NP-MRD: Showing NP-Card for 16,18-dimethyl (2r,4s,9r,18r,19r,22r)-14,18,19-trihydroxy-13-methoxy-3-oxa-6,16-diazaheptacyclo[15.2.2.1¹,⁶.0²,⁴.0⁹,¹⁷.0¹⁰,¹⁵.0⁹,²²]docosa-10(15),11,13-triene-16,18-dicarboxylate (NP0219503)

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Record Information

Version

2.0

Created at

2022-09-05 20:30:47 UTC

Updated at

2022-09-05 20:30:47 UTC

NP-MRD ID

NP0219503

Secondary Accession Numbers

None

Natural Product Identification

Common Name

16,18-dimethyl (2r,4s,9r,18r,19r,22r)-14,18,19-trihydroxy-13-methoxy-3-oxa-6,16-diazaheptacyclo[15.2.2.1¹,⁶.0²,⁴.0⁹,¹⁷.0¹⁰,¹⁵.0⁹,²²]docosa-10(15),11,13-triene-16,18-dicarboxylate

Description

Kopsimaline C 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. 16,18-dimethyl (2r,4s,9r,18r,19r,22r)-14,18,19-trihydroxy-13-methoxy-3-oxa-6,16-diazaheptacyclo[15.2.2.1¹,⁶.0²,⁴.0⁹,¹⁷.0¹⁰,¹⁵.0⁹,²²]docosa-10(15),11,13-triene-16,18-dicarboxylate is found in Kopsia singapurensis. Based on a literature review very few articles have been published on Kopsimaline C.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309052222302D          

 35 41  0  0  1  0            999 V2000
    9.3622    1.4481    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8314    2.0796    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.0190    1.9356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4882    2.5672    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7375    1.1602    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.1555    0.4361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5391   -0.1122    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7058   -0.9202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4889   -1.1799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1053   -0.6315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8884   -0.8912    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.5048   -0.3428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9386    0.1765    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5550    0.7248    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6721   -0.0489    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.7579   -0.9062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2566   -1.5711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5773   -1.0544    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.7636   -1.3117    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0878   -0.7977    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.3988   -0.3439    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1363    0.0259    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.9473    0.3611    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5983    0.7108    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3132    0.5085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9394    0.8680    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1672    1.3777    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.7927    1.9156    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8209    2.1265    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2962    2.8008    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9993    2.2010    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6530    2.9498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2637    1.2356    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.7386    1.8719    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7173   -0.1867    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 10 13  2  0  0  0  0
  6 13  1  0  0  0  0
 13 14  1  0  0  0  0
 15  7  1  6  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  6  0  0  0
 22 21  1  6  0  0  0
 20 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
  5 26  1  0  0  0  0
 15 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  6  0  0  0
 27 29  1  0  0  0  0
 29 30  2  0  0  0  0
 29 31  1  0  0  0  0
 31 32  1  0  0  0  0
 27 33  1  0  0  0  0
 23 33  1  0  0  0  0
 33 34  1  1  0  0  0
 23 35  1  0  0  0  0
 35 18  1  1  0  0  0
 15 35  1  0  0  0  0
M  END


  Mrv1652309052222302D          

 35 41  0  0  1  0            999 V2000
    9.3622    1.4481    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8314    2.0796    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.0190    1.9356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4882    2.5672    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7375    1.1602    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.1555    0.4361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5391   -0.1122    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7058   -0.9202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4889   -1.1799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1053   -0.6315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8884   -0.8912    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.5048   -0.3428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9386    0.1765    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5550    0.7248    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6721   -0.0489    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.7579   -0.9062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2566   -1.5711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5773   -1.0544    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.7636   -1.3117    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0878   -0.7977    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.3988   -0.3439    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1363    0.0259    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.9473    0.3611    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5983    0.7108    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3132    0.5085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9394    0.8680    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1672    1.3777    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.7927    1.9156    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8209    2.1265    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2962    2.8008    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9993    2.2010    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6530    2.9498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2637    1.2356    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.7386    1.8719    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7173   -0.1867    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 10 13  2  0  0  0  0
  6 13  1  0  0  0  0
 13 14  1  0  0  0  0
 15  7  1  6  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  6  0  0  0
 22 21  1  6  0  0  0
 20 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
  5 26  1  0  0  0  0
 15 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  6  0  0  0
 27 29  1  0  0  0  0
 29 30  2  0  0  0  0
 29 31  1  0  0  0  0
 31 32  1  0  0  0  0
 27 33  1  0  0  0  0
 23 33  1  0  0  0  0
 33 34  1  1  0  0  0
 23 35  1  0  0  0  0
 35 18  1  1  0  0  0
 15 35  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0219503

