NP-MRD: Showing NP-Card for 6-(acetyloxy)-4-(butanoyloxy)-3,3a-dihydroxy-3,6,9-trimethyl-8-[(2-methylbut-2-enoyl)oxy]-2-oxo-4h,5h,6ah,7h,8h,9bh-azuleno[4,5-b]furan-7-yl octanoate (NP0211844)

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Record Information

Version

2.0

Created at

2022-09-05 10:17:15 UTC

Updated at

2022-09-05 10:17:15 UTC

NP-MRD ID

NP0211844

Secondary Accession Numbers

None

Natural Product Identification

Common Name

6-(acetyloxy)-4-(butanoyloxy)-3,3a-dihydroxy-3,6,9-trimethyl-8-[(2-methylbut-2-enoyl)oxy]-2-oxo-4h,5h,6ah,7h,8h,9bh-azuleno[4,5-b]furan-7-yl octanoate

Description

67526-95-8, Also known as thapsigargin, belongs to the class of organic compounds known as pentacarboxylic acids and derivatives. These are carboxylic acids containing exactly five carboxyl groups. 6-(acetyloxy)-4-(butanoyloxy)-3,3a-dihydroxy-3,6,9-trimethyl-8-[(2-methylbut-2-enoyl)oxy]-2-oxo-4h,5h,6ah,7h,8h,9bh-azuleno[4,5-b]furan-7-yl octanoate is found in Thapsia garganica. 67526-95-8 Is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004161509182D          

 46 48  0  0  0  0            999 V2000
    4.7706   -3.5805    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4851   -3.1680    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1996   -3.5805    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9140   -3.1680    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6285   -3.5805    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3430   -3.1680    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0575   -3.5805    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7719   -3.1680    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7719   -2.3430    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.4864   -3.5805    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.2009   -3.1680    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2871   -2.3476    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6740   -1.7955    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   11.6302   -0.7336    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.2324   -0.4365    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    9.4478   -0.6915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   12.4296   -1.4224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
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 20 46  1  0  0  0  0
M  END

     RDKit          3D

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M  END


  Mrv1533004161509182D          

 46 48  0  0  0  0            999 V2000
    4.7706   -3.5805    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4851   -3.1680    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1996   -3.5805    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9140   -3.1680    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6285   -3.5805    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3430   -3.1680    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0575   -3.5805    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7719   -3.1680    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7719   -2.3430    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.4864   -3.5805    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.2009   -3.1680    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2871   -2.3476    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6740   -1.7955    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.8455   -0.9886    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6302   -0.7336    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.2324   -0.4365    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4040    0.3704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1886    0.6254    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4478   -0.6915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0941   -2.1760    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5066   -2.8905    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3301   -2.9398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8249   -2.2797    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.6057   -2.5464    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2803   -2.0715    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.5933   -3.3713    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4150   -3.2973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7528   -4.1807    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.8050   -3.6145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3927   -4.1934    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.5736   -4.4064    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8103   -4.7192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0897   -4.3175    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2662   -4.2681    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8583   -5.1094    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.0569   -5.3049    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8255   -6.0968    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.4867   -4.7086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9545   -3.5036    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1867   -4.9584    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.0152   -5.7654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2306   -6.0203    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.6283   -6.3174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4568   -7.1244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0699   -7.6764    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4296   -1.4224    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  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
  7  8  1  0  0  0  0
  8  9  2  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  1  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  2  0  0  0  0
 17 18  1  4  0  0  0
 16 19  1  0  0  0  0
 12 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 24 26  1  0  0  0  0
 26 27  1  0  0  0  0
 26 28  1  0  0  0  0
 26 29  1  0  0  0  0
 22 29  1  0  0  0  0
 29 30  1  0  0  0  0
 29 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 33 35  1  0  0  0  0
 35 36  1  0  0  0  0
 36 37  2  0  0  0  0
 36 38  1  0  0  0  0
 33 39  1  0  0  0  0
 11 39  1  0  0  0  0
 21 39  1  0  0  0  0
 31 40  1  0  0  0  0
 40 41  1  0  0  0  0
 41 42  2  0  0  0  0
 41 43  1  0  0  0  0
 43 44  1  0  0  0  0
 44 45  1  0  0  0  0
 20 46  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0211844

