NP-MRD: Showing NP-Card for (1r,13r,14e,19s,21s)-14-ethylidene-10-[(1r,12s,13r,14e,17r,19s,21s)-14-ethylidene-9-oxo-8,16-diazahexacyclo[11.5.2.1¹,⁸.0²,⁷.0¹⁶,¹⁹.0¹²,²¹]henicosa-2,4,6,10-tetraen-17-yl]-8,16-diazahexacyclo[11.5.2.1¹,⁸.0²,⁷.0¹⁶,¹⁹.0¹²,²¹]henicosa-2,4,6,10-tetraen-9-one (NP0317218)

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Record Information

Version

2.0

Created at

2022-09-11 16:57:29 UTC

Updated at

2022-09-11 16:57:29 UTC

NP-MRD ID

NP0317218

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1r,13r,14e,19s,21s)-14-ethylidene-10-[(1r,12s,13r,14e,17r,19s,21s)-14-ethylidene-9-oxo-8,16-diazahexacyclo[11.5.2.1¹,⁸.0²,⁷.0¹⁶,¹⁹.0¹²,²¹]henicosa-2,4,6,10-tetraen-17-yl]-8,16-diazahexacyclo[11.5.2.1¹,⁸.0²,⁷.0¹⁶,¹⁹.0¹²,²¹]henicosa-2,4,6,10-tetraen-9-one

Description

Sungucine belongs to the class of organic compounds known as strychnos alkaloids. These are alkaloids having a core structure based on the strychnan, stemmadenine (seco-curan), or the akuammicine (curan) skeleton. (1r,13r,14e,19s,21s)-14-ethylidene-10-[(1r,12s,13r,14e,17r,19s,21s)-14-ethylidene-9-oxo-8,16-diazahexacyclo[11.5.2.1¹,⁸.0²,⁷.0¹⁶,¹⁹.0¹²,²¹]henicosa-2,4,6,10-tetraen-17-yl]-8,16-diazahexacyclo[11.5.2.1¹,⁸.0²,⁷.0¹⁶,¹⁹.0¹²,²¹]henicosa-2,4,6,10-tetraen-9-one is found in Strychnos icaja. (1r,13r,14e,19s,21s)-14-ethylidene-10-[(1r,12s,13r,14e,17r,19s,21s)-14-ethylidene-9-oxo-8,16-diazahexacyclo[11.5.2.1¹,⁸.0²,⁷.0¹⁶,¹⁹.0¹²,²¹]henicosa-2,4,6,10-tetraen-17-yl]-8,16-diazahexacyclo[11.5.2.1¹,⁸.0²,⁷.0¹⁶,¹⁹.0¹²,²¹]henicosa-2,4,6,10-tetraen-9-one was first documented in 2002 (PMID: 12398531). Based on a literature review a significant number of articles have been published on Sungucine (PMID: 24593048) (PMID: 16375888) (PMID: 34817185) (PMID: 33602083) (PMID: 27305659) (PMID: 12644898).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309112218572D          

 48 59  0  0  1  0            999 V2000
    4.0693   -1.5360    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3076   -0.7462    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1108   -0.5577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3369    0.3012    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1806    0.5249    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.8898    1.0215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5763    0.5223    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3859   -0.3452    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.2532   -0.2785    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6968    0.4170    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5210    0.3807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9016   -0.3513    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4580   -1.0469    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6338   -1.0105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    8.0191   -2.4530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    5.7094   -1.2424    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
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    6.5981   -0.1490    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
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  8  7  1  6  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
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  9 14  1  0  0  0  0
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 21 37  1  0  0  0  0
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  8 45  1  0  0  0  0
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  3 46  1  0  0  0  0
 46 47  1  1  0  0  0
 48 47  1  6  0  0  0
  5 48  1  0  0  0  0
  8 48  1  0  0  0  0
M  END

     RDKit          3D

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 15 14  1  0
 14 13  2  0
 13 12  1  0
 12 11  2  0
 11 10  1  0
 10  9  2  0
 46  3  1  0
 45 44  1  0
  9 14  1  0
 48  5  1  0
 38 19  1  0
 45  8  1  0
  9  8  1  0
 34 21  1  0
 22 27  1  0
 22 21  1  0
 38 37  1  0
 34 33  1  0
  1 49  1  0
  1 50  1  0
  1 51  1  0
  2 52  1  0
  4 53  1  0
  4 54  1  0
  6 55  1  0
  6 56  1  0
  7 57  1  0
  7 58  1  0
 48 90  1  1
 47 88  1  0
 47 89  1  0
 46 87  1  1
 44 85  1  1
 43 84  1  0
 19 63  1  1
 20 64  1  0
 20 65  1  0
 37 77  1  6
 36 75  1  0
 36 76  1  0
 35 74  1  6
 33 72  1  1
 32 71  1  0
 31 70  1  0
 34 73  1  1
 26 69  1  0
 25 68  1  0
 24 67  1  0
 23 66  1  0
 39 78  1  0
 39 79  1  0
 41 80  1  0
 42 81  1  0
 42 82  1  0
 42 83  1  0
 45 86  1  6
 13 62  1  0
 12 61  1  0
 11 60  1  0
 10 59  1  0
M  END


