NP-MRD: Showing NP-Card for (9s,12s,15s,18s,21s,26as)-1,4,7,10,13,16,19-heptahydroxy-15-(hydroxymethyl)-18,21-bis[(4-hydroxyphenyl)methyl]-9-isopropyl-12-(2-methylpropyl)-3h,6h,9h,12h,15h,18h,21h,24h,25h,26h,26ah-pyrrolo[1,2-a]1,4,7,10,13,16,19,22-octaazacyclotetracosan-22-one (NP0173454)

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Record Information

Version

2.0

Created at

2022-09-03 10:35:30 UTC

Updated at

2022-09-03 10:35:30 UTC

NP-MRD ID

NP0173454

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(9s,12s,15s,18s,21s,26as)-1,4,7,10,13,16,19-heptahydroxy-15-(hydroxymethyl)-18,21-bis[(4-hydroxyphenyl)methyl]-9-isopropyl-12-(2-methylpropyl)-3h,6h,9h,12h,15h,18h,21h,24h,25h,26h,26ah-pyrrolo[1,2-a]1,4,7,10,13,16,19,22-octaazacyclotetracosan-22-one

Description

Cyclosquamosin D belongs to the class of organic compounds known as oligopeptides. These are organic compounds containing a sequence of between three and ten alpha-amino acids joined by peptide bonds. (9s,12s,15s,18s,21s,26as)-1,4,7,10,13,16,19-heptahydroxy-15-(hydroxymethyl)-18,21-bis[(4-hydroxyphenyl)methyl]-9-isopropyl-12-(2-methylpropyl)-3h,6h,9h,12h,15h,18h,21h,24h,25h,26h,26ah-pyrrolo[1,2-a]1,4,7,10,13,16,19,22-octaazacyclotetracosan-22-one is found in Annona squamosa. (9s,12s,15s,18s,21s,26as)-1,4,7,10,13,16,19-heptahydroxy-15-(hydroxymethyl)-18,21-bis[(4-hydroxyphenyl)methyl]-9-isopropyl-12-(2-methylpropyl)-3h,6h,9h,12h,15h,18h,21h,24h,25h,26h,26ah-pyrrolo[1,2-a]1,4,7,10,13,16,19,22-octaazacyclotetracosan-22-one was first documented in 2008 (PMID: 18072745). Based on a literature review very few articles have been published on Cyclosquamosin D (PMID: 20801649).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309032212352D          