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCCCCCC(=O)OC1C(OC(=O)C(C)=CC)C(C)=C2C3OC(=O)C(C)(O)C3(O)C(CC(C)(OC(C)=O)C12)OC(=O)CCC

> <INCHI_IDENTIFIER>
InChI=1S/C34H50O12/c1-9-12-13-14-15-17-24(37)43-28-26-25(20(5)27(28)44-30(38)19(4)11-3)29-34(41,33(8,40)31(39)45-29)22(42-23(36)16-10-2)18-32(26,7)46-21(6)35/h11,22,26-29,40-41H,9-10,12-18H2,1-8H3

> <INCHI_KEY>
IXFPJGBNCFXKPI-UHFFFAOYSA-N

> <FORMULA>
C34H50O12

> <MOLECULAR_WEIGHT>
650.762

> <EXACT_MASS>
650.33022705

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
96

> <JCHEM_AVERAGE_POLARIZABILITY>
70.81121584066497

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
6-(acetyloxy)-4-(butanoyloxy)-3,3a-dihydroxy-3,6,9-trimethyl-8-[(2-methylbut-2-enoyl)oxy]-2-oxo-2H,3H,3aH,4H,5H,6H,6aH,7H,8H,9bH-azuleno[4,5-b]furan-7-yl octanoate

> <ALOGPS_LOGP>
4.07

> <JCHEM_LOGP>
4.384525495666665

> <ALOGPS_LOGS>
-5.09

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.498704796841494

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.135565750741481

> <JCHEM_PKA_STRONGEST_BASIC>
-4.307623186172571

> <JCHEM_POLAR_SURFACE_AREA>
171.95999999999998

> <JCHEM_REFRACTIVITY>
163.81580000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
17

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
5.30e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
6-(acetyloxy)-4-(butanoyloxy)-3,3a-dihydroxy-3,6,9-trimethyl-8-[(2-methylbut-2-enoyl)oxy]-2-oxo-4H,5H,6aH,7H,8H,9bH-azuleno[4,5-b]furan-7-yl octanoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 16-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   16-APR-15         0                                  
HETATM    1  C   UNK     0       8.905  -6.684   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      10.239  -5.914   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      11.573  -6.684   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      12.906  -5.914   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      14.240  -6.684   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      15.574  -5.914   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      16.907  -6.684   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      18.241  -5.914   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      18.241  -4.374   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0      19.575  -6.684   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      20.908  -5.914   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      21.069  -4.382   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      19.925  -3.352   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      20.245  -1.845   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      21.710  -1.369   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      19.101  -0.815   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      19.421   0.692   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      20.885   1.167   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      17.636  -1.291   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      22.576  -4.062   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      23.346  -5.396   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      24.883  -5.488   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      25.807  -4.256   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      27.264  -4.753   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      28.523  -3.867   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      27.241  -6.293   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      28.775  -6.155   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      27.538  -7.804   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      25.769  -6.747   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      26.866  -7.828   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      25.337  -8.225   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      23.912  -8.809   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      22.567  -8.059   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      21.030  -7.967   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0      22.136  -9.537   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0      20.639  -9.903   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0      20.208 -11.381   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0      19.575  -8.789   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      22.315  -6.540   0.000  0.00  0.00           C+0
HETATM   40  O   UNK     0      26.482  -9.256   0.000  0.00  0.00           O+0
HETATM   41  C   UNK     0      26.162 -10.762   0.000  0.00  0.00           C+0
HETATM   42  O   UNK     0      24.697 -11.238   0.000  0.00  0.00           O+0
HETATM   43  C   UNK     0      27.306 -11.792   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0      26.986 -13.299   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0      28.130 -14.329   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0      23.202  -2.655   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10   12   39                                                  
CONECT   12   11   13   20                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17   19                                                  
CONECT   17   16   18                                                       
CONECT   18   17                                                            
CONECT   19   16                                                            
CONECT   20   12   21   46                                                  
CONECT   21   20   22   39                                                  
CONECT   22   21   23   29                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   27   28   29                                             
CONECT   27   26                                                            
CONECT   28   26                                                            
CONECT   29   26   22   30   31                                             
CONECT   30   29                                                            
CONECT   31   29   32   40                                                  
CONECT   32   31   33                                                       
CONECT   33   32   34   35   39                                             
CONECT   34   33                                                            
CONECT   35   33   36                                                       
CONECT   36   35   37   38                                                  
CONECT   37   36                                                            
CONECT   38   36                                                            
CONECT   39   33   11   21                                                  
CONECT   40   31   41                                                       
CONECT   41   40   42   43                                                  
CONECT   42   41                                                            
CONECT   43   41   44                                                       
CONECT   44   43   45                                                       
CONECT   45   44                                                            
CONECT   46   20                                                            
MASTER        0    0    0    0    0    0    0    0   46    0   96    0
END