  Mrv1652309112218572D          

 48 59  0  0  1  0            999 V2000
    4.0693   -1.5360    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3076   -0.7462    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1108   -0.5577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3369    0.3012    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1806    0.5249    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.8898    1.0215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5763    0.5223    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3859   -0.3452    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.2532   -0.2785    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6968    0.4170    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5210    0.3807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9016   -0.3513    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4580   -1.0469    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6338   -1.0105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0407   -1.6135    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.0191   -2.4530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7307   -2.8704    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3021   -2.8784    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3176   -3.7032    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.0185   -4.1834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8527   -5.0585    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.7233   -4.9757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1540   -4.2720    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9788   -4.2932    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3728   -5.0180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9421   -5.7217    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1173   -5.7005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5388   -6.3153    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.5378   -7.1544    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2593   -7.5545    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8310   -7.5968    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0952   -7.2163    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0289   -6.3948    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.7978   -5.9398    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.2033   -5.9973    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.5773   -5.5094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0630   -4.8793    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.6237   -4.2180    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.7860   -4.4624    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5840   -5.3292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7866   -5.5407    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5711   -6.3371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5743   -2.4828    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5273   -1.6594    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3062   -1.2236    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.7094   -1.2424    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.0956   -0.7664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5981   -0.1490    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  8  7  1  6  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
  9 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
 19 18  1  1  0  0  0
 19 20  1  0  0  0  0
 21 20  1  6  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 22 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 29 31  1  0  0  0  0
 31 32  2  0  0  0  0
 33 32  1  1  0  0  0
 33 34  1  0  0  0  0
 34 28  1  1  0  0  0
 21 34  1  0  0  0  0
 33 35  1  0  0  0  0
 35 36  1  1  0  0  0
 37 36  1  6  0  0  0
 21 37  1  0  0  0  0
 37 38  1  0  0  0  0
 19 38  1  0  0  0  0
 38 39  1  0  0  0  0
 39 40  1  0  0  0  0
 35 40  1  0  0  0  0
 40 41  2  0  0  0  0
 41 42  1  0  0  0  0
 18 43  2  0  0  0  0
 43 44  1  0  0  0  0
 44 45  1  0  0  0  0
 45 15  1  1  0  0  0
  8 45  1  0  0  0  0
 44 46  1  0  0  0  0
  3 46  1  0  0  0  0
 46 47  1  1  0  0  0
 48 47  1  6  0  0  0
  5 48  1  0  0  0  0
  8 48  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0317218

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C\C=C1\CN2CC[C@@]34[C@@H]2C[C@@H]1C1C=C([C@H]2C[C@@]56[C@@H]7C[C@H]([C@@H]8C=CC(=O)N([C@H]58)C5=CC=CC=C65)\C(CN27)=C/C)C(=O)N([C@H]31)C1=CC=CC=C41

> <INCHI_IDENTIFIER>
InChI=1S/C42H42N4O2/c1-3-23-21-43-16-15-41-30-9-5-8-12-33(30)46-39(41)28(27(23)18-35(41)43)17-29(40(46)48)34-20-42-31-10-6-7-11-32(31)45-37(47)14-13-25(38(42)45)26-19-36(42)44(34)22-24(26)4-2/h3-14,17,25-28,34-36,38-39H,15-16,18-22H2,1-2H3/b23-3-,24-4-/t25-,26-,27-,28?,34+,35-,36-,38-,39-,41+,42+/m0/s1

> <INCHI_KEY>
VCDMHIARBYKHSB-GGFWQZPHSA-N

> <FORMULA>
C42H42N4O2

> <MOLECULAR_WEIGHT>
634.824

> <EXACT_MASS>
634.330776608

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
90

> <JCHEM_AVERAGE_POLARIZABILITY>
71.72346582122938

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,13R,14E,19S,21S)-14-ethylidene-10-[(1R,12S,13R,14E,17R,19S,21S)-14-ethylidene-9-oxo-8,16-diazahexacyclo[11.5.2.1^{1,8}.0^{2,7}.0^{16,19}.0^{12,21}]henicosa-2,4,6,10-tetraen-17-yl]-8,16-diazahexacyclo[11.5.2.1^{1,8}.0^{2,7}.0^{16,19}.0^{12,21}]henicosa-2,4,6,10-tetraen-9-one

