NP-MRD: Showing NP-Card for (1e,4r)-2-methyl-1-[(2r,3s,4s,6r,10z,14s,16r,18s,21r,22s,23s)-14,16,18-tris(acetyloxy)-4,6,22-trihydroxy-3,11,21,23-tetramethyl-24-oxo-1-oxacyclotetracos-10-en-2-yl]hept-1-en-4-yl acetate (NP0272537)

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Record Information

Version

2.0

Created at

2022-09-08 19:11:44 UTC

Updated at

2022-09-08 19:11:44 UTC

NP-MRD ID

NP0272537

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1e,4r)-2-methyl-1-[(2r,3s,4s,6r,10z,14s,16r,18s,21r,22s,23s)-14,16,18-tris(acetyloxy)-4,6,22-trihydroxy-3,11,21,23-tetramethyl-24-oxo-1-oxacyclotetracos-10-en-2-yl]hept-1-en-4-yl acetate

Description

Dolabelide C belongs to the class of organic compounds known as pentacarboxylic acids and derivatives. These are carboxylic acids containing exactly five carboxyl groups. (1e,4r)-2-methyl-1-[(2r,3s,4s,6r,10z,14s,16r,18s,21r,22s,23s)-14,16,18-tris(acetyloxy)-4,6,22-trihydroxy-3,11,21,23-tetramethyl-24-oxo-1-oxacyclotetracos-10-en-2-yl]hept-1-en-4-yl acetate is found in Dolabella auricularia. (1e,4r)-2-methyl-1-[(2r,3s,4s,6r,10z,14s,16r,18s,21r,22s,23s)-14,16,18-tris(acetyloxy)-4,6,22-trihydroxy-3,11,21,23-tetramethyl-24-oxo-1-oxacyclotetracos-10-en-2-yl]hept-1-en-4-yl acetate was first documented in 2011 (PMID: 21534597). Based on a literature review a small amount of articles have been published on dolabelide C (PMID: 30589270) (PMID: 25518970) (PMID: 21528846) (PMID: 35577918).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309082221112D          

 56 56  0  0  1  0            999 V2000
   -1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000   -4.1250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0000   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -5.3625    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4289   -5.7750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -7.0125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -7.0125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1434   -7.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -6.6000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.8579   -5.7750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -7.0125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.5724   -7.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013   -7.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7158   -6.6000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.7158   -7.4250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013   -7.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013   -8.6625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4302   -7.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1447   -6.6000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -7.1447   -7.4250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8592   -7.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8592   -8.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5737   -7.4250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8592   -7.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5737   -6.6000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -9.2881   -7.0125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  -10.0026   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.7171   -7.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.0026   -5.7750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5737   -5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8592   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8592   -4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5737   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1447   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4302   -4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7158   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013   -4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868   -4.1250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.2868   -3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -4.1250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.8579   -3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -4.5375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4289   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  2  0  0  0  0
  9  8  1  6  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
 13 14  1  1  0  0  0
 13 15  1  0  0  0  0
 15 16  1  6  0  0  0
 15 17  1  0  0  0  0
 17 18  1  6  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  1  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 23 25  2  0  0  0  0
 21 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  6  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 29 31  2  0  0  0  0
 27 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  1  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
 35 37  2  0  0  0  0
 33 38  1  0  0  0  0
 38 39  1  0  0  0  0
 39 40  1  0  0  0  0
 40 41  1  0  0  0  0
 40 42  2  0  0  0  0
 42 43  1  0  0  0  0
 43 44  1  0  0  0  0
 44 45  1  0  0  0  0
 45 46  1  0  0  0  0
 46 47  1  1  0  0  0
 46 48  1  0  0  0  0
 48 49  1  0  0  0  0
 49 50  1  6  0  0  0
 49 51  1  0  0  0  0
  9 51  1  0  0  0  0
 51 52  1  6  0  0  0
  4 53  1  1  0  0  0
 53 54  1  0  0  0  0
 54 55  1  0  0  0  0
 54 56  2  0  0  0  0
M  END

     RDKit          3D

128128  0  0  0  0  0  0  0  0999 V2000
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    1.3327    5.2583   -1.6685 O   0  0  0  0  0  0  0  0  0  0  0  0
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    4.6581   -0.4746    0.6189 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -6.6720   -3.1622   -4.5672 H   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


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M  END
> <DATABASE_ID>
NP0272537

