NP-MRD: Showing NP-Card for Kopsinitarine D (NP0066906)

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Record Information

Version

2.0

Created at

2022-04-28 11:07:55 UTC

Updated at

2022-04-28 11:07:55 UTC

NP-MRD ID

NP0066906

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Kopsinitarine D

Description

Methyl (1R,2R,4R,5R,7R,11S,12S,15S,23R)-4,11-dihydroxy-18-methoxy-3-oxo-6-oxa-8,16-diazaoctacyclo[10.10.1.0¹,¹⁵.0²,⁷.0⁴,¹⁵.0⁵,¹².0⁸,²³.0¹⁷,²²]Tricosa-17(22),18,20-triene-16-carboxylate 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. Kopsinitarine D is found in Kopsia teoi. Based on a literature review very few articles have been published on methyl (1R,2R,4R,5R,7R,11S,12S,15S,23R)-4,11-dihydroxy-18-methoxy-3-oxo-6-oxa-8,16-diazaoctacyclo[10.10.1.0¹,¹⁵.0²,⁷.0⁴,¹⁵.0⁵,¹².0⁸,²³.0¹⁷,²²]Tricosa-17(22),18,20-triene-16-carboxylate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282213072D          

 32 39  0  0  1  0            999 V2000
    5.9834   -1.4408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3499   -0.7017    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8930   -0.0147    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0697   -0.0669    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7032   -0.8060    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1601   -1.4930    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6909   -0.6015    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.3535   -0.0726    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.1730   -0.7289    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.7010   -1.6829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5628   -1.7602    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8099   -2.6093    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1485   -3.1024    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8111    0.7607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9367    0.6146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9032   -0.5306    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7151    0.1487    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7652   -0.1630    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3251   -0.9096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7699   -1.6034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5768   -1.4653    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7523   -2.3084    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2159    0.2356    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1741   -0.8626    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0994   -1.1804    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.0545   -0.8801    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.1012   -1.7555    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9915    0.2052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5645    0.9478    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2459    0.0947    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.3704    0.7228    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2162    0.9297    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  6  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  1  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
 21 22  1  1  0  0  0
 23 18  1  1  0  0  0
 23 24  1  0  0  0  0
 25 24  1  6  0  0  0
 16 25  1  0  0  0  0
 25 26  1  0  0  0  0
  8 26  1  0  0  0  0
 26 27  1  6  0  0  0
 26 28  1  0  0  0  0
 28 29  2  0  0  0  0
 30 28  1  6  0  0  0
  7 30  1  0  0  0  0
 23 30  1  0  0  0  0
  3 31  1  0  0  0  0
 31 32  1  0  0  0  0
M  END

     RDKit          3D

 56 63  0  0  0  0  0  0  0  0999 V2000
    3.5044    3.2293    1.8759 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4733    2.4668    1.2802 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6597    1.1577    0.8347 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8594    0.7421    1.0298 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6581    0.3743    0.2382 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8429   -0.9340   -0.2875 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9607   -1.5905   -0.7517 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1890   -0.9798   -0.7767 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3657   -1.6128   -1.2442 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8791   -2.9135   -1.2191 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6637   -3.5509   -1.2090 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5713   -2.8836   -0.7470 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6035   -1.5936   -0.2820 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3774   -0.6782    0.2267 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7147   -0.8136    1.6774 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2179    0.4799    2.2833 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2118    0.6601    3.3849 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4182    1.4368    1.1292 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0195    2.7122    1.3943 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9248    1.3693    0.8422 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.6109    0.5752    1.7386 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2266   -0.7653    1.6561 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.5506   -1.3642    0.3876 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9272   -1.3154    0.0401 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5014    0.0625   -0.0903 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5862    0.9136   -0.9386 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.7137    0.4842   -2.2624 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1560    0.7876   -0.5407 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3339    1.6344   -1.5024 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0956    1.2451   -1.3261 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2899    0.6963    0.0588 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.6831   -0.6528   -0.5278 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1390    3.6888    2.7947 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4167    2.6031    2.0549 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8184    3.9876    1.1026 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2583   -0.9806   -1.1079 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5067   -2.6231   -0.7696 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2256   -1.8041   -2.3276 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7905   -3.3783   -1.5715 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6378   -4.5713   -1.5765 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3990   -3.4044   -0.7435 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3045   -1.6842    2.1726 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0373    2.8585    2.3690 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3640    2.3851    0.8870 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5935   -1.3075    2.5265 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4995   -1.8405    0.8302 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0731   -1.8853   -0.8957 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4610   -0.0448   -0.6735 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7784    0.5324    0.8649 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8602    1.9794   -0.9257 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6569    0.6200   -2.5843 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6562    1.3408   -2.5228 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5384    2.6833   -1.2578 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7696    2.0937   -1.4547 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4261    0.4567   -2.0395 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6331   -1.0848   -1.5243 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  1  0
  7 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 14 13  1  6
 14 15  1  0
 15 22  1  0
 22 21  1  0
 21 20  1  0
 20 18  1  0
 18 19  1  1
 18 16  1  0
 16 17  2  0
 18 31  1  0
 31 30  1  0
 30 29  1  0
 28 29  1  6
 28 32  1  0
 32 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 31  5  1  1
 26 28  1  0
 13  6  1  0
 31 14  1  0
 32 14  1  0
 16 15  1  0
 23 22  1  0
 28 20  1  0
  1 33  1  0
  1 34  1  0
  1 35  1  0
  9 36  1  0
  9 37  1  0
  9 38  1  0
 10 39  1  0
 11 40  1  0
 12 41  1  0
 15 42  1  1
 22 45  1  1
 20 44  1  6
 19 43  1  0
 30 54  1  0
 30 55  1  0
 29 52  1  0
 29 53  1  0
 32 56  1  6
 24 46  1  0
 24 47  1  0
 25 48  1  0
 25 49  1  0
 26 50  1  6
 27 51  1  0
M  END


