NP-MRD: Showing NP-Card for Phallisacin (NP0350698)

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Record Information

Version

2.0

Created at

2025-02-04 14:55:22 UTC

Updated at

2025-10-22 19:35:49 UTC

NP-MRD ID

NP0350698

Natural Product DOI

https://doi.org/10.57994/3678

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Phallisacin

Description

Phallisacin was first documented in 2011 (PMID: 21471295). Based on a literature review very few articles have been published on Phallisacin (PMID: 37929913).

Structure

MOL SDF PDB SMILES InChI


  Mrv2104 05042315032D          

 60 64  0  0  1  0            999 V2000
    2.0722   -2.7942    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6949   -2.2530    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8537   -1.3458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2232   -1.9499    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.2860   -1.6860    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3538   -0.7776    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1062   -0.3186    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.9692   -0.4205    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.2536    0.3539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7252    0.9875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1967    1.6210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3838    1.4801    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0916    0.4590    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3172    0.7434    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3587    1.5159    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6896   -0.8991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    6.1171   -4.7477    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
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    6.9240   -5.9270    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    2.3893   -4.7974    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.5564   -2.8964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7980   -3.6853    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2357   -4.2889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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  2  1  1  1  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  5  4  1  1  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  8  7  1  0  0  0  0
  8  9  1  1  0  0  0
  9 10  1  0  0  0  0
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 13 14  1  0  0  0  0
 10 15  1  0  0  0  0
  8 16  1  0  0  0  0
 16 17  1  0  0  0  0
 18 17  1  0  0  0  0
 18 19  1  1  0  0  0
 19 20  1  0  0  0  0
 19 21  1  0  0  0  0
 18 22  1  0  0  0  0
 22 23  1  0  0  0  0
 24 23  1  0  0  0  0
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 25 26  1  6  0  0  0
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 30 56  2  0  0  0  0
 22 57  2  0  0  0  0
 16 58  2  0  0  0  0
  6 59  2  0  0  0  0
  3 60  2  0  0  0  0
M  END


  Mrv2104 05042315032D          

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  3 60  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0350698

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)[C@@H]1NC(=O)[C@H](CC(O)(CO)CO)NC(=O)[C@@H]2CC3=C(NC4=C3C=CC=C4)SC[C@H](NC(=O)[C@H](NC1=O)[C@@H](O)C(O)=O)C(=O)N1C[C@@H](O)C[C@H]1C(=O)N[C@@H](C)C(=O)N2

> <INCHI_IDENTIFIER>
InChI=1S/C37H50N8O14S/c1-15(2)25-32(54)44-26(27(49)36(57)58)33(55)41-23-12-60-34-19(18-6-4-5-7-20(18)42-34)9-21(29(51)40-22(30(52)43-25)10-37(59,13-46)14-47)39-28(50)16(3)38-31(53)24-8-17(48)11-45(24)35(23)56/h4-7,15-17,21-27,42,46-49,59H,8-14H2,1-3H3,(H,38,53)(H,39,50)(H,40,51)(H,41,55)(H,43,52)(H,44,54)(H,57,58)/t16-,17-,21-,22-,23-,24-,25-,26+,27+/m0/s1

> <INCHI_KEY>
CUMAQJMTVOVGKD-TWWVSFTESA-N

> <FORMULA>
C37H50N8O14S

> <MOLECULAR_WEIGHT>
862.91

> <EXACT_MASS>
862.316719496

> <JCHEM_ACCEPTOR_COUNT>
14

> <JCHEM_ATOM_COUNT>
110

> <JCHEM_AVERAGE_POLARIZABILITY>
83.75469119236325

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
13

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R)-2-[(1S,14R,18S,20S,23S,28S,31S,34R)-28-[2,3-dihydroxy-2-(hydroxymethyl)propyl]-18-hydroxy-23-methyl-15,21,24,26,29,32,35-heptaoxo-31-(propan-2-yl)-12-thia-10,16,22,25,27,30,33,36-octaazapentacyclo[12.11.11.0^{3,11}.0^{4,9}.0^{16,20}]hexatriaconta-3(11),4(9),5,7-tetraen-34-yl]-2-hydroxyacetic acid

