NP-MRD: Showing NP-Card for 2,18-dimethyl (1r,9s,16s,17s,18s,21s)-17,18-dihydroxy-2,12-diazahexacyclo[14.2.2.1⁹,¹².0¹,⁹.0³,⁸.0¹⁶,²¹]henicosa-3,5,7,14-tetraene-2,18-dicarboxylate (NP0225608)

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Record Information

Version

2.0

Created at

2022-09-06 04:22:32 UTC

Updated at

2022-09-06 04:22:32 UTC

NP-MRD ID

NP0225608

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2,18-dimethyl (1r,9s,16s,17s,18s,21s)-17,18-dihydroxy-2,12-diazahexacyclo[14.2.2.1⁹,¹².0¹,⁹.0³,⁸.0¹⁶,²¹]henicosa-3,5,7,14-tetraene-2,18-dicarboxylate

Description

Kopsaporine 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. 2,18-dimethyl (1r,9s,16s,17s,18s,21s)-17,18-dihydroxy-2,12-diazahexacyclo[14.2.2.1⁹,¹².0¹,⁹.0³,⁸.0¹⁶,²¹]henicosa-3,5,7,14-tetraene-2,18-dicarboxylate is found in Kopsia singapurensis. Based on a literature review very few articles have been published on Kopsaporine.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309062206222D          

 31 36  0  0  1  0            999 V2000
    6.0919    3.9541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7841    3.1886    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2930    2.5393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1098    2.6555    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9852    1.7739    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.3782    1.0360    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1520    0.7498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2909   -0.0635    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6562   -0.5904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8824   -0.3042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7434    0.5091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8791    0.6020    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.9355   -0.2578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4119   -0.9051    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7506   -0.3655    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9286   -0.5948    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2707   -0.0580    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3496    0.7876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1693    1.0707    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.8319    1.3979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5395    1.1713    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1776    1.5092    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.4232    2.0450    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.0667    2.5613    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1027    2.8052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6008    3.4629    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2841    2.9077    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9636    3.6679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5154    1.9338    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.0124    2.5878    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9201    0.4969    0.0000 C   0  0  2  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  1  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  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  2  0  0  0  0
 19 18  1  1  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22  5  1  1  0  0  0
 12 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  1  0  0  0
 23 25  1  0  0  0  0
 25 26  2  0  0  0  0
 25 27  1  0  0  0  0
 27 28  1  0  0  0  0
 23 29  1  0  0  0  0
 19 29  1  0  0  0  0
 29 30  1  6  0  0  0
 19 31  1  0  0  0  0
 31 15  1  6  0  0  0
 12 31  1  0  0  0  0
M  END

