ID: ALA603622

Max Phase: Preclinical

Molecular Formula: C8H11O6P

Molecular Weight: 234.14

Molecule Type: Small molecule

Representations

Synonyms (2): Cyclophostin | Rac-Cyclophostin
Synonyms from Alternative Forms(2):

Canonical SMILES:  CO[P@]1(=O)OC[C@H]2COC(=O)C2=C(C)O1

Standard InChI:  InChI=1S/C8H11O6P/c1-5-7-6(3-12-8(7)9)4-13-15(10,11-2)14-5/h6H,3-4H2,1-2H3/t6-,15-/m1/s1

Standard InChI Key:  OMPQJMDGDAAXPE-NPMWZIQKSA-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: 234.14

Molecular Weight (Monoisotopic): 234.0293

AlogP: 1.23

#Rotatable Bonds: 1

Polar Surface Area: 71.06

Molecular Species: NEUTRAL

HBA: 6

HBD: 0

#RO5 Violations: 0

HBA (Lipinski): 6

HBD (Lipinski): 0

#RO5 Violations (Lipinski): 0

CX Acidic pKa:

CX Basic pKa:

CX LogP: -0.09

CX LogD: -0.09

Aromatic Rings: 0

Heavy Atoms: 15

QED Weighted: 0.50

Np Likeness Score: 0.70

References

1. Dutta S, Malla RK, Bandyopadhyay S, Spilling CD, Dupureur CM..  (2010)  Synthesis and kinetic analysis of some phosphonate analogs of cyclophostin as inhibitors of human acetylcholinesterase.,  18  (6): [PMID:20189400] [10.1016/j.bmc.2010.01.063]

2. Point V, Malla RK, Diomande S, Martin BP, Delorme V, Carriere F, Canaan S, Rath NP, Spilling CD, Cavalier JF..  (2012)  Synthesis and kinetic evaluation of cyclophostin and cyclipostins phosphonate analogs as selective and potent inhibitors of microbial lipases.,  55  (22): [PMID:23095026] [10.1021/jm301216x]

3. Vasilieva E, Dutta S, Malla RK, Martin BP, Spilling CD, Dupureur CM..  (2015)  Rat hormone sensitive lipase inhibition by cyclipostins and their analogs.,  23  (5): [PMID:25678014] [10.1016/j.bmc.2015.01.028]

4. Martin BP, Vasilieva E, Dupureur CM, Spilling CD..  (2015)  Synthesis and comparison of the biological activity of monocyclic phosphonate, difluorophosphonate and phosphate analogs of the natural AChE inhibitor cyclophostin.,  23  (24): [PMID:26585276] [10.1016/j.bmc.2015.10.044]

Source

Source(1):

• Scientific Literature