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)N1C2=C(C=CC(OC)=C2O)[C@@]23CCN4C[C@@H]5O[C@@H]5C5(CCC12[C@@](O)([C@@H]5O)C(=O)OC)[C@@H]34

> <INCHI_IDENTIFIER>
InChI=1S/C24H28N2O9/c1-32-12-5-4-11-14(15(12)27)26(20(30)34-3)23-7-6-21(18(28)24(23,31)19(29)33-2)16-13(35-16)10-25-9-8-22(11,23)17(21)25/h4-5,13,16-18,27-28,31H,6-10H2,1-3H3/t13-,16-,17-,18+,21?,22+,23?,24+/m0/s1

> <INCHI_KEY>
GXDHEFQHGXMJAL-RUSVUQAZSA-N

> <FORMULA>
C24H28N2O9

> <MOLECULAR_WEIGHT>
488.493

> <EXACT_MASS>
488.17948049

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
63

> <JCHEM_AVERAGE_POLARIZABILITY>
48.18143369752346

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
16,18-dimethyl (2R,4S,9R,18R,19R,22R)-14,18,19-trihydroxy-13-methoxy-3-oxa-6,16-diazaheptacyclo[15.2.2.1^{1,6}.0^{2,4}.0^{9,17}.0^{10,15}.0^{9,22}]docosa-10(15),11,13-triene-16,18-dicarboxylate

> <JCHEM_LOGP>
-0.6257075921007088

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
10.769297272647066

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.97568354107181

> <JCHEM_PKA_STRONGEST_BASIC>
7.614498509113217

> <JCHEM_POLAR_SURFACE_AREA>
141.53

> <JCHEM_REFRACTIVITY>
116.55569999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
16,18-dimethyl (2R,4S,9R,18R,19R,22R)-14,18,19-trihydroxy-13-methoxy-3-oxa-6,16-diazaheptacyclo[15.2.2.1^{1,6}.0^{2,4}.0^{9,17}.0^{10,15}.0^{9,22}]docosa-10(15),11,13-triene-16,18-dicarboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 05-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   05-SEP-22         0                                  
HETATM    1  C   UNK     0      17.476   2.703   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      16.485   3.882   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      14.969   3.613   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      13.978   4.792   0.000  0.00  0.00           O+0
HETATM    5  N   UNK     0      14.443   2.166   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0      15.224   0.814   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      14.073  -0.210   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      14.384  -1.718   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      15.846  -2.202   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      16.997  -1.179   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      18.458  -1.664   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      19.609  -0.640   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      16.685   0.329   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      17.836   1.353   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      12.455  -0.091   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      12.615  -1.692   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      11.679  -2.933   0.000  0.00  0.00           C+0
HETATM   18  N   UNK     0      10.411  -1.968   0.000  0.00  0.00           N+0
HETATM   19  C   UNK     0       8.892  -2.448   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       7.631  -1.489   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       6.345  -0.642   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       7.721   0.048   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       9.235   0.674   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      10.450   1.327   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      11.785   0.949   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      12.954   1.620   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      11.512   2.572   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      12.680   3.576   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      10.866   3.969   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      11.753   5.228   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0       9.332   4.109   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       8.686   5.506   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       9.826   2.306   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       8.845   3.494   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0      10.672  -0.349   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6   26                                                  
CONECT    6    5    7   13                                                  
CONECT    7    6    8   15                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   13                                                  
CONECT   11   10   12                                                       
CONECT   12   11                                                            
CONECT   13   10    6   14                                                  
CONECT   14   13                                                            
CONECT   15    7   16   26   35                                             
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   35                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20   22                                                       
CONECT   22   21   20   23                                                  
CONECT   23   22   24   33   35                                             
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25    5   15   27                                             
CONECT   27   26   28   29   33                                             
CONECT   28   27                                                            
CONECT   29   27   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29   32                                                       
CONECT   32   31                                                            
CONECT   33   27   23   34                                                  
CONECT   34   33                                                            
CONECT   35   23   18   15                                                  
MASTER        0    0    0    0    0    0    0    0   35    0   82    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₄H₂₈N₂O₉