 60 63  0  0  1  0            999 V2000
   11.7715   -2.6415    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0970   -1.8835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9163   -1.7863    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6033   -1.2225    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7840   -1.3197    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   10.2902   -0.6587    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.8009   -0.0108    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6173   -0.1290    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.4950    0.7554    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   11.0056    1.4034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8221    1.2852    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6997    2.1696    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6785    0.8737    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.5813    1.6929    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2423    2.1867    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.8233    2.0184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1623    1.5247    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.5143    2.0353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6325    2.8518    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7481    1.7294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6299    0.9129    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.8107    0.8158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3169    1.4767    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4852    0.0577    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.7040   -0.2077    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7150   -1.0326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7174   -1.3691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9789   -0.6032    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.4683   -1.2512    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6553   -1.3911    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7742   -2.0174    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.2636   -2.6654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4471   -2.5472    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9365   -3.1952    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1200   -3.0770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8141   -2.3108    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9976   -2.1926    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3247   -1.6628    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1412   -1.7810    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5907   -2.1356    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.6878   -2.9549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0269   -3.4487    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4459   -3.2804    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.5431   -4.0997    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8821   -4.5934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9793   -5.4127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3183   -5.9065    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5603   -5.5810    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8993   -6.0747    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4631   -4.7617    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1241   -4.2679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1068   -2.7866    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.7548   -3.2973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6366   -4.1137    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.5210   -2.9914    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   10.1690   -3.5020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0508   -4.3185    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.6392   -2.1749    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.4585   -2.0777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9523   -2.7387    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  5  4  1  1  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  4  0  0  0
  7  9  1  0  0  0  0
  9 10  1  1  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
  9 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  4  0  0  0
 14 16  1  0  0  0  0
 17 16  1  4  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 18 20  1  0  0  0  0
 21 20  1  4  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 22 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 24 28  1  1  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 29 31  1  0  0  0  0
 31 32  1  1  0  0  0
 32 33  1  0  0  0  0
 33 34  2  0  0  0  0
 34 35  1  0  0  0  0
 35 36  2  0  0  0  0
 36 37  1  0  0  0  0
 36 38  1  0  0  0  0
 38 39  2  0  0  0  0
 33 39  1  0  0  0  0
 31 40  1  0  0  0  0
 40 41  2  0  0  0  0
 41 42  1  4  0  0  0
 41 43  1  0  0  0  0
 43 44  1  1  0  0  0
 44 45  1  0  0  0  0
 45 46  2  0  0  0  0
 46 47  1  0  0  0  0
 47 48  2  0  0  0  0
 48 49  1  0  0  0  0
 48 50  1  0  0  0  0
 50 51  2  0  0  0  0
 45 51  1  0  0  0  0
 43 52  1  0  0  0  0
 52 53  2  0  0  0  0
 53 54  1  4  0  0  0
 53 55  1  0  0  0  0
 55 56  1  1  0  0  0
 56 57  1  0  0  0  0
 55 58  1  0  0  0  0
 58 59  2  0  0  0  0
  5 59  1  0  0  0  0
 59 60  1  4  0  0  0
M  END

     RDKit          3D

116119  0  0  0  0  0  0  0  0999 V2000
    5.7274   -3.0250    2.2175 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4211   -3.6420    1.8384 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1217   -4.7667    2.8099 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2973   -2.6643    1.7714 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5638   -1.5539    0.7299 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.7306   -0.9094    1.1512 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.3778    0.1190    0.9366 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5879    0.4398    1.6035 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9605    1.1431   -0.0487 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.7560    0.8211   -1.3356 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4291    1.7888   -2.4294 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5764   -0.6026   -1.7621 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4167    2.4561    0.3310 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.7647    3.5109    0.5353 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4229    4.7008    0.9030 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3018    3.5704    0.4051 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6903    4.3217    1.5153 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4936    4.7603    1.4176 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8678    5.4754    2.4340 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7638    4.4675    0.1275 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5912    4.8443    0.2962 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6634    4.3333   -0.0816 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8860    4.9199    0.2265 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7113    3.0822   -0.8746 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.8883    3.1939   -2.1440 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9338    3.8353   -3.0577 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0724    2.8689   -2.8438 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0441    2.7636   -1.3562 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1381    2.4237   -0.5398 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1940    3.1767   -0.6421 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3066    1.3433    0.4284 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.1035    1.9026    1.6484 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2695    0.7783    2.6030 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3846    0.4627    3.6022 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6064   -0.6122    4.4522 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7355   -1.4170    4.3285 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9614   -2.4926    5.1749 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6179   -1.0912    3.3217 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4036   -0.0239    2.4736 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1947    0.6988    0.9763 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3801   -0.1759    0.5807 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3196   -0.6543    1.3845 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4382   -0.8147   -0.7963 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.3560   -2.0004   -0.6364 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5849   -2.7592   -1.8718 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8301   -3.8302   -2.2593 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0755   -4.5307   -3.4250 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1111   -4.1682   -4.2555 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3790   -4.8625   -5.4398 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8939   -3.0886   -3.8924 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6258   -2.4112   -2.7278 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2425   -0.9640   -1.4011 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1905   -1.0973   -1.9247 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0425   -0.8436   -3.3099 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0498   -1.5509   -1.2117 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8340   -3.0238   -0.8800 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1629   -3.2013    0.0595 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3900   -0.7508   -0.1060 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3575   -0.7138    0.6823 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2907    0.2833    1.6879 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6070   -2.1831    2.9499 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3294   -3.7882    2.7676 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3565   -2.7431    1.3449 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5621   -4.1070    0.8299 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5695   -5.6921    2.4293 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0272   -4.8540    3.0086 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5986   -4.5617    3.7871 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3015   -3.0764    1.7181 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3328   -2.0878    2.7472 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6344   -2.0803   -0.2465 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4689    0.9140    2.5123 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9171    1.0828   -0.3544 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8189    0.9503   -1.0557 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2339    2.7887   -1.9903 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5691    1.4085   -3.0306 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2897    1.8540   -3.1187 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2367   -0.7698   -2.6405 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5375   -0.8304   -2.0816 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9155   -1.3082   -0.9832 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6463    4.7480    1.9072 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7971    2.6009    0.3601 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0846    4.1037   -0.5563 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1055    5.2731    3.3968 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3165    5.0939   -0.6218 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9425    3.3721   -0.0212 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2616    4.9633    1.1687 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2460    2.2599   -0.2849 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5684    2.2311   -2.5377 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0603    3.8858   -2.1073 H   0  0  0  0  0  0  0  0  0  0  0  0
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 12 79  1  0
M  END


