring system containing a pyrrole ring fused on either side to a benzene ring. 12-methoxyicajine is found in Strychnos icaja. 12-methoxyicajine was first documented in 2012 (Tchinda, A. T., et al.). Based on a literature review very few articles have been published on Vomicine methyl ether.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306212101283D          

 55 60  0  0  0  0            999 V2000
   -4.2011   -0.8568   -3.7675 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8288   -1.1330   -4.0504 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0216   -0.1630   -3.5303 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9652    1.0786   -4.1764 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0615    2.0600   -3.7575 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1822    1.7996   -2.7087 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2213    0.5539   -2.0821 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1551   -0.4143   -2.4699 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9740   -1.5698   -1.6962 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7012   -2.7418   -1.7117 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8934   -2.8458   -1.9903 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8720   -3.9983   -1.4698 C   0  0  1  0  0  0  0  0  0  0  0  0
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    2.3698   -2.0787    1.2651 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9786   -0.8727    1.9659 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4547    0.3897    1.4549 N   0  0  2  0  0  0  0  0  0  0  0  0
    3.1970    1.5309    1.9887 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0125    0.5538    1.6219 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3954    0.9947    0.2886 C   0  0  1  0  0  0  0  0  0  0  0  0
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    2.1655    0.1320   -1.3244 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6539    1.1298   -1.8714 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0864   -1.0476   -1.0322 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4493   -2.2177   -0.2609 C   0  0  2  0  0  0  0  0  0  0  0  0
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  6  5  2  0  0  0  0
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M  END

     RDKit          3D

 55 60  0  0  0  0  0  0  0  0999 V2000
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   -2.8288   -1.1330   -4.0504 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.9740   -1.5698   -1.6962 N   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


  Mrv1652306212101283D          

 55 60  0  0  0  0            999 V2000
   -4.2011   -0.8568   -3.7675 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8288   -1.1330   -4.0504 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0216   -0.1630   -3.5303 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9652    1.0786   -4.1764 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0615    2.0600   -3.7575 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.6064    1.2752   -5.0315 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.5245   -4.7418   -0.9963 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6097   -4.3692   -2.4691 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0733   -4.6746   -0.9218 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8675   -4.9669    1.0915 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7366   -4.8100    2.4302 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7808   -2.9007    3.1172 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0636   -0.9224    1.8049 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8298   -0.9237    3.0528 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8485    2.4659    1.5361 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0955    1.6128    3.0767 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2622    1.4459    1.7465 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5166   -0.3609    1.9629 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7774    1.2984    2.3940 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6891    1.0862    0.4429 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7492    2.0119    0.0678 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4076   -1.4190   -2.0154 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9914   -0.6818   -0.5362 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1179   -3.0747   -0.4330 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3468   -2.5607   -2.0596 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3231   -1.4748    0.2431 H   0  0  0  0  0  0  0  0  0  0  0  0
 13 14  1  0  0  0  0
 27 26  1  0  0  0  0
 13 12  1  0  0  0  0
 26 24  1  0  0  0  0
 12 10  1  0  0  0  0
  9 10  1  0  0  0  0
  8  9  1  0  0  0  0
 10 11  2  0  0  0  0
 23 22  1  0  0  0  0
  8  7  2  0  0  0  0
 29 55  1  1  0  0  0
  9 29  1  0  0  0  0
 22 21  1  0  0  0  0
  7  6  1  0  0  0  0
 27 17  1  0  0  0  0
 23  7  1  0  0  0  0
 17 18  1  0  0  0  0
  6  5  2  0  0  0  0
 18 19  1  0  0  0  0
 21 19  1  0  0  0  0
 23 29  1  0  0  0  0
 19 20  1  0  0  0  0
  5  4  1  0  0  0  0
 17 16  2  0  0  0  0
 23 24  1  6  0  0  0
 16 15  1  0  0  0  0
 15 14  1  0  0  0  0
  4  3  2  0  0  0  0
 27 53  1  1  0  0  0
  3  8  1  0  0  0  0
 28 54  1  6  0  0  0
 29 28  1  0  0  0  0
  3  2  1  0  0  0  0
 28 13  1  0  0  0  0
 24 25  2  0  0  0  0
 28 27  1  0  0  0  0
  2  1  1  0  0  0  0
 26 51  1  0  0  0  0
 26 52  1  0  0  0  0
  6 35  1  0  0  0  0
  5 34  1  0  0  0  0
  4 33  1  0  0  0  0
 13 38  1  6  0  0  0
 12 36  1  0  0  0  0
 12 37  1  0  0  0  0
 22 49  1  0  0  0  0
 22 50  1  0  0  0  0
 21 47  1  0  0  0  0
 21 48  1  0  0  0  0
 18 42  1  0  0  0  0
 18 43  1  0  0  0  0
 20 44  1  0  0  0  0
 20 45  1  0  0  0  0
 20 46  1  0  0  0  0
 16 41  1  0  0  0  0
 15 39  1  0  0  0  0
 15 40  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
M  END
> <DATABASE_ID>
NP0041593

