(2Z,5Z)-2-{[4-(Adamantan-1-yl)-1,3-thiazol-2-yl]imino}-5-(4-hydroxy-3,5-dimethoxy-benzylidene)-1,3-thiazolidin-4-one

ID: ALA606914

PubChem CID: 136066067

Max Phase: Preclinical

Molecular Formula: C25H27N3O4S2

Molecular Weight: 497.64

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cc(/C=C2\S/C(=N\c3nc(C45CC6CC(CC(C6)C4)C5)cs3)NC2=O)cc(OC)c1O

Standard InChI:  InChI=1S/C25H27N3O4S2/c1-31-17-6-13(7-18(32-2)21(17)29)8-19-22(30)27-24(34-19)28-23-26-20(12-33-23)25-9-14-3-15(10-25)5-16(4-14)11-25/h6-8,12,14-16,29H,3-5,9-11H2,1-2H3,(H,26,27,28,30)/b19-8-

Standard InChI Key:  XABMQLCZOSQQOW-UWVJOHFNSA-N

Molfile:  

     RDKit          2D

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   13.9586  -16.1151    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
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   16.4027  -12.0036    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0039  -12.7306    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4313  -13.4338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9760  -11.2975    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   15.1791  -12.7490    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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  4  6  1  0
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 33 34  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA606914

   ---

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: 497.64

Molecular Weight (Monoisotopic): 497.1443

AlogP: 5.23

#Rotatable Bonds: 5

Polar Surface Area: 93.04

Molecular Species: NEUTRAL

HBA: 8

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 7

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 9.18

CX Basic pKa: ┄

CX LogP: 5.37

CX LogD: 5.36

Aromatic Rings: 2

Heavy Atoms: 34

QED Weighted: 0.55

Np Likeness Score: -0.73

References

1. Omar K, Geronikaki A, Zoumpoulakis P, Camoutsis C, Soković M, Cirić A, Glamoclija J..  (2010)  Novel 4-thiazolidinone derivatives as potential antifungal and antibacterial drugs.,  18  (1): [PMID:19914077] [10.1016/j.bmc.2009.10.041]

Source

Source(1):

• Scientific Literature