ID: ALA230741

Max Phase: Preclinical

Molecular Formula: C19H19NO4

Molecular Weight: 325.36

Molecule Type: Small molecule

Representations

Canonical SMILES:  COc1cc(C(=O)c2ccc3c(ccn3C)c2)cc(OC)c1OC

Standard InChI:  InChI=1S/C19H19NO4/c1-20-8-7-12-9-13(5-6-15(12)20)18(21)14-10-16(22-2)19(24-4)17(11-14)23-3/h5-11H,1-4H3

Standard InChI Key:  ZACNDXXBCBNGMV-UHFFFAOYSA-N

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

Properties

Molecular Weight: 325.36

Molecular Weight (Monoisotopic): 325.1314

AlogP: 3.44

#Rotatable Bonds: 5

Polar Surface Area: 49.69

Molecular Species: NEUTRAL

HBA: 5

HBD: 0

#RO5 Violations: 0

HBA (Lipinski): 5

HBD (Lipinski): 0

#RO5 Violations (Lipinski): 0

CX Acidic pKa:

CX Basic pKa:

CX LogP: 3.28

CX LogD: 3.28

Aromatic Rings: 3

Heavy Atoms: 24

QED Weighted: 0.67

Np Likeness Score: -0.28

References

1. Liou JP, Wu CY, Hsieh HP, Chang CY, Chen CM, Kuo CC, Chang JY..  (2007)  4- and 5-aroylindoles as novel classes of potent antitubulin agents.,  50  (18): [PMID:17685504] [10.1021/jm070557q]

2. Hu L, Jiang JD, Qu J, Li Y, Jin J, Li ZR, Boykin DW..  (2007)  Novel potent antimitotic heterocyclic ketones: synthesis, antiproliferative activity, and structure-activity relationships.,  17  (13): [PMID:17482458] [10.1016/j.bmcl.2007.04.048]

3. Alvarez C, Alvarez R, Corchete P, López JL, Pérez-Melero C, Peláez R, Medarde M..  (2008)  Diarylmethyloxime and hydrazone derivatives with 5-indolyl moieties as potent inhibitors of tubulin polymerization.,  16  (11): [PMID:18502133] [10.1016/j.bmc.2008.04.054]

4. Alvarez C, Alvarez R, Corchete P, Pérez-Melero C, Peláez R, Medarde M..  (2010)  Exploring the effect of 2,3,4-trimethoxy-phenyl moiety as a component of indolephenstatins.,  45  (2): [PMID:19939521] [10.1016/j.ejmech.2009.10.047]

5. Alvarez R, Alvarez C, Mollinedo F, Sierra BG, Medarde M, Peláez R..  (2009)  Isocombretastatins A: 1,1-diarylethenes as potent inhibitors of tubulin polymerization and cytotoxic compounds.,  17  (17): [PMID:19647439] [10.1016/j.bmc.2009.07.012]

6. Álvarez R, Puebla P, Díaz JF, Bento AC, García-Navas R, de la Iglesia-Vicente J, Mollinedo F, Andreu JM, Medarde M, Peláez R..  (2013)  Endowing indole-based tubulin inhibitors with an anchor for derivatization: highly potent 3-substituted indolephenstatins and indoleisocombretastatins.,  56  (7): [PMID:23470139] [10.1021/jm3015603]

Source

Source(1):

• Scientific Literature