NP-MRD: Showing NP-Card for (1r,4s,12r,13r,21s)-20-oxo-5,15-diazahexacyclo[11.5.2.1¹,¹².0⁴,¹².0⁶,¹¹.0¹⁵,²¹]henicosa-6,8,10-triene-4-carboxylic acid (NP0327200)

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Record Information

Version

2.0

Created at

2022-09-12 09:32:55 UTC

Updated at

2022-09-12 09:32:55 UTC

NP-MRD ID

NP0327200

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1r,4s,12r,13r,21s)-20-oxo-5,15-diazahexacyclo[11.5.2.1¹,¹².0⁴,¹².0⁶,¹¹.0¹⁵,²¹]henicosa-6,8,10-triene-4-carboxylic acid

Description

Kopsihainanine B belongs to the class of organic compounds known as aspidofractine alkaloids. These are alkaloids with a structure that is based on the hexacyclic aspidofractine core. These compounds are related to the Aspidosperma group by formation of a C-2 to C-18 bond. (1r,4s,12r,13r,21s)-20-oxo-5,15-diazahexacyclo[11.5.2.1¹,¹².0⁴,¹².0⁶,¹¹.0¹⁵,²¹]henicosa-6,8,10-triene-4-carboxylic acid was first documented in 2011 (PMID: 21677983). Based on a literature review very few articles have been published on Kopsihainanine B (PMID: 24756124).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309122211322D          

 25 30  0  0  1  0            999 V2000
    3.3601   -0.8586    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6344   -1.2511    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5684   -1.0773    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4710   -0.2329    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6506   -0.4487    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4949   -1.2711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1147   -1.8335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9323   -1.5782    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9679   -1.8755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3707   -1.8453    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.9039   -0.7638    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.7828   -0.8917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0997   -1.6534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9178   -1.7598    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4190   -1.1045    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1021   -0.3428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2840   -0.2364    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8120    0.4380    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0445    0.1321    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.2533    0.9302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6665    1.5101    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0489    1.1484    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5128    0.7900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7042    0.5866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0588   -0.6243    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  4  3  1  1  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
 10  9  1  6  0  0  0
  2 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  6  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 12 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 11 19  1  0  0  0  0
 19 20  1  1  0  0  0
 20 21  2  0  0  0  0
 20 22  1  0  0  0  0
 19 23  1  0  0  0  0
 23 24  1  0  0  0  0
  4 24  1  0  0  0  0
 11 25  1  0  0  0  0
 25  8  1  1  0  0  0
  4 25  1  0  0  0  0
M  END

     RDKit          3D

 47 52  0  0  0  0  0  0  0  0999 V2000
    1.3173   -3.1293    0.6765 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2500   -1.9404    0.5353 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2000   -1.2231   -0.3028 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6703    0.0794   -0.8495 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8252    1.0344   -1.0165 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8985    2.0579    0.0821 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3102    1.5824    1.3902 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9830    1.0659    1.2978 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.9134   -0.1545    2.0846 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1760   -1.1801    1.2296 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4997   -0.3181    0.2129 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.7641    0.3246    0.6686 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2936    0.7249    1.8713 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5304    1.3243    1.9061 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2742    1.5424    0.7492 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7569    1.1464   -0.4695 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5167    0.5458   -0.4911 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8340    0.0402   -1.6416 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9425   -0.9884   -1.0291 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.8122   -2.1383   -0.7814 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8734   -2.3144   -1.5170 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6608   -3.1207    0.1827 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0916   -1.3026   -2.0285 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0954   -0.1867   -2.2340 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5930    0.7130   -0.0447 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5212   -1.8386   -1.1681 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1640   -1.0024    0.2431 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7751    1.5997   -1.9754 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7601    0.4388   -1.0742 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9897    2.2308    0.2884 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4926    3.0425   -0.2329 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3747    2.4559    2.0932 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0129    0.8084    1.7967 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5015   -0.0077    3.0734 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9599   -0.5517    2.2644 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4901   -1.8040    1.8193 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7203    0.5567    2.7850 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9148    1.6231    2.8734 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2268    2.0090    0.8030 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3540    1.3281   -1.3475 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8753    0.2590   -2.6297 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3773   -3.3627    0.8601 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4067   -1.4477   -3.0189 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6483   -2.2289   -1.8251 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5872    0.7311   -2.5785 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8614   -0.5683   -2.9421 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1511    1.5437   -0.5886 H   0  0  0  0  0  0  0  0  0  0  0  0
 22 20  1  0
 20 21  2  0
 19 20  1  1
 19 23  1  0
 23 24  1  0
  4 24  1  6
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10  2  1  0
  2  1  2  0
  2  3  1  0
 10 11  1  0
 11 25  1  0
 11 12  1  1
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 11 19  1  0
 17 12  1  0
 18 19  1  0
  3  4  1  0
 25  4  1  0
 25  8  1  0
 22 42  1  0
 23 43  1  0
 23 44  1  0
 24 45  1  0
 24 46  1  0
  5 28  1  0
  5 29  1  0
  6 30  1  0
  6 31  1  0
  7 32  1  0
  7 33  1  0
  9 34  1  0
  9 35  1  0
 10 36  1  1
  3 26  1  0
  3 27  1  0
 25 47  1  6
 13 37  1  0
 14 38  1  0
 15 39  1  0
 16 40  1  0
 18 41  1  0
M  END


