NP-MRD: Showing NP-Card for (6s,9s,15s,18s,21s,24s)-6-benzyl-5,8,17,20,23-pentahydroxy-21-[(1r)-1-hydroxyethyl]-15-(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 (NP0201979)

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Record Information

Version

2.0

Created at

2022-09-04 21:06:37 UTC

Updated at

2022-09-04 21:06:37 UTC

NP-MRD ID

NP0201979

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(6s,9s,15s,18s,21s,24s)-6-benzyl-5,8,17,20,23-pentahydroxy-21-[(1r)-1-hydroxyethyl]-15-(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

Phakellistatin 13 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. (6s,9s,15s,18s,21s,24s)-6-benzyl-5,8,17,20,23-pentahydroxy-21-[(1r)-1-hydroxyethyl]-15-(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 is found in Phakellia fusca. (6s,9s,15s,18s,21s,24s)-6-benzyl-5,8,17,20,23-pentahydroxy-21-[(1r)-1-hydroxyethyl]-15-(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 a small amount of articles have been published on Phakellistatin 13 (PMID: 19760191) (PMID: 15151396) (PMID: 17190452) (PMID: 20345147).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309042223062D          

 58 63  0  0  1  0            999 V2000
    3.8741    7.9449    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7390    8.7587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3762    9.2827    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9666    9.0486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3293    8.5246    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5569    8.8145    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.5446    9.6394    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2528   10.0626    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8240   10.0412    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8117   10.8661    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5199   11.2892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0911   11.2679    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1158    9.6180    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5368   10.1227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4261   10.9402    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3002    9.8098    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.0435   10.1678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6136    9.5715    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2864    9.0695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4109    8.9923    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2124    8.7967    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9389    9.1877    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4438    8.0048    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8737    7.4085    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2204    6.6600    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0421    6.5860    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7456    5.9853    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.0924    5.2368    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9140    5.1628    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2608    4.4142    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0825    4.3403    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5574    5.0149    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2106    5.7635    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3889    5.8374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9239    6.0593    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5549    5.3214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0093    4.6329    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2687    5.2721    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7831    4.6271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5554    4.9170    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5822    5.5167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7232    5.9606    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.5301    5.7891    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0151    5.1216    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0822    6.4022    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8891    6.2306    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1441    5.4460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6592    4.7786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1441    4.1111    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.9287    4.3661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6432    3.9536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3576    4.3661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3576    5.1911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6432    5.6036    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9287    5.1911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8272    7.1868    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4645    7.7108    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2369    7.4209    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  6  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
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 16 20  1  1  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 21 23  1  0  0  0  0
 24 23  1  4  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 25 27  1  0  0  0  0
 27 28  1  1  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 30 31  1  0  0  0  0
 31 32  2  0  0  0  0
 32 33  1  0  0  0  0
 33 34  2  0  0  0  0
 29 34  1  0  0  0  0
 27 35  1  0  0  0  0
 35 36  2  0  0  0  0
 36 37  1  4  0  0  0
 36 38  1  0  0  0  0
 38 39  1  0  0  0  0
 39 40  1  0  0  0  0
 40 41  1  0  0  0  0
 41 42  1  0  0  0  0
 38 42  1  1  0  0  0
 42 43  1  0  0  0  0
 43 44  2  0  0  0  0
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 47 55  1  0  0  0  0
 50 55  1  0  0  0  0
 45 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
   -2.9864    1.3050    1.9745 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0190    1.3537    0.8798 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1034    2.3277    1.3639 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4403    1.8244   -0.4412 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3540    0.8750   -0.8704 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.6933    1.1620   -2.0738 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0079    2.0379   -2.5972 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4900    1.9637   -3.9178 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6298    3.2938   -1.9081 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.2529    4.4383   -2.7258 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.7540    4.3891   -2.7084 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.7974    3.4402   -2.0912 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6677    3.9308   -1.3424 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.3801    4.5016   -0.0175 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5399    6.0256   -0.1380 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9253    6.2260    0.4445 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8856    5.2808    1.6053 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2962    4.0745    0.9993 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5533    2.7144    1.3328 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7338    2.4283    1.6546 O   0  0  0  0  0  0  0  0  0  0  0  0
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    1.4262   -4.1913    1.9100 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3390   -5.4305    1.0531 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7278   -5.0353   -0.2457 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3534   -3.6430   -0.0382 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7582   -2.9293   -0.5408 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0399   -3.1435   -1.7692 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6128   -1.9728    0.2092 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1613   -2.6418    1.4811 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9714   -3.8288    1.2137 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5762   -5.1344    1.2964 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.5450    1.1721    2.9418 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.5307    0.3844    0.8138 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7911    3.3726    1.3081 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0663    2.0988    0.8752 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.8592    4.3511   -3.7687 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.0422    3.3281   -2.9416 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1644    4.7367   -1.7440 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9843    6.3866   -2.9120 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2824    4.4674   -2.6024 H   0  0  0  0  0  0  0  0  0  0  0  0
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    2.2273    5.7008    2.3838 H   0  0  0  0  0  0  0  0  0  0  0  0
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    4.3422    1.0775   -0.5972 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2365   -0.3072   -1.6876 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6626   -2.2721   -1.4505 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7384   -3.2236   -0.5357 H   0  0  0  0  0  0  0  0  0  0  0  0
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 12 75  1  0
M  END


