NP-MRD: Showing NP-Card for methyl (3as,4s,5s,11ar)-4-{[(2s,3s)-3-(acetyloxy)-2-hydroxy-2-methylbutanoyl]oxy}-10-methyl-5-{[(2r)-2-methylbutanoyl]oxy}-3-methylidene-2-oxo-3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-6-carboxylate (NP0165271)

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Record Information

Version

2.0

Created at

2022-09-03 00:20:57 UTC

Updated at

2022-09-03 00:20:57 UTC

NP-MRD ID

NP0165271

Secondary Accession Numbers

None

Natural Product Identification

Common Name

methyl (3as,4s,5s,11ar)-4-{[(2s,3s)-3-(acetyloxy)-2-hydroxy-2-methylbutanoyl]oxy}-10-methyl-5-{[(2r)-2-methylbutanoyl]oxy}-3-methylidene-2-oxo-3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-6-carboxylate

Description

Methyl (3aS,4S,5S,11aR)-4-{[(2S,3S)-3-(acetyloxy)-2-hydroxy-2-methylbutanoyl]oxy}-10-methyl-5-{[(2R)-2-methylbutanoyl]oxy}-3-methylidene-2-oxo-2H,3H,3aH,4H,5H,8H,9H,11aH-cyclodeca[b]furan-6-carboxylate belongs to the class of organic compounds known as germacranolides and derivatives. These are sesquiterpene lactones with a structure based on the germacranolide skeleton, characterized by a gamma lactone fused to a 1,7-dimethylcyclodec-1-ene moiety. methyl (3as,4s,5s,11ar)-4-{[(2s,3s)-3-(acetyloxy)-2-hydroxy-2-methylbutanoyl]oxy}-10-methyl-5-{[(2r)-2-methylbutanoyl]oxy}-3-methylidene-2-oxo-3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-6-carboxylate is found in Tetragonotheca helianthoides. Based on a literature review very few articles have been published on methyl (3aS,4S,5S,11aR)-4-{[(2S,3S)-3-(acetyloxy)-2-hydroxy-2-methylbutanoyl]oxy}-10-methyl-5-{[(2R)-2-methylbutanoyl]oxy}-3-methylidene-2-oxo-2H,3H,3aH,4H,5H,8H,9H,11aH-cyclodeca[b]furan-6-carboxylate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309032202202D          

 39 40  0  0  1  0            999 V2000
   -1.8175   -0.6051    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7540    0.2856    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5180   -0.0258    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0980   -0.6664    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0502    0.6046    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6151    1.3056    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.8449    2.0979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2736    2.6931    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0726    1.9228    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5034    3.4854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9321    4.0806    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1310    3.8834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9012    3.0911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0996    3.7862    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.2681    4.6222    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.4725    2.4959    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4915    2.3577    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.0691    3.1215    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3390    2.2845    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7172    1.5120    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2178    2.4675    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0204    2.1321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2427    1.7036    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
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   -0.2600   -1.5837    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7581   -0.8019    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6688   -1.3468    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4763   -2.1490    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.8140    1.1084    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  3  5  1  0  0  0  0
  6  5  1  6  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
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 13 18  1  0  0  0  0
 18 19  1  1  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 20 22  1  0  0  0  0
 22 23  1  1  0  0  0
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 18 26  1  0  0  0  0
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 35 36  1  0  0  0  0
 36 37  1  0  0  0  0
 36 38  2  0  0  0  0
 26 39  1  0  0  0  0
 39  2  1  1  0  0  0
  6 39  1  0  0  0  0
M  END

     RDKit          3D

 77 78  0  0  0  0  0  0  0  0999 V2000
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   -2.4918    0.1827   -0.0899 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.1518    0.0510   -1.3866 C   0  0  0  0  0  0  0  0  0  0  0  0
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    4.5845   -2.7695   -0.1007 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2681   -4.2101    0.0316 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.7430    2.2567    0.8971 C   0  0  1  0  0  0  0  0  0  0  0  0
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   -1.3094    6.4150   -1.5381 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.3671    3.3819   -0.5821 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4806    3.7181   -2.3157 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.8774    1.6641   -2.8827 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1453    1.1506   -0.8652 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2713   -1.3998    2.6141 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9711   -2.0049    1.0864 H   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


