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Tigilanol tiglate

CAT: 0931-T28975Size: 25 mgDry Ice: NoHazardous: No
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CAT#:0931-T28975Size:25 mg
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24/48H Stock Items & 2 to 6 Weeks non Stock Items.
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CAS Number
943001-56-7
Target
PKC, Caspase
Related Pathways
Chromatin/Epigenetic, Proteases/Proteasome, Apoptosis, Cytoskeletal Signaling
Bioactivity
Tigilanol tiglate (EBC-46) is a PKC/C1 domain activator. Tigilanol tiglate promotes mitochondrial/endoplasmic reticulum dysfunction, leading to ATP depletion, caspase activation, and gasdermin E cleavage. It induces immunogenic cell death, enhancing the response to immune checkpoint blockade in both target tumours and non-injected tumours, resulting in tumour regression.
Smiles
O(C([C@H](CC)C)=O)[C@@]12[C@@](C1(C)C)([C@@]3([C@]4([C@](CO)(O4)[C@@H](O)[C@@]5(O)[C@]([C@@]3(O)[C@H](C)[C@H]2OC(/C(=C/C)/C)=O)(C=C(C)C5=O)[H])[H])[H])[H]
Molecular Formula
C30H42O10
Molecular Weight
562.65
Shipping Conditions
Ice Packs
Storage Temperature
-20°C

Chemical Information

Tigilanol Tiglate

Tigilanol tiglate is a diterpenoid natural product isolated from the kernels of the Australian blushwood tree (Fontainea picrosperma). It is approved as a veterinary pharmaceutical for the treatment of non-metastatic and non-resectable canine mast cell tumours. It has a role as an antineoplastic agent, a protein kinase C agonist and a plant metabolite. It is a diterpenoid, a phorbol ester, an organic heteropentacyclic compound and a diester.

CAS Number943001-56-7
PubChem CID92135637
IUPAC Name[(1R,2S,4R,5S,6S,10S,11R,12R,13R,14S,16R)-5,6,11-trihydroxy-4-(hydroxymethyl)-8,12,15,15-tetramethyl-13-[(E)-2-methylbut-2-enoyl]oxy-7-oxo-3-oxapentacyclo[9.5.0.02,4.06,10.014,16]hexadec-8-en-14-yl] (2S)-2-methylbutanoate
Molecular FormulaC30H42O10
Molecular Weight562.6
XLogP2.1
Topological Polar Surface Area163
Hydrogen Bond Donor Count4
Hydrogen Bond Acceptor Count10
Rotatable Bond Count8
Heavy Atom Count40
Formal Charge0
Complexity1220
SMILES
CC[C@H](C)C(=O)O[C@@]12[C@@H](C1(C)C)[C@@H]3[C@H]4[C@](O4)([C@H]([C@]5([C@H]([C@]3([C@@H]([C@H]2OC(=O)/C(=C/C)/C)C)O)C=C(C5=O)C)O)O)CO
InChI
InChI=1S/C30H42O10/c1-9-13(3)23(33)38-21-16(6)28(36)17-11-15(5)20(32)29(17,37)25(35)27(12-31)22(39-27)18(28)19-26(7,8)30(19,21)40-24(34)14(4)10-2/h9,11,14,16-19,21-22,25,31,35-37H,10,12H2,1-8H3/b13-9+/t14-,16+,17-,18+,19+,21+,22-,25+,27-,28-,29+,30+/m0/s1
InChIKey
YLQZMOUMDYVSQR-FOWZUWBHSA-N
Chemical Structure
2D Structure
2D structure of Tigilanol Tiglate
CAS: 943001-56-7
CID: 92135637
Formula: C30H42O10
MW: 562.6
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight562.6
XLogP32.1
Hydrogen Bond Donor Count4
Hydrogen Bond Acceptor Count10
Rotatable Bond Count8
Exact Mass562.27779753
Monoisotopic Mass562.27779753
Topological Polar Surface Area163 Ų
Heavy Atom Count40
Formal Charge0
Complexity1220
Isotope Atom Count0
Defined Atom Stereocenter Count12
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count1
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count1
Compound Is CanonicalizedYes

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Alternative Products

CatalogName
HY-109076-01Tigilanol tiglate
HY-N10967-01Isoatriplicolide tiglate
283661-01Methyl tiglate
OR1013262Ethyl Tiglate
GTR19172584-01Geranyl Tiglate
sc-475218Isobutyl Tiglate
GTR19230335-01Helenalin tiglate
MBS3609108-01Geranyl Tiglate
7493-71-2ALLYL TIGLATE
GTR19159395-01Geranyl?Tiglate

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