NP-MRD: Showing NP-Card for (3s,6s,12r,15s,18r,21z,24s,25s,26s)-18-[(2s)-butan-2-yl]-8,17,24-trihydroxy-6,15-diisopropyl-3,4,10,13,21,25-hexamethyl-12-(2-methylpropyl)-26-[(2z)-pent-2-en-2-yl]-1,19-dioxa-4,7,10,13,16-pentaazacyclohexacosa-7,16,21-triene-2,5,11,14,20-pentone (NP0235021)

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Record Information

Version

2.0

Created at

2022-09-06 17:25:00 UTC

Updated at

2022-09-06 17:25:00 UTC

NP-MRD ID

NP0235021

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(3s,6s,12r,15s,18r,21z,24s,25s,26s)-18-[(2s)-butan-2-yl]-8,17,24-trihydroxy-6,15-diisopropyl-3,4,10,13,21,25-hexamethyl-12-(2-methylpropyl)-26-[(2z)-pent-2-en-2-yl]-1,19-dioxa-4,7,10,13,16-pentaazacyclohexacosa-7,16,21-triene-2,5,11,14,20-pentone

Description

Aurilide belongs to the class of organic compounds known as cyclic depsipeptides. These are natural or synthetic compounds having sequences of amino and hydroxy carboxylic acid residues (usually α-amino and α-hydroxy acids) connected in a ring. The residues are commonly but not necessarily regularly alternating. (3s,6s,12r,15s,18r,21z,24s,25s,26s)-18-[(2s)-butan-2-yl]-8,17,24-trihydroxy-6,15-diisopropyl-3,4,10,13,21,25-hexamethyl-12-(2-methylpropyl)-26-[(2z)-pent-2-en-2-yl]-1,19-dioxa-4,7,10,13,16-pentaazacyclohexacosa-7,16,21-triene-2,5,11,14,20-pentone is found in Dolabella auricularia. (3s,6s,12r,15s,18r,21z,24s,25s,26s)-18-[(2s)-butan-2-yl]-8,17,24-trihydroxy-6,15-diisopropyl-3,4,10,13,21,25-hexamethyl-12-(2-methylpropyl)-26-[(2z)-pent-2-en-2-yl]-1,19-dioxa-4,7,10,13,16-pentaazacyclohexacosa-7,16,21-triene-2,5,11,14,20-pentone was first documented in 2011 (PMID: 21903231). Based on a literature review a small amount of articles have been published on aurilide (PMID: 28515454) (PMID: 22822361) (PMID: 33498789) (PMID: 29670702).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309062219252D          

 59 59  0  0  1  0            999 V2000
    2.1462    2.9971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  6  4  1  1  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  1  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
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 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
 16 20  1  0  0  0  0
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 23 24  1  0  0  0  0
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 28 29  1  6  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
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 33 34  1  0  0  0  0
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 37 38  1  6  0  0  0
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  6 58  1  0  0  0  0
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M  END

     RDKit          3D

134134  0  0  0  0  0  0  0  0999 V2000
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M  END


  Mrv1652309062219252D          

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  6 58  1  0  0  0  0
 58 59  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0235021

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC\C=C(\C)[C@H]1OC(=O)[C@H](C)N(C)C(=O)[C@@H](N=C(O)CN(C)C(=O)[C@@H](CC(C)C)N(C)C(=O)[C@@H](N=C(O)[C@H](OC(=O)\C(C)=C/C[C@H](O)[C@@H]1C)[C@@H](C)CC)C(C)C)C(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C44H75N5O10/c1-17-19-28(10)37-30(12)33(50)21-20-29(11)43(56)59-38(27(9)18-2)39(52)46-36(26(7)8)42(55)49(16)32(22-24(3)4)40(53)47(14)23-34(51)45-35(25(5)6)41(54)48(15)31(13)44(57)58-37/h19-20,24-27,30-33,35-38,50H,17-18,21-23H2,1-16H3,(H,45,51)(H,46,52)/b28-19-,29-20-/t27-,30-,31-,32+,33-,35-,36-,37+,38+/m0/s1

