ID: ALA53982

Max Phase: Preclinical

Molecular Formula: C12H21NO8P2

Molecular Weight: 369.25

Molecule Type: Small molecule

Representations

Canonical SMILES:  CN(CCOc1ccccc1)CCC(O)(P(=O)(O)O)P(=O)(O)O

Standard InChI:  InChI=1S/C12H21NO8P2/c1-13(9-10-21-11-5-3-2-4-6-11)8-7-12(14,22(15,16)17)23(18,19)20/h2-6,14H,7-10H2,1H3,(H2,15,16,17)(H2,18,19,20)

Standard InChI Key:  ZEQNCEOOAYAQEG-UHFFFAOYSA-N

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

Properties

Molecular Weight: 369.25

Molecular Weight (Monoisotopic): 369.0742

AlogP: 0.39

#Rotatable Bonds: 9

Polar Surface Area: 147.76

Molecular Species: ZWITTERION

HBA: 5

HBD: 5

#RO5 Violations: 0

HBA (Lipinski): 9

HBD (Lipinski): 5

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 0.66

CX Basic pKa: 9.07

CX LogP: -2.57

CX LogD: -4.95

Aromatic Rings: 1

Heavy Atoms: 23

QED Weighted: 0.39

Np Likeness Score: -0.44

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. Kotsikorou E, Oldfield E..  (2003)  A quantitative structure-activity relationship and pharmacophore modeling investigation of aryl-X and heterocyclic bisphosphonates as bone resorption agents.,  46  (14): [PMID:12825934] [10.1021/jm030054u]

3. 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]

4. 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]

5. Hudock MP, Sanz-Rodríguez CE, Song Y, Chan JM, Zhang Y, Odeh S, Kosztowski T, Leon-Rossell A, Concepción JL, Yardley V, Croft SL, Urbina JA, Oldfield E..  (2006)  Inhibition of Trypanosoma cruzi hexokinase by bisphosphonates.,  49  (1): [PMID:16392806] [10.1021/jm0582625]

6. 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]

7. 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]

Source

Source(1):

• Scientific Literature