  Mrv1652309032212352D          

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 31 32  1  1  0  0  0
 32 33  1  0  0  0  0
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 35 36  2  0  0  0  0
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 38 39  2  0  0  0  0
 33 39  1  0  0  0  0
 31 40  1  0  0  0  0
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 43 44  1  1  0  0  0
 44 45  1  0  0  0  0
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 46 47  1  0  0  0  0
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 50 51  2  0  0  0  0
 45 51  1  0  0  0  0
 43 52  1  0  0  0  0
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 53 54  1  4  0  0  0
 53 55  1  0  0  0  0
 55 56  1  1  0  0  0
 56 57  1  0  0  0  0
 55 58  1  0  0  0  0
 58 59  2  0  0  0  0
  5 59  1  0  0  0  0
 59 60  1  4  0  0  0
M  END
> <DATABASE_ID>
NP0173454

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)C[C@@H]1N=C(O)[C@@H](N=C(O)CN=C(O)CN=C(O)[C@@H]2CCCN2C(=O)[C@H](CC2=CC=C(O)C=C2)N=C(O)[C@H](CC2=CC=C(O)C=C2)N=C(O)[C@H](CO)N=C1O)C(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C41H56N8O11/c1-22(2)16-28-36(55)47-31(21-50)38(57)44-29(17-24-7-11-26(51)12-8-24)37(56)46-30(18-25-9-13-27(52)14-10-25)41(60)49-15-5-6-32(49)39(58)43-19-33(53)42-20-34(54)48-35(23(3)4)40(59)45-28/h7-14,22-23,28-32,35,50-52H,5-6,15-21H2,1-4H3,(H,42,53)(H,43,58)(H,44,57)(H,45,59)(H,46,56)(H,47,55)(H,48,54)/t28-,29-,30-,31-,32-,35-/m0/s1

> <INCHI_KEY>
ZHNAXZUOHRJIJT-ZABOXFJKSA-N

> <FORMULA>
C41H56N8O11

> <MOLECULAR_WEIGHT>
836.944

> <EXACT_MASS>
836.406854655

> <JCHEM_ACCEPTOR_COUNT>
18

> <JCHEM_ATOM_COUNT>
116

> <JCHEM_AVERAGE_POLARIZABILITY>
86.37403467259318

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
10

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(9S,12S,15S,18S,21S,26aS)-1,4,7,10,13,16,19-heptahydroxy-15-(hydroxymethyl)-18,21-bis[(4-hydroxyphenyl)methyl]-12-(2-methylpropyl)-9-(propan-2-yl)-3H,6H,9H,12H,15H,18H,21H,22H,24H,25H,26H,26aH-pyrrolo[1,2-a]1,4,7,10,13,16,19,22-octaazacyclotetracosan-22-one