> <JCHEM_LOGP>
-5.799180448666667

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
10.05756079716475

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.3892332049579794

> <JCHEM_PKA_STRONGEST_BASIC>
-4.154697501729098

> <JCHEM_POLAR_SURFACE_AREA>
349.1499999999999

> <JCHEM_REFRACTIVITY>
206.21480000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(R)-[(1S,14R,18S,20S,23S,28S,31S,34R)-28-[2,3-dihydroxy-2-(hydroxymethyl)propyl]-18-hydroxy-31-isopropyl-23-methyl-15,21,24,26,29,32,35-heptaoxo-12-thia-10,16,22,25,27,30,33,36-octaazapentacyclo[12.11.11.0^{3,11}.0^{4,9}.0^{16,20}]hexatriaconta-3(11),4(9),5,7-tetraen-34-yl](hydroxy)acetic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 04-MAY-23   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-MAY-23         0                                  
HETATM    1  C   UNK     0       3.868  -5.216   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.030  -4.206   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.327  -2.512   0.000  0.00  0.00           C+0
HETATM    4  N   UNK     0       6.017  -3.640   0.000  0.00  0.00           N+0
HETATM    5  C   UNK     0       4.267  -3.147   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.394  -1.452   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0       5.798  -0.595   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0       7.409  -0.785   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.940   0.661   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.954   1.843   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.967   3.026   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       4.450   2.763   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       5.771   0.857   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       4.325   1.388   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0       8.136   2.830   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       8.754  -1.678   0.000  0.00  0.00           C+0
HETATM   17  N   UNK     0       9.852  -2.857   0.000  0.00  0.00           N+0
HETATM   18  C   UNK     0      10.753  -4.193   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      12.108  -3.461   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      13.419  -4.268   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      12.152  -1.921   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      11.376  -5.680   0.000  0.00  0.00           C+0
HETATM   23  N   UNK     0      11.716  -7.261   0.000  0.00  0.00           N+0
HETATM   24  C   UNK     0      11.419  -8.862   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      12.807  -9.528   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      12.925 -11.064   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      14.078  -8.659   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      13.961  -7.123   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0      15.467  -9.325   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0      10.355 -10.098   0.000  0.00  0.00           C+0
HETATM   31  N   UNK     0       8.860 -10.722   0.000  0.00  0.00           N+0
HETATM   32  C   UNK     0       7.274 -10.403   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       5.738  -9.929   0.000  0.00  0.00           C+0
HETATM   34  S   UNK     0       4.460  -8.955   0.000  0.00  0.00           S+0
HETATM   35  C   UNK     0       3.552  -7.618   0.000  0.00  0.00           C+0
HETATM   36  N   UNK     0       2.322  -8.544   0.000  0.00  0.00           N+0
HETATM   37  C   UNK     0       1.061  -7.660   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       1.512  -6.188   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       0.462  -5.061   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      -1.039  -5.407   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0      -1.490  -6.879   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0      -0.440  -8.006   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0       3.052  -6.162   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0       3.253  -4.475   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0       7.896  -8.973   0.000  0.00  0.00           C+0
HETATM   46  N   UNK     0       8.669  -7.632   0.000  0.00  0.00           N+0
HETATM   47  C   UNK     0       8.118  -6.193   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0       6.673  -6.708   0.000  0.00  0.00           C+0
HETATM   49  N   UNK     0       5.561  -5.669   0.000  0.00  0.00           N+0
HETATM   50  O   UNK     0       6.361  -8.216   0.000  0.00  0.00           O+0
HETATM   51  C   UNK     0       9.316  -5.225   0.000  0.00  0.00           C+0
HETATM   52  C   UNK     0      10.606  -6.065   0.000  0.00  0.00           C+0
HETATM   53  O   UNK     0      11.446  -4.774   0.000  0.00  0.00           O+0
HETATM   54  C   UNK     0      10.207  -7.552   0.000  0.00  0.00           C+0
HETATM   55  O   UNK     0       6.374  -8.740   0.000  0.00  0.00           O+0
HETATM   56  O   UNK     0      11.260 -11.344   0.000  0.00  0.00           O+0
HETATM   57  O   UNK     0      12.845  -5.218   0.000  0.00  0.00           O+0
HETATM   58  O   UNK     0       9.750  -0.504   0.000  0.00  0.00           O+0
HETATM   59  O   UNK     0       3.080  -0.648   0.000  0.00  0.00           O+0
HETATM   60  O   UNK     0       5.039  -0.999   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   49                                                  
CONECT    3    2    4   60                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   44                                                  
CONECT    6    5    7   59                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   16                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   13   15                                             
CONECT   11   10   12                                                       
CONECT   12   11                                                            
CONECT   13   10   14                                                       
CONECT   14   13                                                            
CONECT   15   10                                                            
CONECT   16    8   17   58                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19   22                                                  
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19                                                            
CONECT   22   18   23   57                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25   30                                                  
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27                                                            
CONECT   30   24   31   56                                                  
CONECT   31   30   32                                                       
CONECT   32   31   33   45                                                  
CONECT   33   32   34                                                       
CONECT   34   33   35                                                       
CONECT   35   34   36   43                                                  
CONECT   36   35   37                                                       
CONECT   37   36   38   42                                                  
CONECT   38   37   39   43                                                  
CONECT   39   38   40                                                       
CONECT   40   39   41                                                       
CONECT   41   40   42                                                       
CONECT   42   41   37                                                       
CONECT   43   35   38   44                                                  
CONECT   44   43    5                                                       
CONECT   45   32   46   55                                                  
CONECT   46   45   47   54                                                  
CONECT   47   46   48   51                                                  
CONECT   48   47   49   50                                                  
CONECT   49   48    2                                                       
CONECT   50   48                                                            
CONECT   51   47   52                                                       
CONECT   52   51   53   54                                                  
CONECT   53   52                                                            
CONECT   54   52   46                                                       
CONECT   55   45                                                            
CONECT   56   30                                                            
CONECT   57   22                                                            
CONECT   58   16                                                            
CONECT   59    6                                                            
CONECT   60    3                                                            
MASTER        0    0    0    0    0    0    0    0   60    0  128    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₇H₅₀N₈O₁₄S

