NP-MRD: Showing NP-Card for Methyl chanofruticosinate (NP0066923)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-04-28 11:08:44 UTC

Updated at

2022-04-28 11:08:44 UTC

NP-MRD ID

NP0066923

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Methyl chanofruticosinate

Description

Methyl chanofruticosinate 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. Methyl chanofruticosinate is found in Kopsia arborea, Kopsia dasyrachis and Kopsia officinalis. Methyl chanofruticosinate was first documented in 2003 (PMID: 12608641). Based on a literature review a small amount of articles have been published on Methyl chanofruticosinate (PMID: 28230294) (PMID: 29295627) (PMID: 17631924).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282213082D          

 30 35  0  0  1  0            999 V2000
    5.8139    1.1232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3828    0.5257    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1498   -0.2657    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3479   -0.4597    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7790    0.1378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0120    0.9292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9278   -0.1068    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.0497   -0.9559    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.8855   -1.1411    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.1902   -1.9078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6786   -2.5550    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0065   -2.0273    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3112   -2.7940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3622   -1.4477    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5937   -1.1083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5794   -0.2426    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.0013    0.1143    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6240    0.9665    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8172    1.0932    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3623    0.4047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7358   -0.3455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3417    1.2996    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1409    0.6868    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.7997    1.2214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9743    2.0278    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9797    0.6884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2148   -1.7642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2082   -2.5892    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5973   -2.3113    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7623   -3.1197    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  1  6  1  0  0  0  0
  7  5  1  1  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  4  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
  8 14  1  0  0  0  0
 14 15  1  0  0  0  0
 16 15  1  6  0  0  0
 16 17  1  0  0  0  0
  7 17  1  0  0  0  0
 17 18  1  6  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 16 21  1  0  0  0  0
 18 22  1  0  0  0  0
 23 22  1  1  0  0  0
  7 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 24 26  1  0  0  0  0
 16 26  1  0  0  0  0
  8 27  1  6  0  0  0
 27 28  2  0  0  0  0
 27 29  1  0  0  0  0
 29 30  1  0  0  0  0
M  END

     RDKit          3D

 56 61  0  0  0  0  0  0  0  0999 V2000
   -5.5610    0.7333    1.3539 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3135    0.1252    1.2281 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2521    0.6204    0.5048 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4382    1.7117   -0.0855 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0136   -0.0955    0.4482 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6956   -1.3308    1.0560 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4862   -2.1421    1.8586 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9977   -3.3197    2.3806 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7090   -3.7122    2.1122 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0711   -2.8818    1.3021 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4029   -1.7040    0.7734 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1611   -0.6351   -0.0905 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3431    0.0305    0.6738 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2178   -1.0840    0.7868 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5134   -0.7584    1.3227 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1068    0.4865    0.7224 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1627    1.6189    0.5514 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8500    1.1720   -0.1105 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8182    2.2819    0.0051 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5507    1.7450    0.3065 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8350    0.4023   -0.3101 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3871    0.5963   -1.6708 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3474   -0.0911   -2.1262 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8722    1.5563   -2.5078 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3456    1.8100   -3.8156 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1392    0.9717   -1.5507 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4327   -0.1814   -2.1465 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2797   -0.2680   -3.3314 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9340   -1.2176   -1.2000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2422   -1.6746   -0.5029 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9796    0.6362    2.3967 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5568    1.7803    1.0294 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2814    0.1461    0.7127 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5101   -1.8327    2.0735 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6122   -3.9598    3.0099 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3334   -4.6379    2.5261 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0701   -3.2578    1.1538 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9234    0.3921    1.6185 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1812   -1.6074    1.1748 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4005   -0.5923    2.4137 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6171    0.2080   -0.2354 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9224    0.8158    1.4006 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6120    2.3402   -0.1715 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9800    2.1724    1.4750 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7983    2.8850   -0.9249 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1719    2.9584    0.8084 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2711    2.4691   -0.1254 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6939    1.7709    1.4038 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6693    2.8800   -3.8312 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2853    1.2230   -4.0316 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5868    1.6866   -4.5885 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8042    1.8845   -2.1285 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2368    0.9430   -1.7783 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4578   -2.0712   -1.7163 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1415   -1.2639   -1.0830 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3986   -2.7346   -0.5205 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 12 11  1  1
 12 29  1  0
 29 30  1  0
 30 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 18 17  1  1
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  6
 22 23  2  0
 22 24  1  0
 24 25  1  0
 18 26  1  0
 26 27  1  0
 27 28  2  0
 18 13  1  0
 21  5  1  0
 11  6  1  0
 21 12  1  0
 13 12  1  0
 27 29  1  0
 13 14  1  0
  1 31  1  0
  1 32  1  0
  1 33  1  0
  7 34  1  0
  8 35  1  0
  9 36  1  0
 10 37  1  0
 29 54  1  6
 30 55  1  0
 30 56  1  0
 15 39  1  0
 15 40  1  0
 16 41  1  0
 16 42  1  0
 17 43  1  0
 17 44  1  0
 19 45  1  0
 19 46  1  0
 20 47  1  0
 20 48  1  0
 25 49  1  0
 25 50  1  0
 25 51  1  0
 26 52  1  0
 26 53  1  0
 13 38  1  1
M  END


