sodium (E)-((5-hydroxy-4-methylpent-3-enyl)oxidophosphoryl)methylphosphonate

ID: ALA4089656

PubChem CID: 137641445

Max Phase: Preclinical

Molecular Formula: C7H13Na3O6P2

Molecular Weight: 258.15

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C/C(=C\CCP(=O)([O-])CP(=O)([O-])[O-])CO.[Na+].[Na+].[Na+]

Standard InChI:  InChI=1S/C7H16O6P2.3Na/c1-7(5-8)3-2-4-14(9,10)6-15(11,12)13;;;/h3,8H,2,4-6H2,1H3,(H,9,10)(H2,11,12,13);;;/q;3*+1/p-3/b7-3+;;;

Standard InChI Key:  KXFOALMBZYBRLI-XAEFZVGHSA-K

Molfile:  

     RDKit          2D

 18 14  0  0  0  0  0  0  0  0999 V2000
   17.1899  -25.5517    0.0000 Na  0  0  0  0  0 15  0  0  0  0  0  0
   16.6369  -23.6903    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   15.9270  -24.0989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2212  -23.6903    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   16.6369  -22.8731    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.2171  -24.5034    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.2212  -22.8731    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.3899  -23.6903    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0957  -24.0989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3426  -24.0989    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.6327  -24.5034    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.5113  -24.0989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8056  -23.6903    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9743  -23.6903    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.6842  -24.0989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3899  -22.8731    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9612  -25.4567    0.0000 Na  0  0  0  0  0 15  0  0  0  0  0  0
   18.0236  -23.8182    0.0000 Na  0  0  0  0  0 15  0  0  0  0  0  0
  3  2  1  0
  4  3  1  0
  5  2  2  0
  6  4  1  0
  7  4  2  0
  8  9  2  0
  9 13  1  0
 10  2  1  0
 11  2  1  0
 12  4  1  0
 13 12  1  0
 14 15  1  0
 15  8  1  0
 16  8  1  0
M  CHG  6   1   1   6  -1  10  -1  11  -1  17   1  18   1
M  END

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: 258.15

Molecular Weight (Monoisotopic): 258.0422

AlogP: 0.72

#Rotatable Bonds: 6

Polar Surface Area: 115.06

Molecular Species: ACID

HBA: 3

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 1.32

CX Basic pKa: ┄

CX LogP: -1.48

CX LogD: -6.15

Aromatic Rings: ┄

Heavy Atoms: 15

QED Weighted: 0.41

Np Likeness Score: 1.44

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]

Source

Source(1):

• Scientific Literature