NP-MRD: Showing NP-Card for (3s,6s,12r,15s,18r,21e,24s,25s,26s)-12-benzyl-6-[(2r)-butan-2-yl]-18,26-bis[(2s)-butan-2-yl]-8,17,24-trihydroxy-3,4,10,13,15,21,25-heptamethyl-1,19-dioxa-4,7,10,13,16-pentaazacyclohexacosa-7,16,21-triene-2,5,11,14,20-pentone (NP0242112)

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Record Information

Version

2.0

Created at

2022-09-07 02:21:24 UTC

Updated at

2022-09-07 02:21:24 UTC

NP-MRD ID

NP0242112

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(3s,6s,12r,15s,18r,21e,24s,25s,26s)-12-benzyl-6-[(2r)-butan-2-yl]-18,26-bis[(2s)-butan-2-yl]-8,17,24-trihydroxy-3,4,10,13,15,21,25-heptamethyl-1,19-dioxa-4,7,10,13,16-pentaazacyclohexacosa-7,16,21-triene-2,5,11,14,20-pentone

Description

Lagunamide A 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,21e,24s,25s,26s)-12-benzyl-6-[(2r)-butan-2-yl]-18,26-bis[(2s)-butan-2-yl]-8,17,24-trihydroxy-3,4,10,13,15,21,25-heptamethyl-1,19-dioxa-4,7,10,13,16-pentaazacyclohexacosa-7,16,21-triene-2,5,11,14,20-pentone was first documented in 2012 (PMID: 22824869). Based on a literature review a small amount of articles have been published on Lagunamide A (PMID: 30717076) (PMID: 29578725) (PMID: 27715057) (PMID: 24090274).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309072204212D          

 60 61  0  0  1  0            999 V2000
   16.4328    5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4328    6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7184    6.6000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   15.7184    7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0039    6.1875    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   15.7184    5.7750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.7184    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4328    4.5375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.0039    4.5375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   15.0039    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2894    4.9500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.2894    5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5749    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5749    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.8605    4.9500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   12.8605    4.1250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   13.1960    3.3713    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1460    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4315    4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1460    4.5375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.4315    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4315    5.7750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.7171    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0026    4.9500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.0026    5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737    4.9500    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
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    7.1447    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    7.1447    5.7750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592    7.0125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.1447    7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    9.2881    7.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7730    6.3451    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.0026    7.4250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   10.0026    8.2500    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   10.7171    8.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881    8.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881    9.4875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7171    7.0125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.4315    7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4315    8.2500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.1460    7.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1460    6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8605    7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5749    7.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2894    7.4250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   14.2894    8.2500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.0039    7.0125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   15.3394    7.7662    0.0000 C   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  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  6  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
 15 16  1  1  0  0  0
 16 17  1  6  0  0  0
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
 15 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  4  0  0  0
 21 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 24 26  1  0  0  0  0
 26 27  2  0  0  0  0
 26 28  1  0  0  0  0
 28 29  1  1  0  0  0
 29 30  1  0  0  0  0
 30 31  2  0  0  0  0
 31 32  1  0  0  0  0
 32 33  2  0  0  0  0
 33 34  1  0  0  0  0
 34 35  2  0  0  0  0
 30 35  1  0  0  0  0
 28 36  1  0  0  0  0
 36 37  1  0  0  0  0
 36 38  1  0  0  0  0
 38 39  2  0  0  0  0
 38 40  1  0  0  0  0
 40 41  1  6  0  0  0
 40 42  1  0  0  0  0
 42 43  2  0  0  0  0
 43 44  1  4  0  0  0
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 53 55  2  0  0  0  0
 55 56  1  0  0  0  0
 56 57  1  0  0  0  0
 57 58  1  6  0  0  0
 57 59  1  0  0  0  0
  5 59  1  0  0  0  0
 59 60  1  6  0  0  0
M  END

     RDKit          3D

131132  0  0  0  0  0  0  0  0999 V2000
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M  END