     RDKit          3D

 57 62  0  0  0  0  0  0  0  0999 V2000
    3.9974   -3.5965    0.2447 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4343   -2.3205    0.2064 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0745   -2.0951   -0.1066 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4442   -3.1425   -0.3405 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5424   -0.8152   -0.1373 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3480    0.3634    0.1263 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6967    0.6463    0.0363 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2317    1.8761    0.3413 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4029    2.8873    0.7578 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0404    2.6036    0.8496 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5334    1.3788    0.5427 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1311    0.8255    0.5700 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2875    0.6421    1.9392 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0602    1.9325    2.3188 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5129    2.4689    1.0787 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9053    2.6965    0.9535 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4454    2.7367   -0.4187 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8748    2.0215   -1.3730 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7081    1.2045   -1.0192 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.8038    1.0808   -2.2557 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5001    0.4970   -1.7623 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2546   -0.2897   -0.4032 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8799   -1.1330   -0.7088 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7768   -1.5175   -2.0932 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1595   -2.3731   -0.0131 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1424   -2.5116    1.2134 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4908   -3.5634   -0.7227 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7613   -4.7524   -0.0089 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1251   -0.2026   -0.6906 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.8784   -0.3535    0.4355 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8396    1.8383    0.0149 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.1670   -4.3252    0.4409 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4316   -3.8146   -0.7581 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8047   -3.6836    0.9909 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3955   -0.1400   -0.2946 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2838    2.0198    0.2476 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7730    3.8853    1.0134 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4118    3.4287    1.1832 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6221    0.6504    2.6181 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9001   -0.1583    2.2827 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3603    2.6658    2.7783 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8422    1.7353    3.0496 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5312    2.0383    1.6018 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0955    3.7294    1.3826 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2993    3.3424   -0.6483 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2474    2.0272   -2.3977 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5978    2.1335   -2.6260 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3009    0.5125   -3.0389 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2367    1.2725   -1.5447 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8240   -0.2768   -2.4661 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5512   -2.1299   -2.2974 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3469   -4.6436    1.0143 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8538   -4.9295    0.1075 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2581   -5.6313   -0.4816 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7952   -0.5235   -1.5434 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7289   -0.8471    0.3132 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2213    2.6293   -0.5025 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
 11 12  1  0
 12 13  1  1
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 19 18  1  6
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  6
 23 29  1  0
 29 30  1  0
 23 25  1  0
 25 26  2  0
 25 27  1  0
 27 28  1  0
 19 31  1  0
 22  5  1  1
 11  6  1  0
 22 12  1  0
 31 12  1  0
 31 15  1  0
 29 19  1  0
  1 32  1  0
  1 33  1  0
  1 34  1  0
  7 35  1  0
  8 36  1  0
  9 37  1  0
 10 38  1  0
 13 39  1  0
 13 40  1  0
 14 41  1  0
 14 42  1  0
 16 43  1  0
 16 44  1  0
 17 45  1  0
 18 46  1  0
 20 47  1  0
 20 48  1  0
 21 49  1  0
 21 50  1  0
 24 51  1  0
 29 55  1  6
 30 56  1  0
 28 52  1  0
 28 53  1  0
 28 54  1  0
 31 57  1  6
M  END


  Mrv1652309062206222D          

 31 36  0  0  1  0            999 V2000
    6.0919    3.9541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7841    3.1886    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2930    2.5393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1098    2.6555    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9852    1.7739    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.3782    1.0360    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1520    0.7498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2909   -0.0635    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6562   -0.5904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8824   -0.3042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7434    0.5091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8791    0.6020    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.9355   -0.2578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4119   -0.9051    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7506   -0.3655    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9286   -0.5948    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2707   -0.0580    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3496    0.7876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1693    1.0707    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.8319    1.3979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5395    1.1713    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1776    1.5092    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.4232    2.0450    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.0667    2.5613    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1027    2.8052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6008    3.4629    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2841    2.9077    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9636    3.6679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5154    1.9338    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.0124    2.5878    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9201    0.4969    0.0000 C   0  0  2  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  1  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  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  2  0  0  0  0
 19 18  1  1  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22  5  1  1  0  0  0
 12 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  1  0  0  0
 23 25  1  0  0  0  0
 25 26  2  0  0  0  0
 25 27  1  0  0  0  0
 27 28  1  0  0  0  0
 23 29  1  0  0  0  0
 19 29  1  0  0  0  0
 29 30  1  6  0  0  0
 19 31  1  0  0  0  0
 31 15  1  6  0  0  0
 12 31  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0225608

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)N1C2=CC=CC=C2[C@]23CCN4CC=C[C@@]5(CC[C@@]12[C@](O)([C@H]5O)C(=O)OC)[C@H]34

> <INCHI_IDENTIFIER>
InChI=1S/C23H26N2O6/c1-30-18(27)23(29)17(26)20-8-5-12-24-13-11-21(16(20)24)14-6-3-4-7-15(14)25(19(28)31-2)22(21,23)10-9-20/h3-8,16-17,26,29H,9-13H2,1-2H3/t16-,17+,20-,21+,22-,23+/m1/s1

> <INCHI_KEY>
HVUPNDMRYTUMME-JLCSSFLSSA-N

> <FORMULA>
C23H26N2O6

> <MOLECULAR_WEIGHT>
426.469

> <EXACT_MASS>
426.179086565

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
57

> <JCHEM_AVERAGE_POLARIZABILITY>
43.426322063851444

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2,18-dimethyl (1R,9S,16S,17S,18S,21S)-17,18-dihydroxy-2,12-diazahexacyclo[14.2.2.1^{9,12}.0^{1,9}.0^{3,8}.0^{16,21}]henicosa-3,5,7,14-tetraene-2,18-dicarboxylate

