NP-MRD: Showing NP-Card for Pauciflorine A (NP0066932)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-04-28 11:09:10 UTC

Updated at

2022-04-28 11:09:10 UTC

NP-MRD ID

NP0066932

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Pauciflorine A

Description

2,21-Dimethyl (1S,12S,21S)-21-hydroxy-24-oxo-5,7-dioxa-2,15-diazahexacyclo[17.2.2.1¹²,¹⁵.0¹,¹².0³,¹¹.0⁴,⁸]Tetracosa-3(11),4(8),9,19(23)-tetraene-2,21-dicarboxylate belongs to the class of organic compounds known as indolecarboxylic acids. Indolecarboxylic acids are compounds containing a carboxylic acid group linked to an indole. Pauciflorine A is found in Kopsia pauciflora. Based on a literature review very few articles have been published on 2,21-dimethyl (1S,12S,21S)-21-hydroxy-24-oxo-5,7-dioxa-2,15-diazahexacyclo[17.2.2.1¹²,¹⁵.0¹,¹².0³,¹¹.0⁴,⁸]Tetracosa-3(11),4(8),9,19(23)-tetraene-2,21-dicarboxylate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282213092D          

 34 39  0  0  1  0            999 V2000
    2.5583   -0.5536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9043    0.1953    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4286    0.8694    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6070    0.7946    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2611    0.0456    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7367   -0.6285    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7563    0.3383    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6493    0.4089    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9803    1.2387    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.4771    2.1060    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9178    2.9895    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3725    2.4904    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0428    2.0094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0139    0.1082    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4950    0.9768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1272    1.7578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6308    1.3860    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4720    0.5205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6541    2.4914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4893    2.7438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2624    2.3330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5384    1.5221    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9059    1.2700    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8327    2.0297    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0546    0.7820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5519    0.1070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1212   -0.8545    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0749   -1.7229    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7392   -1.5075    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5417   -1.3160    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0102    0.2411    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9228    1.5301    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7038    1.2643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6924    0.4394    0.0000 O   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  1  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
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
  8 18  1  0  0  0  0
 16 19  1  0  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 23  1  0  0  0  0
  7 23  1  0  0  0  0
 23 24  2  0  0  0  0
 22 25  1  0  0  0  0
 25 26  1  0  0  0  0
  7 26  1  0  0  0  0
 14 27  1  0  0  0  0
 27 28  2  0  0  0  0
 27 29  1  0  0  0  0
 29 30  1  0  0  0  0
 14 31  1  1  0  0  0
  3 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
  2 34  1  0  0  0  0
M  END

     RDKit          3D

 60 65  0  0  0  0  0  0  0  0999 V2000
    1.7154    4.5660   -1.0088 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1187    3.2859   -0.9221 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7925    2.1140   -0.6492 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0498    2.3389   -0.4816 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2316    0.8271   -0.5618 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0979   -0.3377   -0.4739 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3536   -1.4309   -0.1268 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9966   -2.6459   -0.0251 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3465   -2.7799   -0.2593 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1120   -1.6978   -0.6075 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4603   -0.4854   -0.7083 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4967    0.3944   -1.0723 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7445   -0.1466   -0.6336 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4808   -1.5332   -0.9012 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0953   -1.0144    0.0817 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3307   -1.1775    1.5309 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9413   -2.5584    1.6663 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7385   -2.5645    0.3985 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1180   -2.9238    0.3741 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0074   -2.3716   -0.6568 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0192   -0.8908   -0.5769 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8267   -0.1544   -1.0326 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0293   -0.2440   -2.0577 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5575    0.0244   -1.9988 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1286    0.3026   -0.5379 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0379    1.3640   -0.1522 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.1548    2.2509   -1.2820 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7595    2.2809    0.9610 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0285    3.5137    0.9916 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1532    1.8690    2.1204 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1395    2.7074    3.2183 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4972    0.9644   -0.0464 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8159   -2.1697   -0.5902 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5196   -2.5528   -1.7642 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8122    4.4927   -1.1827 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2085    5.2394   -1.6951 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6224    5.0134    0.0232 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4594   -3.5270    0.2302 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8349   -3.7523   -0.1723 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5871    0.2279   -1.2020 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7899    0.0081    0.4537 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6256   -1.1015    2.0963 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1217   -0.5472    1.9810 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2583   -3.3827    1.7422 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5924   -2.6058    2.5620 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6273   -2.7318    1.3683 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1705   -4.0538    0.3031 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0178   -2.7461   -0.5237 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6174   -2.6882   -1.6669 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2297   -0.7209    0.5284 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9888   -0.5069   -1.0218 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2156   -0.4888   -3.1147 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3567    1.0452   -2.4943 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0947   -0.6152   -2.5458 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8324    2.9219   -1.1118 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1316    2.5299    3.6524 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1009    3.7606    2.8278 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6927    2.5769    3.9498 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7225    0.7411    0.9757 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2007    1.7869   -0.3502 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 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 10  1  0
 10  9  2  0
  9  8  1  0
  8  7  2  0
  7 15  1  0
 15 16  1  1
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  6
 26 32  1  0
 26 28  1  0
 28 29  2  0
 28 30  1  0
 30 31  1  0
 18 33  1  0
 33 34  2  0
 25  5  1  6
  7  6  1  0
 25 15  1  0
 10 11  1  0
 33 15  1  0
 32 22  1  0
  1 35  1  0
  1 36  1  0
  1 37  1  0
 13 40  1  0
 13 41  1  0
  9 39  1  0
  8 38  1  0
 16 42  1  0
 16 43  1  0
 17 44  1  0
 17 45  1  0
 19 46  1  0
 19 47  1  0
 20 48  1  0
 20 49  1  0
 21 50  1  0
 21 51  1  0
 23 52  1  0
 24 53  1  0
 24 54  1  0
 27 55  1  0
 32 59  1  0
 32 60  1  0
 31 56  1  0
 31 57  1  0
 31 58  1  0
M  END


