N-(4-fluorobenzyl)-(1,3,6,7-Tetramethoxyxanthone-4-yl)-sulfonamide

ID: ALA1096716

PubChem CID: 46887525

Max Phase: Preclinical

Molecular Formula: C24H22FNO8S

Molecular Weight: 503.50

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cc2oc3c(S(=O)(=O)NCc4ccc(F)cc4)c(OC)cc(OC)c3c(=O)c2cc1OC

Standard InChI:  InChI=1S/C24H22FNO8S/c1-30-17-9-15-16(10-18(17)31-2)34-23-21(22(15)27)19(32-3)11-20(33-4)24(23)35(28,29)26-12-13-5-7-14(25)8-6-13/h5-11,26H,12H2,1-4H3

Standard InChI Key:  GTIXGRYGQGNEOV-UHFFFAOYSA-N

Molfile:  

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   16.2772  -13.7336    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.2583  -12.3083    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   18.8039  -16.5449    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

Alternative Forms

1. Parent:

   

   ALA1096716

   N-[(4-fluorophenyl)methyl]-1,3,6,7-tetramethoxy-9-oxoxanthene-4-sulfonamide

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: 503.50

Molecular Weight (Monoisotopic): 503.1050

AlogP: 3.60

#Rotatable Bonds: 8

Polar Surface Area: 113.30

Molecular Species: NEUTRAL

HBA: 8

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 9

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 9.06

CX Basic pKa: ┄

CX LogP: 3.03

CX LogD: 3.02

Aromatic Rings: 4

Heavy Atoms: 35

QED Weighted: 0.36

Np Likeness Score: -0.28

References

1. Hu H, Liao H, Zhang J, Wu W, Yan J, Yan Y, Zhao Q, Zou Y, Chai X, Yu S, Wu Q..  (2010)  First identification of xanthone sulfonamides as potent acyl-CoA:cholesterol acyltransferase (ACAT) inhibitors.,  20  (10): [PMID:20403694] [10.1016/j.bmcl.2010.03.101]

2. Pokhrel, Laxman and 5 more authors.  2012-10-25  Inhibition of Acyl-CoA: cholesterol acyltransferase (ACAT), overexpression of cholesterol transporter gene, and protection of amyloid β (Aβ) oligomers-induced neuronal cell death by tricyclic pyrone molecules.  [PMID:23025824]

3. Ting, Pauline C PC and 10 more authors.  2013-02-15  Lead optimization of a pyridine-carboxamide series as DGAT-1 inhibitors.  [PMID:23317570]

4. Eguchi, Keisuke K and 10 more authors.  2013-07-01  Manzamine A, a marine-derived alkaloid, inhibits accumulation of cholesterol ester in macrophages and suppresses hyperlipidemia and atherosclerosis in vivo.  [PMID:23665143]

Source

Source(1):

• Scientific Literature