Average Mass

862.9100 Da

Monoisotopic Mass

862.31672 Da

IUPAC Name

(2R)-2-[(1S,14R,18S,20S,23S,28S,31S,34R)-28-[2,3-dihydroxy-2-(hydroxymethyl)propyl]-18-hydroxy-23-methyl-15,21,24,26,29,32,35-heptaoxo-31-(propan-2-yl)-12-thia-10,16,22,25,27,30,33,36-octaazapentacyclo[12.11.11.0^{3,11}.0^{4,9}.0^{16,20}]hexatriaconta-3(11),4(9),5,7-tetraen-34-yl]-2-hydroxyacetic acid

Traditional Name

(R)-[(1S,14R,18S,20S,23S,28S,31S,34R)-28-[2,3-dihydroxy-2-(hydroxymethyl)propyl]-18-hydroxy-31-isopropyl-23-methyl-15,21,24,26,29,32,35-heptaoxo-12-thia-10,16,22,25,27,30,33,36-octaazapentacyclo[12.11.11.0^{3,11}.0^{4,9}.0^{16,20}]hexatriaconta-3(11),4(9),5,7-tetraen-34-yl](hydroxy)acetic acid

CAS Registry Number

Not Available

SMILES

CC(C)[C@@H]1NC(=O)[C@H](CC(O)(CO)CO)NC(=O)[C@@H]2CC3=C(NC4=C3C=CC=C4)SC[C@H](NC(=O)[C@H](NC1=O)[C@@H](O)C(O)=O)C(=O)N1C[C@@H](O)C[C@H]1C(=O)N[C@@H](C)C(=O)N2

InChI Identifier

InChI=1S/C37H50N8O14S/c1-15(2)25-32(54)44-26(27(49)36(57)58)33(55)41-23-12-60-34-19(18-6-4-5-7-20(18)42-34)9-21(29(51)40-22(30(52)43-25)10-37(59,13-46)14-47)39-28(50)16(3)38-31(53)24-8-17(48)11-45(24)35(23)56/h4-7,15-17,21-27,42,46-49,59H,8-14H2,1-3H3,(H,38,53)(H,39,50)(H,40,51)(H,41,55)(H,43,52)(H,44,54)(H,57,58)/t16-,17-,21-,22-,23-,24-,25-,26+,27+/m0/s1

