NP-MRD: Showing NP-Card for (-)-Tamandarin A (NP0079329)

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Record Information

Version

2.0

Created at

2022-04-29 00:21:39 UTC

Updated at

2022-04-29 00:21:39 UTC

NP-MRD ID

NP0079329

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(-)-Tamandarin A

Description

TAMANDARIN A, also known as 2-hiv-didemnin b or tamandarin-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. (-)-Tamandarin A is found in Didemnum sp. (-)-Tamandarin A was first documented in 2003 (PMID: 12526689). Based on a literature review very few articles have been published on TAMANDARIN A (PMID: 15509169).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304292202212D          

 75 78  0  0  1  0            999 V2000
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M  END

     RDKit          3D

160163  0  0  0  0  0  0  0  0999 V2000
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M  END


  Mrv1652304292202212D          

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  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
 12 13  1  6  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  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 18 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 22 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
  1 27  1  0  0  0  0
 26 28  1  1  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 28 31  1  1  0  0  0
 25 32  1  1  0  0  0
 20 33  1  1  0  0  0
 33 34  1  0  0  0  0
 33 35  1  0  0  0  0
 16 36  1  6  0  0  0
 36 37  1  0  0  0  0
 37 38  1  0  0  0  0
 37 39  1  0  0  0  0
 13 40  1  0  0  0  0
 40 41  1  0  0  0  0
 41 42  1  0  0  0  0
 12 42  1  0  0  0  0
  9 43  1  0  0  0  0
  8 44  1  1  0  0  0
 44 45  1  0  0  0  0
 45 46  2  0  0  0  0
 46 47  1  0  0  0  0
 47 48  2  0  0  0  0
 48 49  1  0  0  0  0
 49 50  2  0  0  0  0
 45 50  1  0  0  0  0
 48 51  1  0  0  0  0
 51 52  1  0  0  0  0
  4 53  1  1  0  0  0
  3 54  1  1  0  0  0
 54 55  1  0  0  0  0
 55 56  2  0  0  0  0
 55 57  1  0  0  0  0
 57 58  1  6  0  0  0
 58 59  1  0  0  0  0
 58 60  1  0  0  0  0
 60 61  2  0  0  0  0
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 62 66  1  0  0  0  0
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 72 73  1  0  0  0  0
 73 74  1  0  0  0  0
 73 75  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0079329

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C54H85N7O14/c1-14-32(8)44-42(63)28-43(64)75-46(31(6)7)49(67)55-37(25-29(2)3)51(69)61-24-16-18-39(61)53(71)59(12)41(27-35-19-21-36(73-13)22-20-35)54(72)74-34(10)45(48(66)56-44)57-47(65)40(26-30(4)5)58(11)52(70)38-17-15-23-60(38)50(68)33(9)62/h19-22,29-34,37-42,44-46,62-63H,14-18,23-28H2,1-13H3,(H,55,67)(H,56,66)(H,57,65)/t32-,33-,34+,37-,38-,39-,40+,41-,42-,44+,45-,46-/m0/s1

> <INCHI_KEY>
OSGNLULODCTKKR-NBUCEWDXSA-N

> <FORMULA>
C54H85N7O14

> <MOLECULAR_WEIGHT>
1056.309

> <EXACT_MASS>
1055.615450445

> <JCHEM_ACCEPTOR_COUNT>
12

> <JCHEM_ATOM_COUNT>
160

> <JCHEM_AVERAGE_POLARIZABILITY>
112.73044510283913

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R)-N-[(3S,6R,7S,10R,11S,15S,18S,23aS)-10-[(2S)-butan-2-yl]-11-hydroxy-3-[(4-methoxyphenyl)methyl]-2,6-dimethyl-18-(2-methylpropyl)-1,4,8,13,16,19-hexaoxo-15-(propan-2-yl)-icosahydro-1H-pyrrolo[1,2-g]1,13-dioxa-4,7,10,17-tetraazacyclohenicosan-7-yl]-2-{1-[(2S)-1-[(2S)-2-hydroxypropanoyl]pyrrolidin-2-yl]-N-methylformamido}-4-methylpentanamide