  Mrv1652309032202202D          

 39 40  0  0  1  0            999 V2000
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   -1.7540    0.2856    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5180   -0.0258    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.0204    2.1321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2427    1.7036    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5367    0.9551    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0033    0.1463    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8365   -0.0347    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0584   -0.7676    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2600   -1.5837    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7581   -0.8019    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6688   -1.3468    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4763   -2.1490    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4598   -1.1124    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0583   -1.6802    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8493   -1.4458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8658   -2.4824    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8140    1.1084    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  3  5  1  0  0  0  0
  6  5  1  6  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  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
 13 18  1  0  0  0  0
 18 19  1  1  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 20 22  1  0  0  0  0
 22 23  1  1  0  0  0
 22 24  1  0  0  0  0
 24 25  1  0  0  0  0
 18 26  1  0  0  0  0
 26 27  1  1  0  0  0
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
 28 30  1  0  0  0  0
 30 31  1  1  0  0  0
 30 32  1  6  0  0  0
 30 33  1  0  0  0  0
 33 34  1  1  0  0  0
 33 35  1  0  0  0  0
 35 36  1  0  0  0  0
 36 37  1  0  0  0  0
 36 38  2  0  0  0  0
 26 39  1  0  0  0  0
 39  2  1  1  0  0  0
  6 39  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0165271

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC[C@@H](C)C(=O)O[C@@H]1[C@@H](OC(=O)[C@@](C)(O)[C@H](C)OC(C)=O)[C@@H]2[C@H](OC(=O)C2=C)\C=C(C)\CC\C=C1\C(=O)OC

> <INCHI_IDENTIFIER>
InChI=1S/C28H38O11/c1-9-15(3)24(30)38-22-19(26(32)35-8)12-10-11-14(2)13-20-21(16(4)25(31)37-20)23(22)39-27(33)28(7,34)17(5)36-18(6)29/h12-13,15,17,20-23,34H,4,9-11H2,1-3,5-8H3/b14-13+,19-12+/t15-,17+,20-,21+,22+,23+,28+/m1/s1

> <INCHI_KEY>
HHSMOWSETHYQGC-JMFZUNKNSA-N

> <FORMULA>
C28H38O11

> <MOLECULAR_WEIGHT>
550.601

> <EXACT_MASS>
550.241412044

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
77

> <JCHEM_AVERAGE_POLARIZABILITY>
55.93637963688451

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
methyl (3aS,4S,5S,11aR)-4-{[(2S,3S)-3-(acetyloxy)-2-hydroxy-2-methylbutanoyl]oxy}-10-methyl-5-{[(2R)-2-methylbutanoyl]oxy}-3-methylidene-2-oxo-2H,3H,3aH,4H,5H,8H,9H,11aH-cyclodeca[b]furan-6-carboxylate

