NP-MRD: Showing NP-Card for methyl (2s,3r,12s,14r)-12-hydroxy-13-oxo-10,16-diazaheptacyclo[9.8.2.1¹,¹².0²,¹⁶.0³,¹¹.0³,¹⁴.0⁴,⁹]docosa-4,6,8-triene-10-carboxylate (NP0184646)

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Record Information

Version

2.0

Created at

2022-09-03 23:49:22 UTC

Updated at

2022-09-03 23:49:23 UTC

NP-MRD ID

NP0184646

Secondary Accession Numbers

None

Natural Product Identification

Common Name

methyl (2s,3r,12s,14r)-12-hydroxy-13-oxo-10,16-diazaheptacyclo[9.8.2.1¹,¹².0²,¹⁶.0³,¹¹.0³,¹⁴.0⁴,⁹]docosa-4,6,8-triene-10-carboxylate

Description

Kopsine 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 (2s,3r,12s,14r)-12-hydroxy-13-oxo-10,16-diazaheptacyclo[9.8.2.1¹,¹².0²,¹⁶.0³,¹¹.0³,¹⁴.0⁴,⁹]docosa-4,6,8-triene-10-carboxylate was first documented in 2005 (PMID: 15818570). Based on a literature review a small amount of articles have been published on Kopsine (PMID: 28230294) (PMID: 26717050).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309042201492D          

 28 34  0  0  1  0            999 V2000
    4.9243   -1.7325    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1001   -1.6965    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6736   -0.8775    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8746   -1.4679    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2135    0.1487    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0298    0.5759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2086    0.4968    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8665   -0.2539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3455   -0.9255    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1667   -0.8465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5089   -0.0958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4865    0.3072    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.5021    0.1411    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.1840    0.6777    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.9088    0.1793    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8440   -0.6576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0578   -0.9765    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3728   -0.4132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6606    0.6067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0617    1.2759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1498    0.9033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9964    0.0594    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1706   -0.3899    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5665   -0.7207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6527    0.9375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0581    1.6642    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6270    1.1385    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.6087    1.3527    0.0000 C   0  0  0  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  2  0  0  0  0
  6 11  1  0  0  0  0
 12 11  1  6  0  0  0
 12 13  1  0  0  0  0
 13 14  1  1  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 13 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
  5 21  1  0  0  0  0
 12 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  6  0  0  0
 22 24  1  0  0  0  0
 18 24  1  0  0  0  0
 22 25  1  0  0  0  0
 25 26  2  0  0  0  0
 27 25  1  1  0  0  0
 12 27  1  0  0  0  0
 27 28  1  0  0  0  0
 14 28  1  0  0  0  0
M  END

     RDKit          3D

 52 58  0  0  0  0  0  0  0  0999 V2000
    4.7051   -1.5829   -1.9681 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4352   -1.3466   -1.4126 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2403   -0.2331   -0.6144 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2759    0.5201   -0.4413 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0409    0.1394    0.0103 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8973    1.2906    0.8412 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8056    2.0788    1.5519 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3766    3.1566    2.2982 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0407    3.4939    2.3693 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1534    2.7212    1.6727 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5697    1.6449    0.9257 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1631    0.6968    0.1096 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4738    0.2578    0.6476 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.4144    1.0719   -0.0502 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7634    0.6716   -0.0020 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9940   -0.8079   -0.1589 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0166   -1.6437    0.5946 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6111   -1.2189    0.3839 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7073   -1.9110    1.3904 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6852   -1.4396    1.1531 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7792   -0.4857   -0.0164 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2844   -1.0911   -1.2741 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0517   -2.0637   -1.8519 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1350   -1.6184   -0.9755 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0545    0.0782   -2.1664 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2188    0.0845   -3.3587 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3989    1.1797   -1.3071 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.8879    1.4000   -1.3306 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2969   -2.3197   -1.3963 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5204   -1.9719   -3.0105 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2614   -0.6308   -2.0062 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8625    1.8316    1.5104 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1133    3.7423    2.8347 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6664    4.3295    2.9422 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9119    2.9844    1.7251 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5275    0.4174    1.7307 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3050    1.1618   -0.8638 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2546    1.0493    0.9055 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0019   -1.0896   -1.2147 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0117   -1.0133    0.2841 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1932   -2.7051    0.3193 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2201   -1.5916    1.7045 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8136   -3.0094    1.3705 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0011   -1.5753    2.4267 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3109   -2.3117    0.9027 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1514   -0.9475    2.0257 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1196   -2.8216   -1.2459 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8330   -1.3670   -1.7859 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0381   -2.7286   -0.9789 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1880    2.0804   -1.5414 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0328    2.5117   -1.4729 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3953    0.9312   -2.1858 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 27  1  0
 27 28  1  0
 28 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  0
 22 23  1  6
 22 24  1  0
 22 25  1  0
 25 26  2  0
 18 13  1  0
 21  5  1  6
 11  6  1  0
 21 12  1  0
 13 12  1  0
 25 27  1  0
 13 14  1  0
 24 18  1  0
  1 29  1  0
  1 30  1  0
  1 31  1  0
  7 32  1  0
  8 33  1  0
  9 34  1  0
 10 35  1  0
 27 50  1  6
 28 51  1  0
 28 52  1  0
 15 37  1  0
 15 38  1  0
 16 39  1  0
 16 40  1  0
 17 41  1  0
 17 42  1  0
 19 43  1  0
 19 44  1  0
 20 45  1  0
 20 46  1  0
 23 47  1  0
 24 48  1  0
 24 49  1  0
 13 36  1  1
M  END


