Structure Database (LMSD)

O OH O H H O O O O O O O O OH
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

Main

Classification

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

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]

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

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

Admin

Created at
-
Updated at
-