NP-MRD: Showing NP-Card for (3s,6s,12s,15s,21s,24s)-21-benzyl-3,24-bis[(2s)-butan-2-yl]-5,14,23,26-tetrahydroxy-12-[(4-hydroxyphenyl)methyl]-1,4,10,13,19,22,25-heptaazatetracyclo[25.3.0.0⁶,¹⁰.0¹⁵,¹⁹]triaconta-4,13,22,25-tetraene-2,11,20-trione (NP0161844)

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Record Information

Version

2.0

Created at

2022-09-02 20:06:54 UTC

Updated at

2022-09-02 20:06:55 UTC

NP-MRD ID

NP0161844

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(3s,6s,12s,15s,21s,24s)-21-benzyl-3,24-bis[(2s)-butan-2-yl]-5,14,23,26-tetrahydroxy-12-[(4-hydroxyphenyl)methyl]-1,4,10,13,19,22,25-heptaazatetracyclo[25.3.0.0⁶,¹⁰.0¹⁵,¹⁹]triaconta-4,13,22,25-tetraene-2,11,20-trione

Description

Phakellistatin 1 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. (3s,6s,12s,15s,21s,24s)-21-benzyl-3,24-bis[(2s)-butan-2-yl]-5,14,23,26-tetrahydroxy-12-[(4-hydroxyphenyl)methyl]-1,4,10,13,19,22,25-heptaazatetracyclo[25.3.0.0⁶,¹⁰.0¹⁵,¹⁹]triaconta-4,13,22,25-tetraene-2,11,20-trione is found in Gymnocoronis spilanthoides. (3s,6s,12s,15s,21s,24s)-21-benzyl-3,24-bis[(2s)-butan-2-yl]-5,14,23,26-tetrahydroxy-12-[(4-hydroxyphenyl)methyl]-1,4,10,13,19,22,25-heptaazatetracyclo[25.3.0.0⁶,¹⁰.0¹⁵,¹⁹]triaconta-4,13,22,25-tetraene-2,11,20-trione was first documented in 2017 (PMID: 28335479). Based on a literature review very few articles have been published on Phakellistatin 1.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309022222062D          

 60 65  0  0  1  0            999 V2000
    0.6119    1.8725    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8051    1.0705    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5963    0.8368    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7895    0.0347    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1943    1.4051    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.9855    1.1714    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0570    0.3495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3810   -0.1233    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8046    0.0005    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.0454   -0.7885    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8703   -0.8033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9199   -0.1031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4806    0.4734    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.1678    0.0169    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3730   -0.7822    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9067    0.3837    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.5939   -0.0728    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5421   -0.8962    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2293   -1.3527    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1775   -2.1761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4386   -2.5429    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3868   -3.3663    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7514   -2.0864    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8032   -1.2630    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9585    1.2071    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.7439    1.4597    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3553    0.9059    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9178    2.2662    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.6335    2.6766    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4644    3.4840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9731    3.6923    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3063    2.8200    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.5985    3.5916    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3319    3.9694    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0764    4.2304    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.3686    5.0019    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1829    5.1346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4750    5.9062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2893    6.0389    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8114    5.4001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5192    4.6286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7049    4.4958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2622    4.0976    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.8411    4.8071    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2450    5.5265    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0162    4.7972    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5952    5.5067    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.7702    5.4968    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9991    6.2260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5780    6.9355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6123    4.0778    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7951    4.1910    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4845    4.9553    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2885    3.5399    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4656    3.4806    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2677    2.6797    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8885    2.4633    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5991    2.7756    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0011    2.2072    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1764    2.1850    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
  3  4  1  1  0  0  0
  5  3  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  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
  9 13  1  1  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
 16 17  1  1  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 21 23  1  0  0  0  0
 23 24  2  0  0  0  0
 18 24  1  0  0  0  0
 16 25  1  0  0  0  0
 25 26  2  0  0  0  0
 26 27  1  4  0  0  0
 26 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 28 32  1  1  0  0  0
 32 33  1  0  0  0  0
 33 34  2  0  0  0  0
 33 35  1  0  0  0  0
 35 36  1  1  0  0  0
 36 37  1  0  0  0  0
 37 38  2  0  0  0  0
 38 39  1  0  0  0  0
 39 40  2  0  0  0  0
 40 41  1  0  0  0  0
 41 42  2  0  0  0  0
 37 42  1  0  0  0  0
 35 43  1  0  0  0  0
 43 44  2  0  0  0  0
 44 45  1  4  0  0  0
 44 46  1  0  0  0  0
 46 47  1  1  0  0  0
 47 48  1  1  0  0  0
 47 49  1  0  0  0  0
 49 50  1  0  0  0  0
 46 51  1  0  0  0  0
 51 52  2  0  0  0  0
 52 53  1  4  0  0  0
 52 54  1  0  0  0  0
 54 55  1  0  0  0  0
 55 56  1  0  0  0  0
 56 57  1  0  0  0  0
 57 58  1  0  0  0  0
 54 58  1  0  0  0  0
 58 59  1  0  0  0  0
  5 59  1  0  0  0  0
 59 60  2  0  0  0  0
M  END