> <JCHEM_LOGP>
0.6624428536666658

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
13.96271841527286

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.757441951489488

> <JCHEM_PKA_STRONGEST_BASIC>
7.998653936968461

> <JCHEM_POLAR_SURFACE_AREA>
99.54000000000002

> <JCHEM_REFRACTIVITY>
110.0153

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
2,18-dimethyl (1R,9S,16S,17S,18S,21S)-17,18-dihydroxy-2,12-diazahexacyclo[14.2.2.1^{9,12}.0^{1,9}.0^{3,8}.0^{16,21}]henicosa-3,5,7,14-tetraene-2,18-dicarboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-SEP-22         0                                  
HETATM    1  C   UNK     0      11.372   7.381   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      10.797   5.952   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      11.747   4.740   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      13.272   4.957   0.000  0.00  0.00           O+0
HETATM    5  N   UNK     0      11.172   3.311   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0      11.906   1.934   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      13.350   1.400   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      13.610  -0.118   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      12.425  -1.102   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      10.981  -0.568   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      10.721   0.950   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       9.108   1.124   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       9.213  -0.481   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.235  -1.690   0.000  0.00  0.00           C+0
HETATM   15  N   UNK     0       7.001  -0.682   0.000  0.00  0.00           N+0
HETATM   16  C   UNK     0       5.467  -1.110   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.239  -0.108   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.386   1.470   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.916   1.999   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       7.153   2.609   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       8.474   2.186   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       9.665   2.817   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       8.257   3.817   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       9.458   4.781   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       7.658   5.236   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       8.588   6.464   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0       6.130   5.428   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       5.532   6.847   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       6.562   3.610   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       5.623   4.830   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       7.318   0.927   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   22                                                  
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   22   31                                             
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   31                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20   29   31                                             
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21    5   12   23                                             
CONECT   23   22   24   25   29                                             
CONECT   24   23                                                            
CONECT   25   23   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   28                                                       
CONECT   28   27                                                            
CONECT   29   23   19   30                                                  
CONECT   30   29                                                            
CONECT   31   19   15   12                                                  
MASTER        0    0    0    0    0    0    0    0   31    0   72    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₃H₂₆N₂O₆

Average Mass

426.4690 Da

Monoisotopic Mass

426.17909 Da

IUPAC Name

2,18-dimethyl (1R,9S,16S,17S,18S,21S)-17,18-dihydroxy-2,12-diazahexacyclo[14.2.2.1^{9,12}.0^{1,9}.0^{3,8}.0^{16,21}]henicosa-3,5,7,14-tetraene-2,18-dicarboxylate

Traditional Name

2,18-dimethyl (1R,9S,16S,17S,18S,21S)-17,18-dihydroxy-2,12-diazahexacyclo[14.2.2.1^{9,12}.0^{1,9}.0^{3,8}.0^{16,21}]henicosa-3,5,7,14-tetraene-2,18-dicarboxylate

CAS Registry Number

Not Available

SMILES

COC(=O)N1C2=CC=CC=C2[C@]23CCN4CC=C[C@@]5(CC[C@@]12[C@](O)([C@H]5O)C(=O)OC)[C@H]34

InChI Identifier

InChI=1S/C23H26N2O6/c1-30-18(27)23(29)17(26)20-8-5-12-24-13-11-21(16(20)24)14-6-3-4-7-15(14)25(19(28)31-2)22(21,23)10-9-20/h3-8,16-17,26,29H,9-13H2,1-2H3/t16-,17+,20-,21+,22-,23+/m1/s1

InChI Key

HVUPNDMRYTUMME-JLCSSFLSSA-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
Carbazole
Indolecarboxylic acid
Indolecarboxylic acid derivative
Indole or derivatives
Beta-hydroxy acid
Aralkylamine
Hydroxy acid
Benzenoid
N-alkylpyrrolidine
Cyclic alcohol
Methyl ester
Carbamic acid ester
Pyrrolidine
Tertiary alcohol
1,2-diol
Amino acid or derivatives
Carboxylic acid ester
Carbonic acid derivative
Tertiary aliphatic amine
Secondary alcohol
Tertiary amine
Organoheterocyclic compound
Azacycle
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Amine
Carbonyl group
Alcohol
Organonitrogen compound
Organooxygen compound
Organic nitrogen compound
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