  Mrv1652309042223062D          

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 47 55  1  0  0  0  0
 50 55  1  0  0  0  0
 45 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>
NP0201979

> <DATABASE_NAME>
NP-MRD

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

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

> <INCHI_KEY>
GCYCNNNVEBIXIM-SKOSDCFOSA-N

> <FORMULA>
C42H54N8O8

> <MOLECULAR_WEIGHT>
798.942

> <EXACT_MASS>
798.406460731

> <JCHEM_ACCEPTOR_COUNT>
13

> <JCHEM_ATOM_COUNT>
112

> <JCHEM_AVERAGE_POLARIZABILITY>
83.56775730766707

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(6S,9S,15S,18S,21S,24S)-6-benzyl-5,8,17,20,23-pentahydroxy-21-[(1R)-1-hydroxyethyl]-15-[(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

> <JCHEM_LOGP>
4.354144509333333

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
3.7000588196209656

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.1850632124766944

> <JCHEM_PKA_STRONGEST_BASIC>
1.7492901845721351

> <JCHEM_POLAR_SURFACE_AREA>
239.59

> <JCHEM_REFRACTIVITY>
214.53519999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(6S,9S,15S,18S,21S,24S)-6-benzyl-5,8,17,20,23-pentahydroxy-21-[(1R)-1-hydroxyethyl]-15-(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                                 04-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-22         0                                  
HETATM    1  C   UNK     0       7.232  14.830   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.979  16.350   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.169  17.328   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.538  16.891   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.348  15.913   0.000  0.00  0.00           C+0
HETATM    6  N   UNK     0       2.906  16.454   0.000  0.00  0.00           N+0
HETATM    7  C   UNK     0       2.883  17.994   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       4.205  18.783   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       1.538  18.744   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.515  20.283   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.837  21.073   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       0.170  21.033   0.000  0.00  0.00           O+0
HETATM   13  N   UNK     0       0.216  17.954   0.000  0.00  0.00           N+0
HETATM   14  C   UNK     0      -1.002  18.896   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -0.795  20.422   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      -2.427  18.312   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -3.815  18.980   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -4.879  17.867   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -4.268  16.930   0.000  0.00  0.00           C+0
HETATM   20  N   UNK     0      -2.634  16.786   0.000  0.00  0.00           N+0
HETATM   21  C   UNK     0      -4.130  16.421   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      -5.486  17.150   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      -4.562  14.942   0.000  0.00  0.00           C+0
HETATM   24  N   UNK     0      -3.497  13.829   0.000  0.00  0.00           N+0
HETATM   25  C   UNK     0      -4.145  12.432   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      -5.679  12.294   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      -3.258  11.173   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -3.906   9.775   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -5.440   9.637   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -6.087   8.240   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      -7.621   8.102   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -8.507   9.361   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      -7.860  10.758   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      -6.326  10.897   0.000  0.00  0.00           C+0
HETATM   35  N   UNK     0      -1.725  11.311   0.000  0.00  0.00           N+0
HETATM   36  C   UNK     0      -1.036   9.933   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0      -1.884   8.648   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0       0.502   9.841   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       1.462   8.637   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0       2.903   9.178   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0       2.953  10.298   0.000  0.00  0.00           C+0