> <INCHI_KEY>
XCPGQUJQUPDEFX-YWIOOLKYSA-N

> <FORMULA>
C44H75N5O10

> <MOLECULAR_WEIGHT>
834.109

> <EXACT_MASS>
833.551393635

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
134

> <JCHEM_AVERAGE_POLARIZABILITY>
92.8142078619936

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(3S,6S,12R,15S,18R,21Z,24S,25S,26S)-18-[(2S)-butan-2-yl]-8,17,24-trihydroxy-3,4,10,13,21,25-hexamethyl-12-(2-methylpropyl)-26-[(2Z)-pent-2-en-2-yl]-6,15-bis(propan-2-yl)-1,19-dioxa-4,7,10,13,16-pentaazacyclohexacosa-7,16,21-triene-2,5,11,14,20-pentone

> <JCHEM_LOGP>
6.6080407779999994

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
4.730367154849157

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.7519226997327446

> <JCHEM_PKA_STRONGEST_BASIC>
1.4493265427424393

> <JCHEM_POLAR_SURFACE_AREA>
198.93999999999997

> <JCHEM_REFRACTIVITY>
227.32880000000014

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(3S,6S,12R,15S,18R,21Z,24S,25S,26S)-18-[(2S)-butan-2-yl]-8,17,24-trihydroxy-6,15-diisopropyl-3,4,10,13,21,25-hexamethyl-12-(2-methylpropyl)-26-[(2Z)-pent-2-en-2-yl]-1,19-dioxa-4,7,10,13,16-pentaazacyclohexacosa-7,16,21-triene-2,5,11,14,20-pentone

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-SEP-22         0                                  
HETATM    1  C   UNK     0       4.006   5.595   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.116   4.527   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.595   4.954   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.705   3.886   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       9.185   4.313   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.335   2.391   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       8.445   1.323   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       9.925   1.751   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      10.294   3.246   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      11.034   0.683   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      10.664  -0.812   0.000  0.00  0.00           C+0
HETATM   12  N   UNK     0      12.514   1.110   0.000  0.00  0.00           N+0
HETATM   13  C   UNK     0      12.884   2.605   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      13.623   0.042   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      15.103   0.469   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      13.254  -1.453   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      14.733  -1.026   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      15.843  -2.093   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      15.911  -0.034   0.000  0.00  0.00           C+0
HETATM   20  N   UNK     0      14.363  -2.521   0.000  0.00  0.00           N+0
HETATM   21  C   UNK     0      13.993  -4.016   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      15.103  -5.083   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      12.514  -4.443   0.000  0.00  0.00           C+0
HETATM   24  N   UNK     0      11.404  -3.375   0.000  0.00  0.00           N+0
HETATM   25  C   UNK     0      11.774  -1.880   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       9.925  -3.802   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      10.504  -5.229   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       8.815  -2.734   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       8.445  -4.229   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       9.555  -5.297   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      11.003  -5.821   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       9.185  -6.792   0.000  0.00  0.00           C+0
HETATM   33  N   UNK     0       7.335  -3.161   0.000  0.00  0.00           N+0
HETATM   34  C   UNK     0       6.965  -4.656   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       6.226  -2.093   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0       6.595  -0.599   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0       4.746  -2.521   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       4.376  -4.016   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       2.896  -4.443   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0       5.486  -5.083   0.000  0.00  0.00           C+0
HETATM   41  N   UNK     0       3.636  -1.453   0.000  0.00  0.00           N+0
HETATM   42  C   UNK     0       2.157  -1.880   0.000  0.00  0.00           C+0
HETATM   43  O   UNK     0       1.787  -3.375   0.000  0.00  0.00           O+0
HETATM   44  C   UNK     0       1.047  -0.812   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0      -0.433  -1.239   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0      -1.542  -0.171   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0      -0.802  -2.734   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0      -2.282  -3.161   0.000  0.00  0.00           C+0
HETATM   49  O   UNK     0       1.417   0.683   0.000  0.00  0.00           O+0
HETATM   50  C   UNK     0       0.307   1.751   0.000  0.00  0.00           C+0
HETATM   51  O   UNK     0      -1.172   1.323   0.000  0.00  0.00           O+0
HETATM   52  C   UNK     0       0.677   3.246   0.000  0.00  0.00           C+0
HETATM   53  C   UNK     0      -0.433   4.313   0.000  0.00  0.00           C+0
HETATM   54  C   UNK     0       2.157   3.673   0.000  0.00  0.00           C+0
HETATM   55  C   UNK     0       3.266   2.605   0.000  0.00  0.00           C+0
HETATM   56  C   UNK     0       4.746   3.032   0.000  0.00  0.00           C+0
HETATM   57  O   UNK     0       4.167   4.459   0.000  0.00  0.00           O+0
HETATM   58  C   UNK     0       5.856   1.964   0.000  0.00  0.00           C+0
HETATM   59  C   UNK     0       5.486   0.469   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7   58                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17   20                                                  
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17                                                            
CONECT   20   16   21                                                       
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24                                                       
CONECT   24   23   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   29   33                                                  
CONECT   29   28   30                                                       
CONECT   30   29   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30                                                            
CONECT   33   28   34   35                                                  
CONECT   34   33                                                            
CONECT   35   33   36   37                                                  
CONECT   36   35                                                            
CONECT   37   35   38   41                                                  
CONECT   38   37   39   40                                                  
CONECT   39   38                                                            
CONECT   40   38                                                            
CONECT   41   37   42                                                       
CONECT   42   41   43   44                                                  
CONECT   43   42                                                            
CONECT   44   42   45   49                                                  
CONECT   45   44   46   47                                                  
CONECT   46   45                                                            
CONECT   47   45   48                                                       
CONECT   48   47                                                            
CONECT   49   44   50                                                       
CONECT   50   49   51   52                                                  
CONECT   51   50                                                            
CONECT   52   50   53   54                                                  
CONECT   53   52                                                            
CONECT   54   52   55                                                       
CONECT   55   54   56                                                       
CONECT   56   55   57   58                                                  
CONECT   57   56                                                            
CONECT   58   56    6   59                                                  
CONECT   59   58                                                            
MASTER        0    0    0    0    0    0    0    0   59    0  118    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₄₄H₇₅N₅O₁₀