  Mrv1652309072204212D          

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   15.7184    5.7750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.7184    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4328    4.5375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   15.0039    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    9.2881    7.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7730    6.3451    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.0026    7.4250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   10.0026    8.2500    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
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    9.2881    8.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881    9.4875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7171    7.0125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   11.4315    8.2500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   13.5749    7.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2894    7.4250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
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   15.0039    7.0125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   15.3394    7.7662    0.0000 C   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  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  6  0  0  0
  9 11  1  0  0  0  0
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 28 36  1  0  0  0  0
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 38 40  1  0  0  0  0
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 51 53  1  0  0  0  0
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 55 56  1  0  0  0  0
 56 57  1  0  0  0  0
 57 58  1  6  0  0  0
 57 59  1  0  0  0  0
  5 59  1  0  0  0  0
 59 60  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0242112

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC[C@H](C)[C@@H]1OC(=O)[C@H](C)N(C)C(=O)[C@@H](N=C(O)CN(C)C(=O)[C@@H](CC2=CC=CC=C2)N(C)C(=O)[C@H](C)N=C(O)[C@H](OC(=O)\C(C)=C\C[C@H](O)[C@@H]1C)[C@@H](C)CC)[C@H](C)CC

> <INCHI_IDENTIFIER>
InChI=1S/C45H71N5O10/c1-14-26(4)37-43(56)49(12)32(10)45(58)59-38(27(5)15-2)30(8)35(51)23-22-29(7)44(57)60-39(28(6)16-3)40(53)46-31(9)41(54)50(13)34(24-33-20-18-17-19-21-33)42(55)48(11)25-36(52)47-37/h17-22,26-28,30-32,34-35,37-39,51H,14-16,23-25H2,1-13H3,(H,46,53)(H,47,52)/b29-22+/t26-,27+,28+,30+,31+,32+,34-,35+,37+,38+,39-/m1/s1

> <INCHI_KEY>
VOJKUGWTQYFABB-ZJXVFMLESA-N

> <FORMULA>
C45H71N5O10

> <MOLECULAR_WEIGHT>
842.088

> <EXACT_MASS>
841.520093506

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
131

> <JCHEM_AVERAGE_POLARIZABILITY>
93.60545676604679

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <JCHEM_LOGP>
6.4503875193333355