> <ALOGPS_LOGP>
2.25

> <JCHEM_LOGP>
3.6883428496666664

> <ALOGPS_LOGS>
-4.83

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.639849630437139

> <JCHEM_PKA_STRONGEST_BASIC>
-4.2685297716467945

> <JCHEM_POLAR_SURFACE_AREA>
151.73000000000002

> <JCHEM_REFRACTIVITY>
137.3397

> <JCHEM_ROTATABLE_BOND_COUNT>
12

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
8.07e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl (3aS,4S,5S,11aR)-4-{[(2S,3S)-3-(acetyloxy)-2-hydroxy-2-methylbutanoyl]oxy}-10-methyl-5-{[(2R)-2-methylbutanoyl]oxy}-3-methylidene-2-oxo-3aH,4H,5H,8H,9H,11aH-cyclodeca[b]furan-6-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 03-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-SEP-22         0                                  
HETATM    1  C   UNK     0      -3.393  -1.130   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -3.274   0.533   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -4.700  -0.048   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      -5.783  -1.244   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0      -5.694   1.129   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      -4.882   2.437   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -5.310   3.916   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -4.244   5.027   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -3.869   3.589   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -4.673   6.506   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -3.607   7.617   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -2.111   7.249   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.682   5.770   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -0.186   7.068   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       1.447   7.030   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0       0.501   8.628   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       0.459  10.233   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -2.749   4.659   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      -0.917   4.401   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       0.827   4.606   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      -0.129   5.827   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       2.500   4.264   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       3.205   2.822   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       4.140   4.606   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       5.638   3.980   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -2.320   3.180   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      -1.002   1.783   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       0.006   0.273   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       1.561  -0.065   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       0.109  -1.433   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      -0.485  -2.956   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      -1.415  -1.497   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       1.248  -2.514   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       0.889  -4.011   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0       2.725  -2.076   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0       3.842  -3.136   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       5.319  -2.699   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0       3.483  -4.634   0.000  0.00  0.00           O+0
HETATM   39  C   UNK     0      -3.386   2.069   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   39                                                  
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6    5    7   39                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   18                                                  
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17                                                       
CONECT   17   16                                                            
CONECT   18   13   19   26                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25                                                       
CONECT   25   24                                                            
CONECT   26   18   27   39                                                  
CONECT   27   26   28                                                       
CONECT   28   27   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   31   32   33                                             
CONECT   31   30                                                            
CONECT   32   30                                                            
CONECT   33   30   34   35                                                  
CONECT   34   33                                                            
CONECT   35   33   36                                                       
CONECT   36   35   37   38                                                  
CONECT   37   36                                                            
CONECT   38   36                                                            
CONECT   39   26    2    6                                                  
MASTER        0    0    0    0    0    0    0    0   39    0   80    0
END

View in JSmol

Synonyms

Value	Source
Methyl (3as,4S,5S,11ar)-4-{[(2S,3S)-3-(acetyloxy)-2-hydroxy-2-methylbutanoyl]oxy}-10-methyl-5-{[(2R)-2-methylbutanoyl]oxy}-3-methylidene-2-oxo-2H,3H,3ah,4H,5H,8H,9H,11ah-cyclodeca[b]furan-6-carboxylic acid	Generator

Chemical Formula

C₂₈H₃₈O₁₁

Average Mass

550.6010 Da

Monoisotopic Mass

550.24141 Da

IUPAC Name

methyl (3aS,4S,5S,11aR)-4-{[(2S,3S)-3-(acetyloxy)-2-hydroxy-2-methylbutanoyl]oxy}-10-methyl-5-{[(2R)-2-methylbutanoyl]oxy}-3-methylidene-2-oxo-2H,3H,3aH,4H,5H,8H,9H,11aH-cyclodeca[b]furan-6-carboxylate

Traditional Name

methyl (3aS,4S,5S,11aR)-4-{[(2S,3S)-3-(acetyloxy)-2-hydroxy-2-methylbutanoyl]oxy}-10-methyl-5-{[(2R)-2-methylbutanoyl]oxy}-3-methylidene-2-oxo-3aH,4H,5H,8H,9H,11aH-cyclodeca[b]furan-6-carboxylate

CAS Registry Number

Not Available

SMILES

CC[C@@H](C)C(=O)O[C@@H]1[C@@H](OC(=O)[C@@](C)(O)[C@H](C)OC(C)=O)[C@@H]2[C@H](OC(=O)C2=C)\C=C(C)\CC\C=C1\C(=O)OC

InChI Identifier

InChI=1S/C28H38O11/c1-9-15(3)24(30)38-22-19(26(32)35-8)12-10-11-14(2)13-20-21(16(4)25(31)37-20)23(22)39-27(33)28(7,34)17(5)36-18(6)29/h12-13,15,17,20-23,34H,4,9-11H2,1-3,5-8H3/b14-13+,19-12+/t15-,17+,20-,21+,22+,23+,28+/m1/s1

InChI Key

HHSMOWSETHYQGC-JMFZUNKNSA-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
Tetragonotheca helianthoides	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as germacranolides and derivatives. These are sesquiterpene lactones with a structure based on the germacranolide skeleton, characterized by a gamma lactone fused to a 1,7-dimethylcyclodec-1-ene moiety.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Germacranolides and derivatives

