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

ID: ALA1765148

PubChem CID: 54583194

Max Phase: Preclinical

Molecular Formula: C13H31NO6P2

Molecular Weight: 359.34

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C13H31NO6P2/c1-2-3-4-5-6-7-8-9-10-11-14-12-13(21(15,16)17)22(18,19)20/h13-14H,2-12H2,1H3,(H2,15,16,17)(H2,18,19,20)

Standard InChI Key:  KVSGRVWBMQEWPD-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 22 21  0  0  0  0  0  0  0  0999 V2000
   -0.5110   -7.4746    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2052   -7.0612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2273   -7.0612    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.2052   -6.2340    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    0.9214   -7.4746    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    0.9214   -5.8206    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6242   -6.2302    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2146   -5.5124    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6377   -7.0612    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5033   -8.1847    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5020   -8.0520    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9428   -7.4746    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6567   -7.0612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3706   -7.4746    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0845   -7.0612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7984   -7.4746    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5124   -7.0612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2263   -7.4746    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9402   -7.0612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6541   -7.4746    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3729   -7.0621    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0929   -7.4767    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  4  6  2  0
  3 12  1  0
  1  2  1  0
 12 13  1  0
  4  7  1  0
 13 14  1  0
  2  4  1  0
 14 15  1  0
  4  8  1  0
 15 16  1  0
 16 17  1  0
  5  9  2  0
 17 18  1  0
  2  5  1  0
 18 19  1  0
  5 10  1  0
 19 20  1  0
  1  3  1  0
 20 21  1  0
  5 11  1  0
 21 22  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1765148

   1-[(n-Undec-1-ylamino)ethyl]1,1-bisphosphonic 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: 359.34

Molecular Weight (Monoisotopic): 359.1627

AlogP: 2.79

#Rotatable Bonds: 14

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: 0.04

CX LogD: -2.31

Aromatic Rings: ┄

Heavy Atoms: 22

QED Weighted: 0.24

Np Likeness Score: 0.15

References

1. 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]

2. Wu RZ, Zhou HY, Song JF, Xia QH, Hu W, Mou XD, Li X..  (2021)  Chemotherapeutics for Toxoplasma gondii: Molecular Biotargets, Binding Modes, and Structure-Activity Relationship Investigations.,  64  (24.0): [PMID:34894691] [10.1021/acs.jmedchem.1c01569]

Source

Source(1):

• Scientific Literature