> <ALOGPS_LOGP>
1.69

> <JCHEM_LOGP>
4.380431506333332

> <ALOGPS_LOGS>
-4.07

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
3.3438021032876497

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.8565838622720494

> <JCHEM_PKA_STRONGEST_BASIC>
-5.958343579805377

> <JCHEM_POLAR_SURFACE_AREA>
309.13000000000005

> <JCHEM_REFRACTIVITY>
218.14509999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
7.07e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(9S,12S,15S,18S,21S,26aS)-1,4,7,10,13,16,19-heptahydroxy-15-(hydroxymethyl)-18,21-bis[(4-hydroxyphenyl)methyl]-9-isopropyl-12-(2-methylpropyl)-3H,6H,9H,12H,15H,18H,21H,24H,25H,26H,26aH-pyrrolo[1,2-a]1,4,7,10,13,16,19,22-octaazacyclotetracosan-22-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 03-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-SEP-22         0                                  
HETATM    1  C   UNK     0      21.974  -4.931   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      22.581  -3.516   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      24.110  -3.334   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      21.659  -2.282   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      20.130  -2.463   0.000  0.00  0.00           C+0
HETATM    6  N   UNK     0      19.208  -1.230   0.000  0.00  0.00           N+0
HETATM    7  C   UNK     0      20.162  -0.020   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      21.686  -0.241   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      19.591   1.410   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      20.544   2.620   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      22.068   2.399   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      19.973   4.050   0.000  0.00  0.00           C+0
HETATM   13  N   UNK     0      18.067   1.631   0.000  0.00  0.00           N+0
HETATM   14  C   UNK     0      17.885   3.160   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      19.119   4.082   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      16.470   3.768   0.000  0.00  0.00           C+0
HETATM   17  N   UNK     0      15.236   2.846   0.000  0.00  0.00           N+0
HETATM   18  C   UNK     0      14.027   3.799   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      14.247   5.323   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      12.597   3.228   0.000  0.00  0.00           C+0
HETATM   21  N   UNK     0      12.376   1.704   0.000  0.00  0.00           N+0
HETATM   22  C   UNK     0      10.847   1.523   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       9.925   2.756   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      10.239   0.108   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       8.781  -0.388   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       8.801  -1.928   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      10.672  -2.556   0.000  0.00  0.00           C+0
HETATM   28  N   UNK     0      11.161  -1.126   0.000  0.00  0.00           N+0
HETATM   29  C   UNK     0      10.208  -2.336   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       8.690  -2.597   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      10.779  -3.766   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       9.825  -4.975   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       8.301  -4.755   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       7.348  -5.964   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       5.824  -5.744   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       5.253  -4.314   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0       3.729  -4.093   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0       6.206  -3.104   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       7.730  -3.325   0.000  0.00  0.00           C+0
HETATM   40  N   UNK     0      12.303  -3.987   0.000  0.00  0.00           N+0
HETATM   41  C   UNK     0      12.484  -5.516   0.000  0.00  0.00           C+0
HETATM   42  O   UNK     0      11.250  -6.438   0.000  0.00  0.00           O+0
HETATM   43  C   UNK     0      13.899  -6.123   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0      14.080  -7.653   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0      12.847  -8.574   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0      13.028 -10.104   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0      11.794 -11.025   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0      10.379 -10.418   0.000  0.00  0.00           C+0
HETATM   49  O   UNK     0       9.145 -11.339   0.000  0.00  0.00           O+0
HETATM   50  C   UNK     0      10.198  -8.888   0.000  0.00  0.00           C+0
HETATM   51  C   UNK     0      11.432  -7.967   0.000  0.00  0.00           C+0
HETATM   52  N   UNK     0      15.133  -5.202   0.000  0.00  0.00           N+0
HETATM   53  C   UNK     0      16.342  -6.155   0.000  0.00  0.00           C+0
HETATM   54  O   UNK     0      16.122  -7.679   0.000  0.00  0.00           O+0
HETATM   55  C   UNK     0      17.773  -5.584   0.000  0.00  0.00           C+0
HETATM   56  C   UNK     0      18.982  -6.537   0.000  0.00  0.00           C+0
HETATM   57  O   UNK     0      18.762  -8.061   0.000  0.00  0.00           O+0
HETATM   58  N   UNK     0      17.993  -4.060   0.000  0.00  0.00           N+0
HETATM   59  C   UNK     0      19.523  -3.878   0.000  0.00  0.00           C+0
HETATM   60  O   UNK     0      20.444  -5.112   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6   59                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   13                                                  
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10                                                            
CONECT   13    9   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25   28                                                  
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   24   29                                                  
CONECT   29   28   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29   32   40                                                  
CONECT   32   31   33                                                       
CONECT   33   32   34   39                                                  
CONECT   34   33   35                                                       
CONECT   35   34   36                                                       
CONECT   36   35   37   38                                                  
CONECT   37   36                                                            
CONECT   38   36   39                                                       
CONECT   39   38   33                                                       
CONECT   40   31   41                                                       
CONECT   41   40   42   43                                                  
CONECT   42   41                                                            
CONECT   43   41   44   52                                                  
CONECT   44   43   45                                                       
CONECT   45   44   46   51                                                  
CONECT   46   45   47                                                       
CONECT   47   46   48                                                       
CONECT   48   47   49   50                                                  
CONECT   49   48                                                            
CONECT   50   48   51                                                       
CONECT   51   50   45                                                       
CONECT   52   43   53                                                       
CONECT   53   52   54   55                                                  
CONECT   54   53                                                            
CONECT   55   53   56   58                                                  
CONECT   56   55   57                                                       
CONECT   57   56                                                            
CONECT   58   55   59                                                       
CONECT   59   58    5   60                                                  
CONECT   60   59                                                            
MASTER        0    0    0    0    0    0    0    0   60    0  126    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₄₁H₅₆N₈O₁₁