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]C1=C([H])C2=C(N3C(=O)C([H])([H])[C@]4([H])OC([H])([H])C([H])=C5C([H])([H])N(C([H])([H])[H])C([H])([H])C([H])([H])[C@]22C(=O)C([H])([H])[C@]5([H])[C@]4([H])[C@]32[H])C(OC([H])([H])[H])=C1[H]

> <INCHI_IDENTIFIER>
InChI=1S/C23H26N2O4/c1-24-8-7-23-15-4-3-5-16(28-2)21(15)25-19(27)11-17-20(22(23)25)14(10-18(23)26)13(12-24)6-9-29-17/h3-6,14,17,20,22H,7-12H2,1-2H3/t14-,17-,20-,22-,23+/m0/s1

> <INCHI_KEY>
ZKALYGURBPIPGN-PFXBBCFLSA-N

> <FORMULA>
C23H26N2O4

> <MOLECULAR_WEIGHT>
394.471

> <EXACT_MASS>
394.189257325

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
55

> <JCHEM_AVERAGE_POLARIZABILITY>
41.7976680241557

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,10S,11R,12S,22R)-15-methoxy-4-methyl-9-oxa-4,13-diazahexacyclo[9.8.3.2^{10,13}.0^{1,12}.0^{6,22}.0^{14,19}]tetracosa-6,14(19),15,17-tetraene-20,23-dione

> <ALOGPS_LOGP>
1.39

> <JCHEM_LOGP>
0.8138007069999996

> <ALOGPS_LOGS>
-2.56

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
18.923123339019106

> <JCHEM_PKA_STRONGEST_ACIDIC>
17.179246455941424

> <JCHEM_PKA_STRONGEST_BASIC>
8.342781628343564

> <JCHEM_POLAR_SURFACE_AREA>
59.08

> <JCHEM_REFRACTIVITY>
108.40989999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.09e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,10S,11R,12S,22R)-15-methoxy-4-methyl-9-oxa-4,13-diazahexacyclo[9.8.3.2^{10,13}.0^{1,12}.0^{6,22}.0^{14,19}]tetracosa-6,14(19),15,17-tetraene-20,23-dione