Average Mass

834.1090 Da

Monoisotopic Mass

833.55139 Da

IUPAC Name

(3S,6S,12R,15S,18R,21Z,24S,25S,26S)-18-[(2S)-butan-2-yl]-8,17,24-trihydroxy-3,4,10,13,21,25-hexamethyl-12-(2-methylpropyl)-26-[(2Z)-pent-2-en-2-yl]-6,15-bis(propan-2-yl)-1,19-dioxa-4,7,10,13,16-pentaazacyclohexacosa-7,16,21-triene-2,5,11,14,20-pentone

Traditional Name

(3S,6S,12R,15S,18R,21Z,24S,25S,26S)-18-[(2S)-butan-2-yl]-8,17,24-trihydroxy-6,15-diisopropyl-3,4,10,13,21,25-hexamethyl-12-(2-methylpropyl)-26-[(2Z)-pent-2-en-2-yl]-1,19-dioxa-4,7,10,13,16-pentaazacyclohexacosa-7,16,21-triene-2,5,11,14,20-pentone

CAS Registry Number

Not Available

SMILES

CC\C=C(\C)[C@H]1OC(=O)[C@H](C)N(C)C(=O)[C@@H](N=C(O)CN(C)C(=O)[C@@H](CC(C)C)N(C)C(=O)[C@@H](N=C(O)[C@H](OC(=O)\C(C)=C/C[C@H](O)[C@@H]1C)[C@@H](C)CC)C(C)C)C(C)C

InChI Identifier

InChI=1S/C44H75N5O10/c1-17-19-28(10)37-30(12)33(50)21-20-29(11)43(56)59-38(27(9)18-2)39(52)46-36(26(7)8)42(55)49(16)32(22-24(3)4)40(53)47(14)23-34(51)45-35(25(5)6)41(54)48(15)31(13)44(57)58-37/h19-20,24-27,30-33,35-38,50H,17-18,21-23H2,1-16H3,(H,45,51)(H,46,52)/b28-19-,29-20-/t27-,30-,31-,32+,33-,35-,36-,37+,38+/m0/s1

