((2-fluorobenzylamino)(1-hydroxy-2-oxopiperidin-3-yl)phosphoryloxy)methyl pivalate

ID: ALA4800502

Chembl Id: CHEMBL4800502

PubChem CID: 162676484

Max Phase: Preclinical

Molecular Formula: C18H26FN2O6P

Molecular Weight: 416.39

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CC(C)(C)C(=O)OCOP(=O)(NCc1ccccc1F)C1CCCN(O)C1=O

Standard InChI:  InChI=1S/C18H26FN2O6P/c1-18(2,3)17(23)26-12-27-28(25,15-9-6-10-21(24)16(15)22)20-11-13-7-4-5-8-14(13)19/h4-5,7-8,15,24H,6,9-12H2,1-3H3,(H,20,25)

Standard InChI Key:  JIMSHJIMELQWQM-UHFFFAOYSA-N

Alternative Forms

1. Parent:

   

   ALA4800502

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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: 416.39

Molecular Weight (Monoisotopic): 416.1513

AlogP: 3.05

#Rotatable Bonds: 7

Polar Surface Area: 105.17

Molecular Species: NEUTRAL

HBA: 6

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.28

CX Basic pKa: ┄

CX LogP: 2.34

CX LogD: 2.28

Aromatic Rings: 1

Heavy Atoms: 28

QED Weighted: 0.30

Np Likeness Score: -0.23

References

1. Yan VC,Pham CD,Arthur K,Yang KL,Muller FL.  (2020)  Aliphatic amines are viable pro-drug moieties in phosphonoamidate drugs.,  30  (24): [PMID:33130289] [10.1016/j.bmcl.2020.127656]

2. Yan VC, Pham CD, Ballato ES, Yang KL, Arthur K, Khadka S, Barekatain Y, Shrestha P, Tran T, Poral AH, Washington M, Raghavan S, Czako B, Pisaneschi F, Lin YH, Satani N, Hammoudi N, Ackroyd JJ, Georgiou DK, Millward SW, Muller FL..  (2022)  Prodrugs of a 1-Hydroxy-2-oxopiperidin-3-yl Phosphonate Enolase Inhibitor for the Treatment of ENO1-Deleted Cancers.,  65  (20.0): [PMID:36251833] [10.1021/acs.jmedchem.2c01039]

Source

Source(1):

• Scientific Literature