2-(4-(4-tert-butylphenylsulfonylimino)-1-oxo-1,4-dihydronaphthalen-2-ylthio)acetic acid

ID: ALA4526940

Cas Number: 881487-77-0

PubChem CID: 6022998

Max Phase: Preclinical

Molecular Formula: C22H21NO5S2

Molecular Weight: 443.55

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CC(C)(C)c1ccc(S(=O)(=O)/N=C2\C=C(SCC(=O)O)C(=O)c3ccccc32)cc1

Standard InChI:  InChI=1S/C22H21NO5S2/c1-22(2,3)14-8-10-15(11-9-14)30(27,28)23-18-12-19(29-13-20(24)25)21(26)17-7-5-4-6-16(17)18/h4-12H,13H2,1-3H3,(H,24,25)/b23-18+

Standard InChI Key:  BXWWOKYIKNEEHJ-PTGBLXJZSA-N

Molfile:  

 
     RDKit          2D

 30 32  0  0  0  0  0  0  0  0999 V2000
    6.7026  -20.6857    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8854  -20.6857    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    6.2940  -21.3934    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0569  -22.3283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0557  -23.1478    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7638  -23.5568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7620  -21.9194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4706  -22.3247    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4694  -23.1453    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1756  -23.5544    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8875  -23.1473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8887  -22.3267    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1779  -21.9131    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1733  -24.3716    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5941  -23.5579    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    7.3029  -23.1513    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0095  -23.5618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7183  -23.1552    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.0072  -24.3790    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1780  -21.0959    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.8857  -19.8701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5944  -19.4644    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5948  -18.6480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8866  -18.2386    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1765  -18.6515    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1796  -19.4666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8855  -17.4214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5927  -17.0119    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1772  -17.0137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8813  -16.6038    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  2  2  0
  4  5  2  0
  5  6  1  0
  6  9  2  0
  8  7  2  0
  7  4  1  0
  8  9  1  0
  8 13  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 10 14  2  0
 11 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 17 19  2  0
 13 20  2  0
 20  2  1  0
  2 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 21  1  0
 24 27  1  0
 27 28  1  0
 27 29  1  0
 27 30  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4526940

   2-[(4E)-4-(4-tert-butylphenyl)sulfonylimino-1-oxonaphthalen-2-yl]sulfanylacetic acid

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 443.55

Molecular Weight (Monoisotopic): 443.0861

AlogP: 4.06

#Rotatable Bonds: 5

Polar Surface Area: 100.87

Molecular Species: ACID

HBA: 5

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.00

CX Basic pKa: ┄

CX LogP: 3.75

CX LogD: 0.27

Aromatic Rings: 2

Heavy Atoms: 30

QED Weighted: 0.75

Np Likeness Score: -0.93

References

1. Ieda N, Itoh K, Inoue Y, Izumiya Y, Kawaguchi M, Miyata N, Nakagawa H..  (2019)  An irreversible inhibitor of peptidyl-prolyl cis/trans isomerase Pin1 and evaluation of cytotoxicity.,  29  (3): [PMID:30585173] [10.1016/j.bmcl.2018.12.044]

Source

Source(1):

• Scientific Literature