NP-MRD: Showing NP-Card for (3s,9s,15s,18s,21s,24s)-3-benzyl-5,8,17,20,23-pentahydroxy-15-[(1r)-1-hydroxyethyl]-21-(1h-indol-3-ylmethyl)-18-(2-methylpropyl)-1,4,7,13,16,19,22-heptaazatricyclo[22.3.0.0⁹,¹³]heptacosa-4,7,16,19,22-pentaene-2,14-dione (NP0160975)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-02 19:03:15 UTC

Updated at

2022-09-02 19:03:15 UTC

NP-MRD ID

NP0160975

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(3s,9s,15s,18s,21s,24s)-3-benzyl-5,8,17,20,23-pentahydroxy-15-[(1r)-1-hydroxyethyl]-21-(1h-indol-3-ylmethyl)-18-(2-methylpropyl)-1,4,7,13,16,19,22-heptaazatricyclo[22.3.0.0⁹,¹³]heptacosa-4,7,16,19,22-pentaene-2,14-dione

Description

Cyclo-(Pro1-Trp-Leu-Thr-Pro2-Gly-Phe), also known as phakellistatin 13, belongs to the class of organic compounds known as cyclic peptides. Cyclic peptides are compounds containing a cyclic moiety bearing a peptide backbone. (3s,9s,15s,18s,21s,24s)-3-benzyl-5,8,17,20,23-pentahydroxy-15-[(1r)-1-hydroxyethyl]-21-(1h-indol-3-ylmethyl)-18-(2-methylpropyl)-1,4,7,13,16,19,22-heptaazatricyclo[22.3.0.0⁹,¹³]heptacosa-4,7,16,19,22-pentaene-2,14-dione was first documented in 2003 (PMID: 12542366). Based on a literature review very few articles have been published on cyclo-(Pro1-Trp-Leu-Thr-Pro2-Gly-Phe).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309022221032D          

 58 63  0  0  1  0            999 V2000
    5.5076   -2.6049    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4345   -1.7831    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6863   -1.4355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1096   -1.3089    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0365   -0.4872    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.7116   -0.0130    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.3997   -0.4682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3495   -1.2917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.1379   -0.1000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.8260   -0.5552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7758   -1.3787    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0800   -1.8221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2868   -2.6208    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.1102   -2.6710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6239   -3.3165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4398   -3.1944    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7421   -2.4268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2284   -1.7812    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4125   -1.9033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1882    0.7235    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.9730    0.9776    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5856    0.4249    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.1454    1.7844    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    9.8603    2.1961    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6897    3.0033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0906    3.0164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5329    2.3371    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.8236    3.1091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5563    3.4884    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.3003    3.7469    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.5910    4.5190    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4050    4.6533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6957    5.4254    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5097    5.5597    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0330    4.9219    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7423    4.1498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9283    4.0155    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4863    3.6127    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.0639    4.3213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4665    5.0415    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2390    4.3099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8365    3.5897    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.0191    3.7013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7070    4.4651    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5137    3.0492    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.6910    2.9885    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4945    2.1872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9746    1.8268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8258    2.2855    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2288    1.7160    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4042    1.6922    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4236    0.9144    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.8267    0.3449    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.0214   -0.4568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0350    0.5771    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2152    0.6822    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.2883   -0.1396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6132   -0.6138    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
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  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
 18 19  2  0  0  0  0
 11 19  1  0  0  0  0
 14 19  1  0  0  0  0
  9 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  4  0  0  0
 21 23  1  0  0  0  0
 23 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
 23 27  1  1  0  0  0
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
 28 30  1  0  0  0  0
 30 31  1  1  0  0  0
 31 32  1  0  0  0  0
 32 33  2  0  0  0  0
 33 34  1  0  0  0  0
 34 35  2  0  0  0  0
 35 36  1  0  0  0  0
 36 37  2  0  0  0  0
 32 37  1  0  0  0  0
 30 38  1  0  0  0  0
 38 39  2  0  0  0  0
 39 40  1  4  0  0  0
 39 41  1  0  0  0  0
 42 41  1  4  0  0  0
 42 43  2  0  0  0  0
 43 44  1  0  0  0  0
 43 45  1  0  0  0  0
 45 46  1  0  0  0  0
 46 47  1  0  0  0  0
 47 48  1  0  0  0  0
 48 49  1  0  0  0  0
 45 49  1  1  0  0  0
 49 50  1  0  0  0  0
 50 51  2  0  0  0  0
 50 52  1  0  0  0  0
 52 53  1  1  0  0  0
 53 54  1  0  0  0  0
 53 55  1  1  0  0  0
 52 56  1  0  0  0  0
 56 57  2  0  0  0  0
  5 57  1  0  0  0  0
 57 58  1  4  0  0  0
M  END