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
4.758786880729827

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.637857424632502

> <JCHEM_PKA_STRONGEST_BASIC>
1.5177237016068266

> <JCHEM_POLAR_SURFACE_AREA>
198.93999999999997

> <JCHEM_REFRACTIVITY>
228.50560000000013

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(3S,6S,12R,15S,18R,21E,24S,25S,26S)-12-benzyl-6-[(2R)-butan-2-yl]-18,26-bis[(2S)-butan-2-yl]-8,17,24-trihydroxy-3,4,10,13,15,21,25-heptamethyl-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                                 07-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-SEP-22         0                                  
HETATM    1  C   UNK     0      30.675  10.010   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      30.675  11.550   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      29.341  12.320   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      29.341  13.860   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      28.007  11.550   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      29.341  10.780   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      29.341   9.240   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      30.675   8.470   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      28.007   8.470   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      28.007   6.930   0.000  0.00  0.00           C+0
HETATM   11  N   UNK     0      26.674   9.240   0.000  0.00  0.00           N+0
HETATM   12  C   UNK     0      26.674  10.780   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      25.340   8.470   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      25.340   6.930   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      24.006   9.240   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      24.006   7.700   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      24.633   6.293   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      22.673   6.930   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      21.339   7.700   0.000  0.00  0.00           C+0
HETATM   20  N   UNK     0      22.673   8.470   0.000  0.00  0.00           N+0
HETATM   21  C   UNK     0      21.339   9.240   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      21.339  10.780   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      20.005   8.470   0.000  0.00  0.00           C+0
HETATM   24  N   UNK     0      18.672   9.240   0.000  0.00  0.00           N+0
HETATM   25  C   UNK     0      18.672  10.780   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      17.338   8.470   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      17.338   6.930   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      16.004   9.240   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      14.670   8.470   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      14.670   6.930   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      16.004   6.160   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      16.004   4.620   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      14.670   3.850   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      13.337   4.620   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      13.337   6.160   0.000  0.00  0.00           C+0
HETATM   36  N   UNK     0      16.004  10.780   0.000  0.00  0.00           N+0
HETATM   37  C   UNK     0      17.338  11.550   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      14.670  11.550   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0      13.337  10.780   0.000  0.00  0.00           O+0
HETATM   40  C   UNK     0      14.670  13.090   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0      13.337  13.860   0.000  0.00  0.00           C+0
HETATM   42  N   UNK     0      16.004  13.860   0.000  0.00  0.00           N+0
HETATM   43  C   UNK     0      17.338  13.090   0.000  0.00  0.00           C+0
HETATM   44  O   UNK     0      18.243  11.844   0.000  0.00  0.00           O+0
HETATM   45  C   UNK     0      18.672  13.860   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0      18.672  15.400   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0      20.005  16.170   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0      17.338  16.170   0.000  0.00  0.00           C+0
HETATM   49  C   UNK     0      17.338  17.710   0.000  0.00  0.00           C+0
HETATM   50  O   UNK     0      20.005  13.090   0.000  0.00  0.00           O+0
HETATM   51  C   UNK     0      21.339  13.860   0.000  0.00  0.00           C+0
HETATM   52  O   UNK     0      21.339  15.400   0.000  0.00  0.00           O+0
HETATM   53  C   UNK     0      22.673  13.090   0.000  0.00  0.00           C+0
HETATM   54  C   UNK     0      22.673  11.550   0.000  0.00  0.00           C+0
HETATM   55  C   UNK     0      24.006  13.860   0.000  0.00  0.00           C+0
HETATM   56  C   UNK     0      25.340  13.090   0.000  0.00  0.00           C+0
HETATM   57  C   UNK     0      26.674  13.860   0.000  0.00  0.00           C+0
HETATM   58  O   UNK     0      26.674  15.400   0.000  0.00  0.00           O+0
HETATM   59  C   UNK     0      28.007  13.090   0.000  0.00  0.00           C+0
HETATM   60  C   UNK     0      28.634  14.497   0.000  0.00  0.00           C+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   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16   20                                                  
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19                                                       
CONECT   19   18                                                            
CONECT   20   15   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   36                                                  
CONECT   29   28   30                                                       
CONECT   30   29   31   35                                                  
CONECT   31   30   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32   34                                                       
CONECT   34   33   35                                                       
CONECT   35   34   30                                                       
CONECT   36   28   37   38                                                  
CONECT   37   36                                                            
CONECT   38   36   39   40                                                  
CONECT   39   38                                                            
CONECT   40   38   41   42                                                  
CONECT   41   40                                                            
CONECT   42   40   43                                                       
CONECT   43   42   44   45                                                  
CONECT   44   43                                                            
CONECT   45   43   46   50                                                  
CONECT   46   45   47   48                                                  
CONECT   47   46                                                            
CONECT   48   46   49                                                       
CONECT   49   48                                                            
CONECT   50   45   51                                                       
CONECT   51   50   52   53                                                  
CONECT   52   51                                                            
CONECT   53   51   54   55                                                  
CONECT   54   53                                                            
CONECT   55   53   56                                                       
CONECT   56   55   57                                                       
CONECT   57   56   58   59                                                  
CONECT   58   57                                                            
CONECT   59   57    5   60                                                  
CONECT   60   59                                                            
MASTER        0    0    0    0    0    0    0    0   60    0  122    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₄₅H₇₁N₅O₁₀

Average Mass

842.0880 Da

Monoisotopic Mass

841.52009 Da

IUPAC Name

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

Traditional Name

CAS Registry Number

Not Available

SMILES

CC[C@H](C)[C@@H]1OC(=O)[C@H](C)N(C)C(=O)[C@@H](N=C(O)CN(C)C(=O)[C@@H](CC2=CC=CC=C2)N(C)C(=O)[C@H](C)N=C(O)[C@H](OC(=O)\C(C)=C\C[C@H](O)[C@@H]1C)[C@@H](C)CC)[C@H](C)CC