Average Mass

488.4930 Da

Monoisotopic Mass

488.17948 Da

IUPAC Name

16,18-dimethyl (2R,4S,9R,18R,19R,22R)-14,18,19-trihydroxy-13-methoxy-3-oxa-6,16-diazaheptacyclo[15.2.2.1^{1,6}.0^{2,4}.0^{9,17}.0^{10,15}.0^{9,22}]docosa-10(15),11,13-triene-16,18-dicarboxylate

Traditional Name

16,18-dimethyl (2R,4S,9R,18R,19R,22R)-14,18,19-trihydroxy-13-methoxy-3-oxa-6,16-diazaheptacyclo[15.2.2.1^{1,6}.0^{2,4}.0^{9,17}.0^{10,15}.0^{9,22}]docosa-10(15),11,13-triene-16,18-dicarboxylate

CAS Registry Number

Not Available

SMILES

COC(=O)N1C2=C(C=CC(OC)=C2O)[C@@]23CCN4C[C@@H]5O[C@@H]5C5(CCC12[C@@](O)([C@@H]5O)C(=O)OC)[C@@H]34

InChI Identifier

InChI=1S/C24H28N2O9/c1-32-12-5-4-11-14(15(12)27)26(20(30)34-3)23-7-6-21(18(28)24(23,31)19(29)33-2)16-13(35-16)10-25-9-8-22(11,23)17(21)25/h4-5,13,16-18,27-28,31H,6-10H2,1-3H3/t13-,16-,17-,18+,21?,22+,23?,24+/m0/s1

InChI Key

GXDHEFQHGXMJAL-RUSVUQAZSA-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
Kopsia singapurensis	LOTUS Database	35616633

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
Indolecarboxylic acid derivative
Indolecarboxylic acid
Quinolidine
Azaspirodecane
Indolizidine
Indole or derivatives
Anisole
1-hydroxy-4-unsubstituted benzenoid
Aralkylamine
Epoxypiperidine
Beta-hydroxy acid
Alkyl aryl ether
Para-oxazepine
Benzenoid
N-alkylpyrrolidine
Piperidine
Hydroxy acid
Methyl ester
Carbamic acid ester
Tertiary alcohol
Pyrrolidine
Cyclic alcohol
Tertiary aliphatic amine
Tertiary amine
Secondary alcohol
Carbonic acid derivative
Carboxylic acid ester
Amino acid or derivatives
1,2-diol
Oxacycle
Azacycle
Organoheterocyclic compound
Polyol
Monocarboxylic acid or derivatives
Ether
Oxirane
Dialkyl ether
Carboxylic acid derivative
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Carbonyl group
Amine
Alcohol
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	-0.63	ChemAxon
pKa (Strongest Acidic)	8.98	ChemAxon
pKa (Strongest Basic)	7.61	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	141.53 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	116.56 m³·mol⁻¹	ChemAxon
Polarizability	48.18 Å³	ChemAxon
Number of Rings	7	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

C00039584

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

101864232

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 16,18-dimethyl (2r,4s,9r,18r,19r,22r)-14,18,19-trihydroxy-13-methoxy-3-oxa-6,16-diazaheptacyclo[15.2.2.1¹,⁶.0²,⁴.0⁹,¹⁷.0¹⁰,¹⁵.0⁹,²²]docosa-10(15),11,13-triene-16,18-dicarboxylate (NP0219503)