     RDKit          3D

112117  0  0  0  0  0  0  0  0999 V2000
   -5.9437   -0.1862    0.8075 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7731    0.1382    1.6766 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5292    1.6528    1.7574 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5250   -0.6200    1.4406 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8442   -0.5359    0.1279 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.4432    0.6956   -0.2385 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0752    1.7888   -0.5509 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6201    2.5093   -1.6056 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9530    2.4803    0.2004 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.2192    3.8756    0.5358 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4087    4.8640   -0.5134 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1802    4.9060   -1.8523 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5122    6.1239   -2.3677 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9552    6.8725   -1.3552 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3963    8.2022   -1.3596 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7838    8.7790   -0.1758 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7453    8.0648    0.9968 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3110    6.7539    0.9793 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9059    6.1346   -0.2032 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2453    2.4042   -0.5940 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3834    1.9567   -0.4129 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2913    2.0916   -1.4983 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9654    1.2898    0.7742 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9884    2.2428    1.9769 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9469    3.2757    1.4037 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9436    2.4833    0.6122 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4101    1.0970    0.6713 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1156   -0.1025    0.6950 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9118   -0.3018    1.7372 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1853   -1.2505   -0.2151 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.4989   -0.9288   -1.0409 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6480   -0.7511   -0.1444 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0546    0.5236    0.2712 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1052    0.7121    1.1210 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7966   -0.3956    1.5896 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4250   -1.6783    1.1999 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3479   -1.8150    0.3354 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2342   -1.4594   -1.1722 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.2372   -1.6851   -1.7787 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3282   -1.6482   -3.2518 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8519   -2.0108   -1.3766 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5934   -2.4150   -0.0862 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3246   -3.4100    0.6149 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1316   -3.2801    2.0327 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1794   -4.7525    0.1284 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3557   -5.2179   -0.7412 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8408   -6.6113   -1.1046 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6609   -6.5724   -0.8802 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9328   -5.1290   -0.6655 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0078   -4.3964   -1.1506 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1685   -4.3113   -2.4204 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0495   -3.6635   -0.3518 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.1541   -4.7086   -0.1442 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.2431   -4.1655    0.7234 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6208   -5.0961   -1.4181 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5123   -2.5366   -1.0432 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5110   -1.3211   -0.9830 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1411   -0.5543   -1.9613 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7765   -0.6367    1.4459 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3670    0.6964    0.3048 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6764   -1.0293    0.1454 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1081   -0.1097    2.7420 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6166    2.1241    0.7747 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2874    2.0814    2.4530 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5059    1.7375    2.2230 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7146   -1.6615    1.7881 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7661   -0.2456    2.2037 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8545   -1.1587    0.3113 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3619    2.3273   -2.5724 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7772    1.8996    1.1359 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4155    4.2339    1.2490 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1429    3.9018    1.2044 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7703    4.1097   -2.4506 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4160    6.3601   -3.3813 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4121    8.7287   -2.2971 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1135    9.8139   -0.2167 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0610    8.5595    1.9087 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2962    6.2210    1.9107 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9752    2.4561   -2.3825 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3969    0.3893    0.9572 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0744    2.7215    2.2309 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5044    1.7083    2.7971 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3580    3.9648    2.1316 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3737    3.8849    0.6471 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9067    2.5726    1.1689 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1389    2.8139   -0.3956 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4266   -2.1914    0.3625 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6374   -1.6941   -1.7933 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2590    0.0309   -1.5559 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5066    1.3508   -0.1096 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4021    1.7001    1.4309 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.6220   -0.2366    2.2662 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.9384   -2.5495    1.5550 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0756   -2.8438    0.0538 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5433   -2.5575   -3.6764 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3922   -2.6334   -2.1874 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2698   -1.0149   -1.5245 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7109   -3.8925    2.5810 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2059   -5.5350    0.9680 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5169   -4.6116   -1.6287 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2545   -5.3809   -0.1087 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0980   -6.8905   -2.1483 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2308   -7.3748   -0.3968 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1282   -6.9620   -1.8017 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9512   -7.0966    0.0432 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6790   -3.4222    0.6368 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6640   -5.5836    0.3413 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9464   -4.9998    1.0089 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8375   -3.7408    1.6522 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8312   -3.4122    0.1424 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4713   -4.5991   -1.6391 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0841   -0.7316   -2.2610 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  3
  7  8  1  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
  9 20  1  0
 20 21  2  0
 21 22  1  0
 21 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  2  0
 28 30  1  0
 30 31  1  0
 31 32  1  0
 32 33  2  0
 33 34  1  0
 34 35  2  0
 35 36  1  0
 36 37  2  0
 30 38  1  0
 38 39  2  0
 39 40  1  0
 39 41  1  0
 41 42  1  0
 42 43  2  0
 43 44  1  0
 43 45  1  0
 45 46  1  0
 46 47  1  0
 47 48  1  0
 48 49  1  0
 49 50  1  0
 50 51  2  0
 50 52  1  0
 52 56  1  0
 56 57  2  0
 57 58  1  0
 52 53  1  0
 53 54  1  0
 53 55  1  0
 57  5  1  0
 19 11  1  0
 27 23  1  0
 37 32  1  0
 49 45  1  0
 19 14  1  0
  1 59  1  0
  1 60  1  0
  1 61  1  0
  2 62  1  0
  3 63  1  0
  3 64  1  0
  3 65  1  0
  4 66  1  0
  4 67  1  0
  5 68  1  1
  8 69  1  0
  9 70  1  1
 10 71  1  0
 10 72  1  0
 12 73  1  0
 13 74  1  0
 15 75  1  0
 16 76  1  0
 17 77  1  0
 18 78  1  0
 22 79  1  0
 23 80  1  1
 24 81  1  0
 24 82  1  0
 25 83  1  0
 25 84  1  0
 26 85  1  0
 26 86  1  0
 30 87  1  1
 31 88  1  0
 31 89  1  0
 33 90  1  0
 34 91  1  0
 35 92  1  0
 36 93  1  0
 37 94  1  0
 40 95  1  0
 41 96  1  0
 41 97  1  0
 44 98  1  0
 45 99  1  1
 46100  1  0
 46101  1  0
 47102  1  0
 47103  1  0
 48104  1  0
 48105  1  0
 52106  1  1
 58112  1  0
 53107  1  1
 54108  1  0
 54109  1  0
 54110  1  0
 55111  1  0
M  END


