(Z)-2-Methyl-but-2-enoic acid (E)-(1R,8S,10R,11S)-6-acetoxymethyl-11-hydroxy-1,10-dimethyl-5-oxo-4,14-dioxa-tricyclo[9.2.1.0*3,7*]tetradeca-2,6-dien-8-yl ester

ID: ALA3628030

Chembl Id: CHEMBL3628030

PubChem CID: 122193092

Max Phase: Preclinical

Molecular Formula: C22H28O8

Molecular Weight: 420.46

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C/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/C22H28O8/c1-6-12(2)19(24)28-16-9-13(3)22(26)8-7-21(5,30-22)10-17-18(16)15(20(25)29-17)11-27-14(4)23/h6,10,13,16,26H,7-9,11H2,1-5H3/b12-6-,17-10+/t13-,16+,21-,22+/m1/s1

Standard InChI Key:  NPUVRWFJDAPMIA-IIHJLFQTSA-N

Alternative Forms

1. Parent:

   

   ALA3628030

   ---

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: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 420.46

Molecular Weight (Monoisotopic): 420.1784

AlogP: 2.46

#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: 2.34

CX LogD: 2.34

Aromatic Rings: ┄

Heavy Atoms: 30

QED Weighted: 0.42

Np Likeness Score: 2.82

References

1. 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