(3-Amino-1-hydroxy-1-phosphono-butyl)-phosphonic acid

ID: ALA55358

PubChem CID: 9813652

Max Phase: Preclinical

Molecular Formula: C4H13NO7P2

Molecular Weight: 249.10

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(N)CC(O)(P(=O)(O)O)P(=O)(O)O

Standard InChI:  InChI=1S/C4H13NO7P2/c1-3(5)2-4(6,13(7,8)9)14(10,11)12/h3,6H,2,5H2,1H3,(H2,7,8,9)(H2,10,11,12)

Standard InChI Key:  FNPLDQVMNZFNEG-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 14 13  0  0  0  0  0  0  0  0999 V2000
    2.2042   -2.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4417   -1.8542    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    2.1250   -3.5000    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    1.4875   -2.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1792   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6667   -1.5917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9250   -3.0375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5167   -1.0417    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8125   -3.9417    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8667   -4.2792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2292   -2.1417    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7667   -2.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0542   -2.2292    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7667   -3.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  1  1  0
  4  1  1  0
  5  3  2  0
  6  2  2  0
  7  1  1  0
  8  2  1  0
  9  3  1  0
 10  3  1  0
 11  2  1  0
 12  4  1  0
 13 12  1  0
 14 12  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA55358

   (3-Amino-1-hydroxy-1-phosphono-butyl)-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: 249.10

Molecular Weight (Monoisotopic): 249.0167

AlogP: -1.27

#Rotatable Bonds: 4

Polar Surface Area: 161.31

Molecular Species: ZWITTERION

HBA: 4

HBD: 6

#RO5 Violations: 1

HBA (Lipinski): 8

HBD (Lipinski): 7

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 0.67

CX Basic pKa: 10.08

CX LogP: -4.13

CX LogD: -6.50

Aromatic Rings: ┄

Heavy Atoms: 14

QED Weighted: 0.34

Np Likeness Score: 0.41

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. Widler L, Jaeggi KA, Glatt M, Müller K, Bachmann R, Bisping M, Born AR, Cortesi R, Guiglia G, Jeker H, Klein R, Ramseier U, Schmid J, Schreiber G, Seltenmeyer Y, Green JR..  (2002)  Highly potent geminal bisphosphonates. From pamidronate disodium (Aredia) to zoledronic acid (Zometa).,  45  (17): [PMID:12166945] [10.1021/jm020819i]

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. Sanders JM, Gómez AO, Mao J, Meints GA, Van Brussel EM, Burzynska A, Kafarski P, González-Pacanowska D, Oldfield E..  (2003)  3-D QSAR investigations of the inhibition of Leishmania major farnesyl pyrophosphate synthase by bisphosphonates.,  46  (24): [PMID:14613320] [10.1021/jm0302344]

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. Leon A, Liu L, Yang Y, Hudock MP, Hall P, Yin F, Studer D, Puan KJ, Morita CT, Oldfield E..  (2006)  Isoprenoid biosynthesis as a drug target: bisphosphonate inhibition of Escherichia coli K12 growth and synergistic effects of fosmidomycin.,  49  (25): [PMID:17149863] [10.1021/jm060492b]

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