> <ALOGPS_LOGP>
3.10

> <JCHEM_LOGP>
2.672921675666668

> <ALOGPS_LOGS>
-4.35

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.314477013684876

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.726479763114668

> <JCHEM_PKA_STRONGEST_BASIC>
-2.900999651413085

> <JCHEM_POLAR_SURFACE_AREA>
270.83

> <JCHEM_REFRACTIVITY>
274.5195

> <JCHEM_ROTATABLE_BOND_COUNT>
15

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.67e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2R)-N-[(3S,6R,7S,10R,11S,15S,18S,23aS)-10-[(2S)-butan-2-yl]-11-hydroxy-15-isopropyl-3-[(4-methoxyphenyl)methyl]-2,6-dimethyl-18-(2-methylpropyl)-1,4,8,13,16,19-hexaoxo-tetradecahydropyrrolo[1,2-g]1,13-dioxa-4,7,10,17-tetraazacyclohenicosan-7-yl]-2-{1-[(2S)-1-[(2S)-2-hydroxypropanoyl]pyrrolidin-2-yl]-N-methylformamido}-4-methylpentanamide

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 29-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-APR-22         0                                  
HETATM    1  C   UNK     0      -7.142  -7.191   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -6.711  -8.670   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -5.896  -6.286   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -4.650  -7.191   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      -5.126  -8.656   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      -4.508 -10.224   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -3.158  -9.483   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -5.414 -11.469   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0      -4.787 -12.876   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0      -5.692 -14.122   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -7.224 -13.961   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      -5.066 -15.529   0.000  0.00  0.00           C+0
HETATM   13  N   UNK     0      -5.971 -16.775   0.000  0.00  0.00           N+0
HETATM   14  C   UNK     0      -7.503 -16.614   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -8.129 -15.207   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      -8.408 -17.860   0.000  0.00  0.00           C+0
HETATM   17  N   UNK     0      -9.940 -17.699   0.000  0.00  0.00           N+0
HETATM   18  C   UNK     0     -10.566 -16.292   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0     -12.097 -16.131   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      -9.661 -15.046   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0     -10.287 -13.639   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      -9.382 -12.393   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      -7.850 -12.554   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0     -10.008 -10.986   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -9.103  -9.741   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -9.729  -8.334   0.000  0.00  0.00           C+0
HETATM   27  N   UNK     0      -8.824  -7.088   0.000  0.00  0.00           N+0
HETATM   28  C   UNK     0     -11.261  -8.173   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0     -11.887  -6.766   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0     -13.419  -6.605   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0     -12.166  -9.419   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      -7.571  -9.902   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0     -11.192 -14.885   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0     -11.819 -13.478   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0     -12.657 -15.361   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      -7.782 -19.267   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      -8.687 -20.513   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      -8.060 -21.919   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0     -10.218 -20.352   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      -5.066 -18.021   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0      -3.601 -17.545   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0      -3.601 -16.005   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0      -3.256 -13.037   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0      -3.882 -11.630   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0      -2.977 -10.385   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0      -3.603  -8.978   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0      -2.698  -7.732   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0      -1.166  -7.893   0.000  0.00  0.00           C+0
HETATM   49  C   UNK     0      -0.540  -9.300   0.000  0.00  0.00           C+0
HETATM   50  C   UNK     0      -1.445 -10.546   0.000  0.00  0.00           C+0
HETATM   51  O   UNK     0      -0.261  -6.647   0.000  0.00  0.00           O+0
HETATM   52  C   UNK     0       1.270  -6.808   0.000  0.00  0.00           C+0
HETATM   53  C   UNK     0      -3.186  -6.715   0.000  0.00  0.00           C+0
HETATM   54  N   UNK     0      -5.896  -4.746   0.000  0.00  0.00           N+0
HETATM   55  C   UNK     0      -4.563  -3.976   0.000  0.00  0.00           C+0
HETATM   56  O   UNK     0      -3.229  -4.746   0.000  0.00  0.00           O+0
HETATM   57  C   UNK     0      -4.563  -2.436   0.000  0.00  0.00           C+0
HETATM   58  N   UNK     0      -5.896  -1.666   0.000  0.00  0.00           N+0
HETATM   59  C   UNK     0      -7.230  -2.436   0.000  0.00  0.00           C+0
HETATM   60  C   UNK     0      -5.896  -0.126   0.000  0.00  0.00           C+0
HETATM   61  O   UNK     0      -5.070   0.233   0.000  0.00  0.00           O+0
HETATM   62  C   UNK     0      -7.230   0.644   0.000  0.00  0.00           C+0
HETATM   63  C   UNK     0      -8.637   0.018   0.000  0.00  0.00           C+0