  Mrv1652304282213092D          

 34 39  0  0  1  0            999 V2000
    2.5583   -0.5536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9043    0.1953    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4286    0.8694    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6070    0.7946    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2611    0.0456    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7367   -0.6285    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7563    0.3383    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6493    0.4089    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9803    1.2387    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.4771    2.1060    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9178    2.9895    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3725    2.4904    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0428    2.0094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0139    0.1082    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4950    0.9768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1272    1.7578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6308    1.3860    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4720    0.5205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6541    2.4914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4893    2.7438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2624    2.3330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5384    1.5221    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9059    1.2700    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8327    2.0297    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0546    0.7820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5519    0.1070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1212   -0.8545    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0749   -1.7229    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7392   -1.5075    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5417   -1.3160    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0102    0.2411    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9228    1.5301    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7038    1.2643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6924    0.4394    0.0000 O   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  1  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
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
  8 18  1  0  0  0  0
 16 19  1  0  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 23  1  0  0  0  0
  7 23  1  0  0  0  0
 23 24  2  0  0  0  0
 22 25  1  0  0  0  0
 25 26  1  0  0  0  0
  7 26  1  0  0  0  0
 14 27  1  0  0  0  0
 27 28  2  0  0  0  0
 27 29  1  0  0  0  0
 29 30  1  0  0  0  0
 14 31  1  1  0  0  0
  3 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
  2 34  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0066932

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)N1C2=C3OCOC3=CC=C2[C@@]23CCN(CCCC4=CC[C@]12[C@@](O)(C4)C(=O)OC)C3=O

> <INCHI_IDENTIFIER>
InChI=1S/C24H26N2O8/c1-31-20(28)23(30)12-14-4-3-10-25-11-9-22(19(25)27)15-5-6-16-18(34-13-33-16)17(15)26(21(29)32-2)24(22,23)8-7-14/h5-7,30H,3-4,8-13H2,1-2H3/t22-,23-,24+/m1/s1

> <INCHI_KEY>
HNAOVPOBPGXGMD-SMIHKQSGSA-N

> <FORMULA>
C24H26N2O8

> <MOLECULAR_WEIGHT>
470.478

> <EXACT_MASS>
470.168915805

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
60

> <JCHEM_AVERAGE_POLARIZABILITY>
46.99155806709167

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2,21-dimethyl (1S,12S,21S)-21-hydroxy-24-oxo-5,7-dioxa-2,15-diazahexacyclo[17.2.2.1^{12,15}.0^{1,12}.0^{3,11}.0^{4,8}]tetracosa-3,8,10,19(23)-tetraene-2,21-dicarboxylate

