ID: ALA493600

Max Phase: Preclinical

Molecular Formula: C24H34O6

Molecular Weight: 418.53

Molecule Type: Small molecule

Representations

Synonyms (1): (3R, 2'R,5'R,7'R)-Spirolaxine Methyl Ether
Synonyms from Alternative Forms(1):

Canonical SMILES:  COc1cc(OC)c2c(c1)[C@@H](CCCCC[C@H]1CCC[C@]3(CC[C@@H](C)O3)O1)OC2=O

Standard InChI:  InChI=1S/C24H34O6/c1-16-11-13-24(29-16)12-7-9-17(30-24)8-5-4-6-10-20-19-14-18(26-2)15-21(27-3)22(19)23(25)28-20/h14-17,20H,4-13H2,1-3H3/t16-,17+,20-,24-/m1/s1

Standard InChI Key:  JCVYMDCKTLUBAJ-JJLPPOTMSA-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: 418.53

Molecular Weight (Monoisotopic): 418.2355

AlogP: 5.33

#Rotatable Bonds: 8

Polar Surface Area: 63.22

Molecular Species: NEUTRAL

HBA: 6

HBD: 0

#RO5 Violations: 1

HBA (Lipinski): 6

HBD (Lipinski): 0

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 13.64

CX Basic pKa:

CX LogP: 4.92

CX LogD: 4.92

Aromatic Rings: 1

Heavy Atoms: 30

QED Weighted: 0.42

Np Likeness Score: 1.51

References

1. Radcliff FJ, Fraser JD, Wilson ZE, Heapy AM, Robinson JE, Bryant CJ, Flowers CL, Brimble MA..  (2008)  Anti-Helicobacter pylori activity of derivatives of the phthalide-containing antibacterial agents spirolaxine methyl ether, CJ-12,954, CJ-13,013, CJ-13,102, CJ-13,104, CJ-13,108 and CJ-13,015.,  16  (11): [PMID:18457954] [10.1016/j.bmc.2008.04.037]

2. Dimitrov I, Furkert DP, Fraser JD, Radcliff FJ, Finch O, Brimble MA.  (2012)  Synthesis and anti-Helicobacter pylori activity of analogues of spirolaxine methyl ether,  3  (8): [10.1039/C2MD00314G]

Source

Source(1):

• Scientific Literature