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

Predicted Properties

Property	Value	Source
logP	0.66	ChemAxon
pKa (Strongest Acidic)	10.76	ChemAxon
pKa (Strongest Basic)	8	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	99.54 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	110.02 m³·mol⁻¹	ChemAxon
Polarizability	43.43 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

C00024477

Chemspider ID

24717425

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

44575481

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 2,18-dimethyl (1r,9s,16s,17s,18s,21s)-17,18-dihydroxy-2,12-diazahexacyclo[14.2.2.1⁹,¹².0¹,⁹.0³,⁸.0¹⁶,²¹]henicosa-3,5,7,14-tetraene-2,18-dicarboxylate (NP0225608)

MOL for NP0225608 (2,18-dimethyl (1r,9s,16s,17s,18s,21s)-17,18-dihydroxy-2,12-diazahexacyclo[14.2.2.1⁹,¹².0¹,⁹.0³,⁸.0¹⁶,²¹]henicosa-3,5,7,14-tetraene-2,18-dicarboxylate)

3D MOL for NP0225608 (2,18-dimethyl (1r,9s,16s,17s,18s,21s)-17,18-dihydroxy-2,12-diazahexacyclo[14.2.2.1⁹,¹².0¹,⁹.0³,⁸.0¹⁶,²¹]henicosa-3,5,7,14-tetraene-2,18-dicarboxylate)

3D SDF for NP0225608 (2,18-dimethyl (1r,9s,16s,17s,18s,21s)-17,18-dihydroxy-2,12-diazahexacyclo[14.2.2.1⁹,¹².0¹,⁹.0³,⁸.0¹⁶,²¹]henicosa-3,5,7,14-tetraene-2,18-dicarboxylate)

3D-SDF for NP0225608 (2,18-dimethyl (1r,9s,16s,17s,18s,21s)-17,18-dihydroxy-2,12-diazahexacyclo[14.2.2.1⁹,¹².0¹,⁹.0³,⁸.0¹⁶,²¹]henicosa-3,5,7,14-tetraene-2,18-dicarboxylate)

PDB for NP0225608 (2,18-dimethyl (1r,9s,16s,17s,18s,21s)-17,18-dihydroxy-2,12-diazahexacyclo[14.2.2.1⁹,¹².0¹,⁹.0³,⁸.0¹⁶,²¹]henicosa-3,5,7,14-tetraene-2,18-dicarboxylate)

3D PDB for NP0225608 (2,18-dimethyl (1r,9s,16s,17s,18s,21s)-17,18-dihydroxy-2,12-diazahexacyclo[14.2.2.1⁹,¹².0¹,⁹.0³,⁸.0¹⁶,²¹]henicosa-3,5,7,14-tetraene-2,18-dicarboxylate)

SMILES for NP0225608 (2,18-dimethyl (1r,9s,16s,17s,18s,21s)-17,18-dihydroxy-2,12-diazahexacyclo[14.2.2.1⁹,¹².0¹,⁹.0³,⁸.0¹⁶,²¹]henicosa-3,5,7,14-tetraene-2,18-dicarboxylate)

INCHI for NP0225608 (2,18-dimethyl (1r,9s,16s,17s,18s,21s)-17,18-dihydroxy-2,12-diazahexacyclo[14.2.2.1⁹,¹².0¹,⁹.0³,⁸.0¹⁶,²¹]henicosa-3,5,7,14-tetraene-2,18-dicarboxylate)

Structure for NP0225608 (2,18-dimethyl (1r,9s,16s,17s,18s,21s)-17,18-dihydroxy-2,12-diazahexacyclo[14.2.2.1⁹,¹².0¹,⁹.0³,⁸.0¹⁶,²¹]henicosa-3,5,7,14-tetraene-2,18-dicarboxylate)

3D Structure for NP0225608 (2,18-dimethyl (1r,9s,16s,17s,18s,21s)-17,18-dihydroxy-2,12-diazahexacyclo[14.2.2.1⁹,¹².0¹,⁹.0³,⁸.0¹⁶,²¹]henicosa-3,5,7,14-tetraene-2,18-dicarboxylate)