HETATM   64  C   UNK     0      -9.667   1.162   0.000  0.00  0.00           C+0
HETATM   65  C   UNK     0      -8.897   2.496   0.000  0.00  0.00           C+0
HETATM   66  N   UNK     0      -7.391   2.176   0.000  0.00  0.00           N+0
HETATM   67  C   UNK     0      -6.246   3.206   0.000  0.00  0.00           C+0
HETATM   68  O   UNK     0      -4.782   2.730   0.000  0.00  0.00           O+0
HETATM   69  C   UNK     0      -6.567   4.712   0.000  0.00  0.00           C+0
HETATM   70  C   UNK     0      -8.031   5.188   0.000  0.00  0.00           C+0
HETATM   71  O   UNK     0      -5.422   5.743   0.000  0.00  0.00           O+0
HETATM   72  C   UNK     0      -3.229  -1.666   0.000  0.00  0.00           C+0
HETATM   73  C   UNK     0      -3.229  -0.126   0.000  0.00  0.00           C+0
HETATM   74  C   UNK     0      -4.563   0.644   0.000  0.00  0.00           C+0
HETATM   75  C   UNK     0      -1.895   0.644   0.000  0.00  0.00           C+0
CONECT    1    2    3   27                                                  
CONECT    2    1                                                            
CONECT    3    1    4   54                                                  
CONECT    4    3    5   53                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   44                                                  
CONECT    9    8   10   43                                                  
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13   42                                                  
CONECT   13   12   14   40                                                  
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17   36                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21   33                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25                                                       
CONECT   25   24   26   32                                                  
CONECT   26   25   27   28                                                  
CONECT   27   26    1                                                       
CONECT   28   26   29   31                                                  
CONECT   29   28   30                                                       
CONECT   30   29                                                            
CONECT   31   28                                                            
CONECT   32   25                                                            
CONECT   33   20   34   35                                                  
CONECT   34   33                                                            
CONECT   35   33                                                            
CONECT   36   16   37                                                       
CONECT   37   36   38   39                                                  
CONECT   38   37                                                            
CONECT   39   37                                                            
CONECT   40   13   41                                                       
CONECT   41   40   42                                                       
CONECT   42   41   12                                                       
CONECT   43    9                                                            
CONECT   44    8   45                                                       
CONECT   45   44   46   50                                                  
CONECT   46   45   47                                                       
CONECT   47   46   48                                                       
CONECT   48   47   49   51                                                  
CONECT   49   48   50                                                       
CONECT   50   49   45                                                       
CONECT   51   48   52                                                       
CONECT   52   51                                                            
CONECT   53    4                                                            
CONECT   54    3   55                                                       
CONECT   55   54   56   57                                                  
CONECT   56   55                                                            
CONECT   57   55   58   72                                                  
CONECT   58   57   59   60                                                  
CONECT   59   58                                                            
CONECT   60   58   61   62                                                  
CONECT   61   60                                                            
CONECT   62   60   63   66                                                  
CONECT   63   62   64                                                       
CONECT   64   63   65                                                       
CONECT   65   64   66                                                       
CONECT   66   65   62   67                                                  
CONECT   67   66   68   69                                                  
CONECT   68   67                                                            
CONECT   69   67   70   71                                                  
CONECT   70   69                                                            
CONECT   71   69                                                            
CONECT   72   57   73                                                       
CONECT   73   72   74   75                                                  
CONECT   74   73                                                            
CONECT   75   73                                                            
MASTER        0    0    0    0    0    0    0    0   75    0  156    0
END