InChI Identifier

InChI=1S/C45H71N5O10/c1-14-26(4)37-43(56)49(12)32(10)45(58)59-38(27(5)15-2)30(8)35(51)23-22-29(7)44(57)60-39(28(6)16-3)40(53)46-31(9)41(54)50(13)34(24-33-20-18-17-19-21-33)42(55)48(11)25-36(52)47-37/h17-22,26-28,30-32,34-35,37-39,51H,14-16,23-25H2,1-13H3,(H,46,53)(H,47,52)/b29-22+/t26-,27+,28+,30+,31+,32+,34-,35+,37+,38+,39-/m1/s1

InChI Key

VOJKUGWTQYFABB-ZJXVFMLESA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cyclic 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
Alpha-amino acid ester
Macrolide
Macrolactam
Alpha-amino acid or derivatives
Monocyclic benzene moiety
Dicarboxylic acid or derivatives
Benzenoid
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Tertiary carboxylic acid amide
Secondary carboxylic acid amide
Secondary alcohol
Lactone
Lactam
Carboxylic acid ester
Carboxamide group
Carboxylic acid derivative
Oxacycle
Azacycle
Organoheterocyclic compound
Organic nitrogen compound
Hydrocarbon derivative
Alcohol
Organic oxide
Carbonyl group
Organopnictogen compound
Organic oxygen compound
Organooxygen compound
Organonitrogen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

cyclodepsipeptide (CHEBI:70390 )

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	6.45	ChemAxon
pKa (Strongest Acidic)	3.64	ChemAxon
pKa (Strongest Basic)	1.52	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	228.51 m³·mol⁻¹	ChemAxon
Polarizability	93.61 Å³	ChemAxon
Number of Rings	2	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

Not Available

Chemspider ID

26377226

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

50901239

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Luo D, Putra MY, Ye T, Paul VJ, Luesch H: Isolation, Structure Elucidation and Biological Evaluation of Lagunamide D: A New Cytotoxic Macrocyclic Depsipeptide from Marine Cyanobacteria. Mar Drugs. 2019 Feb 1;17(2). pii: md17020083. doi: 10.3390/md17020083. [PubMed:30717076 ]
Gorges J, Kazmaier U: Matteson Homologation-Based Total Synthesis of Lagunamide A. Org Lett. 2018 Apr 6;20(7):2033-2036. doi: 10.1021/acs.orglett.8b00576. Epub 2018 Mar 26. [PubMed:29578725 ]
Huang X, Huang W, Li L, Sun X, Song S, Xu Q, Zhang L, Wei BG, Deng X: Structure Determinants of Lagunamide A for Anticancer Activity and Its Molecular Mechanism of Mitochondrial Apoptosis. Mol Pharm. 2016 Nov 7;13(11):3756-3763. doi: 10.1021/acs.molpharmaceut.6b00564. Epub 2016 Oct 17. [PubMed:27715057 ]
Huang W, Ren RG, Dong HQ, Wei BG, Lin GQ: Diverse synthesis of marine cyclic depsipeptide lagunamide A and its analogues. J Org Chem. 2013 Nov 1;78(21):10747-62. doi: 10.1021/jo401687s. Epub 2013 Oct 23. [PubMed:24090274 ]
Dai L, Chen B, Lei H, Wang Z, Liu Y, Xu Z, Ye T: Total synthesis and stereochemical revision of lagunamide A. Chem Commun (Camb). 2012 Sep 7;48(69):8697-9. doi: 10.1039/c2cc34187e. Epub 2012 Jul 24. [PubMed:22824869 ]
LOTUS database [Link]

Showing NP-Card for (3s,6s,12r,15s,18r,21e,24s,25s,26s)-12-benzyl-6-[(2r)-butan-2-yl]-18,26-bis[(2s)-butan-2-yl]-8,17,24-trihydroxy-3,4,10,13,15,21,25-heptamethyl-1,19-dioxa-4,7,10,13,16-pentaazacyclohexacosa-7,16,21-triene-2,5,11,14,20-pentone (NP0242112)

MOL for NP0242112 ((3s,6s,12r,15s,18r,21e,24s,25s,26s)-12-benzyl-6-[(2r)-butan-2-yl]-18,26-bis[(2s)-butan-2-yl]-8,17,24-trihydroxy-3,4,10,13,15,21,25-heptamethyl-1,19-dioxa-4,7,10,13,16-pentaazacyclohexacosa-7,16,21-triene-2,5,11,14,20-pentone)