  Mrv1652304282213082D          

 30 35  0  0  1  0            999 V2000
    5.8139    1.1232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3828    0.5257    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1498   -0.2657    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3479   -0.4597    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7790    0.1378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0120    0.9292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9278   -0.1068    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.0497   -0.9559    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.8855   -1.1411    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.1902   -1.9078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6786   -2.5550    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0065   -2.0273    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3112   -2.7940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3622   -1.4477    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5937   -1.1083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5794   -0.2426    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.0013    0.1143    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6240    0.9665    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8172    1.0932    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3623    0.4047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7358   -0.3455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3417    1.2996    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1409    0.6868    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.7997    1.2214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9743    2.0278    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9797    0.6884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2148   -1.7642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2082   -2.5892    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5973   -2.3113    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7623   -3.1197    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  1  6  1  0  0  0  0
  7  5  1  1  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  4  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
  8 14  1  0  0  0  0
 14 15  1  0  0  0  0
 16 15  1  6  0  0  0
 16 17  1  0  0  0  0
  7 17  1  0  0  0  0
 17 18  1  6  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 16 21  1  0  0  0  0
 18 22  1  0  0  0  0
 23 22  1  1  0  0  0
  7 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 24 26  1  0  0  0  0
 16 26  1  0  0  0  0
  8 27  1  6  0  0  0
 27 28  2  0  0  0  0
 27 29  1  0  0  0  0
 29 30  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0066923

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)N1C2=CC=CC=C2[C@@]23[C@@H]4CN5CCC[C@@](CC[C@]12C(=O)OC)(CC4=O)[C@@H]35

> <INCHI_IDENTIFIER>
InChI=1S/C23H26N2O5/c1-29-19(27)22-10-9-21-8-5-11-24-13-15(17(26)12-21)23(22,18(21)24)14-6-3-4-7-16(14)25(22)20(28)30-2/h3-4,6-7,15,18H,5,8-13H2,1-2H3/t15-,18+,21-,22-,23+/m1/s1

> <INCHI_KEY>
WLIDZKOEMWHMRI-UYUNAAPYSA-N

> <FORMULA>
C23H26N2O5

> <MOLECULAR_WEIGHT>
410.47

> <EXACT_MASS>
410.184171945

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
56

> <JCHEM_AVERAGE_POLARIZABILITY>
42.377914087543374

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4,5-dimethyl (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-4,5-dicarboxylate

> <ALOGPS_LOGP>
1.79

> <JCHEM_LOGP>
2.0235024189999997

> <ALOGPS_LOGS>
-2.56

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
15.83278857341951

> <JCHEM_PKA_STRONGEST_BASIC>
8.292400844151018

> <JCHEM_POLAR_SURFACE_AREA>
76.15

> <JCHEM_REFRACTIVITY>
106.98439999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.14e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4,5-dimethyl (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-4,5-dicarboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0      10.853   2.097   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      11.915   0.981   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      11.480  -0.496   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       9.983  -0.858   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.921   0.257   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       9.356   1.735   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.332  -0.199   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.559  -1.784   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0       9.120  -2.130   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0       9.688  -3.561   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       8.733  -4.769   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0      11.212  -3.784   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      11.781  -5.215   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.276  -2.702   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.842  -2.069   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.815  -0.453   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.602   0.213   0.000  0.00  0.00           C+0
HETATM   18  N   UNK     0       4.898   1.804   0.000  0.00  0.00           N+0
HETATM   19  C   UNK     0       3.392   2.041   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.543   0.755   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       3.240  -0.645   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       6.238   2.426   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       7.730   1.282   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       7.093   2.280   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       7.419   3.785   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       5.562   1.285   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       7.868  -3.293   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       7.855  -4.833   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0       6.715  -4.314   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       7.023  -5.823   0.000  0.00  0.00           C+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5    9                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5    1                                                       
CONECT    7    5    8   17   23                                             
CONECT    8    7    9   14   27                                             
CONECT    9    8    4   10                                                  
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12                                                            
CONECT   14    8   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   21   26                                             
CONECT   17   16    7   18                                                  
CONECT   18   17   19   22                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   16                                                       
CONECT   22   18   23                                                       
CONECT   23   22    7   24                                                  
CONECT   24   23   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   16                                                       
CONECT   27    8   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   30                                                       
CONECT   30   29                                                            
MASTER        0    0    0    0    0    0    0    0   30    0   70    0
END