  Mrv1652309042201492D          

 28 34  0  0  1  0            999 V2000
    4.9243   -1.7325    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1001   -1.6965    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6736   -0.8775    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8746   -1.4679    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2135    0.1487    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0298    0.5759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2086    0.4968    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8665   -0.2539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3455   -0.9255    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1667   -0.8465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5089   -0.0958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4865    0.3072    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.5021    0.1411    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.1840    0.6777    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.9088    0.1793    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8440   -0.6576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0578   -0.9765    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3728   -0.4132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6606    0.6067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0617    1.2759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1498    0.9033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9964    0.0594    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1706   -0.3899    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5665   -0.7207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6527    0.9375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0581    1.6642    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6270    1.1385    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.6087    1.3527    0.0000 C   0  0  0  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  2  0  0  0  0
  6 11  1  0  0  0  0
 12 11  1  6  0  0  0
 12 13  1  0  0  0  0
 13 14  1  1  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 13 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
  5 21  1  0  0  0  0
 12 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  6  0  0  0
 22 24  1  0  0  0  0
 18 24  1  0  0  0  0
 22 25  1  0  0  0  0
 25 26  2  0  0  0  0
 27 25  1  1  0  0  0
 12 27  1  0  0  0  0
 27 28  1  0  0  0  0
 14 28  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0184646

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)N1C2=CC=CC=C2[C@@]23[C@@H]4CN5CCCC6(CCC12[C@@](O)(C6)C4=O)[C@@H]35

> <INCHI_IDENTIFIER>
InChI=1S/C22H24N2O4/c1-28-18(26)24-15-6-3-2-5-13(15)22-14-11-23-10-4-7-19(17(22)23)8-9-21(22,24)20(27,12-19)16(14)25/h2-3,5-6,14,17,27H,4,7-12H2,1H3/t14-,17+,19?,20-,21?,22+/m1/s1

> <INCHI_KEY>
YROYAGSZNDUMIF-FSZVGSISSA-N

> <FORMULA>
C22H24N2O4

> <MOLECULAR_WEIGHT>
380.444

> <EXACT_MASS>
380.173607261

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
52

> <JCHEM_AVERAGE_POLARIZABILITY>
39.557477286243355

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl (2S,3R,12S,14R)-12-hydroxy-13-oxo-10,16-diazaheptacyclo[9.8.2.1^{1,12}.0^{2,16}.0^{3,11}.0^{3,14}.0^{4,9}]docosa-4,6,8-triene-10-carboxylate