Average Mass

836.9440 Da

Monoisotopic Mass

836.40685 Da

IUPAC Name

(9S,12S,15S,18S,21S,26aS)-1,4,7,10,13,16,19-heptahydroxy-15-(hydroxymethyl)-18,21-bis[(4-hydroxyphenyl)methyl]-12-(2-methylpropyl)-9-(propan-2-yl)-3H,6H,9H,12H,15H,18H,21H,22H,24H,25H,26H,26aH-pyrrolo[1,2-a]1,4,7,10,13,16,19,22-octaazacyclotetracosan-22-one

Traditional Name

(9S,12S,15S,18S,21S,26aS)-1,4,7,10,13,16,19-heptahydroxy-15-(hydroxymethyl)-18,21-bis[(4-hydroxyphenyl)methyl]-9-isopropyl-12-(2-methylpropyl)-3H,6H,9H,12H,15H,18H,21H,24H,25H,26H,26aH-pyrrolo[1,2-a]1,4,7,10,13,16,19,22-octaazacyclotetracosan-22-one

CAS Registry Number

Not Available

SMILES

CC(C)C[C@@H]1N=C(O)[C@@H](N=C(O)CN=C(O)CN=C(O)[C@@H]2CCCN2C(=O)[C@H](CC2=CC=C(O)C=C2)N=C(O)[C@H](CC2=CC=C(O)C=C2)N=C(O)[C@H](CO)N=C1O)C(C)C

InChI Identifier

InChI=1S/C41H56N8O11/c1-22(2)16-28-36(55)47-31(21-50)38(57)44-29(17-24-7-11-26(51)12-8-24)37(56)46-30(18-25-9-13-27(52)14-10-25)41(60)49-15-5-6-32(49)39(58)43-19-33(53)42-20-34(54)48-35(23(3)4)40(59)45-28/h7-14,22-23,28-32,35,50-52H,5-6,15-21H2,1-4H3,(H,42,53)(H,43,58)(H,44,57)(H,45,59)(H,46,56)(H,47,55)(H,48,54)/t28-,29-,30-,31-,32-,35-/m0/s1

