[(4-Heptyl-phenylamino)-phosphono-methyl]-phosphonic acid

ID: ALA433833

PubChem CID: 5277463

Max Phase: Preclinical

Molecular Formula: C14H25NO6P2

Molecular Weight: 365.30

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCCCCCc1ccc(NC(P(=O)(O)O)P(=O)(O)O)cc1

Standard InChI:  InChI=1S/C14H25NO6P2/c1-2-3-4-5-6-7-12-8-10-13(11-9-12)15-14(22(16,17)18)23(19,20)21/h8-11,14-15H,2-7H2,1H3,(H2,16,17,18)(H2,19,20,21)

Standard InChI Key:  IGHWTRWWSFAETJ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 23 23  0  0  0  0  0  0  0  0999 V2000
   15.7101  -14.8490    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7089  -15.6763    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4236  -16.0892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1401  -15.6759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1372  -14.8453    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4218  -14.4363    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8583  -14.4262    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.8554  -13.5971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1389  -13.1826    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   18.5679  -13.1827    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   19.2897  -12.7686    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.4193  -12.7687    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.5552  -12.4618    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.7213  -13.9034    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.9831  -13.9034    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.5613  -12.3575    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.9939  -16.0921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2783  -15.6819    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5651  -16.0967    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8494  -15.6865    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1363  -16.1012    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4206  -15.6910    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7074  -16.1058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  5  6  2  0
  9 12  2  0
  6  1  1  0
  9 13  1  0
  1  2  2  0
  9 14  1  0
  5  7  1  0
 10 15  1  0
  3  4  2  0
 10 16  1  0
  7  8  1  0
  2 17  1  0
 17 18  1  0
  8  9  1  0
 18 19  1  0
  4  5  1  0
 19 20  1  0
  8 10  1  0
 20 21  1  0
  2  3  1  0
 21 22  1  0
 10 11  2  0
 22 23  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA433833

   [(4-Heptylanilino)-phosphono-methyl]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: 365.30

Molecular Weight (Monoisotopic): 365.1157

AlogP: 3.25

#Rotatable Bonds: 10

Polar Surface Area: 127.09

Molecular Species: ACID

HBA: 3

HBD: 5

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 5

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 0.95

CX Basic pKa: ┄

CX LogP: 3.09

CX LogD: -1.74

Aromatic Rings: 1

Heavy Atoms: 23

QED Weighted: 0.32

Np Likeness Score: -0.05

References

1. Ghosh S, Chan JM, Lea CR, Meints GA, Lewis JC, Tovian ZS, Flessner RM, Loftus TC, Bruchhaus I, Kendrick H, Croft SL, Kemp RG, Kobayashi S, Nozaki T, Oldfield E..  (2004)  Effects of bisphosphonates on the growth of Entamoeba histolytica and Plasmodium species in vitro and in vivo.,  47  (1): [PMID:14695831] [10.1021/jm030084x]

2. Hudock MP, Sanz-Rodríguez CE, Song Y, Chan JM, Zhang Y, Odeh S, Kosztowski T, Leon-Rossell A, Concepción JL, Yardley V, Croft SL, Urbina JA, Oldfield E..  (2006)  Inhibition of Trypanosoma cruzi hexokinase by bisphosphonates.,  49  (1): [PMID:16392806] [10.1021/jm0582625]

3. Leon A, Liu L, Yang Y, Hudock MP, Hall P, Yin F, Studer D, Puan KJ, Morita CT, Oldfield E..  (2006)  Isoprenoid biosynthesis as a drug target: bisphosphonate inhibition of Escherichia coli K12 growth and synergistic effects of fosmidomycin.,  49  (25): [PMID:17149863] [10.1021/jm060492b]

4. Sanz-Rodríguez CE, Concepción JL, Pekerar S, Oldfield E, Urbina JA..  (2007)  Bisphosphonates as inhibitors of Trypanosoma cruzi hexokinase: kinetic and metabolic studies.,  282  (17): [PMID:17329254] [10.1074/jbc.m607286200]

5. Song Y, Chan JM, Tovian Z, Secrest A, Nagy E, Krysiak K, Bergan K, Parniak MA, Oldfield E..  (2008)  Bisphosphonate inhibitors of ATP-mediated HIV-1 reverse transcriptase catalyzed excision of chain-terminating 3'-azido, 3'-deoxythymidine: a QSAR investigation.,  16  (19): [PMID:18789701] [10.1016/j.bmc.2008.08.047]

Source

Source(1):

• Scientific Literature