TIGILANOL TIGLATE

ID: ALA3989916

Chembl Id: CHEMBL3989916

Cas Number: 943001-56-7

PubChem CID: 92135637

Max Phase: Phase

First Approval: 2020

Molecular Formula: C30H42O10

Molecular Weight: 562.66

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Tigilanol tiglate | EBC-46 | EBI-46 | Tigilanol tiglate|EBI-46|EBC-46|Stelfonta|943001-56-7|R1ZJT87990|Tigilanol tiglate [USAN]|UNII-R1ZJT87990|12-Tigloyl-13-(2-methylbutanoyl)-6,7-epoxy-4,5,9,12,13,20-hexahydroxy-1-tiglian-3-one|(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|(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,Show More⌵

Trade Names(1): Stelfonta

Canonical SMILES:  C/C=C(\C)C(=O)O[C@@H]1[C@@H](C)[C@@]2(O)[C@H]([C@@H]3C(C)(C)[C@]13OC(=O)[C@@H](C)CC)[C@@H]1O[C@]1(CO)[C@@H](O)[C@]1(O)C(=O)C(C)=C[C@H]12

Standard 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

Standard InChI Key:  YLQZMOUMDYVSQR-FOWZUWBHSA-N

Alternative Forms

1. Parent:

   

   ALA3989916

   TIGILANOL TIGLATE

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: Yes

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 562.66

Molecular Weight (Monoisotopic): 562.2778

AlogP: 1.23

#Rotatable Bonds: 6

Polar Surface Area: 163.12

Molecular Species: NEUTRAL

HBA: 10

HBD: 4

#RO5 Violations: 1

HBA (Lipinski): 10

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 11.64

CX Basic pKa: ┄

CX LogP: 2.17

CX LogD: 2.17

Aromatic Rings: ┄

Heavy Atoms: 40

QED Weighted: 0.21

Np Likeness Score: 3.44

References

1. USP Dictionary of USAN and International Names (2010 edition) and USAN registrations 2007-date, 

2. Unpublished dataset, 

3. Chianese G, Amin HIM, Maioli C, Reddell P, Parsons P, Cullen J, Johns J, Handoko H, Boyle G, Appendino G, Taglialatela-Scafati O, Gaeta S..  (2022)  Cryptic Epoxytiglianes from the Kernels of the Blushwood Tree (Fontainea picrosperma).,  85  (8.0): [PMID:35973043] [10.1021/acs.jnatprod.2c00226]

4. European Medicines Agency, 

Source

Source(4):

• Scientific Literature
• Clinical Candidates
• USP Dictionary of USAN and International Drug Names
• European Medicines Agency