  Mrv1652309122211322D          

 25 30  0  0  1  0            999 V2000
    3.3601   -0.8586    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6344   -1.2511    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5684   -1.0773    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4710   -0.2329    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6506   -0.4487    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4949   -1.2711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1147   -1.8335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9323   -1.5782    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9679   -1.8755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3707   -1.8453    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.9039   -0.7638    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.7828   -0.8917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0997   -1.6534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9178   -1.7598    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4190   -1.1045    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1021   -0.3428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2840   -0.2364    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8120    0.4380    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0445    0.1321    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.2533    0.9302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6665    1.5101    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0489    1.1484    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5128    0.7900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7042    0.5866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0588   -0.6243    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  4  3  1  1  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
 10  9  1  6  0  0  0
  2 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  6  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 12 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 11 19  1  0  0  0  0
 19 20  1  1  0  0  0
 20 21  2  0  0  0  0
 20 22  1  0  0  0  0
 19 23  1  0  0  0  0
 23 24  1  0  0  0  0
  4 24  1  0  0  0  0
 11 25  1  0  0  0  0
 25  8  1  1  0  0  0
  4 25  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0327200

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC(=O)[C@]12CC[C@]34CCCN5C[C@H](C(=O)C3)[C@]1([C@H]45)C1=CC=CC=C1N2

> <INCHI_IDENTIFIER>
InChI=1S/C20H22N2O3/c23-15-10-18-6-3-9-22-11-13(15)20(16(18)22)12-4-1-2-5-14(12)21-19(20,8-7-18)17(24)25/h1-2,4-5,13,16,21H,3,6-11H2,(H,24,25)/t13-,16+,18-,19-,20+/m1/s1

> <INCHI_KEY>
VMYIEWNUGAYDHM-MKCULMFZSA-N

> <FORMULA>
C20H22N2O3

> <MOLECULAR_WEIGHT>
338.407

> <EXACT_MASS>
338.163042576

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
47

> <JCHEM_AVERAGE_POLARIZABILITY>
35.173667406740876

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,4S,12R,13R,21S)-20-oxo-5,15-diazahexacyclo[11.5.2.1^{1,12}.0^{4,12}.0^{6,11}.0^{15,21}]henicosa-6,8,10-triene-4-carboxylic acid

