6-(4-Benzyl-6-oxo-1,6-dihydro-pyrimidin-2-ylsulfanyl)-hexanoic acid hydroxyamide

ID: ALA218027

Chembl Id: CHEMBL218027

PubChem CID: 135513126

Max Phase: Preclinical

Molecular Formula: C17H21N3O3S

Molecular Weight: 347.44

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(CCCCCSc1nc(Cc2ccccc2)cc(=O)[nH]1)NO

Standard InChI:  InChI=1S/C17H21N3O3S/c21-15(20-23)9-5-2-6-10-24-17-18-14(12-16(22)19-17)11-13-7-3-1-4-8-13/h1,3-4,7-8,12,23H,2,5-6,9-11H2,(H,20,21)(H,18,19,22)

Standard InChI Key:  YDVCEIGTXDMBFG-UHFFFAOYSA-N

Alternative Forms

1. Parent:

   

   ALA218027

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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: 347.44

Molecular Weight (Monoisotopic): 347.1304

AlogP: 2.52

#Rotatable Bonds: 9

Polar Surface Area: 95.08

Molecular Species: NEUTRAL

HBA: 5

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 7.69

CX Basic pKa: 0.34

CX LogP: 2.70

CX LogD: 2.54

Aromatic Rings: 2

Heavy Atoms: 24

QED Weighted: 0.21

Np Likeness Score: -1.03

References

1. Mai A, Massa S, Rotili D, Pezzi R, Bottoni P, Scatena R, Meraner J, Brosch G..  (2005)  Exploring the connection unit in the HDAC inhibitor pharmacophore model: novel uracil-based hydroxamates.,  15  (21): [PMID:16165353] [10.1016/j.bmcl.2005.07.081]

2. Mai A, Massa S, Rotili D, Simeoni S, Ragno R, Botta G, Nebbioso A, Miceli M, Altucci L, Brosch G..  (2006)  Synthesis and biological properties of novel, uracil-containing histone deacetylase inhibitors.,  49  (20): [PMID:17004718] [10.1021/jm0605536]

3. Mai A, Rotili D, Massa S, Brosch G, Simonetti G, Passariello C, Palamara AT..  (2007)  Discovery of uracil-based histone deacetylase inhibitors able to reduce acquired antifungal resistance and trailing growth in Candida albicans.,  17  (5): [PMID:17196388] [10.1016/j.bmcl.2006.12.028]

4. Paris M, Porcelloni M, Binaschi M, Fattori D..  (2008)  Histone deacetylase inhibitors: from bench to clinic.,  51  (6): [PMID:18247554] [10.1021/jm7011408]

Source

Source(1):

• Scientific Literature