  Mrv1652309022221032D          

 58 63  0  0  1  0            999 V2000
    5.5076   -2.6049    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4345   -1.7831    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6863   -1.4355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1096   -1.3089    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0365   -0.4872    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.7116   -0.0130    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.3997   -0.4682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3495   -1.2917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.1379   -0.1000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.8260   -0.5552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7758   -1.3787    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0800   -1.8221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2868   -2.6208    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.1102   -2.6710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6239   -3.3165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4398   -3.1944    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7421   -2.4268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2284   -1.7812    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4125   -1.9033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1882    0.7235    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.9730    0.9776    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5856    0.4249    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.1454    1.7844    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    9.8603    2.1961    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6897    3.0033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0906    3.0164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5329    2.3371    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.8236    3.1091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5563    3.4884    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.3003    3.7469    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.5910    4.5190    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4050    4.6533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6957    5.4254    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5097    5.5597    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0330    4.9219    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7423    4.1498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9283    4.0155    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4863    3.6127    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.0639    4.3213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4665    5.0415    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2390    4.3099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8365    3.5897    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.0191    3.7013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7070    4.4651    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5137    3.0492    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.6910    2.9885    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4945    2.1872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9746    1.8268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8258    2.2855    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2288    1.7160    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4042    1.6922    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4236    0.9144    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.8267    0.3449    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.0214   -0.4568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0350    0.5771    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2152    0.6822    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.2883   -0.1396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6132   -0.6138    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
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  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
 18 19  2  0  0  0  0
 11 19  1  0  0  0  0
 14 19  1  0  0  0  0
  9 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  4  0  0  0
 21 23  1  0  0  0  0
 23 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
 23 27  1  1  0  0  0
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
 28 30  1  0  0  0  0
 30 31  1  1  0  0  0
 31 32  1  0  0  0  0
 32 33  2  0  0  0  0
 33 34  1  0  0  0  0
 34 35  2  0  0  0  0
 35 36  1  0  0  0  0
 36 37  2  0  0  0  0
 32 37  1  0  0  0  0
 30 38  1  0  0  0  0
 38 39  2  0  0  0  0
 39 40  1  4  0  0  0
 39 41  1  0  0  0  0
 42 41  1  4  0  0  0
 42 43  2  0  0  0  0
 43 44  1  0  0  0  0
 43 45  1  0  0  0  0
 45 46  1  0  0  0  0
 46 47  1  0  0  0  0
 47 48  1  0  0  0  0
 48 49  1  0  0  0  0
 45 49  1  1  0  0  0
 49 50  1  0  0  0  0
 50 51  2  0  0  0  0
 50 52  1  0  0  0  0
 52 53  1  1  0  0  0
 53 54  1  0  0  0  0
 53 55  1  1  0  0  0
 52 56  1  0  0  0  0
 56 57  2  0  0  0  0
  5 57  1  0  0  0  0
 57 58  1  4  0  0  0
M  END
> <DATABASE_ID>
NP0160975