InChI Key

CUMAQJMTVOVGKD-TWWVSFTESA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, C2D6OS, experimental)	adrien.jagora@universite-paris-saclay.fr	Université Paris-Saclay	Adrien Jagora	2025-02-04	View Spectrum
ROESY NMR	[¹H, ¹H] NMR Spectrum (2D, 500 MHz, C2D6OS, experimental)	adrien.jagora@universite-paris-saclay.fr	Université Paris-Saclay	Adrien Jagora	2025-02-04	View Spectrum
HSQCTOCSY NMR	[¹H, ¹³C] NMR Spectrum (2D, 500 MHz, C2D6OS, experimental)	adrien.jagora@universite-paris-saclay.fr	Université Paris-Saclay	Adrien Jagora	2025-02-04	View Spectrum
HMBC NMR	[¹H, ¹³C] NMR Spectrum (2D, 500 MHz, C2D6OS, experimental)	adrien.jagora@universite-paris-saclay.fr	Université Paris-Saclay	Adrien Jagora	2025-02-04	View Spectrum
TOCSY NMR	[¹H, ¹H] NMR Spectrum (2D, 500 MHz, C2D6OS, experimental)	adrien.jagora@universite-paris-saclay.fr	Université Paris-Saclay	Adrien Jagora	2025-02-04	View Spectrum
HSQC NMR	[¹H, ¹³C] NMR Spectrum (2D, 500 MHz, C2D6OS, experimental)	adrien.jagora@universite-paris-saclay.fr	Université Paris-Saclay	Adrien Jagora	2025-02-04	View Spectrum
COSY NMR	[¹H, ¹H] NMR Spectrum (2D, 500 MHz, C2D6OS, experimental)	adrien.jagora@universite-paris-saclay.fr	Université Paris-Saclay	Adrien Jagora	2025-02-04	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, C2D6OS, experimental)	adrien.jagora@universite-paris-saclay.fr	Université Paris-Saclay	Adrien Jagora	2025-02-04	View Spectrum

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Amanita phalloides		Not Available

Chemical Taxonomy

Classification

Not classified

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	-5.8	ChemAxon
pKa (Strongest Acidic)	3.39	ChemAxon
pKa (Strongest Basic)	-4.2	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	14	ChemAxon
Hydrogen Donor Count	13	ChemAxon
Polar Surface Area	349.15 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	206.21 m³·mol⁻¹	ChemAxon
Polarizability	83.75 Å³	ChemAxon
Number of Rings	5	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

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Yang S, Wen D, Zheng F, Pu S, Chen Z, Chen M, Di B, Liu W, Shi Y: Simple and rapid detection of three amatoxins and three phallotoxins in human body fluids by UPLC-MS-MS and its application in 15 poisoning cases. J Anal Toxicol. 2024 Jan 31;48(1):44-53. doi: 10.1093/jat/bkad081. [PubMed:37929913 ]
Deng WQ, Li TH, Xi PG, Gan LX, Xiao ZD, Jiang ZD: Peptide toxin components of Amanita exitialis basidiocarps. Mycologia. 2011 Sep-Oct;103(5):946-9. doi: 10.3852/10-319. Epub 2011 Apr 6. [PubMed:21471295 ]
DOI: 10.1021/acs.jnatprod.5c00820
PMID: 41077760

Showing NP-Card for Phallisacin (NP0350698)

MOL for NP0350698 (Phallisacin)

3D MOL for NP0350698 (Phallisacin)

3D SDF for NP0350698 (Phallisacin)

3D-SDF for NP0350698 (Phallisacin)

PDB for NP0350698 (Phallisacin)

3D PDB for NP0350698 (Phallisacin)

SMILES for NP0350698 (Phallisacin)

INCHI for NP0350698 (Phallisacin)

Structure for NP0350698 (Phallisacin)

3D Structure for NP0350698 (Phallisacin)