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 55 60  0  0  0  0  0  0  0  0999 V2000
   -4.2011   -0.8568   -3.7675 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8288   -1.1330   -4.0504 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0216   -0.1630   -3.5303 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9652    1.0786   -4.1764 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0615    2.0600   -3.7575 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1822    1.7996   -2.7087 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2213    0.5539   -2.0821 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1551   -0.4143   -2.4699 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9740   -1.5698   -1.6962 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7012   -2.7418   -1.7117 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8934   -2.8458   -1.9903 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8720   -3.9983   -1.4698 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4178   -3.8346   -0.6562 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0606   -3.9570    0.7193 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1523   -4.2841    1.5639 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7984   -3.0287    2.0359 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3698   -2.0787    1.2651 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9786   -0.8727    1.9659 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4547    0.3897    1.4549 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1970    1.5309    1.9887 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0125    0.5538    1.6219 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3954    0.9947    0.2886 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6728    0.0732   -0.9355 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1655    0.1320   -1.3244 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6539    1.1298   -1.8714 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0864   -1.0476   -1.0322 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4493   -2.2177   -0.2609 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1211   -2.5082   -0.9817 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1303   -1.3724   -0.7509 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.3558   -0.5848   -2.7168 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5791   -0.0652   -4.4228 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7756   -1.7652   -3.9724 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6064    1.2752   -5.0315 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0247    3.0178   -4.2707 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5394    2.5551   -2.4070 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5245   -4.7418   -0.9963 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6097   -4.3692   -2.4691 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0733   -4.6746   -0.9218 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8675   -4.9669    1.0915 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7366   -4.8100    2.4302 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7808   -2.9007    3.1172 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0636   -0.9224    1.8049 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8298   -0.9237    3.0528 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8485    2.4659    1.5361 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0955    1.6128    3.0767 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2622    1.4459    1.7465 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5166   -0.3609    1.9629 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7774    1.2984    2.3940 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6891    1.0862    0.4429 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7492    2.0119    0.0678 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4076   -1.4190   -2.0154 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9914   -0.6818   -0.5362 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1179   -3.0747   -0.4330 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3468   -2.5607   -2.0596 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3231   -1.4748    0.2431 H   0  0  0  0  0  0  0  0  0  0  0  0
 13 14  1  0
 27 26  1  0
 13 12  1  0
 26 24  1  0
 12 10  1  0
  9 10  1  0
  8  9  1  0
 10 11  2  0
 23 22  1  0
  8  7  2  0
 29 55  1  1
  9 29  1  0
 22 21  1  0
  7  6  1  0
 27 17  1  0
 23  7  1  0
 17 18  1  0
  6  5  2  0
 18 19  1  0
 21 19  1  0
 23 29  1  0
 19 20  1  0
  5  4  1  0
 17 16  2  0
 23 24  1  6
 16 15  1  0
 15 14  1  0
  4  3  2  0
 27 53  1  1
  3  8  1  0
 28 54  1  6
 29 28  1  0
  3  2  1  0
 28 13  1  0
 24 25  2  0
 28 27  1  0
  2  1  1  0
 26 51  1  0
 26 52  1  0
  6 35  1  0
  5 34  1  0
  4 33  1  0
 13 38  1  6
 12 36  1  0
 12 37  1  0
 22 49  1  0
 22 50  1  0
 21 47  1  0
 21 48  1  0
 18 42  1  0
 18 43  1  0
 20 44  1  0
 20 45  1  0
 20 46  1  0
 16 41  1  0
 15 39  1  0
 15 40  1  0
  1 30  1  0
  1 31  1  0
  1 32  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      -4.201  -0.857  -3.768  0.00  0.00           C+0
HETATM    2  O   UNK     0      -2.829  -1.133  -4.050  0.00  0.00           O+0
HETATM    3  C   UNK     0      -2.022  -0.163  -3.530  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.965   1.079  -4.176  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.062   2.060  -3.757  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.182   1.800  -2.709  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.221   0.554  -2.082  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.155  -0.414  -2.470  0.00  0.00           C+0
HETATM    9  N   UNK     0      -0.974  -1.570  -1.696  0.00  0.00           N+0
HETATM   10  C   UNK     0      -1.701  -2.742  -1.712  0.00  0.00           C+0
HETATM   11  O   UNK     0      -2.893  -2.846  -1.990  0.00  0.00           O+0
HETATM   12  C   UNK     0      -0.872  -3.998  -1.470  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.418  -3.835  -0.656  0.00  0.00           C+0
HETATM   14  O   UNK     0       0.061  -3.957   0.719  0.00  0.00           O+0