InChI Key

ZHNAXZUOHRJIJT-ZABOXFJKSA-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
Annona squamosa	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as oligopeptides. These are organic compounds containing a sequence of between three and ten alpha-amino acids joined by peptide bonds.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Oligopeptides

Alternative Parents

Substituents

Alpha-oligopeptide
Cyclic alpha peptide
Macrolactam
Alpha-amino acid or derivatives
1-hydroxy-2-unsubstituted benzenoid
Phenol
Monocyclic benzene moiety
Benzenoid
Tertiary carboxylic acid amide
Pyrrolidine
Carboxamide group
Lactam
Secondary carboxylic acid amide
Azacycle
Organoheterocyclic compound
Organonitrogen compound
Organic nitrogen compound
Alcohol
Hydrocarbon derivative
Organic oxide
Carbonyl group
Organic oxygen compound
Organooxygen compound
Primary alcohol
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

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

Predicted Properties

Property	Value	Source
logP	1.69	ALOGPS
logP	4.38	ChemAxon
logS	-4.1	ALOGPS
pKa (Strongest Acidic)	2.86	ChemAxon
pKa (Strongest Basic)	-6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	18	ChemAxon
Hydrogen Donor Count	10	ChemAxon
Polar Surface Area	309.13 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	218.15 m³·mol⁻¹	ChemAxon
Polarizability	86.37 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	No	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

23275457

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

15427682

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Yang YL, Hua KF, Chuang PH, Wu SH, Wu KY, Chang FR, Wu YC: New cyclic peptides from the seeds of Annona squamosa L. and their anti-inflammatory activities. J Agric Food Chem. 2008 Jan 23;56(2):386-92. doi: 10.1021/jf072594w. Epub 2007 Dec 12. [PubMed:18072745 ]
Dellai A, Maricic I, Kumar V, Arutyunyan S, Bouraoui A, Nefzi A: Parallel synthesis and anti-inflammatory activity of cyclic peptides cyclosquamosin D and Met-cherimolacyclopeptide B and their analogs. Bioorg Med Chem Lett. 2010 Oct 1;20(19):5653-7. doi: 10.1016/j.bmcl.2010.08.033. Epub 2010 Aug 11. [PubMed:20801649 ]
LOTUS database [Link]

Showing NP-Card for (9s,12s,15s,18s,21s,26as)-1,4,7,10,13,16,19-heptahydroxy-15-(hydroxymethyl)-18,21-bis[(4-hydroxyphenyl)methyl]-9-isopropyl-12-(2-methylpropyl)-3h,6h,9h,12h,15h,18h,21h,24h,25h,26h,26ah-pyrrolo[1,2-a]1,4,7,10,13,16,19,22-octaazacyclotetracosan-22-one (NP0173454)

MOL for NP0173454 ((9s,12s,15s,18s,21s,26as)-1,4,7,10,13,16,19-heptahydroxy-15-(hydroxymethyl)-18,21-bis[(4-hydroxyphenyl)methyl]-9-isopropyl-12-(2-methylpropyl)-3h,6h,9h,12h,15h,18h,21h,24h,25h,26h,26ah-pyrrolo[1,2-a]1,4,7,10,13,16,19,22-octaazacyclotetracosan-22-one)

3D MOL for NP0173454 ((9s,12s,15s,18s,21s,26as)-1,4,7,10,13,16,19-heptahydroxy-15-(hydroxymethyl)-18,21-bis[(4-hydroxyphenyl)methyl]-9-isopropyl-12-(2-methylpropyl)-3h,6h,9h,12h,15h,18h,21h,24h,25h,26h,26ah-pyrrolo[1,2-a]1,4,7,10,13,16,19,22-octaazacyclotetracosan-22-one)

