vernolide-B

ID: ALA2062868

Chembl Id: CHEMBL2062868

Cas Number: 618860-58-5

PubChem CID: 70692803

Max Phase: Preclinical

Molecular Formula: C23H30O8

Molecular Weight: 434.49

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Vernolide-B | Vernolide-B|Vernolide B|CHEMBL2062868|618860-58-5|HY-N8900|BDBM50127004|AKOS040762484|CS-0149341|[(1R,2E,8S,10R,11S)-6-(acetyloxymethyl)-11-methoxy-1,10-dimethyl-5-oxo-4,14-dioxatricyclo[9.2.1.03,7]tetradeca-2,6-dien-8-yl] (E)-2-methylbut-2-enoate

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

Standard InChI:  InChI=1S/C23H30O8/c1-7-13(2)20(25)29-17-10-14(3)23(27-6)9-8-22(5,31-23)11-18-19(17)16(21(26)30-18)12-28-15(4)24/h7,11,14,17H,8-10,12H2,1-6H3/b13-7+,18-11+/t14-,17+,22-,23+/m1/s1

Standard InChI Key:  CIBBPLMBWXKCDP-RRPNGBMBSA-N

Alternative Forms

1. Parent:

   

   ALA2062868

   Vernolide B

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: 434.49

Molecular Weight (Monoisotopic): 434.1941

AlogP: 3.12

#Rotatable Bonds: 5

Polar Surface Area: 97.36

Molecular Species: NEUTRAL

HBA: 8

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 2.98

CX LogD: 2.98

Aromatic Rings: ┄

Heavy Atoms: 31

QED Weighted: 0.37

Np Likeness Score: 2.55

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