NP-MRD: Showing NP-Card for Bannucine (NP0066869)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-04-28 11:06:12 UTC

Updated at

2022-04-28 11:06:12 UTC

NP-MRD ID

NP0066869

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Bannucine

Description

Methyl (1R,9R,10S,11S,12R,19R)-11-(acetyloxy)-12-ethyl-10-hydroxy-4-[(2R)-5-hydroxy-3,4-dihydro-2H-pyrrol-2-yl]-5-methoxy-8-methyl-8,16-diazapentacyclo[10.6.1.0¹,⁹.0²,⁷.0¹⁶,¹⁹]Nonadeca-2,4,6,13-tetraene-10-carboxylate belongs to the class of organic compounds known as plumeran-type alkaloids. These are alkaloids with a structure based on the plumeran skeleton. Plumeran is a pentacyclic compound that consists of a pyrrolidine ring shed to the quinoline moiety of pyrido[3,2-c]carbazole ring system. Bannucine is found in Catharanthus roseus . Based on a literature review very few articles have been published on methyl (1R,9R,10S,11S,12R,19R)-11-(acetyloxy)-12-ethyl-10-hydroxy-4-[(2R)-5-hydroxy-3,4-dihydro-2H-pyrrol-2-yl]-5-methoxy-8-methyl-8,16-diazapentacyclo[10.6.1.0¹,⁹.0²,⁷.0¹⁶,¹⁹]Nonadeca-2,4,6,13-tetraene-10-carboxylate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282213062D          

 39 44  0  0  1  0            999 V2000
    5.4285    1.2096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0125    0.6269    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7998   -0.1702    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0031   -0.3846    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4191    0.1981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6318    0.9952    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6844   -0.1772    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.8144   -0.9919    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.6293   -1.1201    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.0047   -1.8548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1738   -1.5118    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4032   -1.2169    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.2733   -0.4022    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.9139    0.1177    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7840    0.9324    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0135    1.2272    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3729    0.7073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5028   -0.1074    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7529    1.1559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2030    0.4645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6327   -0.9221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8622   -0.6272    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7627   -1.7368    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8926   -2.5515    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2520   -3.0713    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6631   -2.8463    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6710   -2.1701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4897   -2.0687    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3494   -2.9299    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8466   -3.5882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9060   -2.2921    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8091    0.8412    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3931    0.2585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6412    2.0067    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.1213    2.6473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5699    3.3397    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3670    3.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0076    3.6469    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4111    2.3032    0.0000 N   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
  8 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
  7 14  1  0  0  0  0
 14 15  1  6  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 13 18  1  0  0  0  0
 15 19  1  0  0  0  0
 19 20  1  0  0  0  0
  7 20  1  0  0  0  0
 13 21  1  1  0  0  0
 21 22  1  0  0  0  0
 12 23  1  1  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 24 26  1  0  0  0  0
 11 27  1  1  0  0  0
 27 28  2  0  0  0  0
 27 29  1  0  0  0  0
 29 30  1  0  0  0  0
 11 31  1  6  0  0  0
  2 32  1  0  0  0  0
 32 33  1  0  0  0  0
 34  1  1  1  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
 36 37  1  0  0  0  0
 37 38  2  0  0  0  0
 37 39  1  0  0  0  0
 34 39  1  0  0  0  0
M  END