HETATM   15  C   UNK     0       1.152  -4.284   1.564  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.798  -3.029   2.036  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.370  -2.079   1.265  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.979  -0.873   1.966  0.00  0.00           C+0
HETATM   19  N   UNK     0       2.455   0.390   1.455  0.00  0.00           N+0
HETATM   20  C   UNK     0       3.197   1.531   1.989  0.00  0.00           C+0
HETATM   21  C   UNK     0       1.012   0.554   1.622  0.00  0.00           C+0
HETATM   22  C   UNK     0       0.395   0.995   0.289  0.00  0.00           C+0
HETATM   23  C   UNK     0       0.673   0.073  -0.936  0.00  0.00           C+0
HETATM   24  C   UNK     0       2.166   0.132  -1.324  0.00  0.00           C+0
HETATM   25  O   UNK     0       2.654   1.130  -1.871  0.00  0.00           O+0
HETATM   26  C   UNK     0       3.086  -1.048  -1.032  0.00  0.00           C+0
HETATM   27  C   UNK     0       2.449  -2.218  -0.261  0.00  0.00           C+0
HETATM   28  C   UNK     0       1.121  -2.508  -0.982  0.00  0.00           C+0
HETATM   29  C   UNK     0       0.130  -1.372  -0.751  0.00  0.00           C+0
HETATM   30  H   UNK     0      -4.356  -0.585  -2.717  0.00  0.00           H+0
HETATM   31  H   UNK     0      -4.579  -0.065  -4.423  0.00  0.00           H+0
HETATM   32  H   UNK     0      -4.776  -1.765  -3.972  0.00  0.00           H+0
HETATM   33  H   UNK     0      -2.606   1.275  -5.032  0.00  0.00           H+0
HETATM   34  H   UNK     0      -1.025   3.018  -4.271  0.00  0.00           H+0
HETATM   35  H   UNK     0       0.539   2.555  -2.407  0.00  0.00           H+0
HETATM   36  H   UNK     0      -1.525  -4.742  -0.996  0.00  0.00           H+0
HETATM   37  H   UNK     0      -0.610  -4.369  -2.469  0.00  0.00           H+0
HETATM   38  H   UNK     0       1.073  -4.675  -0.922  0.00  0.00           H+0
HETATM   39  H   UNK     0       1.867  -4.967   1.091  0.00  0.00           H+0
HETATM   40  H   UNK     0       0.737  -4.810   2.430  0.00  0.00           H+0
HETATM   41  H   UNK     0       1.781  -2.901   3.117  0.00  0.00           H+0
HETATM   42  H   UNK     0       4.064  -0.922   1.805  0.00  0.00           H+0
HETATM   43  H   UNK     0       2.830  -0.924   3.053  0.00  0.00           H+0
HETATM   44  H   UNK     0       2.849   2.466   1.536  0.00  0.00           H+0
HETATM   45  H   UNK     0       3.095   1.613   3.077  0.00  0.00           H+0
HETATM   46  H   UNK     0       4.262   1.446   1.746  0.00  0.00           H+0
HETATM   47  H   UNK     0       0.517  -0.361   1.963  0.00  0.00           H+0
HETATM   48  H   UNK     0       0.777   1.298   2.394  0.00  0.00           H+0
HETATM   49  H   UNK     0      -0.689   1.086   0.443  0.00  0.00           H+0
HETATM   50  H   UNK     0       0.749   2.012   0.068  0.00  0.00           H+0
HETATM   51  H   UNK     0       3.408  -1.419  -2.015  0.00  0.00           H+0
HETATM   52  H   UNK     0       3.991  -0.682  -0.536  0.00  0.00           H+0
HETATM   53  H   UNK     0       3.118  -3.075  -0.433  0.00  0.00           H+0
HETATM   54  H   UNK     0       1.347  -2.561  -2.060  0.00  0.00           H+0
HETATM   55  H   UNK     0      -0.323  -1.475   0.243  0.00  0.00           H+0
CONECT    1    2   30   31   32                                             
CONECT    2    3    1                                                       
CONECT    3    4    8    2                                                  
CONECT    4    5    3   33                                                  
CONECT    5    6    4   34                                                  
CONECT    6    7    5   35                                                  
CONECT    7    8    6   23                                                  
CONECT    8    9    7    3                                                  
CONECT    9   10    8   29                                                  
CONECT   10   12    9   11                                                  
CONECT   11   10                                                            
CONECT   12   13   10   36   37                                             
CONECT   13   14   12   28   38                                             
CONECT   14   13   15                                                       
CONECT   15   16   14   39   40                                             
CONECT   16   17   15   41                                                  
CONECT   17   27   18   16                                                  
CONECT   18   17   19   42   43                                             
CONECT   19   18   21   20                                                  
CONECT   20   19   44   45   46                                             
CONECT   21   22   19   47   48                                             
CONECT   22   23   21   49   50                                             
CONECT   23   22    7   29   24                                             
CONECT   24   26   23   25                                                  
CONECT   25   24                                                            
CONECT   26   27   24   51   52                                             
CONECT   27   26   17   53   28                                             
CONECT   28   54   29   13   27                                             
CONECT   29   55    9   23   28                                             
CONECT   30    1                                                            
CONECT   31    1                                                            
CONECT   32    1                                                            
CONECT   33    4                                                            
CONECT   34    5                                                            
CONECT   35    6                                                            
CONECT   36   12                                                            
CONECT   37   12                                                            
CONECT   38   13                                                            
CONECT   39   15                                                            
