NP-MRD: Showing NP-Card for Thapsigargin (NP0051968)

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Record Information

Version

2.0

Created at

2022-04-27 23:10:32 UTC

Updated at

2022-04-27 23:10:32 UTC

NP-MRD ID

NP0051968

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Thapsigargin

Description

Thapsigargin, also known as Tg, belongs to the class of organic compounds known as pentacarboxylic acids and derivatives. These are carboxylic acids containing exactly five carboxyl groups. Thus, thapsigargin is considered to be an isoprenoid lipid molecule. Thapsigargin is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Thapsigargin is a potentially toxic compound. An organic heterotricyclic compound that is a hexa-oxygenated 6,7-guaianolide isolated fron the roots of Thapsia garganica L., Apiaceae. A potent skin irritant, it is used in traditional medicine as a counter-irritant. Thapsigargin is found in Thapsia garganica, Thapsia gymnesica and Thapsia villosa. Thapsigargin was first documented in 1996 (PMID: 9014219). Thapsigargin inhibits Ca(2+)-transporting ATPase mediated uptake of calcium ions into sarcoplasmic reticulum and is used in experimentation examining the impacts of increasing cytosolic calcium concentrations (PMID: 10477042) (PMID: 16874404) (PMID: 24598360).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 02241204552D          

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M  END

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M  END


  Mrv0541 02241204552D          

 46 48  0  0  1  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  2  0  0  0  0  0  0  0  0  0
   11.2871   -2.3476    0.0000 C   0  0  1  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
    9.4478   -0.6915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2763   -1.4984    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
   12.4296   -1.4224    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  2  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  1  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  2  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  2  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  2  0  0  0  0  0  0  0  0  0
   11.8583   -5.1094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2662   -4.2681    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.8117   -4.9566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1807   -5.6945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9882   -4.9073    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.9545   -3.5036    0.0000 C   0  0  1  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
   13.6721   -7.3793    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
 11 10  1  6  0  0  0
 11 12  1  0  0  0  0
 12 13  1  1  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
 16 18  2  0  0  0  0
 18 19  1  0  0  0  0
 12 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  2  0  0  0  0
 23 22  1  6  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 25 27  1  0  0  0  0
 27 28  1  6  0  0  0
 27 29  1  1  0  0  0
 27 30  1  0  0  0  0
 23 30  1  0  0  0  0
 30 31  1  6  0  0  0
 30 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  1  0  0  0
 34 36  1  6  0  0  0
 36 37  1  0  0  0  0
 37 38  1  0  0  0  0
 37 39  2  0  0  0  0
 34 40  1  0  0  0  0
 11 40  1  0  0  0  0
 40 22  1  1  0  0  0
 32 41  1  1  0  0  0
 41 42  1  0  0  0  0
 42 43  2  0  0  0  0
 42 44  1  0  0  0  0
 44 45  1  0  0  0  0
 45 46  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0051968

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCCCCCC(=O)O[C@@H]1[C@@H](OC(=O)C(\C)=C/C)C(C)=C2[C@@H]3OC(=O)[C@@](C)(O)[C@@]3(O)[C@H](C[C@](C)(OC(C)=O)[C@@H]12)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/b19-11-/t22-,26+,27-,28-,29-,32-,33+,34+/m0/s1

> <INCHI_KEY>
IXFPJGBNCFXKPI-FSIHEZPISA-N

> <FORMULA>
C34H50O12

> <MOLECULAR_WEIGHT>
650.7536

> <EXACT_MASS>
650.330227064

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_AVERAGE_POLARIZABILITY>
70.87642978517154

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(3S,3aR,4S,6S,6aR,7S,8S,9bS)-6-(acetyloxy)-4-(butanoyloxy)-3,3a-dihydroxy-3,6,9-trimethyl-8-{[(2Z)-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>
thapsigargin