> <JCHEM_LOGP>
4.1584569706666645

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
12

> <JCHEM_PHYSIOLOGICAL_CHARGE>
2

> <JCHEM_PKA_STRONGEST_ACIDIC>
18.394249008497358

> <JCHEM_PKA_STRONGEST_BASIC>
9.680697002715432

> <JCHEM_POLAR_SURFACE_AREA>
47.1

> <JCHEM_REFRACTIVITY>
189.3801

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(1R,13R,14E,19S,21S)-14-ethylidene-10-[(1R,12S,13R,14E,17R,19S,21S)-14-ethylidene-9-oxo-8,16-diazahexacyclo[11.5.2.1^{1,8}.0^{2,7}.0^{16,19}.0^{12,21}]henicosa-2,4,6,10-tetraen-17-yl]-8,16-diazahexacyclo[11.5.2.1^{1,8}.0^{2,7}.0^{16,19}.0^{12,21}]henicosa-2,4,6,10-tetraen-9-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 11-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-SEP-22         0                                  
HETATM    1  C   UNK     0       7.596  -2.867   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.041  -1.393   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       9.540  -1.041   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       9.962   0.562   0.000  0.00  0.00           C+0
HETATM    5  N   UNK     0      11.537   0.980   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0      12.861   1.907   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      14.142   0.975   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      13.787  -0.644   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      15.406  -0.520   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      16.234   0.778   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      17.773   0.711   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      18.483  -0.656   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      17.655  -1.954   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      16.116  -1.886   0.000  0.00  0.00           C+0
HETATM   15  N   UNK     0      15.009  -3.012   0.000  0.00  0.00           N+0
HETATM   16  C   UNK     0      14.969  -4.579   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      16.297  -5.358   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      13.631  -5.373   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      13.659  -6.913   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      14.968  -7.809   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      14.658  -9.443   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      16.284  -9.288   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      17.088  -7.974   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      18.627  -8.014   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      19.363  -9.367   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      18.559 -10.680   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      17.019 -10.641   0.000  0.00  0.00           C+0
HETATM   28  N   UNK     0      15.939 -11.789   0.000  0.00  0.00           N+0
HETATM   29  C   UNK     0      15.937 -13.355   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      17.284 -14.102   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      14.618 -14.181   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      13.244 -13.470   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      13.121 -11.937   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      14.556 -11.088   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      11.579 -11.195   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      12.278 -10.284   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      13.184  -9.108   0.000  0.00  0.00           C+0
HETATM   38  N   UNK     0      12.364  -7.874   0.000  0.00  0.00           N+0
HETATM   39  C   UNK     0      10.801  -8.330   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      10.424  -9.948   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0       8.935 -10.343   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0       8.533 -11.829   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0      12.272  -4.635   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0      12.184  -3.098   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0      13.638  -2.284   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0      10.658  -2.319   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0      11.379  -1.431   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0      12.316  -0.278   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   46                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   48                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   45   48                                             
CONECT    9    8   10   14                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13    9   15                                                  
CONECT   15   14   16   45                                                  
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19   43                                                  
CONECT   19   18   20   38                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22   34   37                                             
CONECT   22   21   23   27                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   22   28                                                  
CONECT   28   27   29   34                                                  
CONECT   29   28   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32   34   35                                                  
CONECT   34   33   28   21                                                  
CONECT   35   33   36   40                                                  
CONECT   36   35   37                                                       
CONECT   37   36   21   38                                                  
CONECT   38   37   19   39                                                  
CONECT   39   38   40                                                       
CONECT   40   39   35   41                                                  
CONECT   41   40   42                                                       
CONECT   42   41                                                            
CONECT   43   18   44                                                       
CONECT   44   43   45   46                                                  
CONECT   45   44   15    8                                                  
CONECT   46   44    3   47                                                  
CONECT   47   46   48                                                       
CONECT   48   47    5    8                                                  
MASTER        0    0    0    0    0    0    0    0   48    0  118    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₄₂H₄₂N₄O₂

Average Mass

634.8240 Da

Monoisotopic Mass

634.33078 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

C\C=C1\CN2CC[C@@]34[C@@H]2C[C@@H]1C1C=C([C@H]2C[C@@]56[C@@H]7C[C@H]([C@@H]8C=CC(=O)N([C@H]58)C5=CC=CC=C65)\C(CN27)=C/C)C(=O)N([C@H]31)C1=CC=CC=C41

InChI Identifier

InChI=1S/C42H42N4O2/c1-3-23-21-43-16-15-41-30-9-5-8-12-33(30)46-39(41)28(27(23)18-35(41)43)17-29(40(46)48)34-20-42-31-10-6-7-11-32(31)45-37(47)14-13-25(38(42)45)26-19-36(42)44(34)22-24(26)4-2/h3-14,17,25-28,34-36,38-39H,15-16,18-22H2,1-2H3/b23-3-,24-4-/t25-,26-,27-,28?,34+,35-,36-,38-,39-,41+,42+/m0/s1