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)C[C@@H]1N=C(O)[C@H](CC2=CNC3=CC=CC=C23)N=C(O)[C@@H]2CCCN2C(=O)[C@H](CC2=CC=CC=C2)N=C(O)CN=C(O)[C@@H]2CCCN2C(=O)[C@@H](N=C1O)[C@@H](C)O

> <INCHI_IDENTIFIER>
InChI=1S/C42H54N8O8/c1-24(2)19-30-38(54)48-36(25(3)51)42(58)50-18-9-15-33(50)39(55)44-23-35(52)45-32(20-26-11-5-4-6-12-26)41(57)49-17-10-16-34(49)40(56)47-31(37(53)46-30)21-27-22-43-29-14-8-7-13-28(27)29/h4-8,11-14,22,24-25,30-34,36,43,51H,9-10,15-21,23H2,1-3H3,(H,44,55)(H,45,52)(H,46,53)(H,47,56)(H,48,54)/t25-,30+,31+,32+,33+,34+,36+/m1/s1

> <INCHI_KEY>
GAMOBFCKXWLTIY-SKOSDCFOSA-N

> <FORMULA>
C42H54N8O8

> <MOLECULAR_WEIGHT>
798.942

> <EXACT_MASS>
798.406460731

> <JCHEM_ACCEPTOR_COUNT>
13

> <JCHEM_ATOM_COUNT>
112

> <JCHEM_AVERAGE_POLARIZABILITY>
82.58687825364296

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(3S,9S,15S,18S,21S,24S)-3-benzyl-5,8,17,20,23-pentahydroxy-15-[(1R)-1-hydroxyethyl]-21-[(1H-indol-3-yl)methyl]-18-(2-methylpropyl)-1,4,7,13,16,19,22-heptaazatricyclo[22.3.0.0^{9,13}]heptacosa-4,7,16,19,22-pentaene-2,14-dione

