((2R,3R,4R)-1,1-Difluoro-3-hexadecanoylamino-2,4-dihydroxy-4-phenyl-butyl)-phosphonic acid

ID: ALA419642

Chembl Id: CHEMBL419642

PubChem CID: 44315516

Max Phase: Preclinical

Molecular Formula: C26H44F2NO6P

Molecular Weight: 535.61

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCCCCCCCCCCCCCC(=O)N[C@H]([C@H](O)c1ccccc1)[C@@H](O)C(F)(F)P(=O)(O)O

Standard InChI:  InChI=1S/C26H44F2NO6P/c1-2-3-4-5-6-7-8-9-10-11-12-13-17-20-22(30)29-23(24(31)21-18-15-14-16-19-21)25(32)26(27,28)36(33,34)35/h14-16,18-19,23-25,31-32H,2-13,17,20H2,1H3,(H,29,30)(H2,33,34,35)/t23-,24-,25-/m1/s1

Standard InChI Key:  OAVAPJLMWSAQST-UBFVSLLYSA-N

Alternative Forms

1. Parent:

   

   ALA419642

   ((2R,3R,4R)-1,1-Difluoro-3-hexadecanoylamino-2,4-dihydroxy-4-phenyl-butyl)-phosphonic acid

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: 535.61

Molecular Weight (Monoisotopic): 535.2874

AlogP: 5.82

#Rotatable Bonds: 20

Polar Surface Area: 127.09

Molecular Species: ACID

HBA: 4

HBD: 5

#RO5 Violations: 2

HBA (Lipinski): 7

HBD (Lipinski): 5

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 0.54

CX Basic pKa: ┄

CX LogP: 5.29

CX LogD: 2.55

Aromatic Rings: 1

Heavy Atoms: 36

QED Weighted: 0.11

Np Likeness Score: 0.01

References

1. Yokomatsu T, Murano T, Akiyama T, Koizumi J, Shibuya S, Tsuji Y, Soeda S, Shimeno H..  (2003)  Synthesis of non-competitive inhibitors of sphingomyelinases with significant activity.,  13  (2): [PMID:12482429] [10.1016/s0960-894x(02)00888-0]

2. Yokomatsu T, Murano T, Akiyama T, Koizumi J, Shibuya S, Tsuji Y, Soeda S, Shimeno H..  (2003)  Synthesis of non-competitive inhibitors of sphingomyelinases with significant activity.,  13  (2): [PMID:12482429] [10.1016/s0960-894x(02)00888-0]

Source

Source(1):

• Scientific Literature