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

ID: ALA1765150

PubChem CID: 54583195

Max Phase: Preclinical

Molecular Formula: C16H37NO6P2

Molecular Weight: 401.42

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C16H37NO6P2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-17-15-16(24(18,19)20)25(21,22)23/h16-17H,2-15H2,1H3,(H2,18,19,20)(H2,21,22,23)

Standard InChI Key:  IBUPDMMMNDTFGH-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 25 24  0  0  0  0  0  0  0  0999 V2000
   26.9889   -6.6624    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.7050   -6.2489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.2727   -6.2489    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   27.7050   -5.4220    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   28.4211   -6.6624    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   28.4211   -5.0085    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.8757   -5.4180    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.2852   -4.7003    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   29.1373   -6.2489    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   28.0030   -7.3723    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   29.0016   -7.2396    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.5573   -6.6624    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.8435   -6.2489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.1296   -6.6624    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.4158   -6.2489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.7019   -6.6624    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.9882   -6.2489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.2743   -6.6624    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.5605   -6.2489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8466   -6.6624    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1300   -6.2500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4143   -6.6643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6976   -6.2519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9820   -6.6664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2653   -6.2540    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  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
  4  6  2  0
 22 23  1  0
  3 12  1  0
 23 24  1  0
  1  2  1  0
 24 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1765150

   1-[(n-Tetradec-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: 401.42

Molecular Weight (Monoisotopic): 401.2096

AlogP: 3.96

#Rotatable Bonds: 17

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: 1.30

CX LogD: -1.05

Aromatic Rings: ┄

Heavy Atoms: 25

QED Weighted: 0.18

Np Likeness Score: 0.14

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