     RDKit          3D

121126  0  0  0  0  0  0  0  0999 V2000
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   -4.4233   -4.7928    0.4754 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.3852   -5.9987   -0.0571 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.2948   -2.5162   -1.0462 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7791   -1.4263   -0.8847 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6238   -0.9219   -1.9140 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.3603   -1.0613    1.4769 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.7897    4.6498    0.1343 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.9018    6.4056   -1.7817 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3959    7.2969   -2.7186 O   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


  Mrv1652309022222062D          

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M  END
> <DATABASE_ID>
NP0161844

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC[C@H](C)[C@@H]1N=C(O)C2CCCN2C(=O)[C@@H](N=C(O)[C@@H]2CCCN2C(=O)[C@H](CC2=CC=C(O)C=C2)N=C(O)[C@@H]2CCCN2C(=O)[C@H](CC2=CC=CC=C2)N=C1O)[C@@H](C)CC

> <INCHI_IDENTIFIER>
InChI=1S/C45H61N7O8/c1-5-27(3)37-42(57)47-33(25-29-13-8-7-9-14-29)44(59)50-22-10-15-34(50)39(54)46-32(26-30-18-20-31(53)21-19-30)43(58)51-23-11-16-35(51)41(56)49-38(28(4)6-2)45(60)52-24-12-17-36(52)40(55)48-37/h7-9,13-14,18-21,27-28,32-38,53H,5-6,10-12,15-17,22-26H2,1-4H3,(H,46,54)(H,47,57)(H,48,55)(H,49,56)/t27-,28-,32-,33-,34-,35-,36?,37-,38-/m0/s1

> <INCHI_KEY>
QKAAFOFCOXIVQV-GWHVZCMOSA-N

> <FORMULA>
C45H61N7O8

> <MOLECULAR_WEIGHT>
828.024

> <EXACT_MASS>
827.458161952

> <JCHEM_ACCEPTOR_COUNT>
12

> <JCHEM_ATOM_COUNT>
121

> <JCHEM_AVERAGE_POLARIZABILITY>
88.85086947881832

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(3S,6S,12S,15S,21S,24S)-21-benzyl-3,24-bis[(2S)-butan-2-yl]-5,14,23,26-tetrahydroxy-12-[(4-hydroxyphenyl)methyl]-1,4,10,13,19,22,25-heptaazatetracyclo[25.3.0.0^{6,10}.0^{15,19}]triaconta-4,13,22,25-tetraene-2,11,20-trione

> <ALOGPS_LOGP>
3.32

> <JCHEM_LOGP>
6.013995446000001

> <ALOGPS_LOGS>
-4.36

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
4.114960570419633

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.5747949551916682

> <JCHEM_PKA_STRONGEST_BASIC>
1.7359599541212447

> <JCHEM_POLAR_SURFACE_AREA>
211.51999999999995

> <JCHEM_REFRACTIVITY>
224.648

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.63e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3S,6S,12S,15S,21S,24S)-21-benzyl-3,24-bis[(2S)-butan-2-yl]-5,14,23,26-tetrahydroxy-12-[(4-hydroxyphenyl)methyl]-1,4,10,13,19,22,25-heptaazatetracyclo[25.3.0.0^{6,10}.0^{15,19}]triaconta-4,13,22,25-tetraene-2,11,20-trione