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C43H72O13/c1-11-14-36(52-31(7)44)21-27(3)22-41-29(5)40(49)23-35(48)16-13-12-15-26(2)17-19-37(53-32(8)45)24-39(55-34(10)47)25-38(54-33(9)46)20-18-28(4)42(50)30(6)43(51)56-41/h15,22,28-30,35-42,48-50H,11-14,16-21,23-25H2,1-10H3/b26-15-,27-22+/t28-,29+,30+,35-,36-,37+,38+,39+,40+,41-,42+/m1/s1

> <INCHI_KEY>
YSRKJBBLDLGINZ-CJFAINIPSA-N

> <FORMULA>
C43H72O13

> <MOLECULAR_WEIGHT>
797.036

> <EXACT_MASS>
796.497292378

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
128

> <JCHEM_AVERAGE_POLARIZABILITY>
88.29653921822762

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1E,4R)-2-methyl-1-[(2R,3S,4S,6R,10Z,14S,16R,18S,21R,22S,23S)-14,16,18-tris(acetyloxy)-4,6,22-trihydroxy-3,11,21,23-tetramethyl-24-oxo-1-oxacyclotetracos-10-en-2-yl]hept-1-en-4-yl acetate

> <JCHEM_LOGP>
4.986569427666666

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.811194590573692

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.23465279214388

> <JCHEM_PKA_STRONGEST_BASIC>
-2.7213607751095017

> <JCHEM_POLAR_SURFACE_AREA>
192.19

> <JCHEM_REFRACTIVITY>
211.74470000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
13

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(1E,4R)-2-methyl-1-[(2R,3S,4S,6R,10Z,14S,16R,18S,21R,22S,23S)-14,16,18-tris(acetyloxy)-4,6,22-trihydroxy-3,11,21,23-tetramethyl-24-oxo-1-oxacyclotetracos-10-en-2-yl]hept-1-en-4-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 08-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   08-SEP-22         0                                  
HETATM    1  C   UNK     0      -2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.334  -5.390   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.334  -6.930   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.000  -7.700   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.000  -9.240   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.334 -10.010   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.334 -11.550   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -2.667  -9.240   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -4.001 -10.010   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      -2.667 -10.780   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      -2.667 -12.320   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      -1.334 -13.090   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      -4.001 -13.090   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -4.001 -14.630   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -5.335 -12.320   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -5.335 -10.780   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      -6.668 -13.090   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -6.668 -14.630   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -8.002 -12.320   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -9.336 -13.090   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0     -10.669 -12.320   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0     -10.669 -13.860   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      -9.336 -14.630   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -8.002 -13.860   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      -9.336 -16.170   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0     -12.003 -13.090   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0     -13.337 -12.320   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0     -13.337 -13.860   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0     -14.670 -14.630   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0     -14.670 -16.170   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0     -16.004 -13.860   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0     -14.670 -13.090   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0     -16.004 -12.320   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0     -17.338 -13.090   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0     -18.672 -12.320   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0     -20.005 -13.090   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0     -18.672 -10.780   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0     -16.004 -10.780   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0     -14.670 -10.010   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0     -14.670  -8.470   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0     -16.004  -7.700   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0     -13.337  -7.700   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0     -12.003  -8.470   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0     -10.669  -7.700   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0      -9.336  -8.470   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0      -8.002  -7.700   0.000  0.00  0.00           C+0
HETATM   47  O   UNK     0      -8.002  -6.160   0.000  0.00  0.00           O+0
HETATM   48  C   UNK     0      -6.668  -8.470   0.000  0.00  0.00           C+0
HETATM   49  C   UNK     0      -5.335  -7.700   0.000  0.00  0.00           C+0
HETATM   50  O   UNK     0      -5.335  -6.160   0.000  0.00  0.00           O+0
HETATM   51  C   UNK     0      -4.001  -8.470   0.000  0.00  0.00           C+0
HETATM   52  C   UNK     0      -2.667  -7.700   0.000  0.00  0.00           C+0
HETATM   53  O   UNK     0       1.334  -6.930   0.000  0.00  0.00           O+0
HETATM   54  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   55  C   UNK     0      -0.000  -4.620   0.000  0.00  0.00           C+0
HETATM   56  O   UNK     0       2.667  -4.620   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5   53                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9    8   10   51                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22   26                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23                                                            
CONECT   26   21   27                                                       
CONECT   27   26   28   32                                                  
CONECT   28   27   29                                                       
CONECT   29   28   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29                                                            
CONECT   32   27   33                                                       
CONECT   33   32   34   38                                                  
CONECT   34   33   35                                                       
CONECT   35   34   36   37                                                  
CONECT   36   35                                                            
CONECT   37   35                                                            
CONECT   38   33   39                                                       
CONECT   39   38   40                                                       
CONECT   40   39   41   42                                                  
CONECT   41   40                                                            
CONECT   42   40   43                                                       
CONECT   43   42   44                                                       
CONECT   44   43   45                                                       
CONECT   45   44   46                                                       
CONECT   46   45   47   48                                                  
CONECT   47   46                                                            
CONECT   48   46   49                                                       
CONECT   49   48   50   51                                                  
CONECT   50   49                                                            
CONECT   51   49    9   52                                                  
CONECT   52   51                                                            
CONECT   53    4   54                                                       
CONECT   54   53   55   56                                                  
CONECT   55   54                                                            
CONECT   56   54                                                            
MASTER        0    0    0    0    0    0    0    0   56    0  112    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₄₃H₇₂O₁₃