CONECT   40   15                                                            
CONECT   41   16                                                            
CONECT   42   18                                                            
CONECT   43   18                                                            
CONECT   44   20                                                            
CONECT   45   20                                                            
CONECT   46   20                                                            
CONECT   47   21                                                            
CONECT   48   21                                                            
CONECT   49   22                                                            
CONECT   50   22                                                            
CONECT   51   26                                                            
CONECT   52   26                                                            
CONECT   53   27                                                            
CONECT   54   28                                                            
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
   -4.2011   -0.8568   -3.7675 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8288   -1.1330   -4.0504 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0216   -0.1630   -3.5303 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9652    1.0786   -4.1764 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0615    2.0600   -3.7575 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1822    1.7996   -2.7087 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2213    0.5539   -2.0821 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1551   -0.4143   -2.4699 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9740   -1.5698   -1.6962 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7012   -2.7418   -1.7117 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8934   -2.8458   -1.9903 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8720   -3.9983   -1.4698 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4178   -3.8346   -0.6562 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0606   -3.9570    0.7193 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1523   -4.2841    1.5639 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7984   -3.0287    2.0359 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3698   -2.0787    1.2651 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9786   -0.8727    1.9659 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4547    0.3897    1.4549 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1970    1.5309    1.9887 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0125    0.5538    1.6219 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3954    0.9947    0.2886 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6728    0.0732   -0.9355 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1655    0.1320   -1.3244 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6539    1.1298   -1.8714 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0864   -1.0476   -1.0322 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4493   -2.2177   -0.2609 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1211   -2.5082   -0.9817 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1303   -1.3724   -0.7509 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.3558   -0.5848   -2.7168 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5791   -0.0652   -4.4228 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7756   -1.7652   -3.9724 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6064    1.2752   -5.0315 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0247    3.0178   -4.2707 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5394    2.5551   -2.4070 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5245   -4.7418   -0.9963 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6097   -4.3692   -2.4691 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0733   -4.6746   -0.9218 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8675   -4.9669    1.0915 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7366   -4.8100    2.4302 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7808   -2.9007    3.1172 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0636   -0.9224    1.8049 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8298   -0.9237    3.0528 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8485    2.4659    1.5361 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0955    1.6128    3.0767 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2622    1.4459    1.7465 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5166   -0.3609    1.9629 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7774    1.2984    2.3940 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6891    1.0862    0.4429 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7492    2.0119    0.0678 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4076   -1.4190   -2.0154 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9914   -0.6818   -0.5362 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1179   -3.0747   -0.4330 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3468   -2.5607   -2.0596 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3231   -1.4748    0.2431 H   0  0  0  0  0  0  0  0  0  0  0  0
 13 14  1  0
 27 26  1  0
 13 12  1  0
 26 24  1  0
 12 10  1  0
  9 10  1  0
  8  9  1  0
 10 11  2  0
 23 22  1  0
  8  7  2  0
 29 55  1  1
  9 29  1  0
 22 21  1  0
  7  6  1  0
 27 17  1  0
 23  7  1  0
 17 18  1  0
  6  5  2  0
 18 19  1  0
 21 19  1  0
 23 29  1  0
 19 20  1  0
  5  4  1  0
 17 16  2  0
 23 24  1  6
 16 15  1  0
 15 14  1  0
  4  3  2  0
 27 53  1  1
  3  8  1  0
 28 54  1  6
 29 28  1  0
  3  2  1  0
 28 13  1  0
 24 25  2  0
 28 27  1  0
  2  1  1  0
 26 51  1  0
 26 52  1  0
  6 35  1  0
  5 34  1  0
  4 33  1  0
 13 38  1  6
 12 36  1  0
 12 37  1  0
 22 49  1  0
 22 50  1  0
 21 47  1  0
 21 48  1  0
 18 42  1  0
 18 43  1  0
 20 44  1  0
 20 45  1  0
 20 46  1  0
 16 41  1  0
 15 39  1  0
 15 40  1  0
  1 30  1  0
  1 31  1  0
  1 32  1  0
M  END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₃H₂₆N₂O₄