     RDKit          3D

 76 81  0  0  0  0  0  0  0  0999 V2000
   -3.5078   -2.5340   -0.4738 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0831   -2.1024   -0.2377 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8999   -1.0817    0.8714 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.4589   -1.7718    2.1025 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7199   -2.5221    2.8429 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2850   -2.7272    2.5013 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2432   -1.4995    2.0301 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5400   -0.5749    3.0811 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3258    0.8032    2.5354 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0237    0.5831    1.0612 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3579    0.7238    0.3607 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5589    0.0364    0.5174 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6897    0.3012   -0.2270 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9531   -0.4520   -0.0282 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.8300   -1.6042    0.9393 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9504   -2.5564    0.5299 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0929   -2.2554   -0.9430 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6390   -3.0711   -1.7246 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5316   -0.9799   -1.2193 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5818    1.3060   -1.1625 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6713    1.6223   -1.9384 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7246    2.6053   -2.9215 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4033    1.9894   -1.3246 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2586    1.7219   -0.5720 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0434    2.2877   -0.5622 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4841    3.3305   -1.4691 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8071    1.6553    0.4932 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1467    1.2983   -0.0262 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.0233    2.3731    0.3759 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2838    1.2063   -1.4760 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5533    0.5490   -2.2655 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3265    1.9020   -2.1390 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4858    1.8322   -3.5418 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7409    0.1038    0.6667 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.9760   -0.1920    0.0991 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2025    0.0572    0.7153 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4956   -0.2718    0.0793 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1817    0.5785    1.8468 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4267   -0.8211    0.9728 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.4782   -3.5960   -0.8743 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0050   -1.9583   -1.2642 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0848   -2.4971    0.4562 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4981   -3.0365    0.0086 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6922   -1.7827   -1.2174 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5099   -1.6329    2.3699 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1707   -2.9991    3.7191 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2895   -2.9682    3.4449 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1949   -3.5395    1.7927 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5981   -0.7658    3.4109 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0584   -0.7576    4.0029 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5020    1.3429    3.0407 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2090    1.4673    2.6254 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6133   -0.7380    1.2555 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6618    0.2796    0.4605 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0183   -1.3145    1.9860 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9045   -2.1900    0.8267 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6818   -3.6063    0.6511 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8930   -2.3590    1.0412 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5510   -0.5261   -2.1447 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7852    2.9931   -2.9381 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5355    2.2312   -3.9479 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1095    3.5096   -2.6936 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3046    2.7954   -2.0706 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3603    2.9945   -2.5160 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4850    3.7008   -1.2118 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2742    4.1570   -1.3553 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9346    2.4237    1.3457 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5472    2.6973   -0.3719 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7228    2.8653   -3.8821 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3590    1.2045   -3.8027 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5837    1.4704   -4.0548 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0071    0.5208    1.7135 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2262    0.5465    0.2941 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4183   -0.3566   -1.0233 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9197   -1.1863    0.5365 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0852   -1.2387    0.0167 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  3  2  1  6
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
 10  9  1  1
 10 39  1  0
 10 27  1  0
 27 25  1  0
 25 26  1  0
 25 24  1  0
 24 23  2  0
 23 20  1  0
 20 21  1  0
 21 22  1  0
 20 13  2  0
 13 12  1  0
 12 11  2  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 17 19  1  0
 27 28  1  0
 28 29  1  1
 28 34  1  0
 34 35  1  0
 35 36  1  0
 36 37  1  0
 36 38  2  0
 28 30  1  0
 30 31  2  0
 30 32  1  0
 32 33  1  0
 39  3  1  0
 11 24  1  0
 19 14  1  0
 34  3  1  0
 39  7  1  0
 11 10  1  0
  1 40  1  0
  1 41  1  0
  1 42  1  0
  2 43  1  0
  2 44  1  0
  4 45  1  0
  5 46  1  0
  6 47  1  0
  6 48  1  0
  8 49  1  0
  8 50  1  0
  9 51  1  0
  9 52  1  0
 39 76  1  6
 27 67  1  1
 26 64  1  0
 26 65  1  0
 26 66  1  0
 23 63  1  0
 22 60  1  0
 22 61  1  0
 22 62  1  0
 12 53  1  0
 14 54  1  1
 15 55  1  0
 15 56  1  0
 16 57  1  0
 16 58  1  0
 19 59  1  0
 29 68  1  0
 34 72  1  1
 37 73  1  0
 37 74  1  0
 37 75  1  0
 33 69  1  0
 33 70  1  0
 33 71  1  0
M  END


  Mrv1652304282213062D          

 39 44  0  0  1  0            999 V2000
    5.4285    1.2096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0125    0.6269    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7998   -0.1702    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0031   -0.3846    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4191    0.1981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6318    0.9952    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6844   -0.1772    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.8144   -0.9919    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.6293   -1.1201    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.0047   -1.8548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1738   -1.5118    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4032   -1.2169    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.2733   -0.4022    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.9139    0.1177    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7840    0.9324    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0135    1.2272    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3729    0.7073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5028   -0.1074    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7529    1.1559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2030    0.4645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6327   -0.9221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8622   -0.6272    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7627   -1.7368    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8926   -2.5515    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2520   -3.0713    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6631   -2.8463    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6710   -2.1701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4897   -2.0687    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3494   -2.9299    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8466   -3.5882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9060   -2.2921    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8091    0.8412    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3931    0.2585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6412    2.0067    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.1213    2.6473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5699    3.3397    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3670    3.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0076    3.6469    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4111    2.3032    0.0000 N   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
  8 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
  7 14  1  0  0  0  0
 14 15  1  6  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 13 18  1  0  0  0  0
 15 19  1  0  0  0  0
 19 20  1  0  0  0  0
  7 20  1  0  0  0  0
 13 21  1  1  0  0  0
 21 22  1  0  0  0  0
 12 23  1  1  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 24 26  1  0  0  0  0
 11 27  1  1  0  0  0
 27 28  2  0  0  0  0
 27 29  1  0  0  0  0
 29 30  1  0  0  0  0
 11 31  1  6  0  0  0
  2 32  1  0  0  0  0
 32 33  1  0  0  0  0
 34  1  1  1  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
 36 37  1  0  0  0  0
 37 38  2  0  0  0  0
 37 39  1  0  0  0  0
 34 39  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0066869