> <ALOGPS_LOGP>
2.39

> <JCHEM_LOGP>
4.030106554803218

> <ALOGPS_LOGS>
-4.27

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
3.838427263541531

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.364106144876445

> <JCHEM_PKA_STRONGEST_BASIC>
2.0553426692391286

> <JCHEM_POLAR_SURFACE_AREA>
239.59

> <JCHEM_REFRACTIVITY>
214.5352

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.24e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3S,9S,15S,18S,21S,24S)-3-benzyl-5,8,17,20,23-pentahydroxy-15-[(1R)-1-hydroxyethyl]-21-(1H-indol-3-ylmethyl)-18-(2-methylpropyl)-1,4,7,13,16,19,22-heptaazatricyclo[22.3.0.0^{9,13}]heptacosa-4,7,16,19,22-pentaene-2,14-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 02-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-SEP-22         0                                  
HETATM    1  C   UNK     0      10.281  -4.862   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      10.144  -3.328   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.748  -2.680   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      11.405  -2.443   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      11.268  -0.909   0.000  0.00  0.00           C+0
HETATM    6  N   UNK     0      12.528  -0.024   0.000  0.00  0.00           N+0
HETATM    7  C   UNK     0      13.813  -0.874   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      13.719  -2.411   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      15.191  -0.187   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      16.475  -1.036   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      16.381  -2.574   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      15.083  -3.401   0.000  0.00  0.00           C+0
HETATM   13  N   UNK     0      15.469  -4.892   0.000  0.00  0.00           N+0
HETATM   14  C   UNK     0      17.006  -4.986   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      17.965  -6.191   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      19.488  -5.963   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      20.052  -4.530   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      19.093  -3.325   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      17.570  -3.553   0.000  0.00  0.00           C+0
HETATM   20  N   UNK     0      15.285   1.351   0.000  0.00  0.00           N+0
HETATM   21  C   UNK     0      16.750   1.825   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      17.893   0.793   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      17.071   3.331   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      18.406   4.099   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      18.087   5.606   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      16.969   5.631   0.000  0.00  0.00           C+0
HETATM   27  N   UNK     0      15.928   4.363   0.000  0.00  0.00           N+0
HETATM   28  C   UNK     0      16.471   5.804   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      17.838   6.512   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0      15.494   6.994   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      16.037   8.436   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      17.556   8.686   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      18.099  10.127   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      19.618  10.378   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      20.595   9.188   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      20.052   7.746   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      18.533   7.496   0.000  0.00  0.00           C+0
HETATM   38  N   UNK     0      13.974   6.744   0.000  0.00  0.00           N+0
HETATM   39  C   UNK     0      13.186   8.066   0.000  0.00  0.00           C+0
HETATM   40  O   UNK     0      13.937   9.411   0.000  0.00  0.00           O+0
HETATM   41  C   UNK     0      11.646   8.045   0.000  0.00  0.00           C+0
HETATM   42  N   UNK     0      10.895   6.701   0.000  0.00  0.00           N+0
HETATM   43  C   UNK     0       9.369   6.909   0.000  0.00  0.00           C+0
HETATM   44  O   UNK     0       8.786   8.335   0.000  0.00  0.00           O+0
HETATM   45  C   UNK     0       8.426   5.692   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0       6.890   5.578   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0       6.523   4.083   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0       7.419   3.410   0.000  0.00  0.00           C+0
HETATM   49  N   UNK     0       9.008   4.266   0.000  0.00  0.00           N+0
HETATM   50  C   UNK     0       7.894   3.203   0.000  0.00  0.00           C+0
HETATM   51  O   UNK     0       6.354   3.159   0.000  0.00  0.00           O+0
HETATM   52  C   UNK     0       8.257   1.707   0.000  0.00  0.00           C+0
HETATM   53  C   UNK     0       7.143   0.644   0.000  0.00  0.00           C+0
HETATM   54  C   UNK     0       7.507  -0.853   0.000  0.00  0.00           C+0
HETATM   55  O   UNK     0       5.665   1.077   0.000  0.00  0.00           O+0
HETATM   56  N   UNK     0       9.735   1.273   0.000  0.00  0.00           N+0
HETATM   57  C   UNK     0       9.872  -0.261   0.000  0.00  0.00           C+0
HETATM   58  O   UNK     0       8.611  -1.146   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   57                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   20                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   19                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   19                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   11   14                                                  
CONECT   20    9   21                                                       
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24   27                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   23   28                                                  
CONECT   28   27   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   31   38                                                  
CONECT   31   30   32                                                       
CONECT   32   31   33   37                                                  
CONECT   33   32   34                                                       
CONECT   34   33   35                                                       
CONECT   35   34   36                                                       
CONECT   36   35   37                                                       
CONECT   37   36   32                                                       
CONECT   38   30   39                                                       
CONECT   39   38   40   41                                                  
CONECT   40   39                                                            
CONECT   41   39   42                                                       
CONECT   42   41   43                                                       
CONECT   43   42   44   45                                                  
CONECT   44   43                                                            
CONECT   45   43   46   49                                                  
CONECT   46   45   47                                                       
CONECT   47   46   48                                                       
CONECT   48   47   49                                                       
CONECT   49   48   45   50                                                  
CONECT   50   49   51   52                                                  
CONECT   51   50                                                            
CONECT   52   50   53   56                                                  
CONECT   53   52   54   55                                                  
CONECT   54   53                                                            
CONECT   55   53                                                            
CONECT   56   52   57                                                       
CONECT   57   56    5   58                                                  
CONECT   58   57                                                            
MASTER        0    0    0    0    0    0    0    0   58    0  126    0
END