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         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      19.100  -0.815   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      19.421   0.691   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      17.636  -1.291   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      17.316  -2.797   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      23.202  -2.655   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      23.346  -5.396   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      24.883  -5.488   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      25.806  -4.255   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      27.264  -4.753   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      28.523  -3.867   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      27.241  -6.293   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      28.775  -6.155   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      27.539  -7.804   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0      25.769  -6.747   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      26.866  -7.828   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0      25.337  -8.225   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      23.913  -8.809   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      22.567  -8.059   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      22.135  -9.538   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0      21.030  -7.967   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0      20.182  -9.252   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      20.871 -10.630   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0      18.645  -9.160   0.000  0.00  0.00           O+0
HETATM   40  C   UNK     0      22.315  -6.540   0.000  0.00  0.00           C+0
HETATM   41  O   UNK     0      26.482  -9.256   0.000  0.00  0.00           O+0
HETATM   42  C   UNK     0      26.162 -10.762   0.000  0.00  0.00           C+0
HETATM   43  O   UNK     0      24.697 -11.238   0.000  0.00  0.00           O+0
HETATM   44  C   UNK     0      27.306 -11.792   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0      26.986 -13.299   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0      25.521 -13.775   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   40                                                  
CONECT   12   11   13   20                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19                                                       
CONECT   19   18                                                            
CONECT   20   12   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23   40                                                  
CONECT   23   22   24   30                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   28   29   30                                             
CONECT   28   27                                                            
CONECT   29   27                                                            
CONECT   30   27   23   31   32                                             
CONECT   31   30                                                            
CONECT   32   30   33   41                                                  
CONECT   33   32   34                                                       
CONECT   34   33   35   36   40                                             
CONECT   35   34                                                            
CONECT   36   34   37                                                       
CONECT   37   36   38   39                                                  
CONECT   38   37                                                            
CONECT   39   37                                                            
CONECT   40   34   11   22                                                  
CONECT   41   32   42                                                       
CONECT   42   41   43   44                                                  
CONECT   43   42                                                            
CONECT   44   42   45                                                       
CONECT   45   44   46                                                       
CONECT   46   45                                                            
MASTER        0    0    0    0    0    0    0    0   46    0   96    0
END

View in JSmol

Synonyms

Value	Source
Octanoic acid {3S-[3alpha,3abeta,4alpha,6beta,6abeta,7beta,8alpha(Z),9balpha]}-6-(acetoxy)-2,3,3a,4,5,6,6a,7,8,9b-decahydro-3,3a-dihydroxy-3,6,9-trimethyl-8-[(2-methyl-1-oxo-2-butenyl)oxy]-2-oxo-4-(1-oxobutoxy)-azuleno[4,5-b]furan-7-yl ester	ChEBI
Tg	ChEBI
Thapsigargine	ChEBI
Octanoate {3S-[3a,3abeta,4a,6b,6abeta,7b,8a(Z),9balpha]}-6-(acetoxy)-2,3,3a,4,5,6,6a,7,8,9b-decahydro-3,3a-dihydroxy-3,6,9-trimethyl-8-[(2-methyl-1-oxo-2-butenyl)oxy]-2-oxo-4-(1-oxobutoxy)-azuleno[4,5-b]furan-7-yl ester	Generator
Octanoate {3S-[3alpha,3abeta,4alpha,6beta,6abeta,7beta,8alpha(Z),9balpha]}-6-(acetoxy)-2,3,3a,4,5,6,6a,7,8,9b-decahydro-3,3a-dihydroxy-3,6,9-trimethyl-8-[(2-methyl-1-oxo-2-butenyl)oxy]-2-oxo-4-(1-oxobutoxy)-azuleno[4,5-b]furan-7-yl ester	Generator
Octanoate {3S-[3α,3abeta,4α,6β,6abeta,7β,8α(Z),9balpha]}-6-(acetoxy)-2,3,3a,4,5,6,6a,7,8,9b-decahydro-3,3a-dihydroxy-3,6,9-trimethyl-8-[(2-methyl-1-oxo-2-butenyl)oxy]-2-oxo-4-(1-oxobutoxy)-azuleno[4,5-b]furan-7-yl ester	Generator
Octanoic acid {3S-[3a,3abeta,4a,6b,6abeta,7b,8a(Z),9balpha]}-6-(acetoxy)-2,3,3a,4,5,6,6a,7,8,9b-decahydro-3,3a-dihydroxy-3,6,9-trimethyl-8-[(2-methyl-1-oxo-2-butenyl)oxy]-2-oxo-4-(1-oxobutoxy)-azuleno[4,5-b]furan-7-yl ester	Generator
Octanoic acid {3S-[3α,3abeta,4α,6β,6abeta,7β,8α(Z),9balpha]}-6-(acetoxy)-2,3,3a,4,5,6,6a,7,8,9b-decahydro-3,3a-dihydroxy-3,6,9-trimethyl-8-[(2-methyl-1-oxo-2-butenyl)oxy]-2-oxo-4-(1-oxobutoxy)-azuleno[4,5-b]furan-7-yl ester	Generator

