1-[(n-oct-1-ylamino)ethyl]-1,1-bisphosphonic acid

ID: ALA260601

PubChem CID: 44451417

Max Phase: Preclinical

Molecular Formula: C10H25NO6P2

Molecular Weight: 317.26

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C10H25NO6P2/c1-2-3-4-5-6-7-8-11-9-10(18(12,13)14)19(15,16)17/h10-11H,2-9H2,1H3,(H2,12,13,14)(H2,15,16,17)

Standard InChI Key:  NTUHKTMOLKDMDP-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 19 18  0  0  0  0  0  0  0  0999 V2000
   -2.6584   -3.5109    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6584   -4.3359    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3728   -3.0984    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9438   -3.0984    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2375   -2.6766    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0884   -2.6859    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9605   -2.3837    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7843   -3.8134    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5261   -3.8097    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3595   -2.3857    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3728   -4.7484    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3728   -5.5734    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0873   -5.9859    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0873   -6.8109    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8017   -7.2234    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8017   -8.0484    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5162   -8.4609    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5162   -9.2859    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2307   -9.6984    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  4 10  2  0
  1  3  1  0
  2 11  1  0
  3  6  2  0
 11 12  1  0
  1  2  1  0
 12 13  1  0
  3  7  1  0
 13 14  1  0
  1  4  1  0
 14 15  1  0
  3  8  1  0
 15 16  1  0
 16 17  1  0
  4  9  1  0
 17 18  1  0
  4  5  1  0
 18 19  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA260601

   [2-(Octylamino)-1-phosphono-ethyl]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: 317.26

Molecular Weight (Monoisotopic): 317.1157

AlogP: 1.62

#Rotatable Bonds: 11

Polar Surface Area: 127.09

Molecular Species: ZWITTERION

HBA: 3

HBD: 5

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 5

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 0.71

CX Basic pKa: 11.31

CX LogP: -1.22

CX LogD: -3.57

Aromatic Rings: ┄

Heavy Atoms: 19

QED Weighted: 0.29

Np Likeness Score: 0.18

References

1. Szajnman SH, García Liñares GE, Li ZH, Jiang C, Galizzi M, Bontempi EJ, Ferella M, Moreno SN, Docampo R, Rodriguez JB..  (2008)  Synthesis and biological evaluation of 2-alkylaminoethyl-1,1-bisphosphonic acids against Trypanosoma cruzi and Toxoplasma gondii targeting farnesyl diphosphate synthase.,  16  (6): [PMID:18096393] [10.1016/j.bmc.2007.12.010]

2. Rosso VS, Szajnman SH, Malayil L, Galizzi M, Moreno SN, Docampo R, Rodriguez JB..  (2011)  Synthesis and biological evaluation of new 2-alkylaminoethyl-1,1-bisphosphonic acids against Trypanosoma cruzi and Toxoplasma gondii targeting farnesyl diphosphate synthase.,  19  (7): [PMID:21419634] [10.1016/j.bmc.2011.02.037]

Source

Source(1):

• Scientific Literature