> <ALOGPS_LOGP>
0.65

> <JCHEM_LOGP>
0.811613820666667

> <ALOGPS_LOGS>
-2.52

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.522092351555829

> <JCHEM_PKA_STRONGEST_BASIC>
-1.418460125900963

> <JCHEM_POLAR_SURFACE_AREA>
114.84000000000002

> <JCHEM_REFRACTIVITY>
116.63469999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.41e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2,21-dimethyl (1S,12S,21S)-21-hydroxy-24-oxo-5,7-dioxa-2,15-diazahexacyclo[17.2.2.1^{12,15}.0^{1,12}.0^{3,11}.0^{4,8}]tetracosa-3,8,10,19(23)-tetraene-2,21-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       4.776  -1.033   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.421   0.365   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.533   1.623   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.000   1.483   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.354   0.085   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.242  -1.173   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.278   0.631   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.212   0.763   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0       1.830   2.312   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0       0.891   3.931   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       1.713   5.580   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0      -0.695   4.649   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      -1.947   3.751   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -0.026   0.202   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.924   1.823   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.237   3.281   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -1.178   2.587   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -0.881   0.972   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.221   4.651   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.780   5.122   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.223   4.355   0.000  0.00  0.00           C+0
HETATM   22  N   UNK     0       4.738   2.841   0.000  0.00  0.00           N+0
HETATM   23  C   UNK     0       3.558   2.371   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       3.421   3.789   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       5.702   1.460   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       4.764   0.200   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -0.226  -1.595   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       0.140  -3.216   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0      -1.380  -2.814   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0      -2.878  -2.457   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      -1.886   0.450   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0       5.456   2.856   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       6.914   2.360   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       6.892   0.820   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3   34                                                  
CONECT    3    2    4   32                                                  
CONECT    4    3    5    9                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5    1                                                       
CONECT    7    5    8   23   26                                             
CONECT    8    7    9   14   18                                             
CONECT    9    8    4   10                                                  
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12                                                            
CONECT   14    8   15   27   31                                             
CONECT   15   14   16                                                       
CONECT   16   15   17   19                                                  
CONECT   17   16   18                                                       
CONECT   18   17    8                                                       
CONECT   19   16   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23   25                                                  
CONECT   23   22    7   24                                                  
CONECT   24   23                                                            
CONECT   25   22   26                                                       
CONECT   26   25    7                                                       
CONECT   27   14   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   30                                                       
CONECT   30   29                                                            
CONECT   31   14                                                            
CONECT   32    3   33                                                       
CONECT   33   32   34                                                       
CONECT   34   33    2                                                       
MASTER        0    0    0    0    0    0    0    0   34    0   78    0
END

View in JSmol

Synonyms

Value	Source
2,21-Dimethyl (1S,12S,21S)-21-hydroxy-24-oxo-5,7-dioxa-2,15-diazahexacyclo[17.2.2.1,.0,.0,.0,]tetracosa-3(11),4(8),9,19(23)-tetraene-2,21-dicarboxylic acid	Generator

Chemical Formula

C₂₄H₂₆N₂O₈

Average Mass

470.4780 Da

Monoisotopic Mass

470.16892 Da

IUPAC Name

2,21-dimethyl (1S,12S,21S)-21-hydroxy-24-oxo-5,7-dioxa-2,15-diazahexacyclo[17.2.2.1^{12,15}.0^{1,12}.0^{3,11}.0^{4,8}]tetracosa-3,8,10,19(23)-tetraene-2,21-dicarboxylate

Traditional Name

2,21-dimethyl (1S,12S,21S)-21-hydroxy-24-oxo-5,7-dioxa-2,15-diazahexacyclo[17.2.2.1^{12,15}.0^{1,12}.0^{3,11}.0^{4,8}]tetracosa-3,8,10,19(23)-tetraene-2,21-dicarboxylate

CAS Registry Number

Not Available

SMILES

COC(=O)N1C2=C3OCOC3=CC=C2[C@@]23CCN(CCCC4=CC[C@]12[C@@](O)(C4)C(=O)OC)C3=O

InChI Identifier

InChI=1S/C24H26N2O8/c1-31-20(28)23(30)12-14-4-3-10-25-11-9-22(19(25)27)15-5-6-16-18(34-13-33-16)17(15)26(21(29)32-2)24(22,23)8-7-14/h5-7,30H,3-4,8-13H2,1-2H3/t22-,23-,24+/m1/s1

InChI Key

HNAOVPOBPGXGMD-SMIHKQSGSA-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 pauciflora	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as indolecarboxylic acids. Indolecarboxylic acids are compounds containing a carboxylic acid group linked to an indole.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Indoles and derivatives

Sub Class

Indolecarboxylic acids and derivatives

Direct Parent

Indolecarboxylic acids

Alternative Parents

Substituents

Indolecarboxylic acid
Benzodioxole
Pyrrolidone
2-pyrrolidone
N-alkylpyrrolidine
Benzenoid
Pyrrolidine
Tertiary alcohol
Tertiary carboxylic acid amide
Methyl ester
Carbamic acid ester
Carboxamide group
Carboxylic acid ester
Lactam
Acetal
Azacycle
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Oxacycle
Organooxygen compound
Organonitrogen compound
Hydrocarbon derivative
Organic oxygen compound
Organic oxide
Organopnictogen compound
Carbonyl group
Alcohol
Organic nitrogen 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	0.65	ALOGPS
logP	0.81	ChemAxon
logS	-2.5	ALOGPS
pKa (Strongest Acidic)	11.52	ChemAxon
pKa (Strongest Basic)	-1.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	114.84 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	116.63 m³·mol⁻¹	ChemAxon
Polarizability	46.99 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

Not Available

Chemspider ID

8727698

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10552307

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Pauciflorine A (NP0066932)

MOL for NP0066932 (Pauciflorine A)

3D MOL for NP0066932 (Pauciflorine A)

3D SDF for NP0066932 (Pauciflorine A)

3D-SDF for NP0066932 (Pauciflorine A)

PDB for NP0066932 (Pauciflorine A)

3D PDB for NP0066932 (Pauciflorine A)

SMILES for NP0066932 (Pauciflorine A)

INCHI for NP0066932 (Pauciflorine A)

Structure for NP0066932 (Pauciflorine A)

3D Structure for NP0066932 (Pauciflorine A)