5-hydroxy-4-methylpent-3-enylphosphonic acid

Names and Identifiers

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

Standard InChI: InChI=1S/C6H13O4P/c1-6(5-7)3-2-4-11(8,9)10/h3,7H,2,4-5H2,1H3,(H2,8,9,10)/b6-3+

Standard InChI Key: INJCOBJBYNCOEW-ZZXKWVIFSA-N

Molfile:

     RDKit          2D

 11 10  0  0  0  0  0  0  0  0999 V2000
   11.7959   -3.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5104   -2.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0815   -2.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.5104   -1.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2249   -3.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9393   -2.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6538   -3.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3683   -2.6500    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   16.0827   -3.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.3683   -1.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.0793   -2.2292    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  1  3  1  0
  2  4  1  0
  2  5  2  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  8 10  2  0
  8 11  1  0
M  END

Alternative Forms

Parent:

ALA4060737
[(E)-5-hydroxy-4-methylpent-3-enyl]phosphonic acid
Alternative Forms:

ALA4060737
disodium;(E)-2-methyl-5-phosphonatopent-2-en-1-ol

Associated Targets(Human)

BTN3A1 Tchem Butyrophilin subfamily 3 member A1 (291 Activities)

Discover Target: BTN3A1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

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

Drug Indications

MESH ID	MESH Heading	EFO IDs	EFO Terms	Max Phase for Indication	References

Mechanisms of Action

Mechanism of Action	Action Type	target ID	Target Name	Target Type	Target Organism	Binding Site Name	References

Calculated Properties

Molecular Weight: 180.14	Molecular Weight (Monoisotopic): 180.0551	AlogP: 0.49	#Rotatable Bonds: 4
Polar Surface Area: 77.76	Molecular Species: ACID	HBA: 2	HBD: 3
#RO5 Violations: ┄	HBA (Lipinski): 4	HBD (Lipinski): 3	#RO5 Violations (Lipinski): ┄
CX Acidic pKa: 1.81	CX Basic pKa: ┄	CX LogP: -0.82	CX LogD: -3.18
Aromatic Rings: ┄	Heavy Atoms: 11	QED Weighted: 0.43	Np Likeness Score: 2.05

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]
3. Harmon NM, Poe MM, Huang X, Singh R, Foust BJ, Hsiao CC, Wiemer DF, Wiemer AJ.. (2022) Synthesis and Metabolism of BTN3A1 Ligands: Studies on Diene Modifications to the Phosphoantigen Scaffold., 13 (2.0): [PMID:35178171] [10.1021/acsmedchemlett.1c00408]

Source

Source(1):

Scientific Literature