[(Isoquinolin-1-ylamino)-phosphono-methyl]-phosphonic acid

ID: ALA291727

Chembl Id: CHEMBL291727

PubChem CID: 405731

Max Phase: Preclinical

Molecular Formula: C10H12N2O6P2

Molecular Weight: 318.16

Molecule Type: Small molecule

Names and Identifiers

Synonyms: (Isoquinolin-1-Ylamino)Methylenediphosphonic Acid | [(ISOQUINOLIN-1-YLAMINO)-PHOSPHONO-METHYL]-PHOSPHONIC ACID|CHEMBL291727|(Isoquinolin-1-Ylamino)Methylenediphosphonic Acid|1t1r|IMB|[(isoquinolin-1-ylamino)methanediyl]bis(phosphonic acid)|(3-ISOQUINOLYLAMINE) METHYLENE-1,1-BISPHOSPHONATE|BDBM50135835|NSC723273|NSC-723273|(3-isoquinolylamine)methylene-1,1-bisphosphonate|1-[(Bis-phosphono-methyl)-amino]-isoquinolinium|Q27461456

Canonical SMILES:  O=P(O)(O)C(Nc1nccc2ccccc12)P(=O)(O)O

Standard InChI:  InChI=1S/C10H12N2O6P2/c13-19(14,15)10(20(16,17)18)12-9-8-4-2-1-3-7(8)5-6-11-9/h1-6,10H,(H,11,12)(H2,13,14,15)(H2,16,17,18)

Standard InChI Key:  JPVMIOWESIQIGB-UHFFFAOYSA-N

Alternative Forms

1. Parent:

   

   ALA291727

   [(Isoquinolin-1-ylamino)-phosphono-methyl]-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: 318.16

Molecular Weight (Monoisotopic): 318.0171

AlogP: 1.29

#Rotatable Bonds: 4

Polar Surface Area: 139.98

Molecular Species: ACID

HBA: 4

HBD: 5

#RO5 Violations: 0

HBA (Lipinski): 8

HBD (Lipinski): 5

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 0.87

CX Basic pKa: 6.74

CX LogP: -1.59

CX LogD: -4.43

Aromatic Rings: 2

Heavy Atoms: 20

QED Weighted: 0.53

Np Likeness Score: -0.33

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. 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]

3. Ling Y, Sahota G, Odeh S, Chan JM, Araujo FG, Moreno SN, Oldfield E..  (2005)  Bisphosphonate inhibitors of Toxoplasma gondi growth: in vitro, QSAR, and in vivo investigations.,  48  (9): [PMID:15857119] [10.1021/jm040132t]

4. Deng L, Sundriyal S, Rubio V, Shi ZZ, Song Y..  (2009)  Coordination chemistry based approach to lipophilic inhibitors of 1-deoxy-D-xylulose-5-phosphate reductoisomerase.,  52  (21): [PMID:19888756] [10.1021/jm9012592]

5. 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]

6. Deng L, Endo K, Kato M, Cheng G, Yajima S, Song Y..  (2011)  Structures of 1-Deoxy-D-Xylulose-5-Phosphate Reductoisomerase/Lipophilic Phosphonate Complexes.,  2  (2): [PMID:21379374] [10.1021/ml100243r]

7. Deng L, Diao J, Chen P, Pujari V, Yao Y, Cheng G, Crick DC, Prasad BV, Song Y..  (2011)  Inhibition of 1-deoxy-D-xylulose-5-phosphate reductoisomerase by lipophilic phosphonates: SAR, QSAR, and crystallographic studies.,  54  (13): [PMID:21561155] [10.1021/jm200363d]

8. Kesharwani S, Sundriyal S..  (2021)  Non-hydroxamate inhibitors of 1-deoxy-d-xylulose 5-phosphate reductoisomerase (DXR): A critical review and future perspective.,  213  [PMID:33303239] [10.1016/j.ejmech.2020.113055]

Source

Source(1):

• Scientific Literature