  Mrv1652304282213072D          

 32 39  0  0  1  0            999 V2000
    5.9834   -1.4408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3499   -0.7017    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8930   -0.0147    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0697   -0.0669    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7032   -0.8060    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1601   -1.4930    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6909   -0.6015    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.3535   -0.0726    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.1730   -0.7289    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.7010   -1.6829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5628   -1.7602    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8099   -2.6093    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1485   -3.1024    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8111    0.7607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9367    0.6146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9032   -0.5306    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7151    0.1487    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7652   -0.1630    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3251   -0.9096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7699   -1.6034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5768   -1.4653    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7523   -2.3084    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2159    0.2356    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1741   -0.8626    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0994   -1.1804    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.0545   -0.8801    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.1012   -1.7555    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9915    0.2052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5645    0.9478    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2459    0.0947    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.3704    0.7228    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2162    0.9297    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  6  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  1  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
 21 22  1  1  0  0  0
 23 18  1  1  0  0  0
 23 24  1  0  0  0  0
 25 24  1  6  0  0  0
 16 25  1  0  0  0  0
 25 26  1  0  0  0  0
  8 26  1  0  0  0  0
 26 27  1  6  0  0  0
 26 28  1  0  0  0  0
 28 29  2  0  0  0  0
 30 28  1  6  0  0  0
  7 30  1  0  0  0  0
 23 30  1  0  0  0  0
  3 31  1  0  0  0  0
 31 32  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0066906

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)N1C2=C(OC)C=CC=C2[C@@]23[C@@H]4[C@H]5O[C@H]6[C@@](O)(C4=O)[C@@]12CC[C@@]61[C@@H]3N5CC[C@@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C23H24N2O7/c1-30-11-5-3-4-10-14(11)25(19(28)31-2)21-8-7-20-12(26)6-9-24-16-13(22(10,21)17(20)24)15(27)23(21,29)18(20)32-16/h3-5,12-13,16-18,26,29H,6-9H2,1-2H3/t12-,13-,16+,17-,18+,20+,21-,22-,23-/m0/s1

> <INCHI_KEY>
PHNDSUUWSBODRA-LBKXKTDYSA-N

> <FORMULA>
C23H24N2O7

> <MOLECULAR_WEIGHT>
440.452

> <EXACT_MASS>
440.158351121

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
56

> <JCHEM_AVERAGE_POLARIZABILITY>
43.37407599150533

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl (1R,2R,4R,5R,7R,11S,12S,15S,23R)-4,11-dihydroxy-18-methoxy-3-oxo-6-oxa-8,16-diazaoctacyclo[10.10.1.0^{1,15}.0^{2,7}.0^{4,15}.0^{5,12}.0^{8,23}.0^{17,22}]tricosa-17,19,21-triene-16-carboxylate

> <ALOGPS_LOGP>
0.46

> <JCHEM_LOGP>
-0.009610503333332299

> <ALOGPS_LOGS>
-1.60

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
8

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.705552301488435

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.124467092824508

> <JCHEM_PKA_STRONGEST_BASIC>
4.073099842335171

> <JCHEM_POLAR_SURFACE_AREA>
108.77000000000002

> <JCHEM_REFRACTIVITY>
106.73179999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.10e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl (1R,2R,4R,5R,7R,11S,12S,15S,23R)-4,11-dihydroxy-18-methoxy-3-oxo-6-oxa-8,16-diazaoctacyclo[10.10.1.0^{1,15}.0^{2,7}.0^{4,15}.0^{5,12}.0^{8,23}.0^{17,22}]tricosa-17,19,21-triene-16-carboxylate