3D MOL for NP0242112 ((3s,6s,12r,15s,18r,21e,24s,25s,26s)-12-benzyl-6-[(2r)-butan-2-yl]-18,26-bis[(2s)-butan-2-yl]-8,17,24-trihydroxy-3,4,10,13,15,21,25-heptamethyl-1,19-dioxa-4,7,10,13,16-pentaazacyclohexacosa-7,16,21-triene-2,5,11,14,20-pentone)

3D SDF for NP0242112 ((3s,6s,12r,15s,18r,21e,24s,25s,26s)-12-benzyl-6-[(2r)-butan-2-yl]-18,26-bis[(2s)-butan-2-yl]-8,17,24-trihydroxy-3,4,10,13,15,21,25-heptamethyl-1,19-dioxa-4,7,10,13,16-pentaazacyclohexacosa-7,16,21-triene-2,5,11,14,20-pentone)

3D-SDF for NP0242112 ((3s,6s,12r,15s,18r,21e,24s,25s,26s)-12-benzyl-6-[(2r)-butan-2-yl]-18,26-bis[(2s)-butan-2-yl]-8,17,24-trihydroxy-3,4,10,13,15,21,25-heptamethyl-1,19-dioxa-4,7,10,13,16-pentaazacyclohexacosa-7,16,21-triene-2,5,11,14,20-pentone)

PDB for NP0242112 ((3s,6s,12r,15s,18r,21e,24s,25s,26s)-12-benzyl-6-[(2r)-butan-2-yl]-18,26-bis[(2s)-butan-2-yl]-8,17,24-trihydroxy-3,4,10,13,15,21,25-heptamethyl-1,19-dioxa-4,7,10,13,16-pentaazacyclohexacosa-7,16,21-triene-2,5,11,14,20-pentone)

3D PDB for NP0242112 ((3s,6s,12r,15s,18r,21e,24s,25s,26s)-12-benzyl-6-[(2r)-butan-2-yl]-18,26-bis[(2s)-butan-2-yl]-8,17,24-trihydroxy-3,4,10,13,15,21,25-heptamethyl-1,19-dioxa-4,7,10,13,16-pentaazacyclohexacosa-7,16,21-triene-2,5,11,14,20-pentone)

SMILES for NP0242112 ((3s,6s,12r,15s,18r,21e,24s,25s,26s)-12-benzyl-6-[(2r)-butan-2-yl]-18,26-bis[(2s)-butan-2-yl]-8,17,24-trihydroxy-3,4,10,13,15,21,25-heptamethyl-1,19-dioxa-4,7,10,13,16-pentaazacyclohexacosa-7,16,21-triene-2,5,11,14,20-pentone)

INCHI for NP0242112 ((3s,6s,12r,15s,18r,21e,24s,25s,26s)-12-benzyl-6-[(2r)-butan-2-yl]-18,26-bis[(2s)-butan-2-yl]-8,17,24-trihydroxy-3,4,10,13,15,21,25-heptamethyl-1,19-dioxa-4,7,10,13,16-pentaazacyclohexacosa-7,16,21-triene-2,5,11,14,20-pentone)

Structure for NP0242112 ((3s,6s,12r,15s,18r,21e,24s,25s,26s)-12-benzyl-6-[(2r)-butan-2-yl]-18,26-bis[(2s)-butan-2-yl]-8,17,24-trihydroxy-3,4,10,13,15,21,25-heptamethyl-1,19-dioxa-4,7,10,13,16-pentaazacyclohexacosa-7,16,21-triene-2,5,11,14,20-pentone)

3D Structure for NP0242112 ((3s,6s,12r,15s,18r,21e,24s,25s,26s)-12-benzyl-6-[(2r)-butan-2-yl]-18,26-bis[(2s)-butan-2-yl]-8,17,24-trihydroxy-3,4,10,13,15,21,25-heptamethyl-1,19-dioxa-4,7,10,13,16-pentaazacyclohexacosa-7,16,21-triene-2,5,11,14,20-pentone)