MOL for NP0219503 (16,18-dimethyl (2r,4s,9r,18r,19r,22r)-14,18,19-trihydroxy-13-methoxy-3-oxa-6,16-diazaheptacyclo[15.2.2.1¹,⁶.0²,⁴.0⁹,¹⁷.0¹⁰,¹⁵.0⁹,²²]docosa-10(15),11,13-triene-16,18-dicarboxylate)

3D MOL for NP0219503 (16,18-dimethyl (2r,4s,9r,18r,19r,22r)-14,18,19-trihydroxy-13-methoxy-3-oxa-6,16-diazaheptacyclo[15.2.2.1¹,⁶.0²,⁴.0⁹,¹⁷.0¹⁰,¹⁵.0⁹,²²]docosa-10(15),11,13-triene-16,18-dicarboxylate)

3D SDF for NP0219503 (16,18-dimethyl (2r,4s,9r,18r,19r,22r)-14,18,19-trihydroxy-13-methoxy-3-oxa-6,16-diazaheptacyclo[15.2.2.1¹,⁶.0²,⁴.0⁹,¹⁷.0¹⁰,¹⁵.0⁹,²²]docosa-10(15),11,13-triene-16,18-dicarboxylate)

3D-SDF for NP0219503 (16,18-dimethyl (2r,4s,9r,18r,19r,22r)-14,18,19-trihydroxy-13-methoxy-3-oxa-6,16-diazaheptacyclo[15.2.2.1¹,⁶.0²,⁴.0⁹,¹⁷.0¹⁰,¹⁵.0⁹,²²]docosa-10(15),11,13-triene-16,18-dicarboxylate)

PDB for NP0219503 (16,18-dimethyl (2r,4s,9r,18r,19r,22r)-14,18,19-trihydroxy-13-methoxy-3-oxa-6,16-diazaheptacyclo[15.2.2.1¹,⁶.0²,⁴.0⁹,¹⁷.0¹⁰,¹⁵.0⁹,²²]docosa-10(15),11,13-triene-16,18-dicarboxylate)

3D PDB for NP0219503 (16,18-dimethyl (2r,4s,9r,18r,19r,22r)-14,18,19-trihydroxy-13-methoxy-3-oxa-6,16-diazaheptacyclo[15.2.2.1¹,⁶.0²,⁴.0⁹,¹⁷.0¹⁰,¹⁵.0⁹,²²]docosa-10(15),11,13-triene-16,18-dicarboxylate)

SMILES for NP0219503 (16,18-dimethyl (2r,4s,9r,18r,19r,22r)-14,18,19-trihydroxy-13-methoxy-3-oxa-6,16-diazaheptacyclo[15.2.2.1¹,⁶.0²,⁴.0⁹,¹⁷.0¹⁰,¹⁵.0⁹,²²]docosa-10(15),11,13-triene-16,18-dicarboxylate)

INCHI for NP0219503 (16,18-dimethyl (2r,4s,9r,18r,19r,22r)-14,18,19-trihydroxy-13-methoxy-3-oxa-6,16-diazaheptacyclo[15.2.2.1¹,⁶.0²,⁴.0⁹,¹⁷.0¹⁰,¹⁵.0⁹,²²]docosa-10(15),11,13-triene-16,18-dicarboxylate)

Structure for NP0219503 (16,18-dimethyl (2r,4s,9r,18r,19r,22r)-14,18,19-trihydroxy-13-methoxy-3-oxa-6,16-diazaheptacyclo[15.2.2.1¹,⁶.0²,⁴.0⁹,¹⁷.0¹⁰,¹⁵.0⁹,²²]docosa-10(15),11,13-triene-16,18-dicarboxylate)

3D Structure for NP0219503 (16,18-dimethyl (2r,4s,9r,18r,19r,22r)-14,18,19-trihydroxy-13-methoxy-3-oxa-6,16-diazaheptacyclo[15.2.2.1¹,⁶.0²,⁴.0⁹,¹⁷.0¹⁰,¹⁵.0⁹,²²]docosa-10(15),11,13-triene-16,18-dicarboxylate)