View in JSmol

Synonyms

Value	Source
2-Hiv-didemnin b	MeSH
Tamandarin-a	MeSH

Chemical Formula

C₅₄H₈₅N₇O₁₄

Average Mass

1056.3090 Da

Monoisotopic Mass

1055.61545 Da

IUPAC Name

(2R)-N-[(3S,6R,7S,10R,11S,15S,18S,23aS)-10-[(2S)-butan-2-yl]-11-hydroxy-3-[(4-methoxyphenyl)methyl]-2,6-dimethyl-18-(2-methylpropyl)-1,4,8,13,16,19-hexaoxo-15-(propan-2-yl)-icosahydro-1H-pyrrolo[1,2-g]1,13-dioxa-4,7,10,17-tetraazacyclohenicosan-7-yl]-2-{1-[(2S)-1-[(2S)-2-hydroxypropanoyl]pyrrolidin-2-yl]-N-methylformamido}-4-methylpentanamide

Traditional Name

(2R)-N-[(3S,6R,7S,10R,11S,15S,18S,23aS)-10-[(2S)-butan-2-yl]-11-hydroxy-15-isopropyl-3-[(4-methoxyphenyl)methyl]-2,6-dimethyl-18-(2-methylpropyl)-1,4,8,13,16,19-hexaoxo-tetradecahydropyrrolo[1,2-g]1,13-dioxa-4,7,10,17-tetraazacyclohenicosan-7-yl]-2-{1-[(2S)-1-[(2S)-2-hydroxypropanoyl]pyrrolidin-2-yl]-N-methylformamido}-4-methylpentanamide

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C54H85N7O14/c1-14-32(8)44-42(63)28-43(64)75-46(31(6)7)49(67)55-37(25-29(2)3)51(69)61-24-16-18-39(61)53(71)59(12)41(27-35-19-21-36(73-13)22-20-35)54(72)74-34(10)45(48(66)56-44)57-47(65)40(26-30(4)5)58(11)52(70)38-17-15-23-60(38)50(68)33(9)62/h19-22,29-34,37-42,44-46,62-63H,14-18,23-28H2,1-13H3,(H,55,67)(H,56,66)(H,57,65)/t32-,33-,34+,37-,38-,39-,40+,41-,42-,44+,45-,46-/m0/s1

InChI Key

OSGNLULODCTKKR-NBUCEWDXSA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Didemnum sp.	Animalia	KNApSAcK

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
Leucine or derivatives
N-acyl-alpha amino acid or derivatives
Alpha-amino acid ester
Proline or derivatives
Macrolactam
Alpha-amino acid amide
Alpha-amino acid or derivatives
N-acylpyrrolidine
Phenoxy compound
Phenol ether
Pyrrolidine carboxylic acid or derivatives
Pyrrolidine-2-carboxamide
Anisole
Methoxybenzene
Alkyl aryl ether
Fatty amide
Benzenoid
Dicarboxylic acid or derivatives
Fatty acyl
N-acyl-amine
Monocyclic benzene moiety
Pyrrolidine
Tertiary carboxylic acid amide
Carboxamide group
Carboxylic acid ester
Secondary carboxylic acid amide
Lactam
Lactone
Secondary alcohol
Ether
Organoheterocyclic compound
Azacycle
Carboxylic acid derivative
Oxacycle
Organic nitrogen compound
Alcohol
Carbonyl group
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	3.1	ALOGPS
logP	2.67	ChemAxon
logS	-4.4	ALOGPS
pKa (Strongest Acidic)	11.73	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	12	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	270.83 Å²	ChemAxon
Rotatable Bond Count	15	ChemAxon
Refractivity	274.52 m³·mol⁻¹	ChemAxon
Polarizability	112.73 Å³	ChemAxon
Number of Rings	4	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

C00043955

Chemspider ID

9248304

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11073155

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Gutierrez-Rodriguez M, Martin-Martinez M, Garcia-Lopez MT, Herranz R, Cuevas F, Polanco C, Rodriguez-Campos I, Manzanares I, Cardenas F, Feliz M, Lloyd-Williams P, Giralt E: Synthesis, conformational analysis, and cytotoxicity of conformationally constrained aplidine and tamandarin A analogues incorporating a spirolactam beta-turn mimetic. J Med Chem. 2004 Nov 4;47(23):5700-12. doi: 10.1021/jm040788m. [PubMed:15509169 ]
Joullie MM, Leonard MS, Portonovo P, Liang B, Ding X, La Clair JJ: Chemical defense in ascidians of the didemnidae family. Bioconjug Chem. 2003 Jan-Feb;14(1):30-7. doi: 10.1021/bc025576n. [PubMed:12526689 ]

Showing NP-Card for (-)-Tamandarin A (NP0079329)

MOL for NP0079329 ((-)-Tamandarin A)

3D MOL for NP0079329 ((-)-Tamandarin A)

3D SDF for NP0079329 ((-)-Tamandarin A)

3D-SDF for NP0079329 ((-)-Tamandarin A)

PDB for NP0079329 ((-)-Tamandarin A)

3D PDB for NP0079329 ((-)-Tamandarin A)

SMILES for NP0079329 ((-)-Tamandarin A)

INCHI for NP0079329 ((-)-Tamandarin A)

Structure for NP0079329 ((-)-Tamandarin A)

3D Structure for NP0079329 ((-)-Tamandarin A)