View in JSmol

Synonyms

Value	Source
Thapsigargin	MeSH
6-(Acetyloxy)-4-(butanoyloxy)-3,3a-dihydroxy-3,6,9-trimethyl-8-[(2-methylbut-2-enoyl)oxy]-2-oxo-2H,3H,3ah,4H,5H,6H,6ah,7H,8H,9BH-azuleno[4,5-b]furan-7-yl octanoic acid	Generator

Chemical Formula

C₃₄H₅₀O₁₂

Average Mass

650.7620 Da

Monoisotopic Mass

650.33023 Da

IUPAC Name

6-(acetyloxy)-4-(butanoyloxy)-3,3a-dihydroxy-3,6,9-trimethyl-8-[(2-methylbut-2-enoyl)oxy]-2-oxo-2H,3H,3aH,4H,5H,6H,6aH,7H,8H,9bH-azuleno[4,5-b]furan-7-yl octanoate

Traditional Name

6-(acetyloxy)-4-(butanoyloxy)-3,3a-dihydroxy-3,6,9-trimethyl-8-[(2-methylbut-2-enoyl)oxy]-2-oxo-4H,5H,6aH,7H,8H,9bH-azuleno[4,5-b]furan-7-yl octanoate

CAS Registry Number

Not Available

SMILES

CCCCCCCC(=O)OC1C(OC(=O)C(C)=CC)C(C)=C2C3OC(=O)C(C)(O)C3(O)C(CC(C)(OC(C)=O)C12)OC(=O)CCC

InChI Identifier

InChI=1S/C34H50O12/c1-9-12-13-14-15-17-24(37)43-28-26-25(20(5)27(28)44-30(38)19(4)11-3)29-34(41,33(8,40)31(39)45-29)22(42-23(36)16-10-2)18-32(26,7)46-21(6)35/h11,22,26-29,40-41H,9-10,12-18H2,1-8H3

InChI Key

IXFPJGBNCFXKPI-UHFFFAOYSA-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
Thapsia garganica	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
Fatty acid ester
Gamma butyrolactone
Fatty acyl
Cyclic alcohol
Tertiary alcohol
Tetrahydrofuran
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Lactone
1,2-diol
Carboxylic acid ester
Organoheterocyclic compound
Oxacycle
Alcohol
Hydrocarbon derivative
Organooxygen compound
Organic oxide
Organic oxygen compound
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	4.07	ALOGPS
logP	4.38	ChemAxon
logS	-5.1	ALOGPS
pKa (Strongest Acidic)	11.14	ChemAxon
pKa (Strongest Basic)	-4.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	171.96 Å²	ChemAxon
Rotatable Bond Count	17	ChemAxon
Refractivity	163.82 m³·mol⁻¹	ChemAxon
Polarizability	70.81 Å³	ChemAxon
Number of Rings	3	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

