8alpha-(2-methylacryloyloxy)-hirsutinolide-13-O-acetate

ID: ALA2062866

Chembl Id: CHEMBL2062866

Cas Number: 67667-71-4

PubChem CID: 70686496

Max Phase: Preclinical

Molecular Formula: C21H26O8

Molecular Weight: 406.43

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C=C(C)C(=O)O[C@H]1C[C@@H](C)[C@]2(O)CC[C@](C)(/C=C3/OC(=O)C(COC(C)=O)=C31)O2

Standard InChI:  InChI=1S/C21H26O8/c1-11(2)18(23)27-15-8-12(3)21(25)7-6-20(5,29-21)9-16-17(15)14(19(24)28-16)10-26-13(4)22/h9,12,15,25H,1,6-8,10H2,2-5H3/b16-9+/t12-,15+,20-,21+/m1/s1

Standard InChI Key:  YKIDGUZXBGGNBZ-GUNZAYKBSA-N

Alternative Forms

1. Parent:

   

   ALA2062866

   8alpha-(2-Methylacryloyloxy)hirsutinolide 13-O-acetate

Molecule Features

Natural Product: Yes

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 406.43

Molecular Weight (Monoisotopic): 406.1628

AlogP: 2.07

#Rotatable Bonds: 4

Polar Surface Area: 108.36

Molecular Species: NEUTRAL

HBA: 8

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 11.83

CX Basic pKa: ┄

CX LogP: 1.95

CX LogD: 1.95

Aromatic Rings: ┄

Heavy Atoms: 29

QED Weighted: 0.43

Np Likeness Score: 2.62

References

1. Youn UJ, Park EJ, Kondratyuk TP, Simmons CJ, Borris RP, Tanamatayarat P, Wongwiwatthananukit S, Toyama O, Songsak T, Pezzuto JM, Chang LC..  (2012)  Anti-inflammatory sesquiterpene lactones from the flower of Vernonia cinerea.,  22  (17): [PMID:22850207] [10.1016/j.bmcl.2012.07.010]

2. Miklossy G, Youn UJ, Yue P, Zhang M, Chen CH, Hilliard TS, Paladino D, Li Y, Choi J, Sarkaria JN, Kawakami JK, Wongwiwatthananukit S, Chen Y, Sun D, Chang LC, Turkson J..  (2015)  Hirsutinolide Series Inhibit Stat3 Activity, Alter GCN1, MAP1B, Hsp105, G6PD, Vimentin, TrxR1, and Importin α-2 Expression, and Induce Antitumor Effects against Human Glioma.,  58  (19): [PMID:26331426] [10.1021/acs.jmedchem.5b00686]

Source

Source(1):

• Scientific Literature