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Tigilanol Tiglate

Tigilanol Tiglate

Synopsis, Chemistry

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Also known as: Ebc-46, Ebi-46, Tigilanol tiglate [usan], 943001-56-7, R1zjt87990, 12-tigloyl-13-(2-methylbutanoyl)-6,7-epoxy-4,5,9,12,13,20-hexahydroxy-1-tiglian-3-one

Molecular Formula

C₃₀H₄₂O₁₀

Molecular Weight

562.6 g/mol

InChI Key

YLQZMOUMDYVSQR-FOWZUWBHSA-N

FDA UNII

R1ZJT87990

Tigilanol Tiglate is a short-chain diterpene ester isolated from the seed of Fontainea picrosperma, with potential antineoplastic activity. Upon intratumoral administration, tigilanol tiglate disrupts mitochondrial functioning and induces mitochondrial swelling, which leads to oncolysis of tumor cells that are in direct contact of the agent. In addition, tigilanol tiglate activates protein kinase C (PKC) signaling cascade, which leads to an acute inflammatory response. This results in hypoxia and activates innate immune cells including neutrophils and macrophages, thereby further killing tumor cells. The activation of the beta-II isoform of PKC (PKC beta II ) also increases tumor vasculature permeability, which leads to the destruction of tumor vasculature.

1 2D Structure

Tigilanol Tiglate

2 Identification

2.1 Computed Descriptors

2.1.1 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

2.1.2 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

2.1.3 InChI Key

YLQZMOUMDYVSQR-FOWZUWBHSA-N

2.1.4 Canonical SMILES

CCC(C)C(=O)OC12C(C1(C)C)C3C4C(O4)(C(C5(C(C3(C(C2OC(=O)C(=CC)C)C)O)C=C(C5=O)C)O)O)CO

2.1.5 Isomeric 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

2.2 Other Identifiers

2.2.1 UNII

R1ZJT87990

2.3 Synonyms

2.3.1 MeSH Synonyms

1. 12-tigloyl-13-(2-methylbutanoyl)-6,7-epoxy-4,5,9,12,13,20-hexahydroxy-1-tigliaen-3-one

2. Ebc-46

2.3.2 Depositor-Supplied Synonyms

1. Ebc-46

2. Ebi-46

3. Tigilanol Tiglate [usan]

4. 943001-56-7

5. R1zjt87990

6. 12-tigloyl-13-(2-methylbutanoyl)-6,7-epoxy-4,5,9,12,13,20-hexahydroxy-1-tiglian-3-one

7. (4s,5s,6r,7s,8r,9r,10s,11r,12r,13s,14r)-12-(2e)-2-methyl-2-enoatyl-13((2s)-2-methylbutyroyl)-6,7-epoxy-4,5,9,12,13,20-hexahydroxy-1-tigliaen-3-one

8. Unii-r1zjt87990

9. Tigilanol Tiglate [mi]

10. Tigilanol Tiglate (usan/inn)

11. Tigilanol Tiglate [inn]

12. Chembl3989916

13. Dtxsid601029530

14. Tigilanol Tiglate [who-dd]

15. D11191

16. (1ar,1br,1cs,2ar,3s,3as,6as,6br,7r,8r,8as)-3,3a,6b-trihydroxy-2a-(hydroxymethyl)-1,1,5,7-tetramethyl-4-oxo-1,1a,1b,1c,2a,3,3a,4,6a,6b,7,8-dodecahydro-8ah-cyclopropa(5',6')benzo(1',2':7,8)azuleno(5,6-b)oxirene-8,8a-diyl 8a-((2s)-2-methylbutanoate) 8-((2e)-2-methylbut-2-enoate)

2.4 Create Date

2015-12-04

3 Chemical and Physical Properties

Molecular Formula	C₃₀H₄₂O₁₀
Molecular Weight	562.6 g/mol
XLogP3	2.1
Hydrogen Bond Donor Count	4
Hydrogen Bond Acceptor Count	10
Rotatable Bond Count	8
Exact Mass	562.27779753 g/mol
Monoisotopic Mass	562.27779753 g/mol
Topological Polar Surface Area	163 Å²
Heavy Atom Count	40
Formal Charge	0
Complexity	1220
Isotope Atom Count	0
Defined Atom Stereocenter Count	12
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	1
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Drug and Medication Information

4.1 Drug Indication

For the treatment of non-resectable, non-metastatic (WHO staging) subcutaneous mast cell tumours located at or distal to the elbow or the hock, and non-resectable, non metastatic cutaneous mast cell tumours in dogs.

5 Pharmacology and Biochemistry

5.1 ATC Code

QL01XX