(R)-4-(2,5-dimethylbenzoyl)-3-hydroxy-5-(4-hydroxyphenyl)-1-phenethyl-1H-pyrrol-2(5H)-one

ID: ALA606193

PubChem CID: 46233561

Max Phase: Preclinical

Molecular Formula: C27H25NO4

Molecular Weight: 427.50

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1ccc(C)c(C(=O)C2=C(O)C(=O)N(CCc3ccccc3)[C@@H]2c2ccc(O)cc2)c1

Standard InChI:  InChI=1S/C27H25NO4/c1-17-8-9-18(2)22(16-17)25(30)23-24(20-10-12-21(29)13-11-20)28(27(32)26(23)31)15-14-19-6-4-3-5-7-19/h3-13,16,24,29,31H,14-15H2,1-2H3/t24-/m1/s1

Standard InChI Key:  SVWUVFBDHGEBNF-XMMPIXPASA-N

Molfile:  

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   -1.5193   -8.6186    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7723  -10.2775    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3815  -11.6482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4990  -12.8612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0073  -12.7034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.5748  -11.7745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

Alternative Forms

1. Parent:

   

   ALA606193

   (4E,5R)-4-[(2,5-dimethylphenyl)-hydroxymethylidene]-5-(4-hydroxyphenyl)-1-(2-phenylethyl)pyrrolidine-2,3-dione

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: 427.50

Molecular Weight (Monoisotopic): 427.1784

AlogP: 4.83

#Rotatable Bonds: 6

Polar Surface Area: 77.84

Molecular Species: NEUTRAL

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.34

CX Basic pKa: ┄

CX LogP: 4.99

CX LogD: 4.98

Aromatic Rings: 3

Heavy Atoms: 32

QED Weighted: 0.55

Np Likeness Score: -0.89

References

1. Podvinec M, Lim SP, Schmidt T, Scarsi M, Wen D, Sonntag LS, Sanschagrin P, Shenkin PS, Schwede T..  (2010)  Novel inhibitors of dengue virus methyltransferase: discovery by in vitro-driven virtual screening on a desktop computer grid.,  53  (4): [PMID:20108931] [10.1021/jm900776m]

Source

Source(1):

• Scientific Literature