> <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      11.169  -2.690   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      11.853  -1.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      11.000  -0.027   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       9.463  -0.125   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.779  -1.505   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       9.632  -2.787   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.890  -1.123   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.126  -0.136   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0       9.656  -1.361   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0      10.642  -3.141   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      12.251  -3.286   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0      10.845  -4.871   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       9.611  -5.791   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.114   1.420   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.482   1.147   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.419  -0.990   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.068   0.278   0.000  0.00  0.00           C+0
HETATM   18  N   UNK     0       3.295  -0.304   0.000  0.00  0.00           N+0
HETATM   19  C   UNK     0       2.474  -1.698   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       3.304  -2.993   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.810  -2.735   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       5.138  -4.309   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       4.136   0.440   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       4.058  -1.610   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       5.786  -2.203   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       7.568  -1.643   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       7.656  -3.277   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       7.451   0.383   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       8.520   1.769   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       6.059   0.177   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      11.891   1.349   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0      13.470   1.735   0.000  0.00  0.00           C+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4   31                                                  
CONECT    4    3    5    9                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5    1                                                       
CONECT    7    5    8   17   30                                             
CONECT    8    7    9   14   26                                             
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   25                                             
CONECT   17   16    7   18                                                  
CONECT   18   17   19   23                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   16   22                                                  
CONECT   22   21                                                            
CONECT   23   18   24   30                                                  
CONECT   24   23   25                                                       
CONECT   25   24   16   26                                                  
CONECT   26   25    8   27   28                                             
CONECT   27   26                                                            
CONECT   28   26   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28    7   23                                                  
CONECT   31    3   32                                                       
CONECT   32   31                                                            
MASTER        0    0    0    0    0    0    0    0   32    0   78    0
END

View in JSmol

Synonyms

Value	Source
Methyl (1R,2R,4R,5R,7R,11S,12S,15S,23R)-4,11-dihydroxy-18-methoxy-3-oxo-6-oxa-8,16-diazaoctacyclo[10.10.1.0,.0,.0,.0,.0,.0,]tricosa-17(22),18,20-triene-16-carboxylic acid	Generator

Chemical Formula

C₂₃H₂₄N₂O₇

Average Mass

440.4520 Da

Monoisotopic Mass

440.15835 Da

IUPAC Name

methyl (1R,2R,4R,5R,7R,11S,12S,15S,23R)-4,11-dihydroxy-18-methoxy-3-oxo-6-oxa-8,16-diazaoctacyclo[10.10.1.0^{1,15}.0^{2,7}.0^{4,15}.0^{5,12}.0^{8,23}.0^{17,22}]tricosa-17,19,21-triene-16-carboxylate

Traditional Name

methyl (1R,2R,4R,5R,7R,11S,12S,15S,23R)-4,11-dihydroxy-18-methoxy-3-oxo-6-oxa-8,16-diazaoctacyclo[10.10.1.0^{1,15}.0^{2,7}.0^{4,15}.0^{5,12}.0^{8,23}.0^{17,22}]tricosa-17,19,21-triene-16-carboxylate

CAS Registry Number

Not Available

SMILES

COC(=O)N1C2=C(OC)C=CC=C2[C@@]23[C@@H]4[C@H]5O[C@H]6[C@@](O)(C4=O)[C@@]12CC[C@@]61[C@@H]3N5CC[C@@H]1O

InChI Identifier

InChI=1S/C23H24N2O7/c1-30-11-5-3-4-10-14(11)25(19(28)31-2)21-8-7-20-12(26)6-9-24-16-13(22(10,21)17(20)24)15(27)23(21,29)18(20)32-16/h3-5,12-13,16-18,26,29H,6-9H2,1-2H3/t12-,13-,16+,17-,18+,20+,21-,22-,23-/m0/s1

InChI Key

PHNDSUUWSBODRA-LBKXKTDYSA-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 teoi	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
Chromenopyridine
Carbazole
2,3-cyclopentanoindoline
Indolecarboxylic acid derivative
Indolecarboxylic acid
Quinolidine
Azaspirodecane
Indolizidine
Indole or derivatives
Anisole
Oxepane
Alkyl aryl ether
Benzenoid
N-alkylpyrrolidine
Piperidine
Oxazinane
Oxane
1,3-oxazinane
Carbamic acid ester
Tertiary alcohol
Pyrrolidine
Cyclic alcohol
Secondary alcohol
Carbonic acid derivative
Ketone
Hemiaminal
Oxacycle
Azacycle
Organoheterocyclic compound
Ether
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Carbonyl group
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	0.46	ALOGPS
logP	-0.0096	ChemAxon
logS	-1.6	ALOGPS
pKa (Strongest Acidic)	11.12	ChemAxon
pKa (Strongest Basic)	4.07	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	108.77 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	106.73 m³·mol⁻¹	ChemAxon
Polarizability	43.37 Å³	ChemAxon
Number of Rings	8	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

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

163105510

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for Kopsinitarine D (NP0066906)

MOL for NP0066906 (Kopsinitarine D)

3D MOL for NP0066906 (Kopsinitarine D)

3D SDF for NP0066906 (Kopsinitarine D)

3D-SDF for NP0066906 (Kopsinitarine D)

PDB for NP0066906 (Kopsinitarine D)

3D PDB for NP0066906 (Kopsinitarine D)

SMILES for NP0066906 (Kopsinitarine D)

INCHI for NP0066906 (Kopsinitarine D)

Structure for NP0066906 (Kopsinitarine D)

3D Structure for NP0066906 (Kopsinitarine D)