3-methylbut-3-enyl trihydrogen diphosphate

ID: ALA356362

Cas Number: 358-71-4

PubChem CID: 1195

Product Number: I611183, Order Now?

Max Phase: Preclinical

Molecular Formula: C5H12O7P2

Molecular Weight: 246.09

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Isopentenyl Pyrophosphate | Isopentenylpyrophosphate | isopentenyl pyrophosphate|isopentenyl diphosphate|358-71-4|3-Methyl-3-butenyl pyrophosphate|Isopentenyl-diphosphate|3-methylbut-3-enyl phosphono hydrogen phosphate|IPPP|Mono(3-methyl-3-butenyl) diphosphate|3-methylbut-3-en-1-yl trihydrogen diphosphate|delta3-Isopentenyl diphosphate|isopentenyl-pp|Diphosphoric acid mono(3-methyl-3-butenyl) ester|delta-3-Isopentenyl pyrophosphat|CHEBI:16584|delta3-methyl-3-butenyl diphosphate|LSC8849M7B|delta-Show More⌵

Canonical SMILES:  C=C(C)CCOP(=O)(O)OP(=O)(O)O

Standard InChI:  InChI=1S/C5H12O7P2/c1-5(2)3-4-11-14(9,10)12-13(6,7)8/h1,3-4H2,2H3,(H,9,10)(H2,6,7,8)

Standard InChI Key:  NUHSROFQTUXZQQ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 14 13  0  0  0  0  0  0  0  0999 V2000
    1.2080    0.0141    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4935   -0.3984    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9224   -0.3984    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6369    0.0141    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3514   -0.3984    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6369    0.8391    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2210    0.0141    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    0.1915    0.7286    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6335   -0.7004    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9355    0.4266    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6499    0.0141    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3644   -0.3984    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0624    0.7286    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2374   -0.7004    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  1  3  1  0
  7  2  1  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  8  7  2  0
  7  9  1  0
 10  7  1  0
 10 11  1  0
 12 11  1  0
 13 11  2  0
 14 11  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA356362

   isopentenyl diphosphate

Molecule Features

Natural Product: Yes

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: 246.09

Molecular Weight (Monoisotopic): 246.0058

AlogP: 1.18

#Rotatable Bonds: 6

Polar Surface Area: 113.29

Molecular Species: ACID

HBA: 4

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 1.78

CX Basic pKa: ┄

CX LogP: 0.20

CX LogD: -4.83

Aromatic Rings: ┄

Heavy Atoms: 14

QED Weighted: 0.48

Np Likeness Score: 1.40

References

1. Reichenberg A, Hintz M, Kletschek Y, Kuhl T, Haug C, Engel R, Moll J, Ostrovsky DN, Jomaa H, Eberl M..  (2003)  Replacing the pyrophosphate group of HMB-PP by a diphosphonate function abrogates Its potential to activate human gammadelta T cells but does not lead to competitive antagonism.,  13  (7): [PMID:12657258] [10.1016/s0960-894x(03)00138-0]

2. Nagaki M, Kannari H, Ishibashi J, Maki Y, Nishino T, Ogura K, Koyama T..  (1998)  Substrate specificity of thermostable farnesyl diphosphate synthase with alkyl group homologs of isopentenyl diphosphate.,  8  (18): [PMID:9873578] [10.1016/s0960-894x(98)00458-2]

3. Gossman W, Oldfield E..  (2002)  Quantitative structure--activity relations for gammadelta T cell activation by phosphoantigens.,  45  (22): [PMID:12383012] [10.1021/jm020224n]

4. Boëdec A, Sicard H, Dessolin J, Herbette G, Ingoure S, Raymond C, Belmant C, Kraus JL..  (2008)  Synthesis and biological activity of phosphonate analogues and geometric isomers of the highly potent phosphoantigen (E)-1-hydroxy-2-methylbut-2-enyl 4-diphosphate.,  51  (6): [PMID:18303828] [10.1021/jm701101g]

5. Breccia P, Angeli F, Cerbara I, Topai A, Auricchio G, Martino A, Colizzi V, Poccia F..  (2009)  Thiopyrophosphoantigens: solid-phase synthesis and in vitro characterization of a new class of Vgamma9 Vdelta2 T cells activators.,  52  (12): [PMID:19453173] [10.1021/jm900054u]

6. Simoni D, Gebbia N, Invidiata FP, Eleopra M, Marchetti P, Rondanin R, Baruchello R, Provera S, Marchioro C, Tolomeo M, Marinelli L, Limongelli V, Novellino E, Kwaasi A, Dunford J, Buccheri S, Caccamo N, Dieli F..  (2008)  Design, synthesis, and biological evaluation of novel aminobisphosphonates possessing an in vivo antitumor activity through a gammadelta-T lymphocytes-mediated activation mechanism.,  51  (21): [PMID:18937434] [10.1021/jm801003y]

7. Masini T, Hirsch AK..  (2014)  Development of inhibitors of the 2C-methyl-D-erythritol 4-phosphate (MEP) pathway enzymes as potential anti-infective agents.,  57  (23): [PMID:25210872] [10.1021/jm5010978]

8. 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]

9. Kadri H,Taher TE,Xu Q,Sharif M,Ashby E,Bryan RT,Willcox BE,Mehellou Y.  (2020)  Aryloxy Diester Phosphonamidate Prodrugs of Phosphoantigens (ProPAgens) as Potent Activators of Vγ9/Vδ2 T-Cell Immune Responses.,  63  (19.0): [PMID:32930595] [10.1021/acs.jmedchem.0c01232]

10. Whitfield H, Hemmings AM, Mills SJ, Baker K, White G, Rushworth S, Riley AM, Potter BVL, Brearley CA..  (2021)  Allosteric Site on SHIP2 Identified Through Fluorescent Ligand Screening and Crystallography: A Potential New Target for Intervention.,  64  (7.0): [PMID:33724834] [10.1021/acs.jmedchem.0c01944]

Source

Source(1):

• Scientific Literature