> <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       1.142   3.495   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.503   1.998   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.980   1.562   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.340   0.065   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.096   2.623   0.000  0.00  0.00           C+0
HETATM    6  N   UNK     0       5.573   2.187   0.000  0.00  0.00           N+0
HETATM    7  C   UNK     0       5.706   0.652   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       4.445  -0.230   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       7.102   0.001   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.551  -1.472   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       9.091  -1.500   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       9.184  -0.192   0.000  0.00  0.00           C+0
HETATM   13  N   UNK     0       8.364   0.884   0.000  0.00  0.00           N+0
HETATM   14  C   UNK     0       9.647   0.032   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      10.030  -1.460   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      11.026   0.716   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      12.309  -0.136   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      12.212  -1.673   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      13.495  -2.525   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      13.398  -4.062   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      12.019  -4.747   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      11.922  -6.284   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      10.736  -3.895   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      10.833  -2.358   0.000  0.00  0.00           C+0
HETATM   25  N   UNK     0      11.123   2.253   0.000  0.00  0.00           N+0
HETATM   26  C   UNK     0      12.589   2.725   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      13.730   1.691   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      12.913   4.230   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      14.249   4.996   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      13.933   6.504   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      13.016   6.892   0.000  0.00  0.00           C+0
HETATM   32  N   UNK     0      11.772   5.264   0.000  0.00  0.00           N+0
HETATM   33  C   UNK     0      12.317   6.704   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0      13.686   7.410   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0      11.343   7.897   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      11.888   9.337   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      13.408   9.585   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      13.953  11.025   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      15.473  11.273   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      16.448  10.080   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0      15.902   8.640   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0      14.383   8.392   0.000  0.00  0.00           C+0
HETATM   43  N   UNK     0       9.823   7.649   0.000  0.00  0.00           N+0
HETATM   44  C   UNK     0       9.037   8.973   0.000  0.00  0.00           C+0
HETATM   45  O   UNK     0       9.791  10.316   0.000  0.00  0.00           O+0
HETATM   46  C   UNK     0       7.497   8.955   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0       6.711  10.279   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0       5.171  10.261   0.000  0.00  0.00           C+0
HETATM   49  C   UNK     0       7.465  11.622   0.000  0.00  0.00           C+0
HETATM   50  C   UNK     0       6.679  12.946   0.000  0.00  0.00           C+0
HETATM   51  N   UNK     0       6.743   7.612   0.000  0.00  0.00           N+0
HETATM   52  C   UNK     0       5.218   7.823   0.000  0.00  0.00           C+0
HETATM   53  O   UNK     0       4.638   9.250   0.000  0.00  0.00           O+0
HETATM   54  C   UNK     0       4.272   6.608   0.000  0.00  0.00           C+0
HETATM   55  C   UNK     0       2.736   6.497   0.000  0.00  0.00           C+0
HETATM   56  C   UNK     0       2.366   5.002   0.000  0.00  0.00           C+0
HETATM   57  C   UNK     0       3.525   4.598   0.000  0.00  0.00           C+0
HETATM   58  N   UNK     0       4.852   5.181   0.000  0.00  0.00           N+0
HETATM   59  C   UNK     0       3.735   4.120   0.000  0.00  0.00           C+0
HETATM   60  O   UNK     0       2.196   4.079   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6   59                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   13                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12    9   14                                                  
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17   25                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19   24                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24                                                       
CONECT   24   23   18                                                       
CONECT   25   16   26                                                       
CONECT   26   25   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   29   32                                                  
CONECT   29   28   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   28   33                                                  
CONECT   33   32   34   35                                                  
CONECT   34   33                                                            
CONECT   35   33   36   43                                                  
CONECT   36   35   37                                                       
CONECT   37   36   38   42                                                  
CONECT   38   37   39                                                       
CONECT   39   38   40                                                       
CONECT   40   39   41                                                       
CONECT   41   40   42                                                       
CONECT   42   41   37                                                       
CONECT   43   35   44                                                       
CONECT   44   43   45   46                                                  
CONECT   45   44                                                            
CONECT   46   44   47   51                                                  
CONECT   47   46   48   49                                                  
CONECT   48   47                                                            
CONECT   49   47   50                                                       
CONECT   50   49                                                            
CONECT   51   46   52                                                       
CONECT   52   51   53   54                                                  
CONECT   53   52                                                            
CONECT   54   52   55   58                                                  
CONECT   55   54   56                                                       
CONECT   56   55   57                                                       
CONECT   57   56   58                                                       
CONECT   58   57   54   59                                                  
CONECT   59   58    5   60                                                  
CONECT   60   59                                                            
MASTER        0    0    0    0    0    0    0    0   60    0  130    0
END