InChI Key

XCPGQUJQUPDEFX-YWIOOLKYSA-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
Dolabella auricularia	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cyclic depsipeptides. These are natural or synthetic compounds having sequences of amino and hydroxy carboxylic acid residues (usually α-amino and α-hydroxy acids) connected in a ring. The residues are commonly but not necessarily regularly alternating.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Peptidomimetics

Sub Class

Depsipeptides

Direct Parent

Cyclic depsipeptides

Alternative Parents

Substituents

Cyclic depsipeptide
Macrolide lactam
Macrolide
Macrolactam
Alpha-amino acid ester
Alpha-amino acid or derivatives
Dicarboxylic acid or derivatives
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Tertiary carboxylic acid amide
Secondary carboxylic acid amide
Secondary alcohol
Lactone
Lactam
Carboxylic acid ester
Carboxamide group
Oxacycle
Azacycle
Organoheterocyclic compound
Carboxylic acid derivative
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Carbonyl group
Alcohol
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic 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	6.61	ChemAxon
pKa (Strongest Acidic)	3.75	ChemAxon
pKa (Strongest Basic)	1.45	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	198.94 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	227.33 m³·mol⁻¹	ChemAxon
Polarizability	92.81 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00034443

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

101999231

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Tripathi A, Puddick J, Prinsep MR, Rottmann M, Chan KP, Chen DY, Tan LT: Lagunamide C, a cytotoxic cyclodepsipeptide from the marine cyanobacterium Lyngbya majuscula. Phytochemistry. 2011 Dec;72(18):2369-75. doi: 10.1016/j.phytochem.2011.08.019. Epub 2011 Sep 6. [PubMed:21903231 ]
Takase S, Kurokawa R, Arai D, Kanemoto Kanto K, Okino T, Nakao Y, Kushiro T, Yoshida M, Matsumoto K: A quantitative shRNA screen identifies ATP1A1 as a gene that regulates cytotoxicity by aurilide B. Sci Rep. 2017 May 17;7(1):2002. doi: 10.1038/s41598-017-02016-4. [PubMed:28515454 ]
Tripathi A, Fang W, Leong DT, Tan LT: Biochemical studies of the lagunamides, potent cytotoxic cyclic depsipeptides from the marine cyanobacterium Lyngbya majuscula. Mar Drugs. 2012 May;10(5):1126-1137. doi: 10.3390/md10051126. Epub 2012 May 23. [PubMed:22822361 ]
Michon S, Cavelier F, Salom-Roig XJ: Synthesis and Biological Activities of Cyclodepsipeptides of Aurilide Family from Marine Origin. Mar Drugs. 2021 Jan 23;19(2):55. doi: 10.3390/md19020055. [PubMed:33498789 ]
Kaneda M, Kawaguchi S, Fujii N, Ohno H, Oishi S: Structure-Activity Relationship Study on Odoamide: Insights into the Bioactivities of Aurilide-Family Hybrid Peptide-Polyketides. ACS Med Chem Lett. 2018 Mar 5;9(4):365-369. doi: 10.1021/acsmedchemlett.8b00028. eCollection 2018 Apr 12. [PubMed:29670702 ]
LOTUS database [Link]

Showing NP-Card for (3s,6s,12r,15s,18r,21z,24s,25s,26s)-18-[(2s)-butan-2-yl]-8,17,24-trihydroxy-6,15-diisopropyl-3,4,10,13,21,25-hexamethyl-12-(2-methylpropyl)-26-[(2z)-pent-2-en-2-yl]-1,19-dioxa-4,7,10,13,16-pentaazacyclohexacosa-7,16,21-triene-2,5,11,14,20-pentone (NP0235021)

MOL for NP0235021 ((3s,6s,12r,15s,18r,21z,24s,25s,26s)-18-[(2s)-butan-2-yl]-8,17,24-trihydroxy-6,15-diisopropyl-3,4,10,13,21,25-hexamethyl-12-(2-methylpropyl)-26-[(2z)-pent-2-en-2-yl]-1,19-dioxa-4,7,10,13,16-pentaazacyclohexacosa-7,16,21-triene-2,5,11,14,20-pentone)