HETATM   42  N   UNK     0       1.350  11.126   0.000  0.00  0.00           N+0
HETATM   43  C   UNK     0       2.856  10.806   0.000  0.00  0.00           C+0
HETATM   44  O   UNK     0       3.761   9.560   0.000  0.00  0.00           O+0
HETATM   45  C   UNK     0       3.887  11.951   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0       5.393  11.631   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0       5.869  10.166   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0       4.964   8.920   0.000  0.00  0.00           C+0
HETATM   49  N   UNK     0       5.869   7.674   0.000  0.00  0.00           N+0
HETATM   50  C   UNK     0       7.334   8.150   0.000  0.00  0.00           C+0
HETATM   51  C   UNK     0       8.667   7.380   0.000  0.00  0.00           C+0
HETATM   52  C   UNK     0      10.001   8.150   0.000  0.00  0.00           C+0
HETATM   53  C   UNK     0      10.001   9.690   0.000  0.00  0.00           C+0
HETATM   54  C   UNK     0       8.667  10.460   0.000  0.00  0.00           C+0
HETATM   55  C   UNK     0       7.334   9.690   0.000  0.00  0.00           C+0
HETATM   56  N   UNK     0       3.411  13.415   0.000  0.00  0.00           N+0
HETATM   57  C   UNK     0       4.600  14.393   0.000  0.00  0.00           C+0
HETATM   58  O   UNK     0       6.042  13.852   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   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   20                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   16   21                                                  
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   28   35                                                  
CONECT   28   27   29                                                       
CONECT   29   28   30   34                                                  
CONECT   30   29   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32   34                                                       
CONECT   34   33   29                                                       
CONECT   35   27   36                                                       
CONECT   36   35   37   38                                                  
CONECT   37   36                                                            
CONECT   38   36   39   42                                                  
CONECT   39   38   40                                                       
CONECT   40   39   41                                                       
CONECT   41   40   42                                                       
CONECT   42   41   38   43                                                  
CONECT   43   42   44   45                                                  
CONECT   44   43                                                            
CONECT   45   43   46   56                                                  
CONECT   46   45   47                                                       
CONECT   47   46   48   55                                                  
CONECT   48   47   49                                                       
CONECT   49   48   50                                                       
CONECT   50   49   51   55                                                  
CONECT   51   50   52                                                       
CONECT   52   51   53                                                       
CONECT   53   52   54                                                       
CONECT   54   53   55                                                       
CONECT   55   54   47   50                                                  
CONECT   56   45   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
Cyclo-(pro1-TRP-leu-THR-pro2-gly-phe)	MeSH

Chemical Formula

C₄₂H₅₄N₈O₈

Average Mass

798.9420 Da

Monoisotopic Mass

798.40646 Da

IUPAC Name

(6S,9S,15S,18S,21S,24S)-6-benzyl-5,8,17,20,23-pentahydroxy-21-[(1R)-1-hydroxyethyl]-15-[(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

(6S,9S,15S,18S,21S,24S)-6-benzyl-5,8,17,20,23-pentahydroxy-21-[(1R)-1-hydroxyethyl]-15-(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](N=C(O)[C@@H]2CCCN2C(=O)CN=C(O)[C@H](CC2=CC=CC=C2)N=C(O)[C@@H]2CCCN2C(=O)[C@H](CC2=CNC3=CC=CC=C23)N=C1O)[C@@H](C)O