View in JSmol

Synonyms

Value	Source
Phakellistatin 13	MeSH

Chemical Formula

C₄₂H₅₄N₈O₈

Average Mass

798.9420 Da

Monoisotopic Mass

798.40646 Da

IUPAC Name

(3S,9S,15S,18S,21S,24S)-3-benzyl-5,8,17,20,23-pentahydroxy-15-[(1R)-1-hydroxyethyl]-21-[(1H-indol-3-yl)methyl]-18-(2-methylpropyl)-1,4,7,13,16,19,22-heptaazatricyclo[22.3.0.0^{9,13}]heptacosa-4,7,16,19,22-pentaene-2,14-dione

Traditional Name

(3S,9S,15S,18S,21S,24S)-3-benzyl-5,8,17,20,23-pentahydroxy-15-[(1R)-1-hydroxyethyl]-21-(1H-indol-3-ylmethyl)-18-(2-methylpropyl)-1,4,7,13,16,19,22-heptaazatricyclo[22.3.0.0^{9,13}]heptacosa-4,7,16,19,22-pentaene-2,14-dione

CAS Registry Number

Not Available

SMILES

CC(C)C[C@@H]1N=C(O)[C@H](CC2=CNC3=CC=CC=C23)N=C(O)[C@@H]2CCCN2C(=O)[C@H](CC2=CC=CC=C2)N=C(O)CN=C(O)[C@@H]2CCCN2C(=O)[C@@H](N=C1O)[C@@H](C)O

InChI Identifier

InChI=1S/C42H54N8O8/c1-24(2)19-30-38(54)48-36(25(3)51)42(58)50-18-9-15-33(50)39(55)44-23-35(52)45-32(20-26-11-5-4-6-12-26)41(57)49-17-10-16-34(49)40(56)47-31(37(53)46-30)21-27-22-43-29-14-8-7-13-28(27)29/h4-8,11-14,22,24-25,30-34,36,43,51H,9-10,15-21,23H2,1-3H3,(H,44,55)(H,45,52)(H,46,53)(H,47,56)(H,48,54)/t25-,30+,31+,32+,33+,34+,36+/m1/s1

InChI Key

GAMOBFCKXWLTIY-SKOSDCFOSA-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

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cyclic peptides. Cyclic peptides are compounds containing a cyclic moiety bearing a peptide backbone.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Cyclic peptides

Alternative Parents

Substituents

Cyclic alpha peptide
Alpha-amino acid or derivatives
3-alkylindole
Indole
Indole or derivatives
Monocyclic benzene moiety
Substituted pyrrole
Benzenoid
Pyrrole
Pyrrolidine
Heteroaromatic compound
Tertiary carboxylic acid amide
Cyclic carboximidic acid
Carboxamide group
Lactam
Secondary alcohol
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Organoheterocyclic compound
Azacycle
Polyol
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic oxygen compound
Organonitrogen compound
Organooxygen 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	2.39	ALOGPS
logP	4.03	ChemAxon
logS	-4.3	ALOGPS
pKa (Strongest Acidic)	3.36	ChemAxon
pKa (Strongest Basic)	2.06	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	13	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	239.59 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	214.54 m³·mol⁻¹	ChemAxon
Polarizability	82.59 Å³	ChemAxon
Number of Rings	6	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

23326979

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

44559452

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Li WL, Yi YH, Wu HM, Xu QZ, Tang HF, Zhou DZ, Lin HW, Wang ZH: Isolation and structure of the cytotoxic cycloheptapeptide phakellistatin 13. J Nat Prod. 2003 Jan;66(1):146-8. doi: 10.1021/np020223y. [PubMed:12542366 ]
LOTUS database [Link]

Showing NP-Card for (3s,9s,15s,18s,21s,24s)-3-benzyl-5,8,17,20,23-pentahydroxy-15-[(1r)-1-hydroxyethyl]-21-(1h-indol-3-ylmethyl)-18-(2-methylpropyl)-1,4,7,13,16,19,22-heptaazatricyclo[22.3.0.0⁹,¹³]heptacosa-4,7,16,19,22-pentaene-2,14-dione (NP0160975)