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

5428

PDB ID

Not Available

ChEBI ID

93880

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 6-(acetyloxy)-4-(butanoyloxy)-3,3a-dihydroxy-3,6,9-trimethyl-8-[(2-methylbut-2-enoyl)oxy]-2-oxo-4h,5h,6ah,7h,8h,9bh-azuleno[4,5-b]furan-7-yl octanoate (NP0211844)

MOL for NP0211844 (6-(acetyloxy)-4-(butanoyloxy)-3,3a-dihydroxy-3,6,9-trimethyl-8-[(2-methylbut-2-enoyl)oxy]-2-oxo-4h,5h,6ah,7h,8h,9bh-azuleno[4,5-b]furan-7-yl octanoate)

3D MOL for NP0211844 (6-(acetyloxy)-4-(butanoyloxy)-3,3a-dihydroxy-3,6,9-trimethyl-8-[(2-methylbut-2-enoyl)oxy]-2-oxo-4h,5h,6ah,7h,8h,9bh-azuleno[4,5-b]furan-7-yl octanoate)

3D SDF for NP0211844 (6-(acetyloxy)-4-(butanoyloxy)-3,3a-dihydroxy-3,6,9-trimethyl-8-[(2-methylbut-2-enoyl)oxy]-2-oxo-4h,5h,6ah,7h,8h,9bh-azuleno[4,5-b]furan-7-yl octanoate)

3D-SDF for NP0211844 (6-(acetyloxy)-4-(butanoyloxy)-3,3a-dihydroxy-3,6,9-trimethyl-8-[(2-methylbut-2-enoyl)oxy]-2-oxo-4h,5h,6ah,7h,8h,9bh-azuleno[4,5-b]furan-7-yl octanoate)

PDB for NP0211844 (6-(acetyloxy)-4-(butanoyloxy)-3,3a-dihydroxy-3,6,9-trimethyl-8-[(2-methylbut-2-enoyl)oxy]-2-oxo-4h,5h,6ah,7h,8h,9bh-azuleno[4,5-b]furan-7-yl octanoate)

3D PDB for NP0211844 (6-(acetyloxy)-4-(butanoyloxy)-3,3a-dihydroxy-3,6,9-trimethyl-8-[(2-methylbut-2-enoyl)oxy]-2-oxo-4h,5h,6ah,7h,8h,9bh-azuleno[4,5-b]furan-7-yl octanoate)

SMILES for NP0211844 (6-(acetyloxy)-4-(butanoyloxy)-3,3a-dihydroxy-3,6,9-trimethyl-8-[(2-methylbut-2-enoyl)oxy]-2-oxo-4h,5h,6ah,7h,8h,9bh-azuleno[4,5-b]furan-7-yl octanoate)

INCHI for NP0211844 (6-(acetyloxy)-4-(butanoyloxy)-3,3a-dihydroxy-3,6,9-trimethyl-8-[(2-methylbut-2-enoyl)oxy]-2-oxo-4h,5h,6ah,7h,8h,9bh-azuleno[4,5-b]furan-7-yl octanoate)

Structure for NP0211844 (6-(acetyloxy)-4-(butanoyloxy)-3,3a-dihydroxy-3,6,9-trimethyl-8-[(2-methylbut-2-enoyl)oxy]-2-oxo-4h,5h,6ah,7h,8h,9bh-azuleno[4,5-b]furan-7-yl octanoate)

3D Structure for NP0211844 (6-(acetyloxy)-4-(butanoyloxy)-3,3a-dihydroxy-3,6,9-trimethyl-8-[(2-methylbut-2-enoyl)oxy]-2-oxo-4h,5h,6ah,7h,8h,9bh-azuleno[4,5-b]furan-7-yl octanoate)