> <JCHEM_LOGP>
1.5731823516666663

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
14.610015663242574

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.241485674148677

> <JCHEM_PKA_STRONGEST_BASIC>
8.76979511415103

> <JCHEM_POLAR_SURFACE_AREA>
70.08000000000001

> <JCHEM_REFRACTIVITY>
100.06939999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
methyl (2S,3R,12S,14R)-12-hydroxy-13-oxo-10,16-diazaheptacyclo[9.8.2.1^{1,12}.0^{2,16}.0^{3,11}.0^{3,14}.0^{4,9}]docosa-4,6,8-triene-10-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 04-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-22         0                                  
HETATM    1  C   UNK     0       9.192  -3.234   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       7.653  -3.167   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       6.857  -1.638   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       5.366  -2.740   0.000  0.00  0.00           O+0
HETATM    5  N   UNK     0       5.999   0.278   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0       5.656   1.075   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.123   0.927   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.484  -0.474   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.378  -1.728   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.911  -1.580   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.550  -0.179   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.375   0.573   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      10.271   0.263   0.000  0.00  0.00           C+0
HETATM   14  N   UNK     0      11.543   1.265   0.000  0.00  0.00           N+0
HETATM   15  C   UNK     0      12.896   0.335   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      12.776  -1.227   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      11.308  -1.823   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      10.029  -0.771   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      10.566   1.132   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       9.449   2.382   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       7.746   1.686   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       7.460   0.111   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       5.918  -0.728   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       8.524  -1.345   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       6.818   1.750   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       5.709   3.107   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       8.637   2.125   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      10.469   2.525   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   21                                                  
CONECT    6    5    7   11                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10    6   12                                                  
CONECT   12   11   13   21   27                                             
CONECT   13   12   14   18                                                  
CONECT   14   13   15   28                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   13   19   24                                             
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20    5   12   22                                             
CONECT   22   21   23   24   25                                             
CONECT   23   22                                                            
CONECT   24   22   18                                                       
CONECT   25   22   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   12   28                                                  
CONECT   28   27   14                                                       
MASTER        0    0    0    0    0    0    0    0   28    0   68    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₂H₂₄N₂O₄

Average Mass

380.4440 Da

Monoisotopic Mass

380.17361 Da

IUPAC Name

methyl (2S,3R,12S,14R)-12-hydroxy-13-oxo-10,16-diazaheptacyclo[9.8.2.1^{1,12}.0^{2,16}.0^{3,11}.0^{3,14}.0^{4,9}]docosa-4,6,8-triene-10-carboxylate

Traditional Name

methyl (2S,3R,12S,14R)-12-hydroxy-13-oxo-10,16-diazaheptacyclo[9.8.2.1^{1,12}.0^{2,16}.0^{3,11}.0^{3,14}.0^{4,9}]docosa-4,6,8-triene-10-carboxylate

CAS Registry Number

Not Available

SMILES

COC(=O)N1C2=CC=CC=C2[C@@]23[C@@H]4CN5CCCC6(CCC12[C@@](O)(C6)C4=O)[C@@H]35

InChI Identifier

InChI=1S/C22H24N2O4/c1-28-18(26)24-15-6-3-2-5-13(15)22-14-11-23-10-4-7-19(17(22)23)8-9-21(22,24)20(27,12-19)16(14)25/h2-3,5-6,14,17,27H,4,7-12H2,1H3/t14-,17+,19?,20-,21?,22+/m1/s1

InChI Key

YROYAGSZNDUMIF-FSZVGSISSA-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
2,3-cyclopentanoindoline
Indolecarboxylic acid derivative
Indolecarboxylic acid
Quinolidine
Azaspirodecane
Indolizidine
Indole or derivatives
Aralkylamine
Benzenoid
N-alkylpyrrolidine
Piperidine
Carbamic acid ester
Tertiary alcohol
Pyrrolidine
Cyclic alcohol
Tertiary aliphatic amine
Tertiary amine
Carbonic acid derivative
Ketone
Azacycle
Organoheterocyclic compound
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	1.57	ChemAxon
pKa (Strongest Acidic)	12.24	ChemAxon
pKa (Strongest Basic)	8.77	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	70.08 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	100.07 m³·mol⁻¹	ChemAxon
Polarizability	39.56 Å³	ChemAxon
Number of Rings	7	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

