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US8987314, B159

ID: ALA3677502

PubChem CID: 89967462

Max Phase: Preclinical

Molecular Formula: C24H29N5O7S3

Molecular Weight: 595.72

Molecule Type: Small molecule

This compound is available for customization.

Associated Items:

Names and Identifiers

Canonical SMILES:  NCCS(=O)(=O)C(C(=O)NCCS(N)(=O)=O)c1nc2ccc(-c3ccc(C(=O)N4CCOCC4)cc3)cc2s1

Standard InChI:  InChI=1S/C24H29N5O7S3/c25-7-13-38(32,33)21(22(30)27-8-14-39(26,34)35)23-28-19-6-5-18(15-20(19)37-23)16-1-3-17(4-2-16)24(31)29-9-11-36-12-10-29/h1-6,15,21H,7-14,25H2,(H,27,30)(H2,26,34,35)

Standard InChI Key:  VUSSSPQHLSKOEZ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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    6.2976   -5.7360    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7968   -5.7302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0505   -4.4281    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    5.2505   -4.4321    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6541   -3.3910    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5497   -4.4224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7974   -5.7210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5974   -5.7189    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5451   -7.0223    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7928   -8.3210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.5882  -10.9189    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1862  -11.9591    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8032   -3.1233    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.0000    1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2990    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2990   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3114   -2.9665    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5987    1.5004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6012    3.0004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9015    3.7484    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1993    2.9963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1969    1.4963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8967    0.7484    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5018    3.7420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5058    4.9420    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7993    2.9876    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1021    3.7310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.3974    2.9744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.3898    1.4745    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0870    0.7310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7918    1.4876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  4  6  2  0
  4  7  1  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 13 15  2  0
 13 16  1  0
  7 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
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 30 31  2  0
 31 26  1  0
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 32 34  1  0
 34 35  1  0
 35 36  1  0
 36 37  1  0
 37 38  1  0
 38 39  1  0
 39 34  1  0
M  END

Associated Targets(Human)

LIPG Tchem Endothelial lipase (1021 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
LIPC Tchem Hepatic lipase (436 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Molecule Features

Natural Product: NoOral: NoChemical Probe: NoParenteral: No
Molecule Type: Small moleculeTopical: NoFirst In Class: NoBlack Box: No
Chirality: NoAvailability: NoProdrug: No

Biocomponents

Calculated Properties

Molecular Weight: 595.72Molecular Weight (Monoisotopic): 595.1229AlogP: 0.26#Rotatable Bonds: 10
Polar Surface Area: 191.85Molecular Species: NEUTRALHBA: 10HBD: 3
#RO5 Violations: 1HBA (Lipinski): 12HBD (Lipinski): 5#RO5 Violations (Lipinski): 2
CX Acidic pKa: 7.29CX Basic pKa: 8.15CX LogP: -1.94CX LogD: -1.95
Aromatic Rings: 3Heavy Atoms: 39QED Weighted: 0.29Np Likeness Score: -1.49

References

1.  (2015)  Amide, urea or sulfone amide linked benzothiazole inhibitors of endothelial lipase, 
2. Goodman, Krista B KB and 24 more authors.  2009-01-01  Discovery of potent, selective sulfonylfuran urea endothelial lipase inhibitors.  [PMID:19058966]
3. Sun, Shaoyi S and 15 more authors.  2013-12-15  Discovery of XEN445: a potent and selective endothelial lipase inhibitor raises plasma HDL-cholesterol concentration in mice.  [PMID:24211162]
4. and Abdel-Magid, Ahmed F AF.  2013-11-14  Endothelial lipase inhibitors for the treatment of atherosclerosis and cardiovascular disorders.  [PMID:24900598]
5. Johnson, James A JA and 22 more authors.  2018-12-13  Sulfonylated Benzothiazoles as Inhibitors of Endothelial Lipase.  [PMID:30613337]
6. Kim, Soong-Hoon SH and 25 more authors.  2019-08-01  Identification of substituted benzothiazole sulfones as potent and selective inhibitors of endothelial lipase.  [PMID:31176700]

Source

Source(1):