3D MOL for NP0235021 ((3s,6s,12r,15s,18r,21z,24s,25s,26s)-18-[(2s)-butan-2-yl]-8,17,24-trihydroxy-6,15-diisopropyl-3,4,10,13,21,25-hexamethyl-12-(2-methylpropyl)-26-[(2z)-pent-2-en-2-yl]-1,19-dioxa-4,7,10,13,16-pentaazacyclohexacosa-7,16,21-triene-2,5,11,14,20-pentone)

3D SDF for NP0235021 ((3s,6s,12r,15s,18r,21z,24s,25s,26s)-18-[(2s)-butan-2-yl]-8,17,24-trihydroxy-6,15-diisopropyl-3,4,10,13,21,25-hexamethyl-12-(2-methylpropyl)-26-[(2z)-pent-2-en-2-yl]-1,19-dioxa-4,7,10,13,16-pentaazacyclohexacosa-7,16,21-triene-2,5,11,14,20-pentone)

3D-SDF for NP0235021 ((3s,6s,12r,15s,18r,21z,24s,25s,26s)-18-[(2s)-butan-2-yl]-8,17,24-trihydroxy-6,15-diisopropyl-3,4,10,13,21,25-hexamethyl-12-(2-methylpropyl)-26-[(2z)-pent-2-en-2-yl]-1,19-dioxa-4,7,10,13,16-pentaazacyclohexacosa-7,16,21-triene-2,5,11,14,20-pentone)

PDB for NP0235021 ((3s,6s,12r,15s,18r,21z,24s,25s,26s)-18-[(2s)-butan-2-yl]-8,17,24-trihydroxy-6,15-diisopropyl-3,4,10,13,21,25-hexamethyl-12-(2-methylpropyl)-26-[(2z)-pent-2-en-2-yl]-1,19-dioxa-4,7,10,13,16-pentaazacyclohexacosa-7,16,21-triene-2,5,11,14,20-pentone)

3D PDB for NP0235021 ((3s,6s,12r,15s,18r,21z,24s,25s,26s)-18-[(2s)-butan-2-yl]-8,17,24-trihydroxy-6,15-diisopropyl-3,4,10,13,21,25-hexamethyl-12-(2-methylpropyl)-26-[(2z)-pent-2-en-2-yl]-1,19-dioxa-4,7,10,13,16-pentaazacyclohexacosa-7,16,21-triene-2,5,11,14,20-pentone)

SMILES for NP0235021 ((3s,6s,12r,15s,18r,21z,24s,25s,26s)-18-[(2s)-butan-2-yl]-8,17,24-trihydroxy-6,15-diisopropyl-3,4,10,13,21,25-hexamethyl-12-(2-methylpropyl)-26-[(2z)-pent-2-en-2-yl]-1,19-dioxa-4,7,10,13,16-pentaazacyclohexacosa-7,16,21-triene-2,5,11,14,20-pentone)

INCHI for NP0235021 ((3s,6s,12r,15s,18r,21z,24s,25s,26s)-18-[(2s)-butan-2-yl]-8,17,24-trihydroxy-6,15-diisopropyl-3,4,10,13,21,25-hexamethyl-12-(2-methylpropyl)-26-[(2z)-pent-2-en-2-yl]-1,19-dioxa-4,7,10,13,16-pentaazacyclohexacosa-7,16,21-triene-2,5,11,14,20-pentone)

Structure for NP0235021 ((3s,6s,12r,15s,18r,21z,24s,25s,26s)-18-[(2s)-butan-2-yl]-8,17,24-trihydroxy-6,15-diisopropyl-3,4,10,13,21,25-hexamethyl-12-(2-methylpropyl)-26-[(2z)-pent-2-en-2-yl]-1,19-dioxa-4,7,10,13,16-pentaazacyclohexacosa-7,16,21-triene-2,5,11,14,20-pentone)

3D Structure for NP0235021 ((3s,6s,12r,15s,18r,21z,24s,25s,26s)-18-[(2s)-butan-2-yl]-8,17,24-trihydroxy-6,15-diisopropyl-3,4,10,13,21,25-hexamethyl-12-(2-methylpropyl)-26-[(2z)-pent-2-en-2-yl]-1,19-dioxa-4,7,10,13,16-pentaazacyclohexacosa-7,16,21-triene-2,5,11,14,20-pentone)