2-(5-{3-[6-(1-methanesulfonyl-1-methyl-ethyl)-quinolin-8-yl]-phenyl}-1-oxy-pyridin-2-yl)-propan-2-ol

ID: ALA436847

PubChem CID: 10005210

Max Phase: Preclinical

Molecular Formula: C27H28N2O4S

Molecular Weight: 476.60

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(C)(O)c1ccc(-c2cccc(-c3cc(C(C)(C)S(C)(=O)=O)cc4cccnc34)c2)c[n+]1[O-]

Standard InChI:  InChI=1S/C27H28N2O4S/c1-26(2,30)24-12-11-21(17-29(24)31)18-8-6-9-19(14-18)23-16-22(27(3,4)34(5,32)33)15-20-10-7-13-28-25(20)23/h6-17,30H,1-5H3

Standard InChI Key:  JFRDONMCKIEZHW-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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    2.6932    0.8727    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4081    0.4598    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.4063    2.1128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1216    1.7037    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    5.8424    2.8390    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6833    2.9625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    5.5564   -1.5868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5515   -0.7640    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2694   -1.9917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2727   -2.8178    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9886   -3.2262    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.9779   -1.5757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6944   -1.9804    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7031   -2.8077    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9933   -4.0512    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.4240   -3.2139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1333   -3.6250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.8333   -2.4977    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0213   -3.9340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  7  8  2  0
 12 17  2  0
  5  4  1  0
  8  9  1  0
 18 19  2  0
  4  1  2  0
 19 20  1  0
  9 10  2  0
 20 21  2  0
 10  5  1  0
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  7 18  1  0
  9 11  1  0
  2  3  2  0
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 11 12  1  0
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  5  6  2  0
 28 27  2  0
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 11 13  1  0
  3  6  1  0
 11 14  1  0
 26 30  1  0
  6  7  1  0
 29 31  1  0
 12 15  1  0
 31 32  1  0
  1  2  1  0
 31 33  1  0
 12 16  2  0
 31 34  1  0
M  CHG  2  26   1  30  -1
M  END

Alternative Forms

1. Parent:

   

   ALA436847

   2-[5-[3-[6-(2-Methylsulfonylpropan-2-yl)quinolin-8-yl]phenyl]-1-oxidopyridin-1-ium-2-yl]propan-2-ol

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: 476.60

Molecular Weight (Monoisotopic): 476.1770

AlogP: 4.71

#Rotatable Bonds: 5

Polar Surface Area: 94.20

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.88

CX Basic pKa: 3.89

CX LogP: 2.92

CX LogD: 2.92

Aromatic Rings: 4

Heavy Atoms: 34

QED Weighted: 0.33

Np Likeness Score: -0.31

References

1. Gallant M, Chauret N, Claveau D, Day S, Deschênes D, Dubé D, Huang Z, Lacombe P, Laliberté F, Lévesque JF, Liu S, Macdonald D, Mancini J, Masson P, Mastracchio A, Nicholson D, Nicoll-Griffith DA, Perrier H, Salem M, Styhler A, Young RN, Girard Y..  (2008)  Design, synthesis, and biological evaluation of 8-biarylquinolines: a novel class of PDE4 inhibitors.,  18  (4): [PMID:18207397] [10.1016/j.bmcl.2008.01.004]

Source

Source(1):

• Scientific Literature