[(3-Hydroxymethyl-phenylamino)-phosphono-methyl]-phosphonic acid

ID: ALA443750

PubChem CID: 5277501

Max Phase: Preclinical

Molecular Formula: C8H13NO7P2

Molecular Weight: 297.14

Molecule Type: Small molecule

Names and Identifiers

Synonyms: (3-(Hydroxymethyl)Phenylamino)Methylenediphosphonic Acid | CHEMBL443750|(3-(Hydroxymethyl)Phenylamino)Methylenediphosphonic Acid|BDBM50173787|[[3-(hydroxymethyl)anilino]-phosphono-methyl]phosphonic acid|[(3-Hydroxymethyl-phenylamino)-phosphono-methyl]-phosphonic acid|Phosphonic acid, [[[3-(hydroxymethyl)phenyl]amino]methylene]bis-

Canonical SMILES:  O=P(O)(O)C(Nc1cccc(CO)c1)P(=O)(O)O

Standard InChI:  InChI=1S/C8H13NO7P2/c10-5-6-2-1-3-7(4-6)9-8(17(11,12)13)18(14,15)16/h1-4,8-10H,5H2,(H2,11,12,13)(H2,14,15,16)

Standard InChI Key:  XNWSSGDDXRUDAG-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 18 18  0  0  0  0  0  0  0  0999 V2000
   13.1021   -5.4425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1010   -6.2675    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8137   -6.6791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5280   -6.2670    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5252   -5.4389    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8119   -5.0309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2442   -5.0209    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.2414   -4.1941    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5268   -3.7808    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   15.9519   -3.7809    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   16.6716   -3.3679    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.8093   -3.3681    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.9419   -3.0621    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.1105   -4.4995    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.3659   -4.4996    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.3813   -5.0147    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6607   -5.4220    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.9453   -2.9581    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  8  9  1  0
  4  5  1  0
  8 10  1  0
  2  3  1  0
 10 11  2  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
  1 16  1  0
  7  8  1  0
 16 17  1  0
 10 18  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA443750

   (3-(Hydroxymethyl)Phenylamino)Methylenediphosphonic 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: 297.14

Molecular Weight (Monoisotopic): 297.0167

AlogP: 0.23

#Rotatable Bonds: 5

Polar Surface Area: 147.32

Molecular Species: ACID

HBA: 4

HBD: 6

#RO5 Violations: 1

HBA (Lipinski): 8

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 0.95

CX Basic pKa: ┄

CX LogP: -0.70

CX LogD: -5.52

Aromatic Rings: 1

Heavy Atoms: 18

QED Weighted: 0.42

Np Likeness Score: -0.13

References

1. Kotsikorou E, Song Y, Chan JM, Faelens S, Tovian Z, Broderick E, Bakalara N, Docampo R, Oldfield E..  (2005)  Bisphosphonate inhibition of the exopolyphosphatase activity of the Trypanosoma brucei soluble vacuolar pyrophosphatase.,  48  (19): [PMID:16162013] [10.1021/jm058220g]

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. 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]

4. 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