C00038124

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

133550442

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 ]
Yap WS, Gan CY, Sim KS, Lim SH, Low YY, Kam TS: Aspidofractinine and Eburnane Alkaloids from a North Borneo Kopsia. Ring-Contracted, Additional Ring-Fused, and Paucidactine-Type Aspidofractinine Alkaloids from K. pauciflora. J Nat Prod. 2016 Jan 22;79(1):230-9. doi: 10.1021/acs.jnatprod.5b00992. Epub 2015 Dec 30. [PubMed:26717050 ]
Glover RP, Yoganathan K, Butler MS: NMR spectral assignments of three aspidofractinine alkaloids, kopsine, fruticosine and fruticosamine. Magn Reson Chem. 2005 Jun;43(6):483-5. doi: 10.1002/mrc.1580. [PubMed:15818570 ]
LOTUS database [Link]

Showing NP-Card for methyl (2s,3r,12s,14r)-12-hydroxy-13-oxo-10,16-diazaheptacyclo[9.8.2.1¹,¹².0²,¹⁶.0³,¹¹.0³,¹⁴.0⁴,⁹]docosa-4,6,8-triene-10-carboxylate (NP0184646)

MOL for NP0184646 (methyl (2s,3r,12s,14r)-12-hydroxy-13-oxo-10,16-diazaheptacyclo[9.8.2.1¹,¹².0²,¹⁶.0³,¹¹.0³,¹⁴.0⁴,⁹]docosa-4,6,8-triene-10-carboxylate)

3D MOL for NP0184646 (methyl (2s,3r,12s,14r)-12-hydroxy-13-oxo-10,16-diazaheptacyclo[9.8.2.1¹,¹².0²,¹⁶.0³,¹¹.0³,¹⁴.0⁴,⁹]docosa-4,6,8-triene-10-carboxylate)

3D SDF for NP0184646 (methyl (2s,3r,12s,14r)-12-hydroxy-13-oxo-10,16-diazaheptacyclo[9.8.2.1¹,¹².0²,¹⁶.0³,¹¹.0³,¹⁴.0⁴,⁹]docosa-4,6,8-triene-10-carboxylate)

3D-SDF for NP0184646 (methyl (2s,3r,12s,14r)-12-hydroxy-13-oxo-10,16-diazaheptacyclo[9.8.2.1¹,¹².0²,¹⁶.0³,¹¹.0³,¹⁴.0⁴,⁹]docosa-4,6,8-triene-10-carboxylate)

PDB for NP0184646 (methyl (2s,3r,12s,14r)-12-hydroxy-13-oxo-10,16-diazaheptacyclo[9.8.2.1¹,¹².0²,¹⁶.0³,¹¹.0³,¹⁴.0⁴,⁹]docosa-4,6,8-triene-10-carboxylate)

3D PDB for NP0184646 (methyl (2s,3r,12s,14r)-12-hydroxy-13-oxo-10,16-diazaheptacyclo[9.8.2.1¹,¹².0²,¹⁶.0³,¹¹.0³,¹⁴.0⁴,⁹]docosa-4,6,8-triene-10-carboxylate)

SMILES for NP0184646 (methyl (2s,3r,12s,14r)-12-hydroxy-13-oxo-10,16-diazaheptacyclo[9.8.2.1¹,¹².0²,¹⁶.0³,¹¹.0³,¹⁴.0⁴,⁹]docosa-4,6,8-triene-10-carboxylate)

INCHI for NP0184646 (methyl (2s,3r,12s,14r)-12-hydroxy-13-oxo-10,16-diazaheptacyclo[9.8.2.1¹,¹².0²,¹⁶.0³,¹¹.0³,¹⁴.0⁴,⁹]docosa-4,6,8-triene-10-carboxylate)

Structure for NP0184646 (methyl (2s,3r,12s,14r)-12-hydroxy-13-oxo-10,16-diazaheptacyclo[9.8.2.1¹,¹².0²,¹⁶.0³,¹¹.0³,¹⁴.0⁴,⁹]docosa-4,6,8-triene-10-carboxylate)

3D Structure for NP0184646 (methyl (2s,3r,12s,14r)-12-hydroxy-13-oxo-10,16-diazaheptacyclo[9.8.2.1¹,¹².0²,¹⁶.0³,¹¹.0³,¹⁴.0⁴,⁹]docosa-4,6,8-triene-10-carboxylate)