View in JSmol

Synonyms

Value	Source
Cyclo(pro-ile-pro-ile-phe-pro-tyr)	MeSH
Cyclo(prolyl-isoleucyl-prolyl-isoleucyl-phenylalanyl-prolyl-tyrosyl)	MeSH

Chemical Formula

C₄₅H₆₁N₇O₈

Average Mass

828.0240 Da

Monoisotopic Mass

827.45816 Da

IUPAC Name

(3S,6S,12S,15S,21S,24S)-21-benzyl-3,24-bis[(2S)-butan-2-yl]-5,14,23,26-tetrahydroxy-12-[(4-hydroxyphenyl)methyl]-1,4,10,13,19,22,25-heptaazatetracyclo[25.3.0.0^{6,10}.0^{15,19}]triaconta-4,13,22,25-tetraene-2,11,20-trione

Traditional Name

CAS Registry Number

Not Available

SMILES

CC[C@H](C)[C@@H]1N=C(O)C2CCCN2C(=O)[C@@H](N=C(O)[C@@H]2CCCN2C(=O)[C@H](CC2=CC=C(O)C=C2)N=C(O)[C@@H]2CCCN2C(=O)[C@H](CC2=CC=CC=C2)N=C1O)[C@@H](C)CC

InChI Identifier

InChI=1S/C45H61N7O8/c1-5-27(3)37-42(57)47-33(25-29-13-8-7-9-14-29)44(59)50-22-10-15-34(50)39(54)46-32(26-30-18-20-31(53)21-19-30)43(58)51-23-11-16-35(51)41(56)49-38(28(4)6-2)45(60)52-24-12-17-36(52)40(55)48-37/h7-9,13-14,18-21,27-28,32-38,53H,5-6,10-12,15-17,22-26H2,1-4H3,(H,46,54)(H,47,57)(H,48,55)(H,49,56)/t27-,28-,32-,33-,34-,35-,36?,37-,38-/m0/s1

InChI Key

QKAAFOFCOXIVQV-GWHVZCMOSA-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
Gymnocoronis spilanthoides	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
Benzenoid
Monocyclic benzene moiety
Tertiary carboxylic acid amide
Pyrrolidine
Secondary carboxylic acid amide
Lactam
Carboxamide group
Azacycle
Organoheterocyclic compound
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Carbonyl group
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	3.32	ALOGPS
logP	6.01	ChemAxon
logS	-4.4	ALOGPS
pKa (Strongest Acidic)	3.57	ChemAxon
pKa (Strongest Basic)	1.74	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	12	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	211.52 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	224.65 m³·mol⁻¹	ChemAxon
Polarizability	88.85 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

57489136

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

197558

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Meli A, Tedesco C, Della Sala G, Schettini R, Albericio F, De Riccardis F, Izzo I: Phakellistatins: An Underwater Unsolved Puzzle. Mar Drugs. 2017 Mar 18;15(3). pii: md15030078. doi: 10.3390/md15030078. [PubMed:28335479 ]
LOTUS database [Link]

Showing NP-Card for (3s,6s,12s,15s,21s,24s)-21-benzyl-3,24-bis[(2s)-butan-2-yl]-5,14,23,26-tetrahydroxy-12-[(4-hydroxyphenyl)methyl]-1,4,10,13,19,22,25-heptaazatetracyclo[25.3.0.0⁶,¹⁰.0¹⁵,¹⁹]triaconta-4,13,22,25-tetraene-2,11,20-trione (NP0161844)

MOL for NP0161844 ((3s,6s,12s,15s,21s,24s)-21-benzyl-3,24-bis[(2s)-butan-2-yl]-5,14,23,26-tetrahydroxy-12-[(4-hydroxyphenyl)methyl]-1,4,10,13,19,22,25-heptaazatetracyclo[25.3.0.0⁶,¹⁰.0¹⁵,¹⁹]triaconta-4,13,22,25-tetraene-2,11,20-trione)