3D SDF for NP0173454 ((9s,12s,15s,18s,21s,26as)-1,4,7,10,13,16,19-heptahydroxy-15-(hydroxymethyl)-18,21-bis[(4-hydroxyphenyl)methyl]-9-isopropyl-12-(2-methylpropyl)-3h,6h,9h,12h,15h,18h,21h,24h,25h,26h,26ah-pyrrolo[1,2-a]1,4,7,10,13,16,19,22-octaazacyclotetracosan-22-one)

3D-SDF for NP0173454 ((9s,12s,15s,18s,21s,26as)-1,4,7,10,13,16,19-heptahydroxy-15-(hydroxymethyl)-18,21-bis[(4-hydroxyphenyl)methyl]-9-isopropyl-12-(2-methylpropyl)-3h,6h,9h,12h,15h,18h,21h,24h,25h,26h,26ah-pyrrolo[1,2-a]1,4,7,10,13,16,19,22-octaazacyclotetracosan-22-one)

PDB for NP0173454 ((9s,12s,15s,18s,21s,26as)-1,4,7,10,13,16,19-heptahydroxy-15-(hydroxymethyl)-18,21-bis[(4-hydroxyphenyl)methyl]-9-isopropyl-12-(2-methylpropyl)-3h,6h,9h,12h,15h,18h,21h,24h,25h,26h,26ah-pyrrolo[1,2-a]1,4,7,10,13,16,19,22-octaazacyclotetracosan-22-one)

3D PDB for NP0173454 ((9s,12s,15s,18s,21s,26as)-1,4,7,10,13,16,19-heptahydroxy-15-(hydroxymethyl)-18,21-bis[(4-hydroxyphenyl)methyl]-9-isopropyl-12-(2-methylpropyl)-3h,6h,9h,12h,15h,18h,21h,24h,25h,26h,26ah-pyrrolo[1,2-a]1,4,7,10,13,16,19,22-octaazacyclotetracosan-22-one)

SMILES for NP0173454 ((9s,12s,15s,18s,21s,26as)-1,4,7,10,13,16,19-heptahydroxy-15-(hydroxymethyl)-18,21-bis[(4-hydroxyphenyl)methyl]-9-isopropyl-12-(2-methylpropyl)-3h,6h,9h,12h,15h,18h,21h,24h,25h,26h,26ah-pyrrolo[1,2-a]1,4,7,10,13,16,19,22-octaazacyclotetracosan-22-one)

INCHI for NP0173454 ((9s,12s,15s,18s,21s,26as)-1,4,7,10,13,16,19-heptahydroxy-15-(hydroxymethyl)-18,21-bis[(4-hydroxyphenyl)methyl]-9-isopropyl-12-(2-methylpropyl)-3h,6h,9h,12h,15h,18h,21h,24h,25h,26h,26ah-pyrrolo[1,2-a]1,4,7,10,13,16,19,22-octaazacyclotetracosan-22-one)

Structure for NP0173454 ((9s,12s,15s,18s,21s,26as)-1,4,7,10,13,16,19-heptahydroxy-15-(hydroxymethyl)-18,21-bis[(4-hydroxyphenyl)methyl]-9-isopropyl-12-(2-methylpropyl)-3h,6h,9h,12h,15h,18h,21h,24h,25h,26h,26ah-pyrrolo[1,2-a]1,4,7,10,13,16,19,22-octaazacyclotetracosan-22-one)

3D Structure for NP0173454 ((9s,12s,15s,18s,21s,26as)-1,4,7,10,13,16,19-heptahydroxy-15-(hydroxymethyl)-18,21-bis[(4-hydroxyphenyl)methyl]-9-isopropyl-12-(2-methylpropyl)-3h,6h,9h,12h,15h,18h,21h,24h,25h,26h,26ah-pyrrolo[1,2-a]1,4,7,10,13,16,19,22-octaazacyclotetracosan-22-one)