> <JCHEM_LOGP>
-1.102130799150521

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.515553627955315

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.644504199036039

> <JCHEM_PKA_STRONGEST_BASIC>
9.698723752060653

> <JCHEM_POLAR_SURFACE_AREA>
69.64

> <JCHEM_REFRACTIVITY>
92.80659999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1R,4S,12R,13R,21S)-20-oxo-5,15-diazahexacyclo[11.5.2.1^{1,12}.0^{4,12}.0^{6,11}.0^{15,21}]henicosa-6,8,10-triene-4-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 12-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   12-SEP-22         0                                  
HETATM    1  O   UNK     0       6.272  -1.603   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       4.918  -2.335   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.928  -2.011   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.746  -0.435   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.214  -0.838   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.924  -2.373   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.081  -3.423   0.000  0.00  0.00           C+0
HETATM    8  N   UNK     0       3.607  -2.946   0.000  0.00  0.00           N+0
HETATM    9  C   UNK     0       5.540  -3.501   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.425  -3.445   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.421  -1.426   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.061  -1.665   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.653  -3.086   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.180  -3.285   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      10.116  -2.062   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       9.524  -0.640   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       7.997  -0.441   0.000  0.00  0.00           C+0
HETATM   18  N   UNK     0       7.116   0.818   0.000  0.00  0.00           N+0
HETATM   19  C   UNK     0       5.683   0.247   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.073   1.736   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       4.977   2.819   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       7.558   2.144   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       4.691   1.475   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       3.181   1.095   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       3.843  -1.165   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   10                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   24   25                                             
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   25                                                  
CONECT    9    8   10                                                       
CONECT   10    9    2   11                                                  
CONECT   11   10   12   19   25                                             
CONECT   12   11   13   17                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   12   18                                                  
CONECT   18   17   19                                                       
CONECT   19   18   11   20   23                                             
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20                                                            
CONECT   23   19   24                                                       
CONECT   24   23    4                                                       
CONECT   25   11    8    4                                                  
MASTER        0    0    0    0    0    0    0    0   25    0   60    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₀H₂₂N₂O₃

Average Mass

338.4070 Da

Monoisotopic Mass

338.16304 Da

IUPAC Name

(1R,4S,12R,13R,21S)-20-oxo-5,15-diazahexacyclo[11.5.2.1^{1,12}.0^{4,12}.0^{6,11}.0^{15,21}]henicosa-6,8,10-triene-4-carboxylic acid

Traditional Name

(1R,4S,12R,13R,21S)-20-oxo-5,15-diazahexacyclo[11.5.2.1^{1,12}.0^{4,12}.0^{6,11}.0^{15,21}]henicosa-6,8,10-triene-4-carboxylic acid

CAS Registry Number

Not Available

SMILES

OC(=O)[C@]12CC[C@]34CCCN5C[C@H](C(=O)C3)[C@]1([C@H]45)C1=CC=CC=C1N2

InChI Identifier

InChI=1S/C20H22N2O3/c23-15-10-18-6-3-9-22-11-13(15)20(16(18)22)12-4-1-2-5-14(12)21-19(20,8-7-18)17(24)25/h1-2,4-5,13,16,21H,3,6-11H2,(H,24,25)/t13-,16+,18-,19-,20+/m1/s1

InChI Key

VMYIEWNUGAYDHM-MKCULMFZSA-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

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as aspidofractine alkaloids. These are alkaloids with a structure that is based on the hexacyclic aspidofractine core. These compounds are related to the Aspidosperma group by formation of a C-2 to C-18 bond.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Aspidofractine alkaloids

Sub Class

Not Available

Direct Parent

Aspidofractine alkaloids

Alternative Parents

Substituents

Aspidofractine skeleton
Aspidosperma alkaloid
Carbazole
Quinoline-7-carboxylic acid
Indolecarboxylic acid
Indolecarboxylic acid derivative
Alpha-amino acid
Alpha-amino acid or derivatives
D-alpha-amino acid
Quinolidine
Indole or derivatives
Dihydroindole
Indolizidine
Azepane
Aralkylamine
Secondary aliphatic/aromatic amine
Benzenoid
N-alkylpyrrolidine
Piperidine
Pyrrolidine
Tertiary amine
Amino acid or derivatives
Amino acid
Ketone
Tertiary aliphatic amine
Secondary amine
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Carboxylic acid
Azacycle
Organoheterocyclic compound
Carbonyl group
Hydrocarbon derivative
Amine
Organooxygen compound
Organonitrogen compound
Organic oxide
Organic nitrogen compound
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

