(4S)-4-(4-methoxyphenyl)-3-(thiophen-2-yl)-1-(3,4,5-trimethoxyphenyl)azetidin-2-one

ID: ALA1766130

PubChem CID: 54583407

Max Phase: Preclinical

Molecular Formula: C23H23NO5S

Molecular Weight: 425.51

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccc([C@@H]2C(c3cccs3)C(=O)N2c2cc(OC)c(OC)c(OC)c2)cc1

Standard InChI:  InChI=1S/C23H23NO5S/c1-26-16-9-7-14(8-10-16)21-20(19-6-5-11-30-19)23(25)24(21)15-12-17(27-2)22(29-4)18(13-15)28-3/h5-13,20-21H,1-4H3/t20?,21-/m1/s1

Standard InChI Key:  UBXLUMZFFJRGAV-BPGUCPLFSA-N

Molfile:  

     RDKit          2D

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    5.1678  -14.9061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2911  -14.0989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5594  -13.7260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9786  -14.3068    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3515  -15.0384    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    8.9059  -13.1582    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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  4  5  1  1
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M  END

Alternative Forms

1. Parent:

   

   ALA1766130

   (4S)-4-(4-methoxyphenyl)-3-thiophen-2-yl-1-(3,4,5-trimethoxyphenyl)azetidin-2-one

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: 425.51

Molecular Weight (Monoisotopic): 425.1297

AlogP: 4.65

#Rotatable Bonds: 7

Polar Surface Area: 57.23

Molecular Species: NEUTRAL

HBA: 6

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 3.76

CX LogD: 3.76

Aromatic Rings: 3

Heavy Atoms: 30

QED Weighted: 0.52

Np Likeness Score: -0.58

References

1. O'Boyle NM, Greene LM, Bergin O, Fichet JB, McCabe T, Lloyd DG, Zisterer DM, Meegan MJ..  (2011)  Synthesis, evaluation and structural studies of antiproliferative tubulin-targeting azetidin-2-ones.,  19  (7): [PMID:21397510] [10.1016/j.bmc.2011.02.022]

Source

Source(1):

• Scientific Literature