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

ID: ALA409012

PubChem CID: 13211562

Max Phase: Preclinical

Molecular Formula: C7H19NO6P2

Molecular Weight: 275.18

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C7H19NO6P2/c1-2-3-4-5-8-6-7(15(9,10)11)16(12,13)14/h7-8H,2-6H2,1H3,(H2,9,10,11)(H2,12,13,14)

Standard InChI Key:  YDYMUJPNPOBLGS-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 16 15  0  0  0  0  0  0  0  0999 V2000
    6.5771    2.8509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5771    2.0259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8626    3.2634    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    7.2916    3.2634    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    7.9979    3.6850    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1471    3.6759    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2748    3.9779    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4512    2.5483    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7092    2.5519    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8759    3.9760    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8626    1.6134    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.8626    0.7884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1481    0.3759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1481   -0.4491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4337   -0.8616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4337   -1.6866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  4  9  1  0
  4  5  1  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
M  END

Alternative Forms

1. Parent:

   

   ALA409012

   [2-(Pentylamino)ethane-1,1-Diyl]bis(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: 275.18

Molecular Weight (Monoisotopic): 275.0688

AlogP: 0.45

#Rotatable Bonds: 8

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: -2.48

CX LogD: -4.83

Aromatic Rings: ┄

Heavy Atoms: 16

QED Weighted: 0.32

Np Likeness Score: 0.15

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. Aripirala S, Szajnman SH, Jakoncic J, Rodriguez JB, Docampo R, Gabelli SB, Amzel LM..  (2012)  Design, synthesis, calorimetry, and crystallographic analysis of 2-alkylaminoethyl-1,1-bisphosphonates as inhibitors of Trypanosoma cruzi farnesyl diphosphate synthase.,  55  (14): [PMID:22715997] [10.1021/jm300425y]

Source

Source(1):

• Scientific Literature