Structure Database (LMSD)

Common Name
Thapsigargin
Systematic Name
Synonyms
LM ID
LMPR0103410001
Formula
C34H50O12
Exact Mass
Calculate m/z
650.33023
Status
Active
Show lipids differing only in stereochemistry/bond geometry

Classification

Category
Main Class
Sub Class
Level 4 Class
Prenol Lipids [PR]
Isoprenoids [PR01]
C15 isoprenoids (sesquiterpenes) [PR0103]
Guaiane sesquiterpenoids [PR010341]

References

Taxonomy Information

Curated from
NCBI taxonomy class
Reference
Thapsia garganica (#79022)
Magnoliopsida (#3398)
Thapsigargin and thapsigargicin, two histamine liberating sesquiterpene lactones from Thapsia garganica. X-ray analysis of the 7,11-epoxide of thapsigargin,
J. Org. Chem, 1982

String Representations

InChiKey (Click to copy)
IXFPJGBNCFXKPI-FSIHEZPISA-N
InChi (Click to copy)
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
SMILES (Click to copy)
O(C(=O)CCC)[C@H]1C[C@](C)(OC(=O)C)[C@]2([C@H](OC(CCCCCCC)=O)[C@@H](OC(=O)/C(=C\C)/C)C(C)=C2[C@@]2(OC([C@]([C@@]12O)(O)C)=O)[H])[H]

Other Databases

Wikipedia
Thapsigargin
KEGG ID
C09561
CHEBI ID
9516
PubChem CID
446378
PDB ID
TG1
GuidePharm ID
5351

Calculated Physicochemical Properties

Heavy Atoms 46
Rings 3
Aromatic Rings 0
Rotatable Bonds 17
Van der Waals Molecular Volume 646.68
Topological Polar Surface Area 174.03
Hydrogen Bond Donors 2
Hydrogen Bond Acceptors 12
logP 5.93
Molar Refractivity 167.37

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Updated at
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