(+/-)-cis-Methyl 5-Dodecyl-2-methoxy-7-methyl-2,3,4,5-tetrahydro-1,2-oxaphosphepine-6-carboxylate 2-Oxide

ID: ALA2179369

Chembl Id: CHEMBL2179369

PubChem CID: 71457279

Max Phase: Preclinical

Molecular Formula: C21H39O5P

Molecular Weight: 402.51

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCCCCCCCCCC[C@@H]1CC[P@@](=O)(OC)OC(C)=C1C(=O)OC

Standard InChI:  InChI=1S/C21H39O5P/c1-5-6-7-8-9-10-11-12-13-14-15-19-16-17-27(23,25-4)26-18(2)20(19)21(22)24-3/h19H,5-17H2,1-4H3/t19-,27-/m1/s1

Standard InChI Key:  ZWCSIELZWHDDDD-XHCCPWGMSA-N

Alternative Forms

1. Parent:

   

   ALA2179369

   methyl (2R,5R)-5-dodecyl-2-methoxy-7-methyl-2-oxo-4,5-dihydro-3H-1,2lambda5-oxaphosphepine-6-carboxylate

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: 402.51

Molecular Weight (Monoisotopic): 402.2535

AlogP: 6.62

#Rotatable Bonds: 13

Polar Surface Area: 61.83

Molecular Species: ┄

HBA: 5

HBD: ┄

#RO5 Violations: 1

HBA (Lipinski): 5

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 5.53

CX LogD: 5.53

Aromatic Rings: ┄

Heavy Atoms: 27

QED Weighted: 0.20

Np Likeness Score: 0.30

References

1. 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]

2. 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]

3. Cavalier JF, Spilling CD, Durand T, Camoin L, Canaan S..  (2021)  Lipolytic enzymes inhibitors: A new way for antibacterial drugs discovery.,  209  [PMID:33071055] [10.1016/j.ejmech.2020.112908]

Source

Source(1):

• Scientific Literature