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

Predicted Properties

Property	Value	Source
logP	-1.1	ChemAxon
pKa (Strongest Acidic)	3.64	ChemAxon
pKa (Strongest Basic)	9.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	69.64 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	92.81 m³·mol⁻¹	ChemAxon
Polarizability	35.17 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	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

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

54590592

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Mizutani M, Yasuda S, Mukai C: Total synthesis of (+)-kopsihainanine A. Chem Commun (Camb). 2014 Jun 1;50(43):5782-5. doi: 10.1039/c4cc01843e. Epub 2014 Apr 22. [PubMed:24756124 ]
Chen J, Chen JJ, Yao X, Gao K: Kopsihainanines A and B, two unusual alkaloids from Kopsia hainanensis. Org Biomol Chem. 2011 Aug 7;9(15):5334-6. doi: 10.1039/c1ob05724c. Epub 2011 Jun 16. [PubMed:21677983 ]
LOTUS database [Link]

Showing NP-Card for (1r,4s,12r,13r,21s)-20-oxo-5,15-diazahexacyclo[11.5.2.1¹,¹².0⁴,¹².0⁶,¹¹.0¹⁵,²¹]henicosa-6,8,10-triene-4-carboxylic acid (NP0327200)

MOL for NP0327200 ((1r,4s,12r,13r,21s)-20-oxo-5,15-diazahexacyclo[11.5.2.1¹,¹².0⁴,¹².0⁶,¹¹.0¹⁵,²¹]henicosa-6,8,10-triene-4-carboxylic acid)

3D MOL for NP0327200 ((1r,4s,12r,13r,21s)-20-oxo-5,15-diazahexacyclo[11.5.2.1¹,¹².0⁴,¹².0⁶,¹¹.0¹⁵,²¹]henicosa-6,8,10-triene-4-carboxylic acid)

3D SDF for NP0327200 ((1r,4s,12r,13r,21s)-20-oxo-5,15-diazahexacyclo[11.5.2.1¹,¹².0⁴,¹².0⁶,¹¹.0¹⁵,²¹]henicosa-6,8,10-triene-4-carboxylic acid)

3D-SDF for NP0327200 ((1r,4s,12r,13r,21s)-20-oxo-5,15-diazahexacyclo[11.5.2.1¹,¹².0⁴,¹².0⁶,¹¹.0¹⁵,²¹]henicosa-6,8,10-triene-4-carboxylic acid)

PDB for NP0327200 ((1r,4s,12r,13r,21s)-20-oxo-5,15-diazahexacyclo[11.5.2.1¹,¹².0⁴,¹².0⁶,¹¹.0¹⁵,²¹]henicosa-6,8,10-triene-4-carboxylic acid)

3D PDB for NP0327200 ((1r,4s,12r,13r,21s)-20-oxo-5,15-diazahexacyclo[11.5.2.1¹,¹².0⁴,¹².0⁶,¹¹.0¹⁵,²¹]henicosa-6,8,10-triene-4-carboxylic acid)

SMILES for NP0327200 ((1r,4s,12r,13r,21s)-20-oxo-5,15-diazahexacyclo[11.5.2.1¹,¹².0⁴,¹².0⁶,¹¹.0¹⁵,²¹]henicosa-6,8,10-triene-4-carboxylic acid)

INCHI for NP0327200 ((1r,4s,12r,13r,21s)-20-oxo-5,15-diazahexacyclo[11.5.2.1¹,¹².0⁴,¹².0⁶,¹¹.0¹⁵,²¹]henicosa-6,8,10-triene-4-carboxylic acid)

Structure for NP0327200 ((1r,4s,12r,13r,21s)-20-oxo-5,15-diazahexacyclo[11.5.2.1¹,¹².0⁴,¹².0⁶,¹¹.0¹⁵,²¹]henicosa-6,8,10-triene-4-carboxylic acid)

3D Structure for NP0327200 ((1r,4s,12r,13r,21s)-20-oxo-5,15-diazahexacyclo[11.5.2.1¹,¹².0⁴,¹².0⁶,¹¹.0¹⁵,²¹]henicosa-6,8,10-triene-4-carboxylic acid)