View in JSmol

Synonyms

Value	Source
Methyl chanofruticosinic acid	Generator

Chemical Formula

C₂₃H₂₆N₂O₅

Average Mass

410.4700 Da

Monoisotopic Mass

410.18417 Da

IUPAC Name

4,5-dimethyl (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-4,5-dicarboxylate

Traditional Name

4,5-dimethyl (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-4,5-dicarboxylate

CAS Registry Number

Not Available

SMILES

COC(=O)N1C2=CC=CC=C2[C@@]23[C@@H]4CN5CCC[C@@](CC[C@]12C(=O)OC)(CC4=O)[C@@H]35

InChI Identifier

InChI=1S/C23H26N2O5/c1-29-19(27)22-10-9-21-8-5-11-24-13-15(17(26)12-21)23(22,18(21)24)14-6-3-4-7-16(14)25(22)20(28)30-2/h3-4,6-7,15,18H,5,8-13H2,1-2H3/t15-,18+,21-,22-,23+/m1/s1

InChI Key

WLIDZKOEMWHMRI-UYUNAAPYSA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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 arborea	LOTUS Database	35616633
Kopsia dasyrachis	Plant	KNApSAcK
Kopsia officinalis	Plant	KNApSAcK

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
Alpha-amino acid ester
Carbazole
Indolecarboxylic acid derivative
Indolecarboxylic acid
Alpha-amino acid or derivatives
Quinolidine
Indole or derivatives
Indolizidine
Azepane
Aralkylamine
Benzenoid
N-alkylpyrrolidine
Piperidine
Methyl ester
Carbamic acid ester
Pyrrolidine
Tertiary aliphatic amine
Amino acid or derivatives
Carboxylic acid ester
Tertiary amine
Ketone
Azacycle
Organoheterocyclic compound
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Carbonyl group
Organic oxygen compound
Organic nitrogen compound
Hydrocarbon derivative
Amine
Organooxygen compound
Organonitrogen 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	1.79	ALOGPS
logP	2.02	ChemAxon
logS	-2.6	ALOGPS
pKa (Strongest Acidic)	15.83	ChemAxon
pKa (Strongest Basic)	8.29	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	76.15 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	106.98 m³·mol⁻¹	ChemAxon
Polarizability	42.38 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

C00024581

Chemspider ID

28424371

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

91895274

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Leng L, Zhou X, Liao Q, Wang F, Song H, Zhang D, Liu XY, Qin Y: Asymmetric Total Syntheses of Kopsia Indole Alkaloids. Angew Chem Int Ed Engl. 2017 Mar 20;56(13):3703-3707. doi: 10.1002/anie.201700831. Epub 2017 Feb 23. [PubMed:28230294 ]
Husain K, Jantan I, Said IM, Aimi N, Takayama H: Two new methyl chanofruticosinates from Kopsia flavida blume. J Asian Nat Prod Res. 2003 Mar;5(1):63-7. doi: 10.1080/1028602031000080487. [PubMed:12608641 ]
Wang JF, Wang Y, Wang HL, Xu CB, Wang HT: Methyl chanofruticosinate type alkaloids from the aerial parts of Kopsia lancibracteolata Merr. J Asian Nat Prod Res. 2019 Mar;21(3):227-233. doi: 10.1080/10286020.2017.1418860. Epub 2018 Jan 3. [PubMed:29295627 ]
Lim KH, Kam TS: Methyl chanofruticosinate alkaloids from Kopsia arborea. Phytochemistry. 2008 Jan;69(2):558-61. doi: 10.1016/j.phytochem.2007.06.001. Epub 2007 Jul 12. [PubMed:17631924 ]

Showing NP-Card for Methyl chanofruticosinate (NP0066923)

MOL for NP0066923 (Methyl chanofruticosinate)

3D MOL for NP0066923 (Methyl chanofruticosinate)

3D SDF for NP0066923 (Methyl chanofruticosinate)

3D-SDF for NP0066923 (Methyl chanofruticosinate)

PDB for NP0066923 (Methyl chanofruticosinate)

3D PDB for NP0066923 (Methyl chanofruticosinate)

SMILES for NP0066923 (Methyl chanofruticosinate)

INCHI for NP0066923 (Methyl chanofruticosinate)

Structure for NP0066923 (Methyl chanofruticosinate)

3D Structure for NP0066923 (Methyl chanofruticosinate)