ID: ALA2062869

Max Phase: Preclinical

Molecular Formula: C17H22O7

Molecular Weight: 338.36

Molecule Type: Small molecule

Representations

Synonyms (1): Hirsutinolide-13-Oacetate
Synonyms from Alternative Forms(1):

Canonical SMILES:  CC(=O)OCC1=C2/C(=C\[C@@]3(C)CC[C@](O)(O3)[C@H](C)C[C@@H]2O)OC1=O

Standard InChI:  InChI=1S/C17H22O7/c1-9-6-12(19)14-11(8-22-10(2)18)15(20)23-13(14)7-16(3)4-5-17(9,21)24-16/h7,9,12,19,21H,4-6,8H2,1-3H3/b13-7+/t9-,12+,16-,17+/m1/s1

Standard InChI Key:  LGGOIMAXQUUDCN-JHVPGQBHSA-N

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

Properties

Molecular Weight: 338.36

Molecular Weight (Monoisotopic): 338.1366

AlogP: 0.95

#Rotatable Bonds: 2

Polar Surface Area: 102.29

Molecular Species: NEUTRAL

HBA: 7

HBD: 2

#RO5 Violations: 0

HBA (Lipinski): 7

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 11.83

CX Basic pKa:

CX LogP: 0.13

CX LogD: 0.13

Aromatic Rings: 0

Heavy Atoms: 24

QED Weighted: 0.72

Np Likeness Score: 2.76

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