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC[C@@]12C=CCN3CC[C@@]4([C@H]13)[C@@H](N(C)C1=CC(OC)=C(C=C41)[C@H]1CCC(=O)N1)[C@](O)([C@H]2OC(C)=O)C(=O)OC

> <INCHI_IDENTIFIER>
InChI=1S/C29H37N3O7/c1-6-27-10-7-12-32-13-11-28(23(27)32)18-14-17(19-8-9-22(34)30-19)21(37-4)15-20(18)31(3)24(28)29(36,26(35)38-5)25(27)39-16(2)33/h7,10,14-15,19,23-25,36H,6,8-9,11-13H2,1-5H3,(H,30,34)/t19-,23+,24-,25+,27-,28-,29+/m1/s1

> <INCHI_KEY>
BJJHBAPHTDPFRO-VMCIFIRHSA-N

> <FORMULA>
C29H37N3O7

> <MOLECULAR_WEIGHT>
539.629

> <EXACT_MASS>
539.263150543

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
76

> <JCHEM_AVERAGE_POLARIZABILITY>
55.98506995115682

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
methyl (1R,9R,10S,11S,12R,19R)-11-(acetyloxy)-12-ethyl-10-hydroxy-5-methoxy-8-methyl-4-[(2R)-5-oxopyrrolidin-2-yl]-8,16-diazapentacyclo[10.6.1.0^{1,9}.0^{2,7}.0^{16,19}]nonadeca-2,4,6,13-tetraene-10-carboxylate

> <ALOGPS_LOGP>
2.39

> <JCHEM_LOGP>
1.114022527333333

> <ALOGPS_LOGS>
-3.01

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
12.774300360805377

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.861694176570015

> <JCHEM_PKA_STRONGEST_BASIC>
8.598760990543573

> <JCHEM_POLAR_SURFACE_AREA>
117.64000000000001

> <JCHEM_REFRACTIVITY>
142.78080000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
5.28e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl (1R,9R,10S,11S,12R,19R)-11-(acetyloxy)-12-ethyl-10-hydroxy-5-methoxy-8-methyl-4-[(2R)-5-oxopyrrolidin-2-yl]-8,16-diazapentacyclo[10.6.1.0^{1,9}.0^{2,7}.0^{16,19}]nonadeca-2,4,6,13-tetraene-10-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      10.133   2.258   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      11.223   1.170   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      10.826  -0.318   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       9.339  -0.718   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.249   0.370   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.646   1.858   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.878  -0.331   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.120  -1.852   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0       8.641  -2.091   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0       9.342  -3.462   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.924  -2.822   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.486  -2.272   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.244  -0.751   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.439   0.220   0.000  0.00  0.00           C+0
HETATM   15  N   UNK     0       5.197   1.740   0.000  0.00  0.00           N+0
HETATM   16  C   UNK     0       3.759   2.291   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.563   1.320   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.805  -0.200   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       7.005   2.158   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       7.846   0.867   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       3.048  -1.721   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       1.609  -1.171   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       3.290  -3.242   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       3.533  -4.763   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       2.337  -5.733   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       4.971  -5.313   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       6.852  -4.051   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       8.381  -3.862   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0       6.252  -5.469   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       7.180  -6.698   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       5.425  -4.279   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0      12.710   1.570   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0      13.800   0.483   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      10.530   3.746   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       9.560   4.942   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      10.397   6.234   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      11.885   5.837   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0      13.081   6.808   0.000  0.00  0.00           O+0
HETATM   39  N   UNK     0      11.967   4.299   0.000  0.00  0.00           N+0
CONECT    1    2    6   34                                                  
CONECT    2    1    3   32                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    9                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5    1                                                       
CONECT    7    5    8   14   20                                             
CONECT    8    7    9   11                                                  
CONECT    9    8    4   10                                                  
CONECT   10    9                                                            
CONECT   11    8   12   27   31                                             
CONECT   12   11   13   23                                                  
CONECT   13   12   14   18   21                                             
CONECT   14   13    7   15                                                  
CONECT   15   14   16   19                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   13                                                       
CONECT   19   15   20                                                       
CONECT   20   19    7                                                       
CONECT   21   13   22                                                       
CONECT   22   21                                                            
CONECT   23   12   24                                                       
CONECT   24   23   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24                                                            
CONECT   27   11   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   30                                                       
CONECT   30   29                                                            
CONECT   31   11                                                            
CONECT   32    2   33                                                       
CONECT   33   32                                                            
CONECT   34    1   35   39                                                  
CONECT   35   34   36                                                       
CONECT   36   35   37                                                       
CONECT   37   36   38   39                                                  
CONECT   38   37                                                            
CONECT   39   37   34                                                       
MASTER        0    0    0    0    0    0    0    0   39    0   88    0
END