InChI Key

VCDMHIARBYKHSB-GGFWQZPHSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Strychnos icaja	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as strychnos alkaloids. These are alkaloids having a core structure based on the strychnan, stemmadenine (seco-curan), or the akuammicine (curan) skeleton.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Strychnos alkaloids

Sub Class

Not Available

Direct Parent

Strychnos alkaloids

Alternative Parents

Substituents

Strychnan skeleton
Akuammicine-skeleton
Stemmadenine-skeleton
Carbazole
Indolizidine
Indole or derivatives
Aralkylamine
Benzenoid
N-alkylpyrrolidine
Piperidine
Tertiary carboxylic acid amide
Pyrrolidine
Tertiary aliphatic amine
Tertiary amine
Lactam
Carboxamide group
Amino acid or derivatives
Azacycle
Organoheterocyclic compound
Carboxylic acid derivative
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Carbonyl group
Amine
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

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

134716700

PDB ID

Not Available

ChEBI ID

141958

Good Scents ID

Not Available

References

General References

Tchinda AT, Jansen O, Nyemb JN, Tits M, Dive G, Angenot L, Frederich M: Strychnobaillonine, an unsymmetrical bisindole alkaloid with an unprecedented skeleton from Strychnos icaja roots. J Nat Prod. 2014 Apr 25;77(4):1078-82. doi: 10.1021/np400908u. Epub 2014 Mar 4. [PubMed:24593048 ]
Philippe G, Nguyen L, Angenot L, Frederich M, Moonen G, Tits M, Rigo JM: Study of the interaction of antiplasmodial strychnine derivatives with the glycine receptor. Eur J Pharmacol. 2006 Jan 13;530(1-2):15-22. doi: 10.1016/j.ejphar.2005.11.048. Epub 2005 Dec 20. [PubMed:16375888 ]
Semenov VA, Krivdin LB: Simple and Versatile Scheme for the Stereochemical Identification of Natural Products and Diverse Organic Compounds with Multiple Asymmetric Centers. J Phys Chem A. 2021 Dec 9;125(48):10359-10372. doi: 10.1021/acs.jpca.1c08687. Epub 2021 Nov 24. [PubMed:34817185 ]
Balkrishna A, Pokhrel S, Varshney A: Phyto-Compounds from a Rather Poisonous Plant, Strychnos nuxvomica, Show High Potency Against SARS-CoV-2 RNA-Dependent RNA Polymerase. Curr Mol Med. 2022;22(10):929-940. doi: 10.2174/1566524021666210218113409. [PubMed:33602083 ]
Zhao S, Teijaro CN, Chen H, Sirasani G, Vaddypally S, Zdilla MJ, Dobereiner GE, Andrade RB: Concise Syntheses of bis-Strychnos Alkaloids (-)-Sungucine, (-)-Isosungucine, and (-)-Strychnogucine B from (-)-Strychnine. Chemistry. 2016 Aug 8;22(33):11593-6. doi: 10.1002/chem.201602663. Epub 2016 Jul 8. [PubMed:27305659 ]
Frederich M, Bentires-Ali M, Tits M, Angenot L, Heinen E, De Pauw-Gillet MC: Apoptosis induction in human cancer cells by sungucine from Strychnos icaja root. Naunyn Schmiedebergs Arch Pharmacol. 2003 Mar;367(3):260-5. doi: 10.1007/s00210-003-0691-x. Epub 2003 Feb 14. [PubMed:12644898 ]
Sauri J, Frederich M, Tchinda AT, Parella T, Williamson RT, Martin GE: Carbon Multiplicity Editing in Long-Range Heteronuclear Correlation NMR Experiments: A Valuable Tool for the Structure Elucidation of Natural Products. J Nat Prod. 2015 Sep 25;78(9):2236-41. doi: 10.1021/acs.jnatprod.5b00447. Epub 2015 Aug 25. [PubMed:26305494 ]
Frederich M, Choi YH, Angenot L, Harnischfeger G, Lefeber AW, Verpoorte R: Metabolomic analysis of Strychnos nux-vomica, Strychnos icaja and Strychnos ignatii extracts by 1H nuclear magnetic resonance spectrometry and multivariate analysis techniques. Phytochemistry. 2004 Jul;65(13):1993-2001. doi: 10.1016/j.phytochem.2004.06.015. [PubMed:15280006 ]
Frederich M, Jacquier MJ, Thepenier P, De Mol P, Tits M, Philippe G, Delaude C, Angenot L, Zeches-Hanrot M: Antiplasmodial activity of alkaloids from various strychnos species. J Nat Prod. 2002 Oct;65(10):1381-6. doi: 10.1021/np020070e. [PubMed:12398531 ]
LOTUS database [Link]