Chemical Formula

C₃₄H₅₀O₁₂

Average Mass

650.7536 Da

Monoisotopic Mass

650.33023 Da

IUPAC Name

(3S,3aR,4S,6S,6aR,7S,8S,9bS)-6-(acetyloxy)-4-(butanoyloxy)-3,3a-dihydroxy-3,6,9-trimethyl-8-{[(2Z)-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

thapsigargin

CAS Registry Number

Not Available

SMILES

CCCCCCCC(=O)O[C@@H]1[C@@H](OC(=O)C(\C)=C/C)C(C)=C2[C@@H]3OC(=O)[C@@](C)(O)[C@@]3(O)[C@H](C[C@](C)(OC(C)=O)[C@@H]12)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/b19-11-/t22-,26+,27-,28-,29-,32-,33+,34+/m0/s1

InChI Key

IXFPJGBNCFXKPI-FSIHEZPISA-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
Thapsia garganica	Plant	KNApSAcK
Thapsia gymnesica	LOTUS Database	35616633
Thapsia villosa	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

butyrate ester (CHEBI:9516 )
organic heterotricyclic compound (CHEBI:9516 )
sesquiterpene lactone (CHEBI:9516 )
Guaiane sesquiterpenoids (C09561 )
Guaianolide (C09561 )
Guaiane sesquiterpenoids (LMPR0103410001 )

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	70.88 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

C00003375

Chemspider ID

Not Available

KEGG Compound ID

C09561

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Thapsigargin

METLIN ID

Not Available

PubChem Compound

446378

PDB ID

Not Available

ChEBI ID

9516

Good Scents ID

Not Available

References

General References

Oriji GK: Endothelin-induced prostacyclin production in rat aortic endothelial cells: role of calcium. Prostaglandins Leukot Essent Fatty Acids. 1999 Jul;61(1):45-9. doi: 10.1054/plef.1999.0072. [PubMed:10477042 ]
Urbina DC, Silva H, Meisel LA: The Ca2+ pump inhibitor, thapsigargin, inhibits root gravitropism in Arabidopsis thaliana. Biol Res. 2006;39(2):289-96. doi: 10.4067/s0716-97602006000200011. Epub 2006 Jul 25. [PubMed:16874404 ]
Schwarzer C, Ravishankar B, Patanwala M, Shuai S, Fu Z, Illek B, Fischer H, Machen TE: Thapsigargin blocks Pseudomonas aeruginosa homoserine lactone-induced apoptosis in airway epithelia. Am J Physiol Cell Physiol. 2014 May 1;306(9):C844-55. doi: 10.1152/ajpcell.00002.2014. Epub 2014 Mar 5. [PubMed:24598360 ]
Oriji GK, Keiser HR: Role of calcium in endothelin-induced contractions and prostacyclin release. Prostaglandins Leukot Essent Fatty Acids. 1996 Dec;55(6):413-7. doi: 10.1016/s0952-3278(96)90124-6. [PubMed:9014219 ]

Showing NP-Card for Thapsigargin (NP0051968)

MOL for NP0051968 (Thapsigargin)

3D MOL for NP0051968 (Thapsigargin)

3D SDF for NP0051968 (Thapsigargin)

3D-SDF for NP0051968 (Thapsigargin)

PDB for NP0051968 (Thapsigargin)

3D PDB for NP0051968 (Thapsigargin)

SMILES for NP0051968 (Thapsigargin)

INCHI for NP0051968 (Thapsigargin)

Structure for NP0051968 (Thapsigargin)

3D Structure for NP0051968 (Thapsigargin)