Phosphoric acid mono-((1R,2S,3S,4R,5R,6S)-3-fluoro-5,6-dihydroxy-2,4-bis-phosphonooxy-cyclohexyl) ester

ID: ALA18162

Chembl Id: CHEMBL18162

PubChem CID: 10251645

Max Phase: Preclinical

Molecular Formula: C6H14FO14P3

Molecular Weight: 422.08

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=P(O)(O)O[C@@H]1[C@H](O)[C@H](O)[C@@H](OP(=O)(O)O)[C@H](OP(=O)(O)O)[C@H]1F

Standard InChI:  InChI=1S/C6H14FO14P3/c7-1-4(19-22(10,11)12)2(8)3(9)6(21-24(16,17)18)5(1)20-23(13,14)15/h1-6,8-9H,(H2,10,11,12)(H2,13,14,15)(H2,16,17,18)/t1-,2+,3-,4-,5+,6+/m0/s1

Standard InChI Key:  DQKWTOBKSULEKU-UZAAGFTCSA-N

Alternative Forms

1. Parent:

   

   ALA18162

   [(1S,2S,3R,4R,5S,6R)-2-fluoro-4,5-dihydroxy-3,6-diphosphonooxycyclohexyl] dihydrogen phosphate

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: 422.08

Molecular Weight (Monoisotopic): 421.9580

AlogP: -2.51

#Rotatable Bonds: 6

Polar Surface Area: 240.74

Molecular Species: ACID

HBA: 8

HBD: 8

#RO5 Violations: 1

HBA (Lipinski): 14

HBD (Lipinski): 8

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 0.33

CX Basic pKa: ┄

CX LogP: -3.26

CX LogD: -14.81

Aromatic Rings: ┄

Heavy Atoms: 24

QED Weighted: 0.21

Np Likeness Score: 0.71

References

1. Guedat P, Poitras M, Spiess B, Guillemette G, Schlewer G.  (1996)  Rapid synthesis and properties of ()-6-Deoxy-6-fluoro-myo-inositol-1,4,5-tris(phosphate) an analogue of myo-inositol-1,4,5-tris(phosphate),  6  (10): [10.1016/0960-894X(96)00193-X]

2. Ballereau S, Guédat P, Poirier SN, Guillemette G, Spiess B, Schlewer G..  (1999)  Synthesis, acid-base behavior, and binding properties of 6-modified myo-inositol 1,4,5-tris(phosphate)s.,  42  (23): [PMID:10579845] [10.1021/jm991084t]

Source

Source(1):

• Scientific Literature