View in JSmol

Synonyms

Value	Source
Methyl (1R,9R,10S,11S,12R,19R)-11-(acetyloxy)-12-ethyl-10-hydroxy-4-[(2R)-5-hydroxy-3,4-dihydro-2H-pyrrol-2-yl]-5-methoxy-8-methyl-8,16-diazapentacyclo[10.6.1.0,.0,.0,]nonadeca-2,4,6,13-tetraene-10-carboxylic acid	Generator

Chemical Formula

C₂₉H₃₇N₃O₇

Average Mass

539.6290 Da

Monoisotopic Mass

539.26315 Da

IUPAC Name

methyl (1R,9R,10S,11S,12R,19R)-11-(acetyloxy)-12-ethyl-10-hydroxy-5-methoxy-8-methyl-4-[(2R)-5-oxopyrrolidin-2-yl]-8,16-diazapentacyclo[10.6.1.0^{1,9}.0^{2,7}.0^{16,19}]nonadeca-2,4,6,13-tetraene-10-carboxylate

Traditional Name

CAS Registry Number

Not Available

SMILES

CC[C@@]12C=CCN3CC[C@@]4([C@H]13)[C@@H](N(C)C1=CC(OC)=C(C=C41)[C@H]1CCC(=O)N1)[C@](O)([C@H]2OC(C)=O)C(=O)OC

InChI Identifier

InChI=1S/C29H37N3O7/c1-6-27-10-7-12-32-13-11-28(23(27)32)18-14-17(19-8-9-22(34)30-19)21(37-4)15-20(18)31(3)24(28)29(36,26(35)38-5)25(27)39-16(2)33/h7,10,14-15,19,23-25,36H,6,8-9,11-13H2,1-5H3,(H,30,34)/t19-,23+,24-,25+,27-,28-,29+/m1/s1

InChI Key

BJJHBAPHTDPFRO-VMCIFIRHSA-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
Catharanthus roseus	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as plumeran-type alkaloids. These are alkaloids with a structure based on the plumeran skeleton. Plumeran is a pentacyclic compound that consists of a pyrrolidine ring shed to the quinoline moiety of pyrido[3,2-c]carbazole ring system.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Plumeran-type alkaloids

Sub Class

Not Available

Direct Parent

Plumeran-type alkaloids

Alternative Parents

Substituents

Plumeran-type alkaloid
Carbazole
2-phenylpyrrolidine
Indole or derivatives
Anisole
Dialkylarylamine
Tertiary aliphatic/aromatic amine
Alkyl aryl ether
Aralkylamine
Dicarboxylic acid or derivatives
Benzenoid
N-alkylpyrrolidine
Pyrrolidone
2-pyrrolidone
Cyclic alcohol
Pyrrole
Pyrrolidine
Methyl ester
Tertiary alcohol
Tertiary amine
Secondary carboxylic acid amide
Tertiary aliphatic amine
Amino acid or derivatives
Lactam
Carboxamide group
Carboxylic acid ester
Organoheterocyclic compound
Azacycle
Ether
Carboxylic acid derivative
Amine
Alcohol
Organic oxide
Hydrocarbon derivative
Carbonyl group
Organopnictogen compound
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	2.39	ALOGPS
logP	1.11	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Acidic)	10.86	ChemAxon
pKa (Strongest Basic)	8.6	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	117.64 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	142.78 m³·mol⁻¹	ChemAxon
Polarizability	55.99 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	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

163033007

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Bannucine (NP0066869)

MOL for NP0066869 (Bannucine)

3D MOL for NP0066869 (Bannucine)

3D SDF for NP0066869 (Bannucine)

3D-SDF for NP0066869 (Bannucine)

PDB for NP0066869 (Bannucine)

3D PDB for NP0066869 (Bannucine)

SMILES for NP0066869 (Bannucine)

INCHI for NP0066869 (Bannucine)

Structure for NP0066869 (Bannucine)

3D Structure for NP0066869 (Bannucine)