1-hydroxy-2-(octylamino)ethane-1,1-diyldiphosphonic acid

ID: ALA3099279

PubChem CID: 73057982

Max Phase: Preclinical

Molecular Formula: C10H25NO7P2

Molecular Weight: 333.26

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C10H25NO7P2/c1-2-3-4-5-6-7-8-11-9-10(12,19(13,14)15)20(16,17)18/h11-12H,2-9H2,1H3,(H2,13,14,15)(H2,16,17,18)

Standard InChI Key:  DWNAIXGVSUHJJI-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 20 19  0  0  0  0  0  0  0  0999 V2000
   18.5792   -3.5833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2917   -3.1708    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   18.5792   -4.4083    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   17.8584   -3.1708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2833   -2.3458    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.8667   -4.8208    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.0042   -2.7542    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.0084   -3.5792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.2959   -4.8208    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.7958   -5.2042    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.1458   -3.5917    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.4273   -3.1863    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7170   -3.6058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9985   -3.2004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2882   -3.6200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5696   -3.2146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2917   -3.9958    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.8592   -3.6342    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1407   -3.2288    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4304   -3.6483    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  1  1  0
  4  1  1  0
  5  2  2  0
  6  3  2  0
  7  2  1  0
  8  2  1  0
  9  3  1  0
 10  3  1  0
 11  4  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
  1 17  1  0
 16 18  1  0
 18 19  1  0
 19 20  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3099279

   [1-Hydroxy-2-(octylamino)-1-phosphonoethyl]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: 333.26

Molecular Weight (Monoisotopic): 333.1106

AlogP: 0.94

#Rotatable Bonds: 11

Polar Surface Area: 147.32

Molecular Species: ZWITTERION

HBA: 4

HBD: 6

#RO5 Violations: 1

HBA (Lipinski): 8

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 0.16

CX Basic pKa: 10.74

CX LogP: -1.52

CX LogD: -4.13

Aromatic Rings: ┄

Heavy Atoms: 20

QED Weighted: 0.24

Np Likeness Score: 0.22

References

1. Ferrer-Casal M, Li C, Galizzi M, Stortz CA, Szajnman SH, Docampo R, Moreno SN, Rodriguez JB..  (2014)  New insights into molecular recognition of 1,1-bisphosphonic acids by farnesyl diphosphate synthase.,  22  (1): [PMID:24300918] [10.1016/j.bmc.2013.11.010]

2. Galaka T, Falcone BN, Li C, Szajnman SH, Moreno SNJ, Docampo R, Rodriguez JB..  (2019)  Synthesis and biological evaluation of 1-alkylaminomethyl-1,1-bisphosphonic acids against Trypanosoma cruzi and Toxoplasma gondii.,  27  (16): [PMID:31296439] [10.1016/j.bmc.2019.07.004]

3. 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