Average Mass

797.0360 Da

Monoisotopic Mass

796.49729 Da

IUPAC Name

(1E,4R)-2-methyl-1-[(2R,3S,4S,6R,10Z,14S,16R,18S,21R,22S,23S)-14,16,18-tris(acetyloxy)-4,6,22-trihydroxy-3,11,21,23-tetramethyl-24-oxo-1-oxacyclotetracos-10-en-2-yl]hept-1-en-4-yl acetate

Traditional Name

(1E,4R)-2-methyl-1-[(2R,3S,4S,6R,10Z,14S,16R,18S,21R,22S,23S)-14,16,18-tris(acetyloxy)-4,6,22-trihydroxy-3,11,21,23-tetramethyl-24-oxo-1-oxacyclotetracos-10-en-2-yl]hept-1-en-4-yl acetate

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C43H72O13/c1-11-14-36(52-31(7)44)21-27(3)22-41-29(5)40(49)23-35(48)16-13-12-15-26(2)17-19-37(53-32(8)45)24-39(55-34(10)47)25-38(54-33(9)46)20-18-28(4)42(50)30(6)43(51)56-41/h15,22,28-30,35-42,48-50H,11-14,16-21,23-25H2,1-10H3/b26-15-,27-22+/t28-,29+,30+,35-,36-,37+,38+,39+,40+,41-,42+/m1/s1

InChI Key

YSRKJBBLDLGINZ-CJFAINIPSA-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 pentacarboxylic acids and derivatives. These are carboxylic acids containing exactly five carboxyl groups.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Pentacarboxylic acids and derivatives

Direct Parent

Pentacarboxylic acids and derivatives

Alternative Parents

Substituents

Pentacarboxylic acid or derivatives
Macrolide
Secondary alcohol
Lactone
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Polyol
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen 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	4.99	ChemAxon
pKa (Strongest Acidic)	14.23	ChemAxon
pKa (Strongest Basic)	-2.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	192.19 Å²	ChemAxon
Rotatable Bond Count	13	ChemAxon
Refractivity	211.74 m³·mol⁻¹	ChemAxon
Polarizability	88.3 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

C00050061

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

53342618

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Tiniakos AF, Wittmann S, Audic A, Prunet J: Novel Synthesis of Trisubstituted Olefins for the Preparation of the C16-C30 Fragment of Dolabelide C. Org Lett. 2019 Feb 1;21(3):589-592. doi: 10.1021/acs.orglett.8b03552. Epub 2018 Dec 27. [PubMed:30589270 ]
Hanson PR, Jayasinghe S, Maitra S, Markley JL: Phosphate tethers in natural product synthesis. Top Curr Chem. 2015;361:253-71. doi: 10.1007/128_2014_572. [PubMed:25518970 ]
Braun MG, Vincent A, Boumediene M, Prunet J: Highly demanding cross-metathesis in the synthesis of the C16-C30 fragment of dolabelide C. J Org Chem. 2011 Jun 17;76(12):4921-9. doi: 10.1021/jo200466t. Epub 2011 May 16. [PubMed:21534597 ]
Hanson PR, Chegondi R, Nguyen J, Thomas CD, Waetzig JD, Whitehead A: Total synthesis of dolabelide C: a phosphate-mediated approach. J Org Chem. 2011 Jun 3;76(11):4358-70. doi: 10.1021/jo2003506. Epub 2011 Apr 29. [PubMed:21528846 ]
Mu Y, Hartrampf FWW, Yu EC, Lounsbury KE, Schrock RR, Romiti F, Hoveyda AH: E- and Z-trisubstituted macrocyclic alkenes for natural product synthesis and skeletal editing. Nat Chem. 2022 Jun;14(6):640-649. doi: 10.1038/s41557-022-00935-y. Epub 2022 May 16. [PubMed:35577918 ]
LOTUS database [Link]

