[(9-ethyl-9H-carbazol-3-ylamino)-phosphono-methyl]-phosphonic acid

ID: ALA200262

PubChem CID: 5277469

Max Phase: Preclinical

Molecular Formula: C15H18N2O6P2

Molecular Weight: 384.27

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCn1c2ccccc2c2cc(NC(P(=O)(O)O)P(=O)(O)O)ccc21

Standard InChI:  InChI=1S/C15H18N2O6P2/c1-2-17-13-6-4-3-5-11(13)12-9-10(7-8-14(12)17)16-15(24(18,19)20)25(21,22)23/h3-9,15-16H,2H2,1H3,(H2,18,19,20)(H2,21,22,23)

Standard InChI Key:  FOIJEVZWWJSXFM-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 25 27  0  0  0  0  0  0  0  0999 V2000
    4.4074    0.0390    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1243    0.4527    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1215    1.2838    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4056    1.6933    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8350    1.6993    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.5515    1.2892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2650    1.7047    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    6.5546    0.4636    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    6.5468   -0.3586    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3803    0.4612    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7290    0.4626    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9771    2.1225    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6816    0.9920    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8485    2.4176    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6920    0.4522    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6932    1.2772    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9070    0.1985    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4230    0.8666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9080    1.5303    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5755    2.2800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7584    2.3672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2748    1.6986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6100    0.9515    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6507   -0.5864    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2022   -1.2007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  7 12  2  0
 15  1  1  0
  7 13  1  0
  5  6  1  0
  7 14  1  0
 15 16  2  0
  2  3  1  0
  6  7  1  0
 16 19  1  0
 18 17  1  0
 17 15  1  0
  6  8  1  0
  3  4  2  0
 18 19  2  0
  8  9  2  0
 19 20  1  0
  4 16  1  0
 20 21  2  0
  8 10  1  0
 21 22  1  0
  1  2  2  0
 22 23  2  0
 23 18  1  0
  8 11  1  0
 17 24  1  0
  3  5  1  0
 24 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA200262

   [[(9-Ethylcarbazol-3-yl)amino]-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: 384.27

Molecular Weight (Monoisotopic): 384.0640

AlogP: 2.87

#Rotatable Bonds: 5

Polar Surface Area: 132.02

Molecular Species: ACID

HBA: 4

HBD: 5

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 5

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 0.95

CX Basic pKa: ┄

CX LogP: 1.86

CX LogD: -2.96

Aromatic Rings: 3

Heavy Atoms: 25

QED Weighted: 0.43

Np Likeness Score: -0.71

References

1. 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]

2. 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]

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. Vermelho AB, Capaci GR, Rodrigues IA, Cardoso VS, Mazotto AM, Supuran CT..  (2017)  Carbonic anhydrases from Trypanosoma and Leishmania as anti-protozoan drug targets.,  25  (5): [PMID:28161253] [10.1016/j.bmc.2017.01.034]

Source

Source(1):

• Scientific Literature