Alternative Parents

Substituents

Germacranolide
Pentacarboxylic acid or derivatives
Germacrane sesquiterpenoid
Sesquiterpenoid
Fatty acid ester
Gamma butyrolactone
Fatty acyl
Enoate ester
Methyl ester
Tetrahydrofuran
Tertiary alcohol
Alpha,beta-unsaturated carboxylic ester
Lactone
Carboxylic acid ester
Organoheterocyclic compound
Oxacycle
Carboxylic acid derivative
Organooxygen compound
Alcohol
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Carbonyl group
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic 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	2.25	ALOGPS
logP	3.69	ChemAxon
logS	-4.8	ALOGPS
pKa (Strongest Acidic)	11.64	ChemAxon
pKa (Strongest Basic)	-4.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	151.73 Å²	ChemAxon
Rotatable Bond Count	12	ChemAxon
Refractivity	137.34 m³·mol⁻¹	ChemAxon
Polarizability	55.94 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

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

163022844

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for methyl (3as,4s,5s,11ar)-4-{[(2s,3s)-3-(acetyloxy)-2-hydroxy-2-methylbutanoyl]oxy}-10-methyl-5-{[(2r)-2-methylbutanoyl]oxy}-3-methylidene-2-oxo-3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-6-carboxylate (NP0165271)

MOL for NP0165271 (methyl (3as,4s,5s,11ar)-4-{[(2s,3s)-3-(acetyloxy)-2-hydroxy-2-methylbutanoyl]oxy}-10-methyl-5-{[(2r)-2-methylbutanoyl]oxy}-3-methylidene-2-oxo-3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-6-carboxylate)

3D MOL for NP0165271 (methyl (3as,4s,5s,11ar)-4-{[(2s,3s)-3-(acetyloxy)-2-hydroxy-2-methylbutanoyl]oxy}-10-methyl-5-{[(2r)-2-methylbutanoyl]oxy}-3-methylidene-2-oxo-3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-6-carboxylate)

3D SDF for NP0165271 (methyl (3as,4s,5s,11ar)-4-{[(2s,3s)-3-(acetyloxy)-2-hydroxy-2-methylbutanoyl]oxy}-10-methyl-5-{[(2r)-2-methylbutanoyl]oxy}-3-methylidene-2-oxo-3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-6-carboxylate)

3D-SDF for NP0165271 (methyl (3as,4s,5s,11ar)-4-{[(2s,3s)-3-(acetyloxy)-2-hydroxy-2-methylbutanoyl]oxy}-10-methyl-5-{[(2r)-2-methylbutanoyl]oxy}-3-methylidene-2-oxo-3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-6-carboxylate)

PDB for NP0165271 (methyl (3as,4s,5s,11ar)-4-{[(2s,3s)-3-(acetyloxy)-2-hydroxy-2-methylbutanoyl]oxy}-10-methyl-5-{[(2r)-2-methylbutanoyl]oxy}-3-methylidene-2-oxo-3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-6-carboxylate)

3D PDB for NP0165271 (methyl (3as,4s,5s,11ar)-4-{[(2s,3s)-3-(acetyloxy)-2-hydroxy-2-methylbutanoyl]oxy}-10-methyl-5-{[(2r)-2-methylbutanoyl]oxy}-3-methylidene-2-oxo-3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-6-carboxylate)

SMILES for NP0165271 (methyl (3as,4s,5s,11ar)-4-{[(2s,3s)-3-(acetyloxy)-2-hydroxy-2-methylbutanoyl]oxy}-10-methyl-5-{[(2r)-2-methylbutanoyl]oxy}-3-methylidene-2-oxo-3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-6-carboxylate)

INCHI for NP0165271 (methyl (3as,4s,5s,11ar)-4-{[(2s,3s)-3-(acetyloxy)-2-hydroxy-2-methylbutanoyl]oxy}-10-methyl-5-{[(2r)-2-methylbutanoyl]oxy}-3-methylidene-2-oxo-3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-6-carboxylate)

Structure for NP0165271 (methyl (3as,4s,5s,11ar)-4-{[(2s,3s)-3-(acetyloxy)-2-hydroxy-2-methylbutanoyl]oxy}-10-methyl-5-{[(2r)-2-methylbutanoyl]oxy}-3-methylidene-2-oxo-3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-6-carboxylate)

3D Structure for NP0165271 (methyl (3as,4s,5s,11ar)-4-{[(2s,3s)-3-(acetyloxy)-2-hydroxy-2-methylbutanoyl]oxy}-10-methyl-5-{[(2r)-2-methylbutanoyl]oxy}-3-methylidene-2-oxo-3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-6-carboxylate)