Showing NP-Card for (1e,4r)-2-methyl-1-[(2r,3s,4s,6r,10z,14s,16r,18s,21r,22s,23s)-14,16,18-tris(acetyloxy)-4,6,22-trihydroxy-3,11,21,23-tetramethyl-24-oxo-1-oxacyclotetracos-10-en-2-yl]hept-1-en-4-yl acetate (NP0272537)

MOL for NP0272537 ((1e,4r)-2-methyl-1-[(2r,3s,4s,6r,10z,14s,16r,18s,21r,22s,23s)-14,16,18-tris(acetyloxy)-4,6,22-trihydroxy-3,11,21,23-tetramethyl-24-oxo-1-oxacyclotetracos-10-en-2-yl]hept-1-en-4-yl acetate)

3D MOL for NP0272537 ((1e,4r)-2-methyl-1-[(2r,3s,4s,6r,10z,14s,16r,18s,21r,22s,23s)-14,16,18-tris(acetyloxy)-4,6,22-trihydroxy-3,11,21,23-tetramethyl-24-oxo-1-oxacyclotetracos-10-en-2-yl]hept-1-en-4-yl acetate)

3D SDF for NP0272537 ((1e,4r)-2-methyl-1-[(2r,3s,4s,6r,10z,14s,16r,18s,21r,22s,23s)-14,16,18-tris(acetyloxy)-4,6,22-trihydroxy-3,11,21,23-tetramethyl-24-oxo-1-oxacyclotetracos-10-en-2-yl]hept-1-en-4-yl acetate)

3D-SDF for NP0272537 ((1e,4r)-2-methyl-1-[(2r,3s,4s,6r,10z,14s,16r,18s,21r,22s,23s)-14,16,18-tris(acetyloxy)-4,6,22-trihydroxy-3,11,21,23-tetramethyl-24-oxo-1-oxacyclotetracos-10-en-2-yl]hept-1-en-4-yl acetate)

PDB for NP0272537 ((1e,4r)-2-methyl-1-[(2r,3s,4s,6r,10z,14s,16r,18s,21r,22s,23s)-14,16,18-tris(acetyloxy)-4,6,22-trihydroxy-3,11,21,23-tetramethyl-24-oxo-1-oxacyclotetracos-10-en-2-yl]hept-1-en-4-yl acetate)

3D PDB for NP0272537 ((1e,4r)-2-methyl-1-[(2r,3s,4s,6r,10z,14s,16r,18s,21r,22s,23s)-14,16,18-tris(acetyloxy)-4,6,22-trihydroxy-3,11,21,23-tetramethyl-24-oxo-1-oxacyclotetracos-10-en-2-yl]hept-1-en-4-yl acetate)

SMILES for NP0272537 ((1e,4r)-2-methyl-1-[(2r,3s,4s,6r,10z,14s,16r,18s,21r,22s,23s)-14,16,18-tris(acetyloxy)-4,6,22-trihydroxy-3,11,21,23-tetramethyl-24-oxo-1-oxacyclotetracos-10-en-2-yl]hept-1-en-4-yl acetate)

INCHI for NP0272537 ((1e,4r)-2-methyl-1-[(2r,3s,4s,6r,10z,14s,16r,18s,21r,22s,23s)-14,16,18-tris(acetyloxy)-4,6,22-trihydroxy-3,11,21,23-tetramethyl-24-oxo-1-oxacyclotetracos-10-en-2-yl]hept-1-en-4-yl acetate)

Structure for NP0272537 ((1e,4r)-2-methyl-1-[(2r,3s,4s,6r,10z,14s,16r,18s,21r,22s,23s)-14,16,18-tris(acetyloxy)-4,6,22-trihydroxy-3,11,21,23-tetramethyl-24-oxo-1-oxacyclotetracos-10-en-2-yl]hept-1-en-4-yl acetate)

3D Structure for NP0272537 ((1e,4r)-2-methyl-1-[(2r,3s,4s,6r,10z,14s,16r,18s,21r,22s,23s)-14,16,18-tris(acetyloxy)-4,6,22-trihydroxy-3,11,21,23-tetramethyl-24-oxo-1-oxacyclotetracos-10-en-2-yl]hept-1-en-4-yl acetate)