(E)-(((((5-Hydroxy-4-methylpent-3-en-1-yl)-((pivaloyloxy)methoxy)phosphoryl)methyl)phosphoryl)bis(oxy))bis-(methylene)Bis(2,2-dimethylpropanoate)

ID: ALA4061531

PubChem CID: 137635930

Max Phase: Preclinical

Molecular Formula: C25H46O12P2

Molecular Weight: 600.58

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C/C(=C\CCP(=O)(CP(=O)(OCOC(=O)C(C)(C)C)OCOC(=O)C(C)(C)C)OCOC(=O)C(C)(C)C)CO

Standard InChI:  InChI=1S/C25H46O12P2/c1-19(14-26)12-11-13-38(30,35-15-32-20(27)23(2,3)4)18-39(31,36-16-33-21(28)24(5,6)7)37-17-34-22(29)25(8,9)10/h12,26H,11,13-18H2,1-10H3/b19-12+

Standard InChI Key:  HLWOIPHPTUUBHH-XDHOZWIPSA-N

Molfile:  

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M  END

Alternative Forms

1. Parent:

   

   ALA4061531

   ---

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: 600.58

Molecular Weight (Monoisotopic): 600.2465

AlogP: 5.43

#Rotatable Bonds: 15

Polar Surface Area: 160.96

Molecular Species: NEUTRAL

HBA: 12

HBD: 1

#RO5 Violations: 3

HBA (Lipinski): 12

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 3

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 5.41

CX LogD: 5.41

Aromatic Rings: ┄

Heavy Atoms: 39

QED Weighted: 0.08

Np Likeness Score: 0.60

References

1. Shippy RR, Lin X, Agabiti SS, Li J, Zangari BM, Foust BJ, Poe MM, Hsiao CC, Vinogradova O, Wiemer DF, Wiemer AJ..  (2017)  Phosphinophosphonates and Their Tris-pivaloyloxymethyl Prodrugs Reveal a Negatively Cooperative Butyrophilin Activation Mechanism.,  60  (6): [PMID:28218845] [10.1021/acs.jmedchem.6b00965]

2. Poe MM, Agabiti SS, Liu C, Li V, Teske KA, Hsiao CC, Wiemer AJ..  (2019)  Probing the Ligand-Binding Pocket of BTN3A1.,  62  (14): [PMID:31268699] [10.1021/acs.jmedchem.9b00825]

Source

Source(1):

• Scientific Literature