6-Nitro-2-(3-nitro-phenyl)-chromen-4-one

ID: ALA292868

Chembl Id: CHEMBL292868

Cas Number: 100914-36-1

PubChem CID: 127714

Max Phase: Preclinical

Molecular Formula: C15H8N2O6

Molecular Weight: 312.24

Molecule Type: Small molecule

Names and Identifiers

Synonyms: 6-3'-Dinitroflavone | 3',6-Dinitroflavone|100914-36-1|6,3'-Dinitroflavone|6-nitro-2-(3-nitrophenyl)chromen-4-one|6-Nitro-2-(3-nitrophenyl)-4H-1-benzopyran-4-one|4H-1-Benzopyran-4-one, 6-nitro-2-(3-nitrophenyl)-|6-3'-Dinitroflavone|Flavone, 3',6-dinitro-|ZZ9K44TRN6|CHEMBL292868|SCHEMBL4607216|DTXSID90143576|PD182983|6-Nitro-2-(3-nitrophenyl)-4H-chromen-4-one

Canonical SMILES:  O=c1cc(-c2cccc([N+](=O)[O-])c2)oc2ccc([N+](=O)[O-])cc12

Standard InChI:  InChI=1S/C15H8N2O6/c18-13-8-15(9-2-1-3-10(6-9)16(19)20)23-14-5-4-11(17(21)22)7-12(13)14/h1-8H

Standard InChI Key:  CNVQMRWAJHEFGZ-UHFFFAOYSA-N

Alternative Forms

1. Parent:

   

   ALA292868

   3',6-Dinitroflavone

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: 312.24

Molecular Weight (Monoisotopic): 312.0382

AlogP: 3.28

#Rotatable Bonds: 3

Polar Surface Area: 116.49

Molecular Species: NEUTRAL

HBA: 6

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 2.85

CX LogD: 2.85

Aromatic Rings: 3

Heavy Atoms: 23

QED Weighted: 0.54

Np Likeness Score: -0.44

References

1. Huang X, Liu T, Gu J, Luo X, Ji R, Cao Y, Xue H, Wong JT, Wong BL, Pei G, Jiang H, Chen K..  (2001)  3D-QSAR model of flavonoids binding at benzodiazepine site in GABAA receptors.,  44  (12): [PMID:11384234] [10.1021/jm000557p]

2. Marde M, Zinczuk J, Colombo MI, Wasowski C, Viola H, Wolfman C, Medina JH, Ruveda EA, Paladini AC.  (1997)  Synthesis of halogenated/nitrated flavone derivatives and evaluation of their affinity for the central benzodiazepine receptor,  7  (15): [10.1016/S0960-894X(97)00343-0]

3. Marder M, Viola H, Wasowski C, Wolfman C, Waterman PG, Medina JH, Paladini AC.  (1995)  6,3'-Dinitroflavone, a novel high affinity ligand for the benzodiazepine receptor with potent anxiolytic properties,  5  (22): [10.1016/0960-894X(95)00464-5]

4. Dekermendjian K, Kahnberg P, Witt MR, Sterner O, Nielsen M, Liljefors T..  (1999)  Structure-activity relationships and molecular modeling analysis of flavonoids binding to the benzodiazepine site of the rat brain GABA(A) receptor complex.,  42  (21): [PMID:10543878] [10.1021/jm991010h]

5. Duchowicz PR, Vitale MG, Castro EA, Autino JC, Romanelli GP, Bennardi DO..  (2008)  QSAR modeling of the interaction of flavonoids with GABA(A) receptor.,  43  (8): [PMID:18158201] [10.1016/j.ejmech.2007.11.009]

6. Singh M, Kaur M, Silakari O..  (2014)  Flavones: an important scaffold for medicinal chemistry.,  84  [PMID:25019478] [10.1016/j.ejmech.2014.07.013]

Source

Source(1):

• Scientific Literature