3D MOL for NP0161844 ((3s,6s,12s,15s,21s,24s)-21-benzyl-3,24-bis[(2s)-butan-2-yl]-5,14,23,26-tetrahydroxy-12-[(4-hydroxyphenyl)methyl]-1,4,10,13,19,22,25-heptaazatetracyclo[25.3.0.0⁶,¹⁰.0¹⁵,¹⁹]triaconta-4,13,22,25-tetraene-2,11,20-trione)

3D SDF for NP0161844 ((3s,6s,12s,15s,21s,24s)-21-benzyl-3,24-bis[(2s)-butan-2-yl]-5,14,23,26-tetrahydroxy-12-[(4-hydroxyphenyl)methyl]-1,4,10,13,19,22,25-heptaazatetracyclo[25.3.0.0⁶,¹⁰.0¹⁵,¹⁹]triaconta-4,13,22,25-tetraene-2,11,20-trione)

3D-SDF for NP0161844 ((3s,6s,12s,15s,21s,24s)-21-benzyl-3,24-bis[(2s)-butan-2-yl]-5,14,23,26-tetrahydroxy-12-[(4-hydroxyphenyl)methyl]-1,4,10,13,19,22,25-heptaazatetracyclo[25.3.0.0⁶,¹⁰.0¹⁵,¹⁹]triaconta-4,13,22,25-tetraene-2,11,20-trione)

PDB for NP0161844 ((3s,6s,12s,15s,21s,24s)-21-benzyl-3,24-bis[(2s)-butan-2-yl]-5,14,23,26-tetrahydroxy-12-[(4-hydroxyphenyl)methyl]-1,4,10,13,19,22,25-heptaazatetracyclo[25.3.0.0⁶,¹⁰.0¹⁵,¹⁹]triaconta-4,13,22,25-tetraene-2,11,20-trione)

3D PDB for NP0161844 ((3s,6s,12s,15s,21s,24s)-21-benzyl-3,24-bis[(2s)-butan-2-yl]-5,14,23,26-tetrahydroxy-12-[(4-hydroxyphenyl)methyl]-1,4,10,13,19,22,25-heptaazatetracyclo[25.3.0.0⁶,¹⁰.0¹⁵,¹⁹]triaconta-4,13,22,25-tetraene-2,11,20-trione)

SMILES for NP0161844 ((3s,6s,12s,15s,21s,24s)-21-benzyl-3,24-bis[(2s)-butan-2-yl]-5,14,23,26-tetrahydroxy-12-[(4-hydroxyphenyl)methyl]-1,4,10,13,19,22,25-heptaazatetracyclo[25.3.0.0⁶,¹⁰.0¹⁵,¹⁹]triaconta-4,13,22,25-tetraene-2,11,20-trione)

INCHI for NP0161844 ((3s,6s,12s,15s,21s,24s)-21-benzyl-3,24-bis[(2s)-butan-2-yl]-5,14,23,26-tetrahydroxy-12-[(4-hydroxyphenyl)methyl]-1,4,10,13,19,22,25-heptaazatetracyclo[25.3.0.0⁶,¹⁰.0¹⁵,¹⁹]triaconta-4,13,22,25-tetraene-2,11,20-trione)

Structure for NP0161844 ((3s,6s,12s,15s,21s,24s)-21-benzyl-3,24-bis[(2s)-butan-2-yl]-5,14,23,26-tetrahydroxy-12-[(4-hydroxyphenyl)methyl]-1,4,10,13,19,22,25-heptaazatetracyclo[25.3.0.0⁶,¹⁰.0¹⁵,¹⁹]triaconta-4,13,22,25-tetraene-2,11,20-trione)

3D Structure for NP0161844 ((3s,6s,12s,15s,21s,24s)-21-benzyl-3,24-bis[(2s)-butan-2-yl]-5,14,23,26-tetrahydroxy-12-[(4-hydroxyphenyl)methyl]-1,4,10,13,19,22,25-heptaazatetracyclo[25.3.0.0⁶,¹⁰.0¹⁵,¹⁹]triaconta-4,13,22,25-tetraene-2,11,20-trione)