diethyl (1RS,3aRS,6aRS)-5-(3-chloro-4-fluorophenyl)-4,6-dioxo-1,3a,4,5,6,6a-hexahydropyrrolo[3,4-c]pyrrol-1-ylphosphonate

ID: ALA4439953

Chembl Id: CHEMBL4439953

PubChem CID: 78114676

Max Phase: Preclinical

Molecular Formula: C16H17ClFN2O5P

Molecular Weight: 402.75

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CCOP(=O)(OCC)C1N=CC2C(=O)N(c3ccc(F)c(Cl)c3)C(=O)C21

Standard InChI:  InChI=1S/C16H17ClFN2O5P/c1-3-24-26(23,25-4-2)14-13-10(8-19-14)15(21)20(16(13)22)9-5-6-12(18)11(17)7-9/h5-8,10,13-14H,3-4H2,1-2H3

Standard InChI Key:  GDBRUKFBBFJPAM-UHFFFAOYSA-N

Alternative Forms

1. Parent:

   

   ALA4439953

   5-(3-chloro-4-fluorophenyl)-3-diethoxyphosphoryl-3a,6a-dihydro-3H-pyrrolo[3,4-c]pyrrole-4,6-dione

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 402.75

Molecular Weight (Monoisotopic): 402.0548

AlogP: 3.26

#Rotatable Bonds: 6

Polar Surface Area: 85.27

Molecular Species: NEUTRAL

HBA: 6

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 10.17

CX Basic pKa: 1.53

CX LogP: 1.98

CX LogD: 1.98

Aromatic Rings: 1

Heavy Atoms: 26

QED Weighted: 0.54

Np Likeness Score: -1.06

References

1. Abás S, Rodríguez-Arévalo S, Bagán A, Griñán-Ferré C, Vasilopoulou F, Brocos-Mosquera I, Muguruza C, Pérez B, Molins E, Luque FJ, Pérez-Lozano P, de Jonghe S, Daelemans D, Naesens L, Brea J, Loza MI, Hernández-Hernández E, García-Sevilla JA, García-Fuster MJ, Radan M, Djikic T, Nikolic K, Pallàs M, Callado LF, Escolano C..  (2020)  Bicyclic α-Iminophosphonates as High Affinity Imidazoline I2 Receptor Ligands for Alzheimer's Disease.,  63  (7): [PMID:32150414] [10.1021/acs.jmedchem.9b02080]

Source

Source(1):

• Scientific Literature