MOL for NP0160975 ((3s,9s,15s,18s,21s,24s)-3-benzyl-5,8,17,20,23-pentahydroxy-15-[(1r)-1-hydroxyethyl]-21-(1h-indol-3-ylmethyl)-18-(2-methylpropyl)-1,4,7,13,16,19,22-heptaazatricyclo[22.3.0.0⁹,¹³]heptacosa-4,7,16,19,22-pentaene-2,14-dione)

3D MOL for NP0160975 ((3s,9s,15s,18s,21s,24s)-3-benzyl-5,8,17,20,23-pentahydroxy-15-[(1r)-1-hydroxyethyl]-21-(1h-indol-3-ylmethyl)-18-(2-methylpropyl)-1,4,7,13,16,19,22-heptaazatricyclo[22.3.0.0⁹,¹³]heptacosa-4,7,16,19,22-pentaene-2,14-dione)

3D SDF for NP0160975 ((3s,9s,15s,18s,21s,24s)-3-benzyl-5,8,17,20,23-pentahydroxy-15-[(1r)-1-hydroxyethyl]-21-(1h-indol-3-ylmethyl)-18-(2-methylpropyl)-1,4,7,13,16,19,22-heptaazatricyclo[22.3.0.0⁹,¹³]heptacosa-4,7,16,19,22-pentaene-2,14-dione)

3D-SDF for NP0160975 ((3s,9s,15s,18s,21s,24s)-3-benzyl-5,8,17,20,23-pentahydroxy-15-[(1r)-1-hydroxyethyl]-21-(1h-indol-3-ylmethyl)-18-(2-methylpropyl)-1,4,7,13,16,19,22-heptaazatricyclo[22.3.0.0⁹,¹³]heptacosa-4,7,16,19,22-pentaene-2,14-dione)

PDB for NP0160975 ((3s,9s,15s,18s,21s,24s)-3-benzyl-5,8,17,20,23-pentahydroxy-15-[(1r)-1-hydroxyethyl]-21-(1h-indol-3-ylmethyl)-18-(2-methylpropyl)-1,4,7,13,16,19,22-heptaazatricyclo[22.3.0.0⁹,¹³]heptacosa-4,7,16,19,22-pentaene-2,14-dione)

3D PDB for NP0160975 ((3s,9s,15s,18s,21s,24s)-3-benzyl-5,8,17,20,23-pentahydroxy-15-[(1r)-1-hydroxyethyl]-21-(1h-indol-3-ylmethyl)-18-(2-methylpropyl)-1,4,7,13,16,19,22-heptaazatricyclo[22.3.0.0⁹,¹³]heptacosa-4,7,16,19,22-pentaene-2,14-dione)

SMILES for NP0160975 ((3s,9s,15s,18s,21s,24s)-3-benzyl-5,8,17,20,23-pentahydroxy-15-[(1r)-1-hydroxyethyl]-21-(1h-indol-3-ylmethyl)-18-(2-methylpropyl)-1,4,7,13,16,19,22-heptaazatricyclo[22.3.0.0⁹,¹³]heptacosa-4,7,16,19,22-pentaene-2,14-dione)

INCHI for NP0160975 ((3s,9s,15s,18s,21s,24s)-3-benzyl-5,8,17,20,23-pentahydroxy-15-[(1r)-1-hydroxyethyl]-21-(1h-indol-3-ylmethyl)-18-(2-methylpropyl)-1,4,7,13,16,19,22-heptaazatricyclo[22.3.0.0⁹,¹³]heptacosa-4,7,16,19,22-pentaene-2,14-dione)

Structure for NP0160975 ((3s,9s,15s,18s,21s,24s)-3-benzyl-5,8,17,20,23-pentahydroxy-15-[(1r)-1-hydroxyethyl]-21-(1h-indol-3-ylmethyl)-18-(2-methylpropyl)-1,4,7,13,16,19,22-heptaazatricyclo[22.3.0.0⁹,¹³]heptacosa-4,7,16,19,22-pentaene-2,14-dione)

3D Structure for NP0160975 ((3s,9s,15s,18s,21s,24s)-3-benzyl-5,8,17,20,23-pentahydroxy-15-[(1r)-1-hydroxyethyl]-21-(1h-indol-3-ylmethyl)-18-(2-methylpropyl)-1,4,7,13,16,19,22-heptaazatricyclo[22.3.0.0⁹,¹³]heptacosa-4,7,16,19,22-pentaene-2,14-dione)