InChI Identifier

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

InChI Key

GCYCNNNVEBIXIM-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

Species Name	Source	Reference
Phakellia fusca	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
3-alkylindole
Indole
Indole or derivatives
Monocyclic benzene moiety
Substituted pyrrole
Benzenoid
Heteroaromatic compound
Pyrrole
Pyrrolidine
Tertiary carboxylic acid amide
Lactam
Carboxamide group
Secondary alcohol
Secondary carboxylic acid amide
Azacycle
Organoheterocyclic compound
Organic nitrogen compound
Organooxygen compound
Organonitrogen compound
Alcohol
Hydrocarbon derivative
Organic oxide
Carbonyl group
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	4.35	ChemAxon
pKa (Strongest Acidic)	3.19	ChemAxon
pKa (Strongest Basic)	1.75	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	83.57 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

C00026792

Chemspider ID

9300779

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Phakellistatin 13

METLIN ID

Not Available

PubChem Compound

11125657

PDB ID

Not Available

ChEBI ID

181743

Good Scents ID

Not Available

References

General References

Wei H, Wen J, Xie R, Lin H, Fan G, Wu Y: Quantitative determination of Phakellistatin 13, a new cyclic heptapeptide, in rat plasma by liquid chromatography/tandem mass spectrometry: application to a pharmacokinetic study. Anal Bioanal Chem. 2009 Nov;395(5):1461-9. doi: 10.1007/s00216-009-3102-4. Epub 2009 Sep 17. [PubMed:19760191 ]
Greenman KL, Hach DM, Van Vranken DL: Synthesis of phakellistatin 13 and oxidation to phakellistatin 3 and isophakellistatin 3. Org Lett. 2004 May 27;6(11):1713-6. doi: 10.1021/ol049614p. [PubMed:15151396 ]
Mohammed R, Peng J, Kelly M, Hamann MT: Cyclic heptapeptides from the Jamaican sponge Stylissa caribica. J Nat Prod. 2006 Dec;69(12):1739-44. doi: 10.1021/np060006n. [PubMed:17190452 ]
Zhang HJ, Yi YH, Yang GJ, Hu MY, Cao GD, Yang F, Lin HW: Proline-containing cyclopeptides from the marine sponge Phakellia fusca. J Nat Prod. 2010 Apr 23;73(4):650-5. doi: 10.1021/np9008267. [PubMed:20345147 ]
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 (6s,9s,15s,18s,21s,24s)-6-benzyl-5,8,17,20,23-pentahydroxy-21-[(1r)-1-hydroxyethyl]-15-(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 (NP0201979)

MOL for NP0201979 ((6s,9s,15s,18s,21s,24s)-6-benzyl-5,8,17,20,23-pentahydroxy-21-[(1r)-1-hydroxyethyl]-15-(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 NP0201979 ((6s,9s,15s,18s,21s,24s)-6-benzyl-5,8,17,20,23-pentahydroxy-21-[(1r)-1-hydroxyethyl]-15-(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 NP0201979 ((6s,9s,15s,18s,21s,24s)-6-benzyl-5,8,17,20,23-pentahydroxy-21-[(1r)-1-hydroxyethyl]-15-(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 NP0201979 ((6s,9s,15s,18s,21s,24s)-6-benzyl-5,8,17,20,23-pentahydroxy-21-[(1r)-1-hydroxyethyl]-15-(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 NP0201979 ((6s,9s,15s,18s,21s,24s)-6-benzyl-5,8,17,20,23-pentahydroxy-21-[(1r)-1-hydroxyethyl]-15-(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 NP0201979 ((6s,9s,15s,18s,21s,24s)-6-benzyl-5,8,17,20,23-pentahydroxy-21-[(1r)-1-hydroxyethyl]-15-(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 NP0201979 ((6s,9s,15s,18s,21s,24s)-6-benzyl-5,8,17,20,23-pentahydroxy-21-[(1r)-1-hydroxyethyl]-15-(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 NP0201979 ((6s,9s,15s,18s,21s,24s)-6-benzyl-5,8,17,20,23-pentahydroxy-21-[(1r)-1-hydroxyethyl]-15-(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 NP0201979 ((6s,9s,15s,18s,21s,24s)-6-benzyl-5,8,17,20,23-pentahydroxy-21-[(1r)-1-hydroxyethyl]-15-(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 NP0201979 ((6s,9s,15s,18s,21s,24s)-6-benzyl-5,8,17,20,23-pentahydroxy-21-[(1r)-1-hydroxyethyl]-15-(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)