(1-Hydroxy-1-phosphono-hexyl)-phosphonic acid

ID: ALA299988

Cas Number: 2809-22-5

PubChem CID: 9881667

Max Phase: Preclinical

Molecular Formula: C6H16O7P2

Molecular Weight: 262.13

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCCCC(O)(P(=O)(O)O)P(=O)(O)O

Standard InChI:  InChI=1S/C6H16O7P2/c1-2-3-4-5-6(7,14(8,9)10)15(11,12)13/h7H,2-5H2,1H3,(H2,8,9,10)(H2,11,12,13)

Standard InChI Key:  LBPHBRVNBKGYTP-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 15 14  0  0  0  0  0  0  0  0999 V2000
    0.1792   -1.8750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4292   -1.0792    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2083   -2.6000    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3500   -0.8167    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9958   -2.3417    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9042   -2.2625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2042   -1.3667    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4917   -0.2667    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4792   -3.0417    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4708   -3.3792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5208   -1.4167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2500   -1.7917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6833   -1.7167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9458   -1.3417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3708   -1.2667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  1  1  0
  4  2  2  0
  5  3  2  0
  6  1  1  0
  7  2  1  0
  8  2  1  0
  9  3  1  0
 10  3  1  0
 11  1  1  0
 12 11  1  0
 13 14  1  0
 14 12  1  0
 15 13  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA299988

   (1-Hydroxy-1-phosphono-hexyl)-phosphonic acid

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: 262.13

Molecular Weight (Monoisotopic): 262.0371

AlogP: 0.57

#Rotatable Bonds: 6

Polar Surface Area: 135.29

Molecular Species: ACID

HBA: 3

HBD: 5

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 5

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 0.69

CX Basic pKa: ┄

CX LogP: -0.46

CX LogD: -5.39

Aromatic Rings: ┄

Heavy Atoms: 15

QED Weighted: 0.35

Np Likeness Score: 0.65

References

1. Ghosh S, Chan JM, Lea CR, Meints GA, Lewis JC, Tovian ZS, Flessner RM, Loftus TC, Bruchhaus I, Kendrick H, Croft SL, Kemp RG, Kobayashi S, Nozaki T, Oldfield E..  (2004)  Effects of bisphosphonates on the growth of Entamoeba histolytica and Plasmodium species in vitro and in vivo.,  47  (1): [PMID:14695831] [10.1021/jm030084x]

2. Szabo CM, Matsumura Y, Fukura S, Martin MB, Sanders JM, Sengupta S, Cieslak JA, Loftus TC, Lea CR, Lee HJ, Koohang A, Coates RM, Sagami H, Oldfield E..  (2002)  Inhibition of geranylgeranyl diphosphate synthase by bisphosphonates and diphosphates: a potential route to new bone antiresorption and antiparasitic agents.,  45  (11): [PMID:12014956] [10.1021/jm010412y]

3. Martin MB, Sanders JM, Kendrick H, de Luca-Fradley K, Lewis JC, Grimley JS, Van Brussel EM, Olsen JR, Meints GA, Burzynska A, Kafarski P, Croft SL, Oldfield E..  (2002)  Activity of bisphosphonates against Trypanosoma brucei rhodesiense.,  45  (14): [PMID:12086478] [10.1021/jm0102809]

4. Szajnman SH, Montalvetti A, Wang Y, Docampo R, Rodriguez JB..  (2003)  Bisphosphonates derived from fatty acids are potent inhibitors of Trypanosoma cruzi farnesyl pyrophosphate synthase.,  13  (19): [PMID:12951099] [10.1016/s0960-894x(03)00663-2]

5. Sanders JM, Ghosh S, Chan JM, Meints G, Wang H, Raker AM, Song Y, Colantino A, Burzynska A, Kafarski P, Morita CT, Oldfield E..  (2004)  Quantitative structure-activity relationships for gammadelta T cell activation by bisphosphonates.,  47  (2): [PMID:14711309] [10.1021/jm0303709]

6. Szajnman SH, Bailey BN, Docampo R, Rodriguez JB..  (2001)  Bisphosphonates derived from fatty acids are potent growth inhibitors of Trypanosoma cruzi.,  11  (6): [PMID:11277521] [10.1016/s0960-894x(01)00057-9]

7. Martin MB, Grimley JS, Lewis JC, Heath HT, Bailey BN, Kendrick H, Yardley V, Caldera A, Lira R, Urbina JA, Moreno SN, Docampo R, Croft SL, Oldfield E..  (2001)  Bisphosphonates inhibit the growth of Trypanosoma brucei, Trypanosoma cruzi, Leishmania donovani, Toxoplasma gondii, and Plasmodium falciparum: a potential route to chemotherapy.,  44  (6): [PMID:11300872] [10.1021/jm0002578]

8. Kotsikorou E, Song Y, Chan JM, Faelens S, Tovian Z, Broderick E, Bakalara N, Docampo R, Oldfield E..  (2005)  Bisphosphonate inhibition of the exopolyphosphatase activity of the Trypanosoma brucei soluble vacuolar pyrophosphatase.,  48  (19): [PMID:16162013] [10.1021/jm058220g]

9. Prado-Prado FJ, García-Mera X, González-Díaz H..  (2010)  Multi-target spectral moment QSAR versus ANN for antiparasitic drugs against different parasite species.,  18  (6): [PMID:20185316] [10.1016/j.bmc.2010.01.068]

10. Barbosa JS, Almeida Paz FA, Braga SS..  (2021)  Bisphosphonates, Old Friends of Bones and New Trends in Clinics.,  64  (3.0): [PMID:33522236] [10.1021/acs.jmedchem.0c01292]

Source

Source(1):

• Scientific Literature