ID: ALA273910

Max Phase: Phase

Molecular Formula: C19H11BrF2N2O4

Molecular Weight: 449.21

Molecule Type: Small molecule

Representations

Synonyms (1): WAY-ARI-509
Synonyms from Alternative Forms(1):

Canonical SMILES:  O=C1CC2(C(=O)N1)C(=O)N(Cc1ccc(Br)cc1F)C(=O)c1ccc(F)cc12

Standard InChI:  InChI=1S/C19H11BrF2N2O4/c20-10-2-1-9(14(22)5-10)8-24-16(26)12-4-3-11(21)6-13(12)19(18(24)28)7-15(25)23-17(19)27/h1-6H,7-8H2,(H,23,25,27)

Standard InChI Key:  BMHZAHGTGIZZCT-UHFFFAOYSA-N

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

Properties

Molecular Weight: 449.21

Molecular Weight (Monoisotopic): 447.9870

AlogP: 2.19

#Rotatable Bonds: 2

Polar Surface Area: 83.55

Molecular Species: NEUTRAL

HBA: 4

HBD: 1

#RO5 Violations: 0

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 9.33

CX Basic pKa:

CX LogP: 2.50

CX LogD: 2.49

Aromatic Rings: 2

Heavy Atoms: 28

QED Weighted: 0.56

Np Likeness Score: -0.92

References

1. Malamas MS, Hohman TC, Millen J..  (1994)  Novel spirosuccinimide aldose reductase inhibitors derived from isoquinoline-1,3-diones: 2-[(4-bromo-2-fluorophenyl)methyl]-6- fluorospiro[isoquinoline-4(1H),3'-pyrrolidine]-1,2',3,5'(2H)-tetrone and congeners. 1.,  37  (13): [PMID:8027986] [10.1021/jm00039a017]

2. Ferrari AM, Degliesposti G, Sgobba M, Rastelli G..  (2007)  Validation of an automated procedure for the prediction of relative free energies of binding on a set of aldose reductase inhibitors.,  15  (24): [PMID:17870536] [10.1016/j.bmc.2007.08.019]

3. Dhagat U, Endo S, Hara A, El-Kabbani O..  (2008)  Inhibition of 3(17)alpha-hydroxysteroid dehydrogenase (AKR1C21) by aldose reductase inhibitors.,  16  (6): [PMID:18165015] [10.1016/j.bmc.2007.12.016]

4. Carbone V, Zhao HT, Chung R, Endo S, Hara A, El-Kabbani O..  (2009)  Correlation of binding constants and molecular modelling of inhibitors in the active sites of aldose reductase and aldehyde reductase.,  17  (3): [PMID:19121944] [10.1016/j.bmc.2008.12.024]

5. Endo S, Matsunaga T, Kuwata K, Zhao HT, El-Kabbani O, Kitade Y, Hara A..  (2010)  Chromene-3-carboxamide derivatives discovered from virtual screening as potent inhibitors of the tumour maker, AKR1B10.,  18  (7): [PMID:20304656] [10.1016/j.bmc.2010.02.050]

6. USP Dictionary of USAN and International Names (2010 edition) and USAN registrations 2007-date, 

Source

Source(2):

• Scientific Literature
• USP Dictionary of USAN and International Drug Names