Average Mass

394.4710 Da

Monoisotopic Mass

394.18926 Da

IUPAC Name

(1S,10S,11R,12S,22R)-15-methoxy-4-methyl-9-oxa-4,13-diazahexacyclo[9.8.3.2^{10,13}.0^{1,12}.0^{6,22}.0^{14,19}]tetracosa-6,14(19),15,17-tetraene-20,23-dione

Traditional Name

(1S,10S,11R,12S,22R)-15-methoxy-4-methyl-9-oxa-4,13-diazahexacyclo[9.8.3.2^{10,13}.0^{1,12}.0^{6,22}.0^{14,19}]tetracosa-6,14(19),15,17-tetraene-20,23-dione

CAS Registry Number

Not Available

SMILES

[H]C1=C([H])C2=C(N3C(=O)C([H])([H])[C@]4([H])OC([H])([H])C([H])=C5C([H])([H])N(C([H])([H])[H])C([H])([H])C([H])([H])[C@]22C(=O)C([H])([H])[C@]5([H])[C@]4([H])[C@]32[H])C(OC([H])([H])[H])=C1[H]

InChI Identifier

InChI=1S/C23H26N2O4/c1-24-8-7-23-15-4-3-5-16(28-2)21(15)25-19(27)11-17-20(22(23)25)14(10-18(23)26)13(12-24)6-9-29-17/h3-6,14,17,20,22H,7-12H2,1-2H3/t14-,17-,20-,22-,23+/m0/s1

InChI Key

ZKALYGURBPIPGN-PFXBBCFLSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
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, 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, 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, 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
Strychnos icaja	JEOL database	Tchinda, A. T., et al, Phytochem. Lett. 5, 108 (2012)

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as carbazoles. Carbazoles are compounds containing a three ring system containing a pyrrole ring fused on either side to a benzene ring.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Indoles and derivatives

Sub Class

Carbazoles

Direct Parent

Carbazoles

Alternative Parents

Substituents

Carbazole
Quinolidine
Anisole
Phenol ether
Alkyl aryl ether
Delta-lactam
Aralkylamine
Piperidinone
Piperidine
Benzenoid
Tertiary carboxylic acid amide
Amino acid or derivatives
Carboxamide group
Ketone
Lactam
Tertiary aliphatic amine
Tertiary amine
Ether
Dialkyl ether
Carboxylic acid derivative
Oxacycle
Azacycle
Organic oxygen compound
Organic nitrogen compound
Hydrocarbon derivative
Amine
Carbonyl group
Organonitrogen compound
Organooxygen compound
Organic oxide
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

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

Predicted Properties

Property	Value	Source
logP	1.39	ALOGPS
logP	0.81	ChemAxon
logS	-2.6	ALOGPS
pKa (Strongest Acidic)	17.18	ChemAxon
pKa (Strongest Basic)	8.34	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	59.08 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	108.41 m³·mol⁻¹	ChemAxon
Polarizability	41.8 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

34991873

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

72710634

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Tchinda, A. T., et al. (2012). Tchinda, A. T., et al, Phytochem. Lett. 5, 108 (2012). Phytochem..

Showing NP-Card for 12-methoxyicajine (NP0041593)

MOL for NP0041593 (12-methoxyicajine)

3D MOL for NP0041593 (12-methoxyicajine)

3D SDF for NP0041593 (12-methoxyicajine)

3D-SDF for NP0041593 (12-methoxyicajine)

PDB for NP0041593 (12-methoxyicajine)

3D PDB for NP0041593 (12-methoxyicajine)

SMILES for NP0041593 (12-methoxyicajine)

INCHI for NP0041593 (12-methoxyicajine)

Structure for NP0041593 